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

ID: ALA130588

Chembl Id: CHEMBL130588

PubChem CID: 44352963

Max Phase: Preclinical

Molecular Formula: C30H38O14

Molecular Weight: 622.62

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

Standard InChI:  InChI=1S/C30H38O14/c1-6-15(2)25(35)42-22-21(32)28(43-23(24(33)34)29(40,26(36)37)30(22,44-28)27(38)39)13-12-16(3)20(41-18(5)31)17(4)14-19-10-8-7-9-11-19/h7-11,15,17,20-23,32,40H,3,6,12-14H2,1-2,4-5H3,(H,33,34)(H,36,37)(H,38,39)/t15-,17+,20+,21+,22+,23?,28?,29?,30?/m0/s1

Standard InChI Key:  LUZUJBRCLNAISU-HVQIROLHSA-N

Alternative Forms

1. Parent:

   

   ALA130588

   (6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-4,7-dihydroxy-6-((S)-2-methyl-butyryloxy)-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: 622.62

Molecular Weight (Monoisotopic): 622.2262

AlogP: 1.30

#Rotatable Bonds: 14

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: 2.89

CX Basic pKa:

CX LogP: 3.22

CX LogD: -5.57

Aromatic Rings: 1

Heavy Atoms: 44

QED Weighted: 0.15

Np Likeness Score: 2.09

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