(3R,4S,5R,6S)-6-(8-chloro-3-cinnamamido-4-hydroxy-2-oxo-2H-chromen-7-yloxy)-5-hydroxy-3-methoxy-2,2-dimethyltetrahydro-2H-pyran-4-yl 5-methyl-1H-pyrrole-2-carboxylate

ID: ALA1275846

Chembl Id: CHEMBL1275846

PubChem CID: 54730369

Max Phase: Preclinical

Molecular Formula: C32H31ClN2O10

Molecular Weight: 639.06

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H]1[C@@H](OC(=O)c2ccc(C)[nH]2)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)/C=C/c4ccccc4)c(=O)oc3c2Cl)OC1(C)C

Standard InChI:  InChI=1S/C32H31ClN2O10/c1-16-10-13-19(34-16)29(39)44-27-25(38)31(45-32(2,3)28(27)41-4)42-20-14-12-18-24(37)23(30(40)43-26(18)22(20)33)35-21(36)15-11-17-8-6-5-7-9-17/h5-15,25,27-28,31,34,37-38H,1-4H3,(H,35,36)/b15-11+/t25-,27+,28-,31-/m1/s1

Standard InChI Key:  YRPQLLNDNYAISI-SNVNZYQNSA-N

Alternative Forms

1. Parent:

   

   ALA1275846

   (3R,4S,5R,6S)-6-(8-chloro-3-cinnamamido-4-hydroxy-2-oxo-2H-chromen-7-yloxy)-5-hydroxy-3-methoxy-2,2-dimethyltetrahydro-2H-pyran-4-yl 5-methyl-1H-pyrrole-2-carboxylate

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: 639.06

Molecular Weight (Monoisotopic): 638.1667

AlogP: 4.56

#Rotatable Bonds: 8

Polar Surface Area: 169.55

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 5.29

CX Basic pKa:

CX LogP: 4.02

CX LogD: 1.98

Aromatic Rings: 4

Heavy Atoms: 45

QED Weighted: 0.12

Np Likeness Score: 0.81

References

1. Anderle C, Stieger M, Burrell M, Reinelt S, Maxwell A, Page M, Heide L..  (2008)  Biological activities of novel gyrase inhibitors of the aminocoumarin class.,  52  (6): [PMID:18347114] [10.1128/aac.01235-07]

Source

Source(1):

• Scientific Literature