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

ID: ALA132738

Chembl Id: CHEMBL132738

PubChem CID: 44352814

Max Phase: Preclinical

Molecular Formula: C27H32O14

Molecular Weight: 580.54

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

Standard InChI:  InChI=1S/C27H32O14/c1-13(18(38-15(3)28)14(2)12-17-8-6-5-7-9-17)10-11-25-19(30)20(39-16(4)29)27(41-25,24(35)36)26(37,23(33)34)21(40-25)22(31)32/h5-9,14,18-21,30,37H,1,10-12H2,2-4H3,(H,31,32)(H,33,34)(H,35,36)/t14-,18-,19-,20-,21?,25?,26?,27?/m1/s1

Standard InChI Key:  ZDTKVVYJPVMYES-ILCGWKQVSA-N

Alternative Forms

1. Parent:

   

   ALA132738

   (6R,7R)-6-Acetoxy-1-((4S,5R)-4-acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-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: 580.54

Molecular Weight (Monoisotopic): 580.1792

AlogP: 0.27

#Rotatable Bonds: 12

Polar Surface Area: 223.42

Molecular Species: ACID

HBA: 11

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.73

CX Basic pKa:

CX LogP: 1.53

CX LogD: -7.48

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.17

Np Likeness Score: 2.13

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