MetaCyc Compound: dehydroepiandrosterone

Synonyms: 3-β-hydroxyandrost-5-en-17-one, dehydroisoandrosterone, DHA, DHEA, androst-5-en-17-one, 3-hydroxy-, (3β)-, androstenolone

Superclasses: a steroida hydroxysteroida sterola 3beta-hydroxy-delta5-steroid

Chemical Formula: C19H28O2

Molecular Weight: 288.43 Daltons

Monoisotopic Molecular Weight: 288.208930143 Daltons

dehydroepiandrosterone compound structure

SMILES: CC24(CCC(O)CC(=CC[CH]1([CH]3(CCC(=O)C(CC[CH]12)(C)3)))4)

InChI: InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1


Unification Links: CAS:53-43-0, ChEBI:28689, ChemSpider:5670, DrugBank:DB01708, HMDB:HMDB00077, KEGG:C01227, LIPID MAPS:LMST02020021, MetaboLights:MTBLC28689, NCI:9896, PubChem:5881

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 254.22136Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

androgen biosynthesis :
dehydroepiandrosterone + NAD+ → 5-androstene-3,17-dione + NADH + H+

Not in pathways:
a steroid + 2 a reduced adrenodoxin + oxygen + 2 H+ → an 11-β-hydroxysteroid + 2 an oxidized adrenodoxin + H2O

Reactions known to produce the compound:

androgen biosynthesis :
17-α-hydroxypregnenolone → dehydroepiandrosterone + acetaldehyde

Not in pathways:
3-β-hydroxyandrost-5-en-17-one 3-sulfate + H2O → dehydroepiandrosterone + sulfate + H+

sphingolipid biosynthesis (plants) :
a dihydroceramide + a sterol 3-β-D-glucoside → a D-glucosyl-N-acylsphinganine + a sterol

Not in pathways:
a steryl-ester + H2O → a fatty acid + a sterol + H+

In Reactions of unknown directionality:

Not in pathways:
androsterone + NADP+ = dehydroepiandrosterone + NADPH + H+

Not in pathways:
a 3β-hydroxy-δ5-steroid + NAD+ = a 3-oxo-δ5-steroid + NADH + H+

Not in pathways:
a sterol + a phosphatidylcholine = a 1-acyl 2-lyso-phosphatidylcholine + a steryl-ester
a sterol + a 1,2-diacyl-sn-glycerol = 1-acyl-sn-glycerol + a steryl-ester
UDP-α-D-glucose + a sterol = UDP + a sterol 3-β-D-glucoside + H+


Chiang08: Chiang YR, Ismail W, Heintz D, Schaeffer C, Van Dorsselaer A, Fuchs G (2008). "Study of anoxic and oxic cholesterol metabolism by Sterolibacterium denitrificans." J Bacteriol 190(3);905-14. PMID: 18039763

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Thu Nov 26, 2015, biocyc12.