4-(10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid

ID: ALA4093171

Cas Number: 7276-59-7

PubChem CID: 2975

Max Phase: Preclinical

Molecular Formula: C24H34O5

Molecular Weight: 402.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(CCC(=O)O)C1CCC2C3C(=O)CC4CC(=O)CCC4(C)C3CC(=O)C12C

Standard InChI:  InChI=1S/C24H34O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-18,22H,4-12H2,1-3H3,(H,28,29)

Standard InChI Key:  OHXPGWPVLFPUSM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   21.2256   -4.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7775   -5.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5854   -5.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8373   -4.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6452   -4.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1969   -5.0683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9013   -3.6701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5212   -6.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7370   -6.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7370   -7.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0238   -7.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3108   -7.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3107   -6.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0238   -6.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0238   -5.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5934   -7.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5934   -8.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8802   -9.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1671   -8.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1671   -7.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8802   -7.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4539   -9.0955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3108   -9.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0238   -8.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7370   -9.0955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5934   -7.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5212   -7.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0062   -7.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8228   -5.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
 10  9  1  0
 10 11  1  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
  9 14  1  0
 14 15  2  0
 12 16  1  0
 17 16  1  0
 17 18  1  0
 19 18  1  0
 20 19  1  0
 21 20  1  0
 16 21  1  0
 19 22  2  0
 23 17  1  0
 24 23  1  0
 11 24  1  0
 24 25  2  0
 16 26  1  0
 27 10  1  0
 28 27  1  0
  8 28  1  0
  9 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4093171

   3,7,12-Trioxocholan-24-oic 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: 402.53

Molecular Weight (Monoisotopic): 402.2406

AlogP: 4.07

#Rotatable Bonds: 4

Polar Surface Area: 88.51

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.35

CX Basic pKa: ┄

CX LogP: 3.64

CX LogD: 0.71

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.77

Np Likeness Score: 2.26

References

1. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

2. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(2):

• Scientific Literature
• IMI-CARE SARS-CoV-2 Data