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Record Information
Version2.0
Creation Date2009-07-21 20:26:13 UTC
Update Date2014-12-24 20:25:49 UTC
Accession NumberT3D2704
Identification
Common NameMenadione
ClassSmall Molecule
DescriptionMenadione is a synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. Despite the fact that it can serve as a precursor to various types of vitamin K, menadione is generally not used as a nutritional supplement. Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia due to G6PD deficiency, neonatal brain or liver damage, or neonatal death in some cases. Moreover, menadione supplements have been banned by the FDA because of their high toxicity. It is sometimes called vitamin K3, although derivatives of naphthoquinone without the sidechain in the 3-position cannot exert all the functions of the K vitamins. Menadione is a vitamin precursor of K2 which utilizes alkylation in the liver to yield menaquinones (MK-n, n=1-13; K2 vitamers), and hence, is better classified as a provitamin.
Compound Type
  • Antifibrinolytic Agent
  • Dietary Supplement
  • Drug
  • Ester
  • Food Toxin
  • Metabolite
  • Micronutrient
  • Nutraceutical
  • Organic Compound
  • Supplement
  • Synthetic Compound
  • Vitamin
Chemical Structure
Thumb
Synonyms
Synonym
2-Methyl-1,4-naftochinon
2-Methyl-1,4-naphthalendione
2-Methyl-1,4-naphthalenedione
2-Methyl-1,4-naphthochinon
2-Methyl-1,4-naphthodione
2-Methyl-1,4-naphthoquinone
2-Methylnaphthoquinone
3-Methyl-1,4-naphthoquinone
Aquakay
Aquinone
Hemodal
Juva-K
K-Thrombyl
K-Vitan
Kaergona
Kanone
Kappaxan
Kappaxin
Karcon
Kareon
Kativ-G
Kayklot
Kaykot
Kaynone
Kayquinone
Kipca
Kipca-Oil Soluble
Klottone
Koaxin
Kolklot
Menadion
Menaphthene
Menaphthon
Menaphthone
Menaphtone
Menaquinone
Menaquinone O
Mitenon
Mitenone
MNQ
Panosine
Prokayvit
Synkavite
Synkay
Thyloquinone
Vitamin K0
Vitamin K2
Vitamin K3
Vitamin K3: 1,4-Dihydro-1,4-dioxo-2-methylnaphthalene
Chemical FormulaC11H8O2
Average Molecular Mass172.180 g/mol
Monoisotopic Mass172.052 g/mol
CAS Registry Number58-27-5
IUPAC Name2-methyl-1,4-dihydronaphthalene-1,4-dione
Traditional Namemenadione
SMILESCC1=CC(=O)C2=CC=CC=C2C1=O
InChI IdentifierInChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
InChI KeyInChIKey=MJVAVZPDRWSRRC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthoquinones
Direct ParentNaphthoquinones
Alternative Parents
Substituents
  • Naphthoquinone
  • Aryl ketone
  • Quinone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Fibroblasts
  • Kidney
  • Liver
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point107°C
Boiling PointNot Available
Solubility160 mg/L (at 30°C)
LogP2.2
Predicted Properties
PropertyValueSource
Water Solubility0.5 g/LALOGPS
logP1.91ALOGPS
logP1.89ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)12.94ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.54 m³·mol⁻¹ChemAxon
Polarizability17.64 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gk9-3900000000-ad6c0e599173ba802f73JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ufr-2910000000-bbd6cf78055e623046a6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ufr-2910000000-5db665917b8c152a80b2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0g4i-6900000000-0c6c7737ff416205089cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gk9-3900000000-ad6c0e599173ba802f73JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ufr-2910000000-bbd6cf78055e623046a6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ufr-2910000000-5db665917b8c152a80b2JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-1900000000-3c2bf459bf04eae7701dJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-074j-1900000000-a62dd17c23ac6e7fa95dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0aor-1900000000-ce35b89eaf766c9398e8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9100000000-65a9c21d7aa7be21de3aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0g4i-6900000000-0c6c7737ff416205089cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-1900000000-b489978f8a44b156f0f3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-1900000000-b489978f8a44b156f0f3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-ea17be197704c13eba82JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-2d0b65ea01fe9dd6b4feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-7900000000-509fb00927321d93a529JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-252f2831b39763f805b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-cea08e3f258cdd275a55JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-6900000000-b84149529316a1f0987fJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0gk9-5900000000-48fb5ac08ce624a689ccJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureVariable and ranges from 10% to 80%
Mechanism of ToxicityMenadione (vitamin K3) is involved as a cofactor in the posttranslational gamma-carboxylation of glutamic acid residues of certain proteins in the body. These proteins include the vitamin K-dependent coagulation factors II (prothrombin), VII (proconvertin), IX (Christmas factor), X (Stuart factor), protein C, protein S, protein Zv and a growth-arrest-specific factor (Gas6). In contrast to the other vitamin K-dependent proteins in the blood coagulation cascade, protein C and protein S serve anticoagulant roles. The two vitamin K-dependent proteins found in bone are osteocalcin, also known as bone G1a (gamma-carboxyglutamate) protein or BGP, and the matrix G1a protein or MGP. Gamma-carboxylation is catalyzed by the vitamin K-dependent gamma-carboxylases. The reduced form of vitamin K, vitamin K hydroquinone, is the actual cofactor for the gamma-carboxylases. Proteins containing gamma-carboxyglutamate are called G1a proteins.
