Details of the Drug

General Information of Drug (ID: DM6VFO1)

Drug Name
Pregnenolone
Synonyms Pregnenolone (schizophrenia); Neurosteroid (schizophrenia), Neuroscience; Pregnenolone (schizophrenia), Neuroscience
Indication
Disease Entry ICD 11 Status REF
Schizophrenia 6A20 Phase 4 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 316.5
Logarithm of the Partition Coefficient (xlogp) 4.2
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C21H32O2
IUPAC Name
1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
Canonical SMILES
CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
InChI
InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1
InChIKey
ORNBQBCIOKFOEO-QGVNFLHTSA-N
Cross-matching ID
PubChem CID
8955
ChEBI ID
CHEMBL16581
CAS Number
145-13-1
UNII
73R90F7MQ8
DrugBank ID
DB02789
TTD ID
D0B4RU
INTEDE ID
DR1336
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP 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 Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Estrogen-related receptor-alpha (ESRRA) TTPNQAC ERR1_HUMAN Agonist [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [3]
Beta-HSD adrenal and gonadal type (HSD3B2) DEN0GVQ 3BHS2_HUMAN Substrate [4]
Sulfotransferase 2A1 (SULT2A1) DE0P6LK ST2A1_HUMAN Substrate [5]
Dihydrotestosterone oxidoreductase (HSD3B1) DERDQWN 3BHS1_HUMAN Substrate [4]
Sulfotransferase 2B1 (SULT2B1) DEZBN53 ST2B1_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Myb-related protein A (MYBL1) OTBJMC2P MYBA_HUMAN Gene/Protein Processing [6]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_HUMAN Gene/Protein Processing [7]
Protein GREB1 (GREB1) OTU6ZA26 GREB1_HUMAN Gene/Protein Processing [6]
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Molecular Expression Atlas of This Drug

ICD Disease Classification 06 Mental, behavioural or neurodevelopmental disorder
Disease Class ICD-11: 6A20 Schizophrenia
The Studied Tissue Pre-frontal cortex
The Studied Disease Schizophrenia [ICD-11:6A20]
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Estrogen-related receptor-alpha (ESRRA) DTT ESRRA 9.34E-01 1.47E-02 0.06
Estrogen-related receptor-alpha (ESRRA) DTT ESRRA 2.09E-01 -0.07 -0.62
Sulfotransferase 2B1 (SULT2B1) DME SULT2B1 9.69E-01 3.48E-03 1.02E-02
Sulfotransferase 2B1 (SULT2B1) DME SULT2B1 8.40E-01 6.15E-02 3.66E-01
Dihydrotestosterone oxidoreductase (HSD3B1) DME HSD3B1 2.84E-01 -8.57E-03 -6.45E-02
Dihydrotestosterone oxidoreductase (HSD3B1) DME HSD3B1 7.78E-01 4.16E-03 5.82E-02
Beta-HSD adrenal and gonadal type (HSD3B2) DME HSD3B2 2.39E-01 5.15E-02 2.14E-01
Beta-HSD adrenal and gonadal type (HSD3B2) DME HSD3B2 8.14E-01 -2.28E-02 -1.48E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 4.66E-01 4.25E-02 1.20E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 4.75E-01 5.15E-02 3.64E-01
Sulfotransferase 2A1 (SULT2A1) DME SULT2A1 7.80E-01 -1.17E-03 -9.90E-03
Sulfotransferase 2A1 (SULT2A1) DME SULT2A1 1.01E-01 -1.06E-02 -1.31E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2376).
2 Suppression of adrenal function by low-dose prednisone: assessment with 24-hour urinary steroid hormone profiles--a review of five cases. Altern Med Rev. 2006 Mar;11(1):40-6.
3 Cytochrome P450 expression and regulation in CYP3A4/CYP2D6 double transgenic humanized mice. Drug Metab Dispos. 2008 Feb;36(2):435-41.
4 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.
5 Expression and characterization of the human 3 beta-hydroxysteroid sulfotransferases (SULT2B1a and SULT2B1b). J Steroid Biochem Mol Biol. 2001 Jun;77(4-5):261-9.
6 A Gene Expression Biomarker Identifies Chemical Modulators of Estrogen Receptor in an MCF-7 Microarray Compendium. Chem Res Toxicol. 2021 Feb 15;34(2):313-329. doi: 10.1021/acs.chemrestox.0c00243. Epub 2021 Jan 6.
7 The pregnane X receptor regulates gene expression in a ligand- and promoter-selective fashion. Mol Endocrinol. 2005 May;19(5):1170-80.