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

ID: ALA131464

Chembl Id: CHEMBL131464

PubChem CID: 44353081

Max Phase: Preclinical

Molecular Formula: C28H35NO14

Molecular Weight: 609.58

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

Standard InChI:  InChI=1S/C28H35NO14/c1-5-29-25(38)41-20-19(31)26(42-21(22(32)33)27(39,23(34)35)28(20,43-26)24(36)37)12-11-14(2)18(40-16(4)30)15(3)13-17-9-7-6-8-10-17/h6-10,15,18-21,31,39H,2,5,11-13H2,1,3-4H3,(H,29,38)(H,32,33)(H,34,35)(H,36,37)/t15-,18-,19-,20-,21?,26?,27?,28?/m1/s1

Standard InChI Key:  DORWMMMQWARLTH-DMFWGQTKSA-N

Alternative Forms

1. Parent:

   

   ALA131464

   (6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-ethylcarbamoyloxy-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: 609.58

Molecular Weight (Monoisotopic): 609.2058

AlogP: 0.46

#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: 2.81

CX Basic pKa:

CX LogP: 1.78

CX LogD: -7.16

Aromatic Rings: 1

Heavy Atoms: 43

QED Weighted: 0.13

Np Likeness Score: 1.79

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