MetabolismHepatic
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (16)
Uses/SourcesThe primary known function of vitamin K is to assist in the normal clotting of blood, but it may also play a role in normal bone calcification.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsMenadione (vitamin K3), which is not used as a nutritional supplemental form of vitamin K for humans, has been reported to cause adverse reactions, including hemolytic anemia. Large doses have also been reported to cause brain damage.
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00170
HMDB IDHMDB01892
PubChem Compound ID4055
ChEMBL IDCHEMBL590
ChemSpider ID3915
KEGG IDC05377
UniProt IDNot Available
OMIM ID109135 , 112260 , 113811 , 115430 , 118650 , 122700 , 137167 , 138140 , 154870 , 176860 , 176880 , 176930 , 188055 , 192090 , 204690 , 214900 , 215100 , 219700 , 227220 , 227500 , 227600 , 245150 , 252650 , 261515 , 277450 , 302960 , 305900 , 306900 , 310400 , 600424 , 600441 , 600646 , 601841 , 602421 , 602497 , 604428 , 604429 , 604824 , 605271 , 607473 , 607542 , 607748 , 608547 , 608838 , 610842
ChEBI ID28869
BioCyc IDCPD-3766
CTD IDNot Available
Stitch IDMenadione
PDB IDVK3
ACToR IDNot Available
Wikipedia LinkMenadione
References
Synthesis Reference

Joachim U. Schneider, Hans Kiefer, “Menadione choline bisulfite adduct, its preparation and antihemorrhagic compositions.” U.S. Patent US4735969, issued January, 1980.

MSDSLink
General References
  1. Robertson DG, Bailey DL, Martin RA: Species differences in response to photohemolytic agents. Photochem Photobiol. 1991 Apr;53(4):455-61. [1857739 ]
  2. Chladek J, Martinkova J, Sispera L: An in vitro study on methotrexate hydroxylation in rat and human liver. Physiol Res. 1997;46(5):371-9. [9728483 ]
  3. Habu D, Shiomi S, Tamori A, Takeda T, Tanaka T, Kubo S, Nishiguchi S: Role of vitamin K2 in the development of hepatocellular carcinoma in women with viral cirrhosis of the liver. JAMA. 2004 Jul 21;292(3):358-61. [15265851 ]
  4. Lasalvia-Prisco E, Cucchi S, Vazquez J, Lasalvia-Galante E, Golomar W, Gordon W: Serum markers variation consistent with autoschizis induced by ascorbic acid-menadione in patients with prostate cancer. Med Oncol. 2003;20(1):45-52. [12665684 ]
  5. Harrington DJ, Soper R, Edwards C, Savidge GF, Hodges SJ, Shearer MJ: Determination of the urinary aglycone metabolites of vitamin K by HPLC with redox-mode electrochemical detection. J Lipid Res. 2005 May;46(5):1053-60. Epub 2005 Feb 1. [15722567 ]
  6. Kwasnicka-Crawford DA, Vincent SR: Role of a novel dual flavin reductase (NR1) and an associated histidine triad protein (DCS-1) in menadione-induced cytotoxicity. Biochem Biophys Res Commun. 2005 Oct 21;336(2):565-71. [16140270 ]
  7. Snider BJ, Moss JL, Revilla FJ, Lee CS, Wheeler VC, Macdonald ME, Choi DW: Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults. Neuroscience. 2003;120(3):617-25. [12895502 ]
  8. Usui Y, Tanimura H, Nishimura N, Kobayashi N, Okanoue T, Ozawa K: Vitamin K concentrations in the plasma and liver of surgical patients. Am J Clin Nutr. 1990 May;51(5):846-52. [2333843 ]
