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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-03-21 06:16:00 UTC
Update Date2019-07-23 07:18:28 UTC
HMDB IDHMDB0062413
Secondary Accession Numbers
  • HMDB62413
Metabolite Identification
Common Name5,9,11-trihydroxyprosta-6E,14Z-dien-1-oate
Descriptionsapintoxin D belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol. sapintoxin D is a moderately basic compound (based on its pKa).
Structure
Data?1563866308
Synonyms
ValueSource
Phorbol 12-(2-methylamino)benzoate 13-acetateChEBI
Phorbol 12-(2-methylamino)benzoic acid 13-acetic acidGenerator
5,9,11-Trihydroxyprosta-6E,14Z-dien-1-Oic acidGenerator
CCRIS 7233HMDB
Chemical FormulaC30H37NO8
Average Molecular Weight539.625
Monoisotopic Molecular Weight539.251917155
IUPAC Name(1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate
Traditional Name(1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate
CAS Registry Number80998-07-8
SMILES
[H][C@]12[C@]3([H])C=C(CO)C[C@]4(O)C(=O)C(C)=C[C@@]4([H])[C@@]3(O)[C@]([H])(C)[C@@]([H])(OC(=O)C3=CC=CC=C3NC)[C@@]1(OC(C)=O)C2(C)C
InChI Identifier
InChI=1S/C30H37NO8/c1-15-11-22-28(36,24(15)34)13-18(14-32)12-20-23-27(4,5)30(23,39-17(3)33)25(16(2)29(20,22)37)38-26(35)19-9-7-8-10-21(19)31-6/h7-12,16,20,22-23,25,31-32,36-37H,13-14H2,1-6H3/t16-,20+,22-,23-,25-,28-,29-,30-/m1/s1
InChI KeyUPAIGGMQTARRMN-CSSCWBSHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentPhorbol esters
Alternative Parents
Substituents
  • Phorbol ester
  • Aminobenzoic acid or derivatives
  • Benzoate ester
  • Benzoic acid or derivatives
  • Benzoyl
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Secondary aliphatic/aromatic amine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Vinylogous amide
  • Tertiary alcohol
  • Cyclic alcohol
  • Amino acid or derivatives
  • Ketone
  • Carboxylic acid ester
  • Secondary amine
  • Carboxylic acid derivative
  • Primary alcohol
  • Amine
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.15 g/lALOGPS
LogP2.78ALOGPS
Predicted Properties
PropertyValueSource
logP2.78ALOGPS
logP2.28ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.57ChemAxon
pKa (Strongest Basic)2.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area142.39 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity144.94 m³·mol⁻¹ChemAxon
Polarizability57.27 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00c0-2626900000-d5a9a4180ebb9cc1801aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0apl-3203496000-c606d131389096e5cb17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ec-0202490000-831cf0690d2cfbb86604Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0704890000-74d2d78011faf97c2a14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-3924100000-975aa5a4626e28efecafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-2300490000-2aa207d114a6433d98a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3803950000-2a93220b5f500db55ae4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5902100000-5cac75cbf7fb4379692aSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound114977
PDB IDNot Available
ChEBI ID72442
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.