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)furan-2-carboxamide

ID: ALA427668

PubChem CID: 44430210

Max Phase: Preclinical

Molecular Formula: C18H27NO11

Molecular Weight: 433.41

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)c1ccco1

Standard InChI:  InChI=1S/C18H27NO11/c20-6-11-14(24)15(25)12(19-16(26)9-2-1-3-28-9)17(30-11)29-10-5-18(27,7-21)4-8(22)13(10)23/h1-3,8,10-15,17,20-25,27H,4-7H2,(H,19,26)/t8-,10-,11-,12-,13-,14-,15-,17+,18+/m1/s1

Standard InChI Key:  OLIKFPQUHJMEKO-XIQAJCNHSA-N

Molfile:  

     RDKit          2D

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   -4.0087   -1.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2880   -2.4426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1030   -0.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9108   -0.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3197   -0.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7645   -1.5455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4446   -0.7746    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4  7  1  6
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  8 31  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA427668

   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]furan-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: 433.41

Molecular Weight (Monoisotopic): 433.1584

AlogP: -3.56

#Rotatable Bonds: 6

Polar Surface Area: 202.31

Molecular Species: NEUTRAL

HBA: 11

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.65

CX Basic pKa: ┄

CX LogP: -4.31

CX LogD: -4.31

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.22

Np Likeness Score: 1.14

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