(8S,9S,10R,11S,13S,14S,17R)-17-((S)-1,2-dihydroxyethyl)-11,17-dihydroxy-10,13-dimethyl-1,7,8,10,11,12,13,15,16,17-decahydro-2H-cyclopenta[a]phenanthren-3(6H,9H,14H)-one

ID: ALA488842

Chembl Id: CHEMBL488842

Cas Number: 1719-79-5

PubChem CID: 256288

Max Phase: Preclinical

Molecular Formula: C21H32O5

Molecular Weight: 364.48

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-82878 | 20alpha-Dihydrocortisol|1719-79-5|(8S,9S,10R,11S,13S,14S,17R)-17-[(1S)-1,2-dihydroxyethyl]-11,17-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one|NSC-82878|20beta-Dihydrocortisol|20-alpha-Dihydrocortisol|MLS002694142|20alpha-hydroxycortisol|CHEMBL488842|SCHEMBL2903879|NSC82878

Canonical SMILES:  C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)[C@@H](O)CO

Standard InChI:  InChI=1S/C21H32O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-18,22,24-26H,3-8,10-11H2,1-2H3/t14-,15-,16-,17-,18+,19-,20-,21-/m0/s1

Standard InChI Key:  AWWCEQOCFFQUKS-FJWDNACWSA-N

Alternative Forms

1. Parent:

   

   ALA488842

   20alpha-Dihydrocortisol

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 364.48

Molecular Weight (Monoisotopic): 364.2250

AlogP: 1.57

#Rotatable Bonds: 2

Polar Surface Area: 97.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.99

CX Basic pKa: ┄

CX LogP: 0.66

CX LogD: 0.66

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.60

Np Likeness Score: 2.68

References

1. Taylor CM, Barda Y, Kisselev OG, Marshall GR..  (2008)  Modulating G-protein coupled receptor/G-protein signal transduction by small molecules suggested by virtual screening.,  51  (17): [PMID:18707087] [10.1021/jm800326q]

Source

Source(1):

• Scientific Literature