(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 (2-oxo-tetrahydro-furan-3-yl)-amide

ID: ALA430525

PubChem CID: 44339722

Max Phase: Preclinical

Molecular Formula: C34H51NO5

Molecular Weight: 553.78

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)NC6CCOC6=O)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O

Standard InChI:  InChI=1S/C34H51NO5/c1-29(2)24-8-12-34(7)26(32(24,5)11-9-25(29)37)23(36)18-20-21-19-31(4,28(39)35-22-10-17-40-27(22)38)14-13-30(21,3)15-16-33(20,34)6/h18,21-22,24-26,37H,8-17,19H2,1-7H3,(H,35,39)/t21-,22?,24?,25-,26?,30+,31-,32-,33+,34+/m0/s1

Standard InChI Key:  NQTDTVZUCHOIOQ-ATTWWDJHSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA430525

   (2S,4aS,6aS,6bR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-N-(2-oxooxolan-3-yl)-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: 553.78

Molecular Weight (Monoisotopic): 553.3767

AlogP: 5.76

#Rotatable Bonds: 2

Polar Surface Area: 92.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.39

CX Basic pKa: 0.02

CX LogP: 5.17

CX LogD: 5.17

Aromatic Rings: ┄

Heavy Atoms: 40

QED Weighted: 0.42

Np Likeness Score: 2.48

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