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

ID: ALA130003

Chembl Id: CHEMBL130003

PubChem CID: 44353105

Max Phase: Preclinical

Molecular Formula: C29H35NO14

Molecular Weight: 621.59

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)NC1CC1)[C@H]2O)[C@@H](OC(C)=O)[C@H](C)Cc1ccccc1

Standard InChI:  InChI=1S/C29H35NO14/c1-14(19(41-16(3)31)15(2)13-17-7-5-4-6-8-17)11-12-27-20(32)21(42-26(39)30-18-9-10-18)29(44-27,25(37)38)28(40,24(35)36)22(43-27)23(33)34/h4-8,15,18-22,32,40H,1,9-13H2,2-3H3,(H,30,39)(H,33,34)(H,35,36)(H,37,38)/t15-,19-,20-,21-,22?,27?,28?,29?/m1/s1

Standard InChI Key:  QKYLAHILVJSRAT-ZBOWUDIFSA-N

Alternative Forms

1. Parent:

   

   ALA130003

   (6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-cyclopropylcarbamoyloxy-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: 621.59

Molecular Weight (Monoisotopic): 621.2058

AlogP: 0.60

#Rotatable Bonds: 13

Polar Surface Area: 235.45

Molecular Species: ACID

HBA: 11

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.79

CX Basic pKa:

CX LogP: 1.88

CX LogD: -6.99

Aromatic Rings: 1

Heavy Atoms: 44

QED Weighted: 0.13

Np Likeness Score: 1.67

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