Details of the Drug

General Information of Drug (ID: DMW6YLS)

Drug Name
deoxycorticosterone
Synonyms 11-deoxycorticosterone; 21-hydroxyprogesterone
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 330.5
Logarithm of the Partition Coefficient (xlogp) 2.9
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C21H30O3
IUPAC Name
(8S,9S,10R,13S,14S,17S)-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Canonical SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)CO)CCC4=CC(=O)CC[C@]34C
InChI
InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1
InChIKey
ZESRJSPZRDMNHY-YFWFAHHUSA-N
Cross-matching ID
PubChem CID
6166
ChEBI ID
CHEBI:16973
CAS Number
64-85-7
TTD ID
D04SQY
INTEDE ID
DR0442

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Glucocorticoid receptor messenger RNA (GCR mRNA) TTOZRK6 GCR_HUMAN Agonist [2]
Mineralocorticoid receptor (MR) TT26PHO MCR_HUMAN Agonist [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Steroid 11-beta-hydroxylase (CYP11B1) DEPE0RD C11B1_HUMAN Substrate [4]
Aldosterone synthase (CYP11B2) DE6TYUK C11B2_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 11B1, mitochondrial (CYP11B1) OTKKL894 C11B1_HUMAN Biotransformations [6]
Cytochrome P450 11B2, mitochondrial (CYP11B2) OTIOLWYN C11B2_HUMAN Biotransformations [7]
Glucocorticoid receptor (NR3C1) OTCI2YDI GCR_HUMAN Post-Translational Modifications [8]
Peroxisome proliferator-activated receptor gamma coactivator 1-alpha (PPARGC1A) OTHCDQ22 PRGC1_HUMAN Gene/Protein Processing [9]
Pro-opiomelanocortin (POMC) OTV41F7T COLI_HUMAN Regulation of Drug Effects [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Glucocorticoid receptor messenger RNA (GCR mRNA) DTT NR3C1 3.19E-02 0.54 1.67
Mineralocorticoid receptor (MR) DTT NR3C2 7.31E-01 -5.31E-04 -1.53E-03
Steroid 11-beta-hydroxylase (CYP11B1) DME CYP11B1 2.70E-01 9.19E-02 9.75E-01
Aldosterone synthase (CYP11B2) DME CYP11B2 1.08E-01 -2.14E-01 -1.14E+00
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: 2871).
2 Functional probing of the human glucocorticoid receptor steroid-interacting surface by site-directed mutagenesis. Gln-642 plays an important role in steroid recognition and binding. J Biol Chem. 2000Jun 23;275(25):19041-9.
3 Pharmacological and functional characterization of human mineralocorticoid and glucocorticoid receptor ligands. Eur J Pharmacol. 1993 Oct 15;247(2):145-54.
4 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
5 Functional expression of human mitochondrial CYP11B2 in fission yeast and identification of a new internal electron transfer protein, etp1. Biochemistry. 2002 Feb 19;41(7):2311-21.
6 Biphasic hormonal responses to the adrenocorticolytic DDT metabolite 3-methylsulfonyl-DDE in human cells. Toxicol Appl Pharmacol. 2010 Feb 1;242(3):281-9.
7 Fine-tuning the selectivity of aldosterone synthase inhibitors: structure-activity and structure-selectivity insights from studies of heteroaryl substituted 1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinolin-4-one derivatives. J Med Chem. 2011 Apr 14;54(7):2307-19.
8 Glucocorticoid receptor phosphorylation differentially affects target gene expression. Mol Endocrinol. 2008 Aug;22(8):1754-66. doi: 10.1210/me.2007-0219. Epub 2008 May 15.
9 A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1 expression and mitochondrial biogenesis. PLoS One. 2012;7(10):e46753. doi: 10.1371/journal.pone.0046753. Epub 2012 Oct 3.
10 Dexamethasone-suppressible hyperaldosteronism. Adrenal transition cell hyperplasia?. Hypertension. 1986 Aug;8(8):669-76. doi: 10.1161/01.hyp.8.8.669.