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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:06:33 UTC
Update Date2021-09-26 23:02:41 UTC
HMDB IDHMDB0250951
Secondary Accession NumbersNone
Metabolite Identification
Common NameDehydroepiandrosterone acetate
Description17-Oxoandrost-5-en-3-yl acetate belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group. 17-Oxoandrost-5-en-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Dehydroepiandrosterone acetate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dehydroepiandrosterone acetate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
17-Oxoandrost-5-en-3-yl acetic acidGenerator
Chemical FormulaC21H30O3
Average Molecular Weight330.468
Monoisotopic Molecular Weight330.219494826
IUPAC Name2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl acetate
Traditional Name2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC1CCC2(C)C3CCC4(C)C(CCC4=O)C3CC=C2C1
InChI Identifier
InChI=1S/C21H30O3/c1-13(22)24-15-8-10-20(2)14(12-15)4-5-16-17-6-7-19(23)21(17,3)11-9-18(16)20/h4,15-18H,5-12H2,1-3H3
InChI KeyNCMZQTLCXHGLOK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androstane-skeleton
  • Oxosteroid
  • 17-oxosteroid
  • Delta-5-steroid
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(3.76) g/LALOGPS
logP10(3.8) g/LChemAxon
logS10(-4.7) g/LALOGPS
pKa (Strongest Acidic)19.96ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.81 m³·mol⁻¹ChemAxon
Polarizability38.17 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dehydroepiandrosterone acetateCC(=O)OC1CCC2(C)C3CCC4(C)C(CCC4=O)C3CC=C2C13219.6Standard polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Dehydroepiandrosterone acetateCC(=O)OC1CCC2(C)C3CCC4(C)C(CCC4=O)C3CC=C2C12545.6Standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Dehydroepiandrosterone acetateCC(=O)OC1CCC2(C)C3CCC4(C)C(CCC4=O)C3CC=C2C12710.3Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
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 Compound540877
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]