Gemfibrozil-1-O-beta-glucuronide

ID: ALA2181817

Cas Number: 91683-38-4

PubChem CID: 88127

Product Number: G647264, Order Now?

Max Phase: Preclinical

Molecular Formula: C21H30O9

Molecular Weight: 426.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C)c(OCCCC(C)(C)C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)c1

Standard InChI:  InChI=1S/C21H30O9/c1-11-6-7-12(2)13(10-11)28-9-5-8-21(3,4)20(27)30-19-16(24)14(22)15(23)17(29-19)18(25)26/h6-7,10,14-17,19,22-24H,5,8-9H2,1-4H3,(H,25,26)/t14-,15-,16+,17-,19-/m0/s1

Standard InChI Key:  CJMNXSKEVNPQOK-LVEJAMMSSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   17.9163  -10.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6611  -10.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2023  -10.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6611   -9.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9554  -10.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9163   -9.3110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9512   -8.9024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6221  -10.5368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2496  -10.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2496   -9.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3751  -10.5368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4965  -10.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7937  -11.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6109  -11.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3669   -8.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0809  -10.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5397  -10.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7908  -10.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3303  -10.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0352  -10.5425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7412  -10.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7464   -9.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0394   -8.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3271   -9.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0431   -8.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4469  -10.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6198   -8.9058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4562   -8.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4428  -11.3675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1566  -10.1453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  1  0
  3  1  1  0
  4  2  1  0
  5  2  2  0
  6  1  2  0
  7  4  2  0
  8  1  1  0
  9  5  1  0
 10  9  2  0
 11 16  1  0
 12  3  1  0
 13  3  1  0
 14  3  1  0
 15  4  1  0
 16 18  1  0
 17  9  1  0
 18 12  1  0
  7 10  1  0
 19  8  1  1
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  1
 21 26  1  1
 24 27  1  6
 22 28  1  6
 26 29  2  0
 26 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2181817

   Gemfibrozil 1-O-β-glucuronide

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: 426.46

Molecular Weight (Monoisotopic): 426.1890

AlogP: 0.92

#Rotatable Bonds: 8

Polar Surface Area: 142.75

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.49

CX Basic pKa: ┄

CX LogP: 2.44

CX LogD: -0.94

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.35

Np Likeness Score: 0.71

References

1. Orr ST, Ripp SL, Ballard TE, Henderson JL, Scott DO, Obach RS, Sun H, Kalgutkar AS..  (2012)  Mechanism-based inactivation (MBI) of cytochrome P450 enzymes: structure-activity relationships and discovery strategies to mitigate drug-drug interaction risks.,  55  (11): [PMID:22409598] [10.1021/jm300065h]

2. Ma Y, Fu Y, Khojasteh SC, Dalvie D, Zhang D..  (2017)  Glucuronides as Potential Anionic Substrates of Human Cytochrome P450 2C8 (CYP2C8).,  60  (21): [PMID:28653847] [10.1021/acs.jmedchem.7b00510]

3. EUbOPEN.  (2023)  EUbOPEN Chemogenomics Library - IncuCyte,  [10.6019/CHEMBL5303304]

Source

Source(2):

• Scientific Literature
• EUbOPEN Chemogenomic Library