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
CHEBI:16814
CAS Number
651-48-9
DrugBank ID
DB05804
VARIDT ID
DR01513

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]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Regulation of Drug Effects [10]
Cytochrome P450 3A7 (CYP3A7) OTTCDHHM CP3A7_HUMAN Biotransformations [11]
Interleukin-1 beta (IL1B) OT0DWXXB IL1B_HUMAN Regulation of Drug Effects [12]
Organic anion transporter 3 (SLC22A8) OT8BY933 S22A8_HUMAN Regulation of Drug Effects [13]
Pro-opiomelanocortin (POMC) OTV41F7T COLI_HUMAN Regulation of Drug Effects [14]
Prolactin (PRL) OTWFQGX7 PRL_HUMAN Regulation of Drug Effects [15]
Solute carrier family 22 member 11 (SLC22A11) OTAJLNJZ S22AB_HUMAN Regulation of Drug Effects [16]
Solute carrier family 22 member 7 (SLC22A7) OTKTNH1W S22A7_HUMAN Regulation of Drug Effects [17]
Steryl-sulfatase (STS) OTXTJQPC STS_HUMAN Regulation of Drug Effects [18]
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 Catalytic activities of human liver cytochrome P-450 IIIA4 expressed in Saccharomyces cerevisiae. Biochemistry. 1990 Dec 25;29(51):11280-92.
11 A common polymorphism in the CYP3A7 gene is associated with a nearly 50% reduction in serum dehydroepiandrosterone sulfate levels. J Clin Endocrinol Metab. 2005 Sep;90(9):5313-6.
12 Dexamethasone or interleukin-10 blocks interleukin-1beta-induced uterine contractions in pregnant rhesus monkeys. Am J Obstet Gynecol. 2003 Jan;188(1):252-63. doi: 10.1067/mob.2003.70.
13 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.
14 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.
15 Hyperprolactinemia and 5-alpha-reductase activity. Acta Eur Fertil. 1986 Mar-Apr;17(2):129-31.
16 Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. J Biol Chem. 2000 Feb 11;275(6):4507-12.
17 Transport mechanism and substrate specificity of human organic anion transporter 2 (hOat2 [SLC22A7]). J Pharm Pharmacol. 2005 May;57(5):573-8.
18 Steroid signalling in the ovarian surface epithelium. Trends Endocrinol Metab. 2005 Sep;16(7):327-33.