(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-hydroxy-ethyl)-amide

ID: ALA113962

PubChem CID: 10436487

Max Phase: Preclinical

Molecular Formula: C32H51NO4

Molecular Weight: 513.76

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

Standard InChI:  InChI=1S/C32H51NO4/c1-27(2)23-8-11-32(7)25(30(23,5)10-9-24(27)36)22(35)18-20-21-19-29(4,26(37)33-16-17-34)13-12-28(21,3)14-15-31(20,32)6/h18,21,23-25,34,36H,8-17,19H2,1-7H3,(H,33,37)/t21-,23?,24-,25?,28+,29-,30-,31+,32+/m0/s1

Standard InChI Key:  CUHQXRIETJJGQE-DGWUYHICSA-N

Molfile:  

     RDKit          2D

 38 42  0  0  1  0  0  0  0  0999 V2000
    0.9250   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9250   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -2.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375   -0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333   -3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3500    1.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375    0.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417    1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6500   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2333   -0.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667    0.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292    2.4333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6500   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167    1.4208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9250   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5208   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6583   -3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3708   -3.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917    1.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792    2.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917    1.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9250    0.2250    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
  5  7  1  0
  6  1  2  0
  7  6  1  0
  8  4  1  0
  9  1  1  0
 10  8  1  0
 11 12  1  0
 12  9  1  0
 13  9  1  0
 14  2  1  0
 11 15  1  1
 16  4  1  0
 17  3  1  0
 18 14  1  0
 19 25  1  0
 20  7  2  0
 21 13  1  0
 22 23  1  0
 23 13  1  0
 24 15  2  0
 25 16  1  0
 26 15  1  0
  2 27  1  1
  4 28  1  1
  3 29  1  6
 30 10  1  0
 31 10  1  0
 19 32  1  1
 11 33  1  6
 13 34  1  1
 35 37  1  0
 36 26  1  0
 37 36  1  0
  9 38  1  1
 21 17  1  0
  5  2  1  0
 11 22  1  0
  8 18  1  0
 10 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA113962

   (2S,4aS,6aS,6bR,10S,12aS,14bR)-10-hydroxy-N-(2-hydroxyethyl)-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: 513.76

Molecular Weight (Monoisotopic): 513.3818

AlogP: 5.44

#Rotatable Bonds: 3

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: ┄

CX LogP: 4.76

CX LogD: 4.76

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.47

Np Likeness Score: 2.64

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