  9. Ono M, Ohta H, Ohhira M, Sekiya C, Namiki M: Measurement of immunoreactive prothrombin, des-gamma-carboxy prothrombin, and vitamin K in human liver tissues: overproduction of immunoreactive prothrombin in hepatocellular carcinoma. Am J Gastroenterol. 1990 Sep;85(9):1149-54. [1697141 ]
  10. Suzuki S, Iwata G, Sutor AH: Vitamin K deficiency during the perinatal and infantile period. Semin Thromb Hemost. 2001;27(2):93-8. [11372776 ]
  11. Wermuth B, Platts KL, Seidel A, Oesch F: Carbonyl reductase provides the enzymatic basis of quinone detoxication in man. Biochem Pharmacol. 1986 Apr 15;35(8):1277-82. [3083821 ]
  12. Price RJ, Mistry H, Wield PT, Renwick AB, Beamand JA, Lake BG: Comparison of the toxicity of allyl alcohol, coumarin and menadione in precision-cut rat, guinea-pig, cynomolgus monkey and human liver slices. Arch Toxicol. 1996;71(1-2):107-11. [9010592 ]
  13. Thijssen HH, Drittij-Reijnders MJ: Vitamin K status in human tissues: tissue-specific accumulation of phylloquinone and menaquinone-4. Br J Nutr. 1996 Jan;75(1):121-7. [8785182 ]
  14. Iioka H, Moriyama IS, Morimoto K, Akada S, Hisanaga H, Ishihara Y, Ichijo M: Pharmacokinetics of vitamin K in mothers and children in the perinatal period: transplacental transport of vitamin K2 (MK-4). Asia Oceania J Obstet Gynaecol. 1991 Mar;17(1):97-100. [2064595 ]
  15. Strunnikova N, Hilmer S, Flippin J, Robinson M, Hoffman E, Csaky KG: Differences in gene expression profiles in dermal fibroblasts from control and patients with age-related macular degeneration elicited by oxidative injury. Free Radic Biol Med. 2005 Sep 15;39(6):781-96. [16109308 ]
  16. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Protein tyrosine phosphatase activity
Specific Function:
Tyrosine protein phosphatase which functions as a dosage-dependent inducer of mitotic progression. Required for G2/M phases of the cell cycle progression and abscission during cytokinesis in a ECT2-dependent manner. Directly dephosphorylates CDK1 and stimulates its kinase activity. The three isoforms seem to have a different level of activity.
Gene Name:
CDC25B
Uniprot ID:
P30305
Molecular Weight:
64986.745 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC502.2 uMNot AvailableBindingDB 24778
IC503.38 uMNot AvailableBindingDB 24778
References
  1. Sarkis M, Tran DN, Kolb S, Miteva MA, Villoutreix BO, Garbay C, Braud E: Design and synthesis of novel bis-thiazolone derivatives as micromolar CDC25 phosphatase inhibitors: effect of dimerisation on phosphatase inhibition. Bioorg Med Chem Lett. 2012 Dec 15;22(24):7345-50. doi: 10.1016/j.bmcl.2012.10.072. Epub 2012 Oct 22. [23141909 ]
  2. Cao S, Murphy BT, Foster C, Lazo JS, Kingston DG: Bioactivities of simplified adociaquinone B and naphthoquinone derivatives against Cdc25B, MKP-1, and MKP-3 phosphatases. Bioorg Med Chem. 2009 Mar 15;17(6):2276-81. doi: 10.1016/j.bmc.2008.10.090. Epub 2008 Nov 8. [19028102 ]
General Function:
Ww domain binding
Specific Function:
Functions as a dosage-dependent inducer in mitotic control. Tyrosine protein phosphatase required for progression of the cell cycle. When phosphorylated, highly effective in activating G2 cells into prophase. Directly dephosphorylates CDK1 and activates its kinase activity.
