4-Bromo-benzoic acid (1R,3R,5S,6R,12S,15S)-6-chloro-5-hydroxy-15-(1-hydroxy-1-methyl-ethyl)-12-methyl-9-methylene-2-oxa-tricyclo[10.3.0.0*1,3*]pentadec-5-ylmethyl ester

ID: ALA497710

Chembl Id: CHEMBL497710

PubChem CID: 13945601

Max Phase: Preclinical

Molecular Formula: C27H36BrClO5

Molecular Weight: 555.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@@H](Cl)[C@@](O)(COC(=O)c2ccc(Br)cc2)C[C@H]2O[C@@]23[C@H](C(C)(C)O)CC[C@@]3(C)CC1

Standard InChI:  InChI=1S/C27H36BrClO5/c1-17-5-10-21(29)26(32,16-33-23(30)18-6-8-19(28)9-7-18)15-22-27(34-22)20(24(2,3)31)12-14-25(27,4)13-11-17/h6-9,20-22,31-32H,1,5,10-16H2,2-4H3/t20-,21+,22+,25+,26-,27-/m0/s1

Standard InChI Key:  IXLSQDRBQLJQKH-OGZANOHWSA-N

Alternative Forms

1. Parent:

   

   ALA497710

   [(1R,3R,5S,6R,12S,15S)-6-chloro-5-hydroxy-15-(2-hydroxypropan-2-yl)-12-methyl-9-methylidene-2-oxatricyclo[10.3.0.01,3]pentadecan-5-yl]methyl 4-bromobenzoate

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: 555.94

Molecular Weight (Monoisotopic): 554.1435

AlogP: 5.79

#Rotatable Bonds: 4

Polar Surface Area: 79.29

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.96

CX Basic pKa: ┄

CX LogP: 5.60

CX LogD: 5.60

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.21

Np Likeness Score: 2.37

References

1. Yabe T, Yamada H, Shimomura M, Miyaoka H, Yamada Y..  (2000)  Induction of choline acetyltransferase activity in cholinergic neurons by stolonidiol: structure-activity relationship.,  63  (4): [PMID:10785408] [10.1021/np990263a]

Source

Source(1):

• Scientific Literature