Pentanoic acid (1R,2S,4R,7R,9R,12aS)-12-hydroxy-4a,6a-dimethyl-12b-(S)-methyl-11-oxo-9-(1S,6S)-pyridin-3-yl-2-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: ALA2398796

Chembl Id: CHEMBL2398796

PubChem CID: 10508383

Max Phase: Preclinical

Molecular Formula: C38H45NO8

Molecular Weight: 643.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC(=O)O[C@H]1C[C@H]2[C@]3(C)CO[C@@H](c4ccccc4C)O[C@H]3CC[C@]2(C)[C@H]2[C@@H](O)c3c(cc(-c4cccnc4)oc3=O)O[C@]12C

Standard InChI:  InChI=1S/C38H45NO8/c1-6-7-14-30(40)45-29-19-27-36(3,16-15-28-37(27,4)21-43-35(46-28)24-13-9-8-11-22(24)2)33-32(41)31-26(47-38(29,33)5)18-25(44-34(31)42)23-12-10-17-39-20-23/h8-13,17-18,20,27-29,32-33,35,41H,6-7,14-16,19,21H2,1-5H3/t27-,28+,29+,32+,33-,35-,36+,37+,38-/m1/s1

Standard InChI Key:  FBZJVGOWLSYPGL-QATYFIILSA-N

Alternative Forms

1. Parent:

   

   ALA2398796

   [(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] pentanoate

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: 643.78

Molecular Weight (Monoisotopic): 643.3145

AlogP: 6.85

#Rotatable Bonds: 6

Polar Surface Area: 117.32

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.84

CX Basic pKa: 4.21

CX LogP: 5.29

CX LogD: 5.29

Aromatic Rings: 3

Heavy Atoms: 47

QED Weighted: 0.29

Np Likeness Score: 1.48

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. 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(1):

• Scientific Literature