(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-acetoxy-4-(acetoxymethyl)-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate

ID: ALA2334539

Chembl Id: CHEMBL2334539

PubChem CID: 71560677

Max Phase: Preclinical

Molecular Formula: C37H38N2O10

Molecular Weight: 670.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@@]1(C)[C@@H]2C[C@H](OC(=O)c3ccc(C#N)cc3)[C@@]3(C)Oc4cc(-c5cccnc5)oc(=O)c4[C@H](O)[C@@H]3[C@@]2(C)CC[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C37H38N2O10/c1-20(40)45-19-36(4)27-16-29(48-33(43)23-10-8-22(17-38)9-11-23)37(5)32(35(27,3)13-12-28(36)46-21(2)41)31(42)30-26(49-37)15-25(47-34(30)44)24-7-6-14-39-18-24/h6-11,14-15,18,27-29,31-32,42H,12-13,16,19H2,1-5H3/t27-,28+,29+,31+,32-,35+,36+,37-/m1/s1

Standard InChI Key:  HBSJDWOXHMSOQS-ZRPSWOMSSA-N

Alternative Forms

1. Parent:

   

   ALA2334539

   [(1S,2S,5S,6R,7R,9S,10S,18R)-5-acetyloxy-6-(acetyloxymethyl)-18-hydroxy-2,6,10-trimethyl-16-oxo-14-pyridin-3-yl-11,15-dioxatetracyclo[8.8.0.02,7.012,17]octadeca-12(17),13-dien-9-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: 670.72

Molecular Weight (Monoisotopic): 670.2526

AlogP: 4.92

#Rotatable Bonds: 6

Polar Surface Area: 175.25

Molecular Species: NEUTRAL

HBA: 12

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.84

CX Basic pKa: 4.21

CX LogP: 2.82

CX LogD: 2.82

Aromatic Rings: 3

Heavy Atoms: 49

QED Weighted: 0.28

Np Likeness Score: 1.47

References

1. Ohtawa M, Yamazaki H, Ohte S, Matsuda D, Ohshiro T, Rudel LL, Omura 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 1.,  23  (5): [PMID:23369538] [10.1016/j.bmcl.2012.12.099]

2. 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]

3. 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