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)-2-naphthamide

ID: ALA232091

PubChem CID: 44430218

Max Phase: Preclinical

Molecular Formula: C24H31NO10

Molecular Weight: 493.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1[C@@H](O[C@@H]2C[C@](O)(CO)C[C@@H](O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O)c1ccc2ccccc2c1

Standard InChI:  InChI=1S/C24H31NO10/c26-10-17-20(30)21(31)18(25-22(32)14-6-5-12-3-1-2-4-13(12)7-14)23(35-17)34-16-9-24(33,11-27)8-15(28)19(16)29/h1-7,15-21,23,26-31,33H,8-11H2,(H,25,32)/t15-,16-,17-,18-,19-,20-,21-,23+,24+/m1/s1

Standard InChI Key:  GYMNNYHHKZEXFO-VABGSTQBSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA232091

   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]naphthalene-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: 493.51

Molecular Weight (Monoisotopic): 493.1948

AlogP: -2.00

#Rotatable Bonds: 6

Polar Surface Area: 189.17

Molecular Species: NEUTRAL

HBA: 10

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.66

CX Basic pKa: ┄

CX LogP: -2.38

CX LogD: -2.38

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.22

Np Likeness Score: 1.11

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