11-O-trans-p-coumaroyl amarolide

ID: ALA450181

Chembl Id: CHEMBL450181

PubChem CID: 10255768

Max Phase: Preclinical

Molecular Formula: C29H34O8

Molecular Weight: 510.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1C[C@H](O)C(=O)[C@]2(C)[C@H]3[C@H](OC(=O)/C=C/c4ccc(O)cc4)C(=O)[C@H](C)[C@@H]4CC(=O)O[C@H](C[C@@H]12)[C@]34C

Standard InChI:  InChI=1S/C29H34O8/c1-14-11-20(31)27(35)29(4)18(14)12-21-28(3)19(13-23(33)36-21)15(2)24(34)25(26(28)29)37-22(32)10-7-16-5-8-17(30)9-6-16/h5-10,14-15,18-21,25-26,30-31H,11-13H2,1-4H3/b10-7+/t14-,15-,18+,19+,20+,21-,25-,26+,28-,29+/m1/s1

Standard InChI Key:  NHJGRRIDYNHGNT-RBASVOMWSA-N

Alternative Forms

1. Parent:

   

   ALA450181

   [(1S,2S,4S,6R,7S,9R,13S,14R,16S,17S)-4-hydroxy-2,6,14,17-tetramethyl-3,11,15-trioxo-10-oxatetracyclo[7.7.1.02,7.013,17]heptadecan-16-yl] (E)-3-(4-hydroxyphenyl)prop-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: 510.58

Molecular Weight (Monoisotopic): 510.2254

AlogP: 3.09

#Rotatable Bonds: 3

Polar Surface Area: 127.20

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.40

CX Basic pKa: ┄

CX LogP: 4.16

CX LogD: 4.16

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.47

Np Likeness Score: 2.64

References

1. Dou J, McChesney JD, Sindelar RD, Goins DK, Walker LA..  (1996)  A new quassinoid from Castela texana.,  59  (1): [PMID:8984156] [10.1021/np960013j]

Source

Source(1):

• Scientific Literature