LITHOCHOL-11-ENIC ACID

ID: ALA3138720

Cas Number: 1053-37-8

PubChem CID: 5283972

Max Phase: Preclinical

Molecular Formula: C24H38O3

Molecular Weight: 374.57

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]4C[C@H](O)CC[C@]4(C)[C@H]3C=C[C@]12C

Standard InChI:  InChI=1S/C24H38O3/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/h11,13,15-21,25H,4-10,12,14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1

Standard InChI Key:  FEGCPHIPSRBREU-HVATVPOCSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    0.3521    0.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0860   -0.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0729   -0.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2733    0.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7398   -0.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1773    0.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3652   -0.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1813    1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9898    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7231   -0.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6152    0.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4065   -0.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0190   -1.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8238    1.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8317   -1.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779   -0.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3322    2.0960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6858    1.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5026    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0069    1.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7106    1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4279    0.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7072   -0.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8025    0.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1364    0.6832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5199   -0.4754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3732    1.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1604   -1.2005    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    0.2905    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5272   -0.7415    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1023    1.1916    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6444   -1.5923    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  1  3  1  0
  4  9  1  0
  3  5  1  0
  6  1  1  0
  2  7  1  0
  1  8  1  0
  9  8  2  0
  3 10  1  0
  2 11  1  0
  6 12  1  0
  5 13  1  0
 14 20  1  0
 15 13  1  0
  7 16  1  0
 17 14  2  0
 18  6  1  0
 18 19  1  0
 20 19  1  0
  1 21  1  1
 22 11  1  0
 23 22  1  0
  2 24  1  1
 25 14  1  0
 23 26  1  6
 18 27  1  6
  3 28  1  6
  5 29  1  1
  4 30  1  6
  6 31  1  6
  7 32  1  1
 12 10  1  0
  5  4  1  0
  7 15  1  0
 23 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3138720

   Lithocholenic 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: 374.57

Molecular Weight (Monoisotopic): 374.2821

AlogP: 5.28

#Rotatable Bonds: 4

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.75

CX Basic pKa: ┄

CX LogP: 4.66

CX LogD: 2.07

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: 2.59

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