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 ZINC000008215740
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Deoxycytidine is a deoxyribonucleoside, a component of deoxyribonucleic acid. It is similar to the ribonucleoside cytidine, but with one hydroxyl group removed from the C2' position. Deoxycytidine can be phosphorylated at C5' of the deoxyribose by deoxycytidine kinase, converting it to deoxycytidine monophosphate (dCMP), a DNA precursor. dCMP can be converted to dUMP and dTMP. It can also be used as a precursor for 5-aza-2′-deoxycytidine, a treatment for MDS patients. This compound slows the cell cycle by interfering with the methylation of the P15/INK4B gene, increasing the expression of P15/INK4B protein which subdues the transformation of MDS to leukemia. Deoxycytidine can also serve as a biomarker for tumor diagnosis. Deoxycytidine can be used as a biomarker for breast cancer patients and healthy individuals. 5-(Hydroxymethyl)-2′-deoxycytidine (5-hmdC), 5-(formyl)-2′-deoxycytidine (5-fodC), and 5-(carboxyl)-2′-deoxycytidine (5-cadC) are intermediates in the DNA demethylation pathway and can act as biomarkers. 5-hmdC levels were significantly reduced in urine samples of breast cancer patients, while 5-fodC and 5-cadC levels were elevated.
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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).
View more via ChEBI Ontology
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 Types Sources
15374110 PubMed citation Europe PMC
18307294 PubMed citation Europe PMC
20797618 PubMed citation Europe PMC
22770225 PubMed citation Europe PMC
9661815 PubMed citation Europe PMC
Last Modified
20 August 2019