CHEBI:16814 - dehydroepiandrosterone sulfate

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ChEBI Name dehydroepiandrosterone sulfate
ChEBI ID CHEBI:16814
Definition A steroid sulfate that is the 3-sulfooxy derivative of dehydroepiandrosterone.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:20247, CHEBI:61003, CHEBI:11912, CHEBI:1724
Supplier Information No supplier information found for this compound.
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Dehydroepiandrosterone sulfate, abbreviated as DHEA sulfate or DHEA-S, also known as androstenolone sulfate, is an endogenous androstane steroid that is produced by the adrenal cortex. It is the 3β-sulfate ester and a metabolite of dehydroepiandrosterone (DHEA) and circulates in far greater relative concentrations than DHEA. The steroid is hormonally inert and is instead an important neurosteroid and neurotrophin.
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Formulae C19H28O5S
C19H28O5S
Net Charge 0
Average Mass 368.489
Monoisotopic Mass 368.16575
InChI InChI=1S/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1
InChIKey CZWCKYRVOZZJNM-USOAJAOKSA-N
SMILES C1[C@@]2([C@@]([C@@]3(C(C[C@@H](OS(O)(=O)=O)CC3)=C1)C)(CC[C@]4([C@]2(CCC4=O)[H])C)[H])[H]
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606) See: PubMed
Roles Classification
Biological Role(s): EC 2.7.1.33 (pantothenate kinase) inhibitor
An EC 2.7.1.* (phosphotransferases with an alcohol group as acceptor) inhibitor that interferes with the action of pantothenate kinase (EC 2.7.1.33).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
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ChEBI Ontology
Outgoing dehydroepiandrosterone sulfate (CHEBI:16814) has functional parent dehydroepiandrosterone (CHEBI:28689)
dehydroepiandrosterone sulfate (CHEBI:16814) has role EC 2.7.1.33 (pantothenate kinase) inhibitor (CHEBI:77194)
dehydroepiandrosterone sulfate (CHEBI:16814) has role human metabolite (CHEBI:77746)
dehydroepiandrosterone sulfate (CHEBI:16814) has role mouse metabolite (CHEBI:75771)
dehydroepiandrosterone sulfate (CHEBI:16814) is a 17-oxo steroid (CHEBI:19168)
dehydroepiandrosterone sulfate (CHEBI:16814) is a steroid sulfate (CHEBI:16158)
dehydroepiandrosterone sulfate (CHEBI:16814) is conjugate acid of dehydroepiandrosterone sulfate(1−) (CHEBI:57905)
Incoming dehydroepiandrosterone sulfate(1−) (CHEBI:57905) is conjugate base of dehydroepiandrosterone sulfate (CHEBI:16814)
IUPAC Name
17-oxoandrost-5-en-3β-yl hydrogen sulfate
Synonyms Sources
(3-beta)-3-(Sulfooxy)androst-5-en-17-one ChemIDplus
17-Ketoandrost-5-en-3beta-yl sulfate ChemIDplus
17-oxoandrost-5-en-3β-yl hydrogen sulphate ChEBI
3-O-Sulfodehydroepiandrosterone ChemIDplus
3beta-Hydroxyandrost-5-en-17-one 3-sulfate KEGG COMPOUND
3beta-hydroxyandrost-5-en-17-one 3-sulfate ChEBI
3beta-Hydroxyandrost-5-en-17-one 3-sulfate KEGG COMPOUND
Androst-5-en-17-on-3beta-yl sulfuric acid ChemIDplus
Dehydroepiandrosterone 3-sulfate ChemIDplus
Dehydroepiandrosterone monosulfate ChemIDplus
Dehydroepiandrosterone sulfate KEGG COMPOUND
Dehydroepiandrosterone sulphate ChemIDplus
Dehydroisoandrosterone sulfate ChemIDplus
Dehydroisoandrosterone-3-sulfate ChemIDplus
DHEA sulfate ChemIDplus
DHEA sulfate KEGG COMPOUND
DHEA-S ChEBI
DHEAS ChemIDplus
Prasterone sulfate ChemIDplus
Manual Xrefs Databases
4049 DrugCentral
C04555 KEGG COMPOUND
DEHYDRO-EPIANDROSTERONE-SULFATE MetaCyc
Dehydroepiandrosterone_sulfate Wikipedia
HMDB0001032 HMDB
LMST05020010 LIPID MAPS
View more database links
Registry Numbers Types Sources
2227078 Reaxys Registry Number Reaxys
651-48-9 CAS Registry Number ChemIDplus
Citations
Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]
Leonardi R, Zhang YM, Yun MK, Zhou R, Zeng FY, Lin W, Cui J, Chen T, Rock CO, White SW, Jackowski S (2010)
Modulation of pantothenate kinase 3 activity by small molecules that interact with the substrate/allosteric regulatory domain.
Chemistry & biology 17, 892-902 [PubMed:20797618]
[show Abstract]
Sato H, Macchiarulo A, Thomas C, Gioiello A, Une M, Hofmann AF, Saladin R, Schoonjans K, Pellicciari R, Auwerx J (2008)
Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies.
Journal of medicinal chemistry 51, 1831-1841 [PubMed:18307294]
[show Abstract]
Hemminki A, Niemi S, Hautoniemi L, Söderlund H, Takkinen K (1998)
Fine tuning of an anti-testosterone antibody binding site by stepwise optimisation of the CDRs.
Immunotechnology : an international journal of immunological engineering 4, 59-69 [PubMed:9661815]
[show Abstract]
Barrou Z, Charru P, Lidy C (1997)
Dehydroepiandrosterone (DHEA) and aging.
Archives of gerontology and geriatrics 24, 233-241 [PubMed:15374110]
[show Abstract]
Last Modified
20 August 2019