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

ID: ALA336406

Chembl Id: CHEMBL336406

PubChem CID: 44353089

Max Phase: Preclinical

Molecular Formula: C28H36O13

Molecular Weight: 580.58

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](OCCC)[C@H]2O)[C@@H](OC(C)=O)[C@H](C)Cc1ccccc1

Standard InChI:  InChI=1S/C28H36O13/c1-5-13-38-21-20(30)26(40-22(23(31)32)27(37,24(33)34)28(21,41-26)25(35)36)12-11-15(2)19(39-17(4)29)16(3)14-18-9-7-6-8-10-18/h6-10,16,19-22,30,37H,2,5,11-14H2,1,3-4H3,(H,31,32)(H,33,34)(H,35,36)/t16-,19-,20-,21-,22?,26?,27?,28?/m1/s1

Standard InChI Key:  HVLJOPVZMQPKIF-JMZZSOILSA-N

Alternative Forms

1. Parent:

   

   ALA336406

   (6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-4,7-dihydroxy-6-propoxy-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: 580.58

Molecular Weight (Monoisotopic): 580.2156

AlogP: 1.14

#Rotatable Bonds: 14

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: 2.90

CX Basic pKa:

CX LogP: 2.61

CX LogD: -6.08

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.15

Np Likeness Score: 1.84

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