(6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-butoxy-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

ID: ALA405288

Chembl Id: CHEMBL405288

PubChem CID: 44353071

Max Phase: Preclinical

Molecular Formula: C29H38O13

Molecular Weight: 594.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(CCC12OC(C(=O)O)C(O)(C(=O)O)C(C(=O)O)(O1)[C@H](OCCCC)[C@H]2O)[C@@H](OC(C)=O)[C@H](C)Cc1ccccc1

Standard InChI:  InChI=1S/C29H38O13/c1-5-6-14-39-22-21(31)27(41-23(24(32)33)28(38,25(34)35)29(22,42-27)26(36)37)13-12-16(2)20(40-18(4)30)17(3)15-19-10-8-7-9-11-19/h7-11,17,20-23,31,38H,2,5-6,12-15H2,1,3-4H3,(H,32,33)(H,34,35)(H,36,37)/t17-,20-,21-,22-,23?,27?,28?,29?/m1/s1

Standard InChI Key:  PYOOJKMTNJGBGV-WGGJGVIXSA-N

Alternative Forms

1. Parent:

   

   ALA405288

   (6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-butoxy-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

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: 594.61

Molecular Weight (Monoisotopic): 594.2312

AlogP: 1.53

#Rotatable Bonds: 15

Polar Surface Area: 206.35

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.94

CX Basic pKa:

CX LogP: 3.05

CX LogD: -5.52

Aromatic Rings: 1

Heavy Atoms: 42

QED Weighted: 0.11

Np Likeness Score: 1.85

References

1. Ponpipom MM, Girotra NN, Bugianesi RL, Roberts CD, Berger GD, Burk RM, Marquis RW, Parsons WH, Bartizal KF, Bergstom JD..  (1994)  Structure-activity relationships of C1 and C6 side chains of zaragozic acid A derivatives.,  37  (23): [PMID:7966163] [10.1021/jm00049a022]

Source

Source(1):

• Scientific Literature