4-Cyano-benzoic acid(4aR,6S,7aS,9R,12R,12bS)-12-hydroxy-4a,6a,12b-trimethyl-11-oxo-9-(R)-pyridin-3-yl-2-((S)-o-tolyl)-4,4a,4b,5,6,6a,12,12a,12b,13,14,14a-dodecahydro-11H-1,3,7,10-tetraoxa-benzo[b]chrysen-6-yl ester

ID: ALA2398804

Chembl Id: CHEMBL2398804

PubChem CID: 71682658

Max Phase: Preclinical

Molecular Formula: C41H40N2O8

Molecular Weight: 688.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1[C@@H]1OC[C@@]2(C)[C@@H]3C[C@H](OC(=O)c4ccc(C#N)cc4)[C@@]4(C)Oc5cc(-c6cccnc6)oc(=O)c5[C@H](O)[C@@H]4[C@@]3(C)CC[C@@H]2O1

Standard InChI:  InChI=1S/C41H40N2O8/c1-23-8-5-6-10-27(23)38-47-22-40(3)30-19-32(49-36(45)25-13-11-24(20-42)12-14-25)41(4)35(39(30,2)16-15-31(40)50-38)34(44)33-29(51-41)18-28(48-37(33)46)26-9-7-17-43-21-26/h5-14,17-18,21,30-32,34-35,38,44H,15-16,19,22H2,1-4H3/t30-,31+,32+,34+,35-,38-,39+,40+,41-/m1/s1

Standard InChI Key:  LSDMSWMTGQIHRK-KFSBURAESA-N

Alternative Forms

1. Parent:

   

   ALA2398804

   [(1S,2S,3R,11S,12S,14R,15R,18R,20S)-3-hydroxy-1,11,15-trimethyl-18-(2-methylphenyl)-5-oxo-7-pyridin-3-yl-6,10,17,19-tetraoxapentacyclo[12.8.0.02,11.04,9.015,20]docosa-4(9),7-dien-12-yl] 4-cyanobenzoate

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: 688.78

Molecular Weight (Monoisotopic): 688.2785

AlogP: 6.85

#Rotatable Bonds: 4

Polar Surface Area: 141.11

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.84

CX Basic pKa: 4.21

CX LogP: 5.61

CX LogD: 5.61

Aromatic Rings: 4

Heavy Atoms: 51

QED Weighted: 0.23

Np Likeness Score: 1.11

References

1. Ohtawa M, Yamazaki H, Ohte S, Matsuda D, Ohshiro T, Rudel LL, Ōmura S, Tomoda H, Nagamitsu T..  (2013)  Synthesis and structure-activity relationship of pyripyropene A derivatives as potent and selective acyl-CoA:cholesterol acyltransferase 2 (ACAT2) inhibitors: part 3.,  23  (13): [PMID:23711919] [10.1016/j.bmcl.2013.04.075]

2.  (2013)  Pyripyropene derivative having ACAT2 inhibiting activity and stable to metabolizing enzymes, 

3.  (2017)  Pyripyropene derivatives having acat2 inhibiting activity and stable to metabolizing enzymes, 

4. Bhattacharjee P, Rutland N, Iyer MR..  (2022)  Targeting Sterol O-Acyltransferase/Acyl-CoA:Cholesterol Acyltransferase (ACAT): A Perspective on Small-Molecule Inhibitors and Their Therapeutic Potential.,  65  (24.0): [PMID:36473091] [10.1021/acs.jmedchem.2c01265]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data