Gene Name:
CDC25C
Uniprot ID:
P30307
Molecular Weight:
53364.17 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC5018.8 uMNot AvailableBindingDB 24778
IC5019 uMNot AvailableBindingDB 24778
References
  1. Contour-Galcera MO, Lavergne O, Brezak MC, Ducommun B, Prevost G: Synthesis of small molecule CDC25 phosphatases inhibitors. Bioorg Med Chem Lett. 2004 Dec 6;14(23):5809-12. [15501045 ]
  2. Lavergne O, Fernandes AC, Brehu L, Sidhu A, Brezak MC, Prevost G, Ducommun B, Contour-Galcera MO: Synthesis and biological evaluation of novel heterocyclic quinones as inhibitors of the dual specificity protein phosphatase CDC25C. Bioorg Med Chem Lett. 2006 Jan 1;16(1):171-5. Epub 2005 Oct 10. [16216500 ]
General Function:
Xanthine dehydrogenase activity
Specific Function:
Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide and N-methylphthalazinium, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal, and vanillin. Plays a key role in the metabolism of xenobiotics and drugs containing aromatic azaheterocyclic substituents. Participates in the bioactivation of prodrugs such as famciclovir, catalyzing the oxidation step from 6-deoxypenciclovir to penciclovir, which is a potent antiviral agent. Is probably involved in the regulation of reactive oxygen species homeostasis. May be a prominent source of superoxide generation via the one-electron reduction of molecular oxygen. Also may catalyze nitric oxide (NO) production via the reduction of nitrite to NO with NADH or aldehyde as electron donor. May play a role in adipogenesis.
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular Weight:
147916.735 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC500.2 uMNot AvailableBindingDB 24778
References
  1. Pryde DC, Dalvie D, Hu Q, Jones P, Obach RS, Tran TD: Aldehyde oxidase: an enzyme of emerging importance in drug discovery. J Med Chem. 2010 Dec 23;53(24):8441-60. doi: 10.1021/jm100888d. Epub 2010 Sep 20. [20853847 ]
General Function:
Serotonin binding
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular Weight:
59681.27 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory26 uMNot AvailableBindingDB 24778
References
  1. Coelho Cerqueira E, Netz PA, Diniz C, Petry do Canto V, Follmer C: Molecular insights into human monoamine oxidase (MAO) inhibition by 1,4-naphthoquinone: evidences for menadione (vitamin K3) acting as a competitive and reversible inhibitor of MAO. Bioorg Med Chem. 2011 Dec 15;19(24):7416-24. doi: 10.1016/j.bmc.2011.10.049. Epub 2011 Oct 20. [22071524 ]
General Function:
Primary amine oxidase activity
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular Weight:
58762.475 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.4 uMNot AvailableBindingDB 24778
References
  1. Coelho Cerqueira E, Netz PA, Diniz C, Petry do Canto V, Follmer C: Molecular insights into human monoamine oxidase (MAO) inhibition by 1,4-naphthoquinone: evidences for menadione (vitamin K3) acting as a competitive and reversible inhibitor of MAO. Bioorg Med Chem. 2011 Dec 15;19(24):7416-24. doi: 10.1016/j.bmc.2011.10.049. Epub 2011 Oct 20. [22071524 ]
General Function:
Nadp binding
Specific Function:
Maintains high levels of reduced glutathione in the cytosol.
Gene Name:
GSR
Uniprot ID:
P00390
Molecular Weight:
56256.565 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory12.1 uMNot AvailableBindingDB 24778
Inhibitory16.1 uMNot AvailableBindingDB 24778
References
  1. Biot C, Bauer H, Schirmer RH, Davioud-Charvet E: 5-substituted tetrazoles as bioisosteres of carboxylic acids. Bioisosterism and mechanistic studies on glutathione reductase inhibitors as antimalarials. J Med Chem. 2004 Nov 18;47(24):5972-83. [15537352 ]
General Function:
Structural molecule activity
Specific Function:
Constitutes 1-2% of the total bone protein. It binds strongly to apatite and calcium.
Gene Name:
BGLAP
Uniprot ID:
P02818
Molecular Weight:
10962.445 Da
References
  1. Price PA: Role of vitamin-K-dependent proteins in bone metabolism. Annu Rev Nutr. 1988;8:565-83. [3060178 ]
General Function:
Lipid binding
Specific Function:
Modulator of adipocyte lipid metabolism. Coats lipid storage droplets to protect them from breakdown by hormone-sensitive lipase (HSL). Its absence may result in leanness. Plays a role in unilocular lipid droplet formation by activating CIDEC. Their interaction promotes lipid droplet enlargement and directional net neutral lipid transfer. May modulate lipolysis and triglyceride levels.
