(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-nitrobenzoate

ID: ALA2334194

Chembl Id: CHEMBL2334194

PubChem CID: 71561054

Max Phase: Preclinical

Molecular Formula: C36H38N2O12

Molecular Weight: 690.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@@]1(C)[C@@H]2C[C@H](OC(=O)c3ccc([N+](=O)[O-])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/C36H38N2O12/c1-19(39)46-18-35(4)26-16-28(49-32(42)21-8-10-23(11-9-21)38(44)45)36(5)31(34(26,3)13-12-27(35)47-20(2)40)30(41)29-25(50-36)15-24(48-33(29)43)22-7-6-14-37-17-22/h6-11,14-15,17,26-28,30-31,41H,12-13,16,18H2,1-5H3/t26-,27+,28+,30+,31-,34+,35+,36-/m1/s1

Standard InChI Key:  DHWSEXMNXLGQJB-HRSZXCBJSA-N

Alternative Forms

1. Parent:

   

   ALA2334194

   [(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-nitrobenzoate

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: 690.70

Molecular Weight (Monoisotopic): 690.2425

AlogP: 4.96

#Rotatable Bonds: 7

Polar Surface Area: 194.60

Molecular Species: NEUTRAL

HBA: 13

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.84

CX Basic pKa: 4.21

CX LogP: 2.90

CX LogD: 2.90

Aromatic Rings: 3

Heavy Atoms: 50

QED Weighted: 0.15

Np Likeness Score: 1.43

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. 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