Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2031)
Drug Name
NSC-63853
Synonyms
(3-beta)-3,17-Dihydroxypregn-5-en-20-one; 17-Hydroxy-delta5-pregnenolone; 17-Hydroxypregnenolone; 17-OH-pregnenolone; 17-alpha-Hydroxypregnenolone; 17a-Hydroxypregnenolone; 17alpha-Hydroxypregnenolone; 3-beta,17-Dihydroxypregn-5-en-20-one; 3-beta,17-alpha-Dihydroxypregn-5-en-20-one; 387-79-1; 3b,17-Dihydroxy-5-pregnen-20-one; 5-Pregnen-3beta,17alpha-diol-20-one; JERGUCIJOXJXHF-TVWVXWENSA-N; 77ME40334S; CHEBI:28750; CHEMBL408706; EINECS 206-862-6; 17 Alpha-Hydroxypregnenolone; Pregn-5-en-20-one, 3-beta,17-dihydroxy-; UNII-77ME40334S
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 332.5 Topological Polar Surface Area 57.5
Heavy Atom Count 24 Rotatable Bond Count 1
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
91451
PubChem SID
841443 ; 855825 ; 10224803 ; 14875321 ; 17425085 ; 24702314 ; 44422400 ; 50019734 ; 53790772 ; 57334862 ; 71831438 ; 76250425 ; 92298057 ; 93167067 ; 103566225 ; 104404818 ; 123080711 ; 124800596 ; 125309465 ; 126523206 ; 128264115 ; 135048384 ; 137236028 ; 164152383 ; 164760906 ; 178101796 ; 179505061 ; 184545691 ; 221121815 ; 227022703 ; 249857761 ; 249910018
ChEBI ID
CHEBI:28750
CAS Number
387-79-1
TTD Drug ID
D06MRM
Formula
C21H32O3
Canonical SMILES
CC(=O)C1(CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
InChI
1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1
InChIKey
JERGUCIJOXJXHF-TVWVXWENSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
17-alpha-hydroxyprogesterone DM002987
6238
Unclear 1 [5]
Androsterone DM004051
5879
Unclear 1 [6]
Cortisol DM004052
5754
Unclear 1 [7]
Dehydroepiandrosterone DM004048
5881
Unclear 1 [4]
Etiocholanolone DM004050
5880
Unclear 1 [6]
Isoandrosteron DM004049 N. A. Unclear 1 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012911 NSC-63853 17-alpha-hydroxyprogesterone Unclear CYB5B [5]
MR012912 NSC-63853 Dehydroepiandrosterone Unclear Unclear [4]
MR012913 NSC-63853 Isoandrosteron Unclear Unclear [6]
MR012914 NSC-63853 Etiocholanolone Unclear Unclear [6]
MR012915 NSC-63853 Androsterone Unclear Unclear [6]
MR012916 NSC-63853 Cortisol Unclear Unclear [7]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-HSD adrenal and gonadal type (HSD3B2) DME0222 Homo sapiens
3BHS2_HUMAN
1.1.1.145
[2]
Cytochrome b5 type B (CYB5B) DMEN196 Homo sapiens
CYB5B_HUMAN
Not Available [3] , [4]
Dihydrotestosterone oxidoreductase (HSD3B1) DME0221 Homo sapiens
3BHS1_HUMAN
1.1.1.145
[2]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Dihydrotestosterone oxidoreductase (HSD3B1) DME0221 Km = 0.0035 microM
3BHS1_HUMAN
[2]
Beta-HSD adrenal and gonadal type (HSD3B2) DME0222 Km = 0.0035 microM
3BHS2_HUMAN
[2]
References
1 The IUPHAR/BPS Guide to PHARMACOLOGY in 2020: extending immunopharmacology content and introducing the IUPHAR/MMV Guide to MALARIA PHARMACOLOGY. Nucleic Acids Res. 2020 Jan 8;48(D1):D1006-D1021. (Ligand id: 5103).
2 Structure/function relationships responsible for the kinetic differences between human type 1 and type 2 3beta-hydroxysteroid dehydrogenase and for the catalysis of the type 1 activity. J Biol Chem. 2002 Nov 8;277(45):42795-801.
3 Blood levels and production rate of 17-hydroxypregnenolone in man
4 The role of cytochrome b5 in the biosynthesis of androgens by human P450c17
5 CONVERSION OF 17-ALPHA-HYDROXYPREGNENOLONE TO 17-ALPHA-HYDROXYPROGESTERONE BY THE CANINE TESTIS IN VIVO
6 The conversion in vivo of 17-alpha-hydroxypregnenolone to dehydroisoandrosterone and other 17-ketosteroids
7 The conversion in vitro of 17-hydroxypregnenolone to cortisol by a human adrenal tumor

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