Debromoaplysiatoxin (T3D4056)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-08-29 04:59:28 UTC
Update Date2014-12-24 20:26:36 UTC
Accession NumberT3D4056
Identification
Common NameDebromoaplysiatoxin
ClassSmall Molecule
DescriptionDebromoaplysiatoxin is an algal toxin found in blue-green algae. It is one of the causative toxins of a series of red alga (Gracilaria coronopifolia) poisonings in Hawaii, which broke out in succession in September of 1994.
Compound Type
  • Animal Toxin
  • Bacterial Toxin
  • Ester
  • Ether
  • Marine Toxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC32H48O10
Average Molecular Mass592.718 g/mol
Monoisotopic Mass592.325 g/mol
CAS Registry Number52423-28-6
IUPAC Name(1S,3R,4S,5S,9R,13S,14R)-13-hydroxy-9-[(1R)-1-hydroxyethyl]-3-[(2S,5S)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1¹,⁵]octadecane-7,11-dione
Traditional Name(1S,3R,4S,5S,9R,13S,14R)-13-hydroxy-9-[(1R)-1-hydroxyethyl]-3-[(2S,5S)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1¹,⁵]octadecane-7,11-dione
SMILES[H][C@](C)(O)[C@@]1([H])CC(=O)O[C@@]2([H])C[C@]3(O[C@]([H])([C@@]([H])(C)CC[C@]([H])(OC)C4=CC(O)=CC=C4)[C@@]2([H])C)O[C@@](O)(CC(=O)O1)[C@]([H])(C)CC3(C)C
InChI IdentifierInChI=1S/C32H48O10/c1-18(11-12-24(38-7)22-9-8-10-23(34)13-22)29-20(3)26-16-32(41-29)30(5,6)15-19(2)31(37,42-32)17-28(36)39-25(21(4)33)14-27(35)40-26/h8-10,13,18-21,24-26,29,33-34,37H,11-12,14-17H2,1-7H3/t18-,19+,20-,21+,24-,25+,26-,29+,31-,32-/m0/s1
InChI KeyInChIKey=REAZZDPREXHWNV-HJUJCDCNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Benzylether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Ketal
  • Phenol
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Oxane
  • Carboxylic acid ester
  • Hemiacetal
  • Secondary alcohol
  • Lactone
  • Acetal
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Actin Filament
  • Cell surface
  • Cytoskeleton
  • Cytosol
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Metabolic PathwaysNot AvailableNot Available
Arachidonic Acid MetabolismSMP00075 map00590
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0091 g/LALOGPS
logP3.41ALOGPS
logP5.27ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.36ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area140.98 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity152.09 m³·mol⁻¹ChemAxon
Polarizability63.29 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pec-0090140000-2c7290e83d3e0d0808a92016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-5490120000-0c366adb120d2e0cbdb42016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-4590000000-b4072cd43070860d52962016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-3011090000-1a9d61ccb670f2dc85f82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-8004290000-4628cc649fb25c5a8e092016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9203000000-1ce386141e77ffb91b412016-08-03View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityDebromoaplysiatoxin have the ability to evoke biological and biochemical responses in cells, and belong to the TPA (12-O-tetradecanoylphorbol 13-acetate) type tumor promoters. Debromoaplysiatoxin is a typical tumor promoter. Debromoaplysiatoxin inhibited the binding of [3H]PDBu or 125I-EGF to their cell receptors in MEM containing 2 mg/ml ovalbumin. Debromoaplysiatoxin also inhibited the binding of [3H]PDBu in MEM containing sera from eight mammalian species tested. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesDebromoaplysiatoxin is an algal toxin found in blue-green algae. It is one of the causative toxins of a series of red alga (Gracilaria coronopifolia) poisonings in Hawaii, which broke out in succession in September of 1994.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID440576
ChEMBL IDNot Available
ChemSpider ID4509004
KEGG IDC05148
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Ueyama H, Sasaki I, Shimomura K, Suganuma M: Specific protein interacting with a tumor promoter, debromoaplysiatoxin, in bovine serum is alpha 1-acid glycoprotein. J Cancer Res Clin Oncol. 1995;121(4):211-8. [7751319 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available