Gene Name:
PLIN1
Uniprot ID:
O60240
Molecular Weight:
55989.785 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC507.895 uMNot AvailableBindingDB 24778
References
  1. Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]
General Function:
Not Available
Specific Function:
Lipid droplet-associated protein that maintains the balance between lipogenesis and lipolysis and also regulates fatty acid oxidation in oxidative tissues. Recruits mitochondria to the surface of lipid droplets and is involved in lipid droplet homeostasis by regulating both the storage of fatty acids in the form of triglycerides and the release of fatty acids for mitochondrial fatty acid oxidation. In lipid droplet triacylglycerol hydrolysis, plays a role as a scaffolding protein for three major key lipolytic players: ABHD5, PNPLA2 and LIPE. Reduces the triacylglycerol hydrolase activity of PNPLA2 by recruiting and sequestering PNPLA2 to lipid droplets. Phosphorylation by PKA enables lipolysis probably by promoting release of ABHD5 from the perilipin scaffold and by facilitating interaction of ABHD5 with PNPLA2. Also increases lipolysis through interaction with LIPE and upon PKA-mediated phosphorylation of LIPE (By similarity).
Gene Name:
PLIN5
Uniprot ID:
Q00G26
Molecular Weight:
50790.96 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC509.468 uMNot AvailableBindingDB 24778
References
  1. Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]
General Function:
Protein-glutamine gamma-glutamyltransferase activity
Specific Function:
Catalyzes the cross-linking of proteins and the conjugation of polyamines to proteins.
Gene Name:
TGM2
Uniprot ID:
P21980
Molecular Weight:
77328.21 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC502.2 uMNot AvailableBindingDB 24778
References
  1. Lai TS, Liu Y, Tucker T, Daniel KR, Sane DC, Toone E, Burke JR, Strittmatter WJ, Greenberg CS: Identification of chemical inhibitors to human tissue transglutaminase by screening existing drug libraries. Chem Biol. 2008 Sep 22;15(9):969-78. doi: 10.1016/j.chembiol.2008.07.015. [18804034 ]
General Function:
Ubiquitin-specific protease activity
Specific Function:
Ubiquitin-protein hydrolase involved both in the processing of ubiquitin precursors and of ubiquitinated proteins. This enzyme is a thiol protease that recognizes and hydrolyzes a peptide bond at the C-terminal glycine of ubiquitin. Also binds to free monoubiquitin and may prevent its degradation in lysosomes. The homodimer may have ATP-independent ubiquitin ligase activity.
Gene Name:
UCHL1
Uniprot ID:
P09936
Molecular Weight:
24824.17 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC50290 uMNot AvailableBindingDB 24778
References
  1. Love KR, Catic A, Schlieker C, Ploegh HL: Mechanisms, biology and inhibitors of deubiquitinating enzymes. Nat Chem Biol. 2007 Nov;3(11):697-705. [17948018 ]
General Function:
Ubiquitin-specific protease activity
Specific Function:
Deubiquitinating enzyme (DUB) that controls levels of cellular ubiquitin through processing of ubiquitin precursors and ubiquitinated proteins. Thiol protease that recognizes and hydrolyzes a peptide bond at the C-terminal glycine of either ubiquitin or NEDD8. Has a 10-fold preference for Arg and Lys at position P3", and exhibits a preference towards 'Lys-48'-linked Ubiquitin chains. Deubiquitinates ENAC in apical compartments, thereby regulating apical membrane recycling. Indirectly increases the phosphorylation of IGFIR, AKT and FOXO1 and promotes insulin-signaling and insulin-induced adipogenesis. Required for stress-response retinal, skeletal muscle and germ cell maintenance. May be involved in working memory. Can hydrolyze UBB(+1), a mutated form of ubiquitin which is not effectively degraded by the proteasome and is associated with neurogenerative disorders.
