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

ID: ALA131651

Chembl Id: CHEMBL131651

PubChem CID: 44352888

Max Phase: Preclinical

Molecular Formula: C29H37NO13S

Molecular Weight: 639.68

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

Standard InChI:  InChI=1S/C29H37NO13S/c1-14(2)30-26(44)41-21-20(32)27(42-22(23(33)34)28(39,24(35)36)29(21,43-27)25(37)38)12-11-15(3)19(40-17(5)31)16(4)13-18-9-7-6-8-10-18/h6-10,14,16,19-22,32,39H,3,11-13H2,1-2,4-5H3,(H,30,44)(H,33,34)(H,35,36)(H,37,38)/t16-,19-,20-,21-,22?,27?,28?,29?/m1/s1

Standard InChI Key:  WHLBCNLGWROAJM-JVDZYOIDSA-N

Alternative Forms

1. Parent:

   

   ALA131651

   (6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-4,7-dihydroxy-6-isopropylthiocarbamoyloxy-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: 639.68

Molecular Weight (Monoisotopic): 639.1986

AlogP: 1.42

#Rotatable Bonds: 13

Polar Surface Area: 218.71

Molecular Species: ZWITTERION

HBA: 11

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.66

CX Basic pKa: 8.61

CX LogP: 3.03

CX LogD: -6.06

Aromatic Rings: 1

Heavy Atoms: 44

QED Weighted: 0.06

Np Likeness Score: 1.80

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