(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 cyclopropylamide

ID: ALA320044

PubChem CID: 44339796

Max Phase: Preclinical

Molecular Formula: C33H51NO3

Molecular Weight: 509.78

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)NC6CC6)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O

Standard InChI:  InChI=1S/C33H51NO3/c1-28(2)24-10-13-33(7)26(31(24,5)12-11-25(28)36)23(35)18-21-22-19-30(4,27(37)34-20-8-9-20)15-14-29(22,3)16-17-32(21,33)6/h18,20,22,24-26,36H,8-17,19H2,1-7H3,(H,34,37)/t22-,24?,25-,26?,29+,30-,31-,32+,33+/m0/s1

Standard InChI Key:  DOBYIOVYOACSOF-DGSIWXLQSA-N

Molfile:  

     RDKit          2D

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    3.1500   -2.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792    0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292    1.8208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7542    1.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292   -0.3875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  5  1  0
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  7  6  1  0
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  9  1  1  0
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 24  7  2  0
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  2 30  1  1
  4 31  1  1
  3 32  1  6
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 23 35  1  1
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  9 38  1  1
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 12 26  1  0
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 21 22  1  0
 23 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA320044

   (2S,4aS,6aS,6bR,10S,12aS,14bR)-N-cyclopropyl-10-hydroxy-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: 509.78

Molecular Weight (Monoisotopic): 509.3869

AlogP: 6.61

#Rotatable Bonds: 2

Polar Surface Area: 66.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 0.05

CX LogP: 5.91

CX LogD: 5.91

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.44

Np Likeness Score: 2.50

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