(2S,4aS,6aS,6bR,10S,12aS,14bR)-10-Hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-picene-2-carboxylic acid (5-hydroxy-pentyl)-amide

ID: ALA322753

PubChem CID: 44339958

Max Phase: Preclinical

Molecular Formula: C35H57NO4

Molecular Weight: 555.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C2CC[C@]3(C)C(C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)NCCCCCO)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O

Standard InChI:  InChI=1S/C35H57NO4/c1-30(2)26-11-14-35(7)28(33(26,5)13-12-27(30)39)25(38)21-23-24-22-32(4,29(40)36-19-9-8-10-20-37)16-15-31(24,3)17-18-34(23,35)6/h21,24,26-28,37,39H,8-20,22H2,1-7H3,(H,36,40)/t24-,26?,27-,28?,31+,32-,33-,34+,35+/m0/s1

Standard InChI Key:  ZQGAWSIJIWWSSR-PGPXYHGTSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA322753

   (2S,4aS,6aS,6bR,10S,12aS,14bR)-10-hydroxy-N-(5-hydroxypentyl)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxamide

Molecule Features

Natural Product: No

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: 555.84

Molecular Weight (Monoisotopic): 555.4288

AlogP: 6.61

#Rotatable Bonds: 6

Polar Surface Area: 86.63

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 0.06

CX LogP: 5.78

CX LogD: 5.78

Aromatic Rings: ┄

Heavy Atoms: 40

QED Weighted: 0.32

Np Likeness Score: 2.52

References

1. Vicker N, Su X, Lawrence H, Cruttenden A, Purohit A, Reed MJ, Potter BV..  (2004)  A novel 18 beta-glycyrrhetinic acid analogue as a potent and selective inhibitor of 11 beta-hydroxysteroid dehydrogenase 2.,  14  (12): [PMID:15149687] [10.1016/s0960-894x(04)00488-3]

Source

Source(1):

• Scientific Literature