Details of the Drug

General Information of Drug (ID: DM4Q80H)

Drug Name
Dehydroepiandrosterone sulfate
Synonyms
Prasterone sulfate; DHEA sulfate; DEHYDROEPIANDROSTERONE SULFATE; Dehydroisoandrosterone sulfate; DHEAS; Dehydroepiandrosterone sulphate; Dehydroepiandrosterone monosulfate; 3-O-Sulfodehydroepiandrosterone; Dehydroepiandrosterone 3-sulfate; Dehydroandrosterone sulfate; Dehydroisoandrosterone-3-sulfate; 17-Ketoandrost-5-en-3beta-yl sulfate; DHEA-S; Androst-5-en-17-on-3beta-yl sulfuric acid; 3beta-Hydroxyandrost-5-en-17-one 3-sulfate; CCRIS 6746; (3-beta)-3-(Sulfooxy)androst-5-en-17-one; DHEA sulphate
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 368.5
Logarithm of the Partition Coefficient (xlogp) 2.8
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C19H28O5S
IUPAC Name
[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate
Canonical SMILES
CC12CCC3C(C1CCC2=O)CC=C4C3(CCC(C4)OS(=O)(=O)O)C
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
Cross-matching ID
PubChem CID
12594
ChEBI ID
CHEMBL16814
CAS Number
651-48-9
UNII
57B09Q7FJR
DrugBank ID
DB05804
VARIDT ID
DR01513
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 3 (ABCC3) DTQ3ZHF MRP3_HUMAN Substrate [1]
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [2]
Multidrug resistance-associated protein 4 (ABCC4) DTCSGPB MRP4_HUMAN Substrate [3]
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTPFTEQ SO2B1_HUMAN Substrate [4]
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTE2B1D SO1A2_HUMAN Substrate [5]
Multidrug resistance-associated protein 1 (ABCC1) DTSYQGK MRP1_HUMAN Substrate [3]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [6]
Organic anion transporting polypeptide 1B1 (SLCO1B1) DT3D8F0 SO1B1_HUMAN Substrate [7]
Organic anion transporting polypeptide 1B3 (SLCO1B3) DT9C1TS SO1B3_HUMAN Substrate [8]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [9]
Organic anion transporter 3 (SLC22A8) OT8BY933 S22A8_HUMAN Regulation of Drug Effects [10]
Pro-opiomelanocortin (POMC) OTV41F7T COLI_HUMAN Regulation of Drug Effects [11]
Solute carrier family 22 member 11 (SLC22A11) OTAJLNJZ S22AB_HUMAN Regulation of Drug Effects [12]
Solute carrier family 22 member 7 (SLC22A7) OTKTNH1W S22A7_HUMAN Regulation of Drug Effects [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Integration of hepatic drug transporters and phase II metabolizing enzymes: mechanisms of hepatic excretion of sulfate, glucuronide, and glutathione metabolites. Eur J Pharm Sci. 2006 Apr;27(5):447-86.
2 Directional trans-epithelial transport of organic anions in porcine LLC-PK1 cells that co-express human OATP1B1 (OATP-C) and MRP2. Biochem Pharmacol. 2005 Feb 1;69(3):415-23.
3 Steroid and bile acid conjugates are substrates of human multidrug-resistance protein (MRP) 4 (ATP-binding cassette C4). Biochem J. 2003 Apr 15;371(Pt 2):361-7.
4 Expression of OATP family members in hormone-related cancers: potential markers of progression. PLoS One. 2011;6(5):e20372.
5 Membrane transporters in drug development. Nat Rev Drug Discov. 2010 Mar;9(3):215-36.
6 A prediction model of substrates and non-substrates of breast cancer resistance protein (BCRP) developed by GA-CG-SVM method. Comput Biol Med. 2011 Nov;41(11):1006-13.
7 Organic anion transporting polypeptide 1B1: a genetically polymorphic transporter of major importance for hepatic drug uptake. Pharmacol Rev. 2011 Mar;63(1):157-81.
8 LST-2, a human liver-specific organic anion transporter, determines methotrexate sensitivity in gastrointestinal cancers. Gastroenterology. 2001 Jun;120(7):1689-99.
9 Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43.
10 Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1. Biochem Pharmacol. 2005 Oct 1;70(7):1104-13.
11 Maintenance of cell proliferation and steroidogenesis in cultured human fetal adrenal cells chronically exposed to adrenocorticotropic hormone: rationalization of in vitro and in vivo findings. Biol Reprod. 1990 Apr;42(4):683-91. doi: 10.1095/biolreprod42.4.683.
12 Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. J Biol Chem. 2000 Feb 11;275(6):4507-12.
13 Transport mechanism and substrate specificity of human organic anion transporter 2 (hOat2 [SLC22A7]). J Pharm Pharmacol. 2005 May;57(5):573-8.