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)thiophene-2-carboxamide

ID: ALA399622

PubChem CID: 44430211

Max Phase: Preclinical

Molecular Formula: C18H27NO10S

Molecular Weight: 449.48

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)c1cccs1

Standard InChI:  InChI=1S/C18H27NO10S/c20-6-10-14(24)15(25)12(19-16(26)11-2-1-3-30-11)17(29-10)28-9-5-18(27,7-21)4-8(22)13(9)23/h1-3,8-10,12-15,17,20-25,27H,4-7H2,(H,19,26)/t8-,9-,10-,12-,13-,14-,15-,17+,18+/m1/s1

Standard InChI Key:  HFIPOAXSLHVMPN-OHRHGBHTSA-N

Molfile:  

     RDKit          2D

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    3.7167    0.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4312    0.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1502    0.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1502    1.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4312    1.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8385    0.0419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8612   -1.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1487   -1.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1537   -2.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8697   -2.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5825   -2.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5792   -1.5285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2990   -2.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3031   -3.5900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4300    2.6641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077   -0.2291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0012    1.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989    1.8280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4322   -1.1328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7199   -1.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0034   -1.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7242   -2.3739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9091   -0.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1013   -0.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925   -0.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2476   -1.4768    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5675   -0.7058    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
 11 16  1  1
  8  9  1  0
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  5 18  1  1
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  6 19  1  1
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  5  6  1  0
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  9 23  1  1
  9 10  1  0
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 10 11  1  0
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 11 12  1  0
 24 26  2  0
 25 27  2  0
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  1  2  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
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 14 15  1  0
  8 31  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA399622

   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]thiophene-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: 449.48

Molecular Weight (Monoisotopic): 449.1356

AlogP: -3.09

#Rotatable Bonds: 6

Polar Surface Area: 189.17

Molecular Species: NEUTRAL

HBA: 11

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.65

CX Basic pKa: ┄

CX LogP: -3.46

CX LogD: -3.46

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.22

Np Likeness Score: 0.92

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