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Record Information
Version2.0
Creation Date2014-09-11 05:20:45 UTC
Update Date2014-12-24 20:26:59 UTC
Accession NumberT3D4883
Identification
Common NameSebacic acid
ClassSmall Molecule
DescriptionSebacic acid is a saturated, straight-chain naturally occurring dicarboxylic acid with 10 carbon atoms. Sebacic acid is a normal urinary acid. In patients with multiple acyl-CoA-dehydrogenase deficiency (MADD) or glutaric aciduria type II (GAII) are a group of metabolic disorders due to deficiency of either electron transfer flavoprotein or electron transfer flavoprotein ubiquinone oxidoreductase, biochemical data shows an increase in urine sebacic acid excretion. Sebacic acid is a white flake or powdered crystal slightly soluble in water that has been proposed as an alternative energy substrate in total parenteral nutrition. Sebacic Acid was named from the Latin sebaceus (tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles. Sebacic Acid and its derivatives such as azelaic acid have a variety of industrial uses as plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. It is used in the synthesis of polyamide and alkyd resins. It is also used as an intermediate for aromatics, antiseptics and painting materials. (1, 2, 3, 4).
Compound Type
  • Animal Toxin
  • Cosmetic Toxin
  • Food Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plasticizer
Chemical Structure
Thumb
Synonyms
Synonym
1,10-Decanedioate
1,10-Decanedioic acid
1,8-Octanedicarboxylate
1,8-Octanedicarboxylic acid
4,7-Dioxosebacic acid
4-Oxodecanedioate
4-Oxodecanedioic acid
Acide sebacique
Decanedicarboxylic acid
Decanedioate
Decanedioic acid
Dicarboxylic acid C10
Ipomic acid
N-Decanedioate
N-Decanedioic acid
Sebacate
Sebacic acids
Sebacinsaeure
Sebacinsaure
Seracic acid
Chemical FormulaC10H18O4
Average Molecular Mass202.248 g/mol
Monoisotopic Mass202.121 g/mol
CAS Registry Number111-20-6
IUPAC Namedecanedioic acid
Traditional Namesebacic acid
SMILESOC(=O)CCCCCCCCC(O)=O
InChI IdentifierInChI=1S/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)
InChI KeyInChIKey=CXMXRPHRNRROMY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point130.8 °C
Boiling Point294.4°C
Solubility1.0 mg/mL
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.91 g/LALOGPS
logP1.93ALOGPS
logP2.27ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.72ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity51.14 m³·mol⁻¹ChemAxon
Polarizability22.61 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00mk-2910000000-944d83241331f8be19a6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00mk-1910000000-2e3fc1189a96874a25c9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00fr-9400000000-d288a779699c505fde08JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00pj-3910000000-87feed2c593dbff7fae8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00mk-2910000000-944d83241331f8be19a6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00mk-1910000000-2e3fc1189a96874a25c9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00fr-9400000000-d288a779699c505fde08JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00pj-3910000000-87feed2c593dbff7fae8JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9600000000-0d93a938bd873800d5e0JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9750000000-c51f62deffa53727f438JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0udi-0290000000-cd204cf662cb75a52f8cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0540-5910000000-d9df3022a95972158b37JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0ue9-9660000000-49a78126c0d15f6e3eb7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0090000000-841b953970b4cd52f8beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0uei-0950000000-001fe11fe26a2d644897JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-0900000000-83a69e4c3ab60df51781JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-08i9-7900000000-951787b9bed084d77a6bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-057i-9000000000-83b9d67dcdf5f385ab57JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0f80-0950000000-7fec916790f882e8630aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-841b953970b4cd52f8beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0uei-0950000000-001fe11fe26a2d644897JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-83a69e4c3ab60df51781JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-08i9-7900000000-951787b9bed084d77a6bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-057i-9000000000-83b9d67dcdf5f385ab57JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0019-0900000000-e9711749ce4f183c8c63JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f80-0950000000-e264d8b786405e562fd4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-007d-8900000000-fb7880caeb9e996f8bbaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0970000000-b21ac000bbddcd19753bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9l-2910000000-aad49769e8652ff2ea40JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rw-9200000000-bab98f63e58992b52316JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0290000000-f600fa6f22d1c40d97d5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-2790000000-3f24f2c725d420658a66JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-1aa6408615ab7e415691JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0532-9200000000-34e843efdffcce316afdJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB00792
PubChem Compound ID5192
ChEMBL IDCHEMBL1232164
ChemSpider ID5004
KEGG IDC08277
UniProt IDNot Available
OMIM ID
ChEBI ID41865
BioCyc IDCPD-3623
CTD IDNot Available
Stitch IDNot Available
PDB IDDEC
ACToR IDNot Available
Wikipedia LinkSebacic acid
References
Synthesis ReferenceLi, Aimin; Jiang, Zhenmao; Cai, Jianguo; Zhang, Xiao; Shi, Hongyan; Zhou, Jiayan; Zhang, Quanxing; Long, Chao; Liu, Fuqiang; Chen, Jinlong. Environmental friendly method for producing sebacic acid using anion exchangers and polymer adsorbents. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 5 pp.
MSDSLink
General References
  1. Capristo E, Mingrone G, De Gaetano A, Addolorato G, Greco AV, Gasbarrini G: A new HPLC method for the direct analysis of triglycerides of dicarboxylic acids in biological samples. Clin Chim Acta. 1999 Nov;289(1-2):11-21. [10556649 ]
  2. Mingrone G, Tacchino RM, Castagneto M, Finotti E, Greco AV: Use of even-numbered carbon atom dicarboxylic salts in parenteral nutrition as fuel substrate. JPEN J Parenter Enteral Nutr. 1992 Jan-Feb;16(1):32-8. [1738216 ]
  3. Bertuzzi A, Finotti E, Mingrone G, Greco AV: Sebacic acid binding to human plasma albumin. Biochem Pharmacol. 1993 Feb 9;45(3):697-702. [8442769 ]
  4. Curcoy A, Olsen RK, Ribes A, Trenchs V, Vilaseca MA, Campistol J, Osorio JH, Andresen BS, Gregersen N: Late-onset form of beta-electron transfer flavoprotein deficiency. Mol Genet Metab. 2003 Apr;78(4):247-9. [12706375 ]
  5. Fleming AB, Saltzman WM: Pharmacokinetics of the carmustine implant. Clin Pharmacokinet. 2002;41(6):403-19. [12074689 ]
  6. Gregersen N, Kolvraa S, Mortensen PB, Rasmussen K: C6-C10-dicarboxylic aciduria: biochemical considerations in relation to diagnosis of beta-oxidation defects. Scand J Clin Lab Invest Suppl. 1982;161:15-27. [6959231 ]
  7. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [2026685 ]
  8. Jakobs C, Sweetman L, Wadman SK, Duran M, Saudubray JM, Nyhan WL: Prenatal diagnosis of glutaric aciduria type II by direct chemical analysis of dicarboxylic acids in amniotic fluid. Eur J Pediatr. 1984 Jan;141(3):153-7. [6698061 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.0187 uMACEA_T47D_80hr_PositiveACEA Biosciences
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]