3-chloro-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)-4-(isopropylsulfonyl)thiophene-2-carboxamide

ID: ALA231889

PubChem CID: 44430227

Max Phase: Preclinical

Molecular Formula: C21H32ClNO12S2

Molecular Weight: 590.07

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)S(=O)(=O)c1csc(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)c1Cl

Standard InChI:  InChI=1S/C21H32ClNO12S2/c1-8(2)37(32,33)12-6-36-18(13(12)22)19(30)23-14-17(29)16(28)11(5-24)35-20(14)34-10-4-21(31,7-25)3-9(26)15(10)27/h6,8-11,14-17,20,24-29,31H,3-5,7H2,1-2H3,(H,23,30)/t9-,10-,11-,14-,15-,16-,17-,20+,21+/m1/s1

Standard InChI Key:  MNDYLVJQYMJCRK-HUHZDMDSSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA231889

   3-chloro-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]-4-propan-2-ylsulfonylthiophene-2-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: 590.07

Molecular Weight (Monoisotopic): 589.1054

AlogP: -2.25

#Rotatable Bonds: 8

Polar Surface Area: 223.31

Molecular Species: NEUTRAL

HBA: 13

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.92

CX Basic pKa: ┄

CX LogP: -2.94

CX LogD: -2.94

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.16

Np Likeness Score: 0.67

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