Gene Name:
UCHL3
Uniprot ID:
P15374
Molecular Weight:
26182.385 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC5071 uMNot AvailableBindingDB 24778
References
  1. Love KR, Catic A, Schlieker C, Ploegh HL: Mechanisms, biology and inhibitors of deubiquitinating enzymes. Nat Chem Biol. 2007 Nov;3(11):697-705. [17948018 ]
General Function:
Serine-type endopeptidase activity
Specific Function:
Factor IX is a vitamin K-dependent plasma protein that participates in the intrinsic pathway of blood coagulation by converting factor X to its active form in the presence of Ca(2+) ions, phospholipids, and factor VIIIa.
Gene Name:
F9
Uniprot ID:
P00740
Molecular Weight:
51778.11 Da
General Function:
Serine-type peptidase activity
Specific Function:
Initiates the extrinsic pathway of blood coagulation. Serine protease that circulates in the blood in a zymogen form. Factor VII is converted to factor VIIa by factor Xa, factor XIIa, factor IXa, or thrombin by minor proteolysis. In the presence of tissue factor and calcium ions, factor VIIa then converts factor X to factor Xa by limited proteolysis. Factor VIIa will also convert factor IX to factor IXa in the presence of tissue factor and calcium.
Gene Name:
F7
Uniprot ID:
P08709
Molecular Weight:
51593.465 Da
General Function:
Serine-type endopeptidase activity
Specific Function:
Factor Xa is a vitamin K-dependent glycoprotein that converts prothrombin to thrombin in the presence of factor Va, calcium and phospholipid during blood clotting.
Gene Name:
F10
Uniprot ID:
P00742
Molecular Weight:
54731.255 Da
General Function:
Superoxide dismutase activity
Specific Function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO1
Uniprot ID:
P15559
Molecular Weight:
30867.405 Da
General Function:
Thrombospondin receptor activity
Specific Function:
Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostasis, inflammation and wound healing.
Gene Name:
F2
Uniprot ID:
P00734
Molecular Weight:
70036.295 Da
General Function:
Nadph dehydrogenase (quinone) activity
Specific Function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO2
Uniprot ID:
P16083
Molecular Weight:
25918.4 Da
General Function:
Vitamin-k-epoxide reductase (warfarin-sensitive) activity
Specific Function:
Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K. Vitamin K is required for the gamma-carboxylation of various proteins, including clotting factors, and is required for normal blood coagulation, but also for normal bone development.
Gene Name:
VKORC1
Uniprot ID:
Q9BQB6
Molecular Weight:
18234.3 Da
General Function:
Vitamin-k-epoxide reductase (warfarin-sensitive) activity
Specific Function:
Involved in vitamin K metabolism. Can reduce inactive vitamin K 2,3-epoxide to active vitamin K (in vitro), and may contribute to vitamin K-mediated protection against oxidative stress. Plays a role in vitamin K-dependent gamma-carboxylation of Glu residues in target proteins.
Gene Name:
VKORC1L1
Uniprot ID:
Q8N0U8
Molecular Weight:
19835.425 Da
General Function:
Gamma-glutamyl carboxylase activity
Specific Function:
Mediates the vitamin K-dependent carboxylation of glutamate residues to calcium-binding gamma-carboxyglutamate (Gla) residues with the concomitant conversion of the reduced hydroquinone form of vitamin K to vitamin K epoxide.
Gene Name:
GGCX
Uniprot ID:
P38435
Molecular Weight:
87560.065 Da
General Function:
Serine-type endopeptidase activity
Specific Function:
Protein C is a vitamin K-dependent serine protease that regulates blood coagulation by inactivating factors Va and VIIIa in the presence of calcium ions and phospholipids (PubMed:25618265). Exerts a protective effect on the endothelial cell barrier function (PubMed:25651845).
Gene Name:
PROC
Uniprot ID:
P04070
Molecular Weight:
52070.82 Da
General Function:
Endopeptidase inhibitor activity
Specific Function:
Anticoagulant plasma protein; it is a cofactor to activated protein C in the degradation of coagulation factors Va and VIIIa. It helps to prevent coagulation and stimulating fibrinolysis.
Gene Name:
PROS1
Uniprot ID:
P07225
Molecular Weight:
75121.905 Da
General Function:
Serine-type endopeptidase activity
Specific Function:
Appears to assist hemostasis by binding thrombin and promoting its association with phospholipid vesicles. Inhibits activity of the coagulation protease factor Xa in the presence of SERPINA10, calcium and phospholipids.
Gene Name:
PROZ
Uniprot ID:
P22891
Molecular Weight:
44743.605 Da