CHOL-11-ENIC ACID

ID: ALA3138713

PubChem CID: 76333167

Max Phase: Preclinical

Molecular Formula: C24H36O3

Molecular Weight: 372.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3C=C[C@]12C

Standard InChI:  InChI=1S/C24H36O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h11,13,15-16,18-21H,4-10,12,14H2,1-3H3,(H,26,27)/t15-,16-,18+,19-,20+,21+,23+,24-/m1/s1

Standard InChI Key:  KGXLWYQCBAUILI-OPTMKGCMSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    1.1666    1.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583   -0.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2500    0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1666    0.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4583   -0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4583    1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2604    1.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8853    1.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583   -1.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6041    0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6875    0.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6041    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4687   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3874    4.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6770   -1.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -1.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3853   -1.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3836    4.6951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8804    2.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9799   -1.3921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1364    2.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3853   -0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1315    3.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1651    1.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9663    0.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2038    3.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4717    2.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9552   -1.6124    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1666   -0.6271    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4583    0.6167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2500   -0.6375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5990    1.8618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  7  1  0
  4  1  1  0
  5  4  1  0
  6  1  1  0
  7  6  2  0
  8  1  1  0
  9  2  1  0
 10  4  1  0
 11  2  1  0
 12  8  1  0
 13  5  1  0
 14 23  1  0
  9 15  1  0
 16 13  1  0
 17 22  1  0
 18 14  2  0
  8 19  1  0
 20 17  2  0
 21 19  1  0
 22 11  1  0
 23 21  1  0
  1 24  1  1
  2 25  1  1
 26 14  1  0
 19 27  1  1
 10 12  1  0
  5  3  1  0
  9 16  1  0
 17 15  1  0
  9 28  1  1
  4 29  1  6
  5 30  1  1
  3 31  1  6
  8 32  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3138713

   (4R)-4-[(5R,8S,9S,10S,13R,14S,17R)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid

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: 372.55

Molecular Weight (Monoisotopic): 372.2664

AlogP: 5.49

#Rotatable Bonds: 4

Polar Surface Area: 54.37

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.75

CX Basic pKa: ┄

CX LogP: 4.87

CX LogD: 2.27

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: 2.46

References

1. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

Source

Source(1):

• Scientific Literature