3-O-(4-Methoxy)cinnamoyl caudatin

ID: ALA2046559

Chembl Id: CHEMBL2046559

PubChem CID: 66573231

Max Phase: Preclinical

Molecular Formula: C38H50O9

Molecular Weight: 650.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/C(=O)O[C@H]2CC[C@@]3(C)C(=CC[C@]4(O)[C@@H]3C[C@@H](OC(=O)/C=C(\C)C(C)C)[C@@]3(C)[C@]4(O)CC[C@@]3(O)C(C)=O)C2)cc1

Standard InChI:  InChI=1S/C38H50O9/c1-23(2)24(3)20-33(41)47-31-22-30-34(5)16-15-29(46-32(40)13-10-26-8-11-28(45-7)12-9-26)21-27(34)14-17-37(30,43)38(44)19-18-36(42,25(4)39)35(31,38)6/h8-14,20,23,29-31,42-44H,15-19,21-22H2,1-7H3/b13-10+,24-20+/t29-,30+,31+,34-,35+,36+,37-,38+/m0/s1

Standard InChI Key:  SEXRIOKVROQFNA-GAKBQJCISA-N

Alternative Forms

1. Parent:

   

   ALA2046559

   [(3S,8S,9R,10R,12R,13S,14R,17S)-17-acetyl-8,14,17-trihydroxy-3-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] (E)-3,4-dimethylpent-2-enoate

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: 650.81

Molecular Weight (Monoisotopic): 650.3455

AlogP: 5.26

#Rotatable Bonds: 8

Polar Surface Area: 139.59

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.39

CX Basic pKa: ┄

CX LogP: 5.19

CX LogD: 5.19

Aromatic Rings: 1

Heavy Atoms: 47

QED Weighted: 0.20

Np Likeness Score: 2.31

References

1. Wang LJ, Geng CA, Ma YB, Luo J, Huang XY, Chen H, Zhou NJ, Zhang XM, Chen JJ..  (2012)  Design, synthesis, and molecular hybrids of caudatin and cinnamic acids as novel anti-hepatitis B virus agents.,  54  [PMID:22687441] [10.1016/j.ejmech.2012.05.012]

2. Huang LJ, Chen SR, Yuan CM, Gu W, Guo BJ, Wang YT, Wang Y, Hao XJ..  (2017)  C21-steroidal pregnane sapogenins and their derivatives as anti-inflammatory agents.,  25  (13): [PMID:28506585] [10.1016/j.bmc.2017.04.045]

Source

Source(1):

• Scientific Literature