1-(3,5-dichlorophenyl)-N-((2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-((1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyloxy)-tetrahydro-2H-pyran-3-yl)-5-propyl-1H-pyrazole-4-carboxamide

ID: ALA233916

PubChem CID: 44430225

Max Phase: Preclinical

Molecular Formula: C26H35Cl2N3O10

Molecular Weight: 620.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1c(C(=O)N[C@H]2[C@@H](O[C@@H]3C[C@](O)(CO)C[C@@H](O)[C@H]3O)O[C@H](CO)[C@@H](O)[C@@H]2O)cnn1-c1cc(Cl)cc(Cl)c1

Standard InChI:  InChI=1S/C26H35Cl2N3O10/c1-2-3-16-15(9-29-31(16)14-5-12(27)4-13(28)6-14)24(38)30-20-23(37)22(36)19(10-32)41-25(20)40-18-8-26(39,11-33)7-17(34)21(18)35/h4-6,9,17-23,25,32-37,39H,2-3,7-8,10-11H2,1H3,(H,30,38)/t17-,18-,19-,20-,21-,22-,23-,25+,26+/m1/s1

Standard InChI Key:  BNFSKTFWRYROQG-SVAYCJTJSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA233916

   1-(3,5-dichlorophenyl)-N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxyoxan-3-yl]-5-propylpyrazole-4-carboxamide

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: 620.48

Molecular Weight (Monoisotopic): 619.1699

AlogP: -0.71

#Rotatable Bonds: 9

Polar Surface Area: 206.99

Molecular Species: NEUTRAL

HBA: 12

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.61

CX Basic pKa: 1.09

CX LogP: -0.91

CX LogD: -0.91

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.18

Np Likeness Score: 0.34

References

1. Metaferia BB, Ray S, Smith JA, Bewley CA..  (2007)  Design and synthesis of substrate-mimic inhibitors of mycothiol-S-conjugate amidase from Mycobacterium tuberculosis.,  17  (2): [PMID:17084627] [10.1016/j.bmcl.2006.10.031]

Source

Source(1):

• Scientific Literature