4-[3''-(Aminosulfonyl)phenyl]-1-(2',3',4',6'-tetra-O-propionyl-beta-D-glucopyranosyl)-1H-1,2,3-triazole

ID: ALA3092938

PubChem CID: 72792903

Max Phase: Preclinical

Molecular Formula: C26H34N4O11S

Molecular Weight: 610.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)OC[C@H]1O[C@@H](n2cc(-c3cccc(S(N)(=O)=O)c3)nn2)[C@H](OC(=O)CC)[C@@H](OC(=O)CC)[C@@H]1OC(=O)CC

Standard InChI:  InChI=1S/C26H34N4O11S/c1-5-19(31)37-14-18-23(39-20(32)6-2)24(40-21(33)7-3)25(41-22(34)8-4)26(38-18)30-13-17(28-29-30)15-10-9-11-16(12-15)42(27,35)36/h9-13,18,23-26H,5-8,14H2,1-4H3,(H2,27,35,36)/t18-,23-,24+,25-,26-/m1/s1

Standard InChI Key:  JILXNVFTERDRCZ-ABNLYDASSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3092938

   [(2R,3R,4S,5R,6R)-3,4,5-tri(propanoyloxy)-6-[4-(3-sulfamoylphenyl)triazol-1-yl]oxan-2-yl]methyl propanoate

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: 610.64

Molecular Weight (Monoisotopic): 610.1945

AlogP: 1.41

#Rotatable Bonds: 12

Polar Surface Area: 205.30

Molecular Species: NEUTRAL

HBA: 14

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.03

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: 2.81

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.27

Np Likeness Score: -0.24

References

1. Carroux CJ, Rankin GM, Moeker J, Bornaghi LF, Katneni K, Morizzi J, Charman SA, Vullo D, Supuran CT, Poulsen SA..  (2013)  A prodrug approach toward cancer-related carbonic anhydrase inhibition.,  56  (23): [PMID:24200125] [10.1021/jm401163e]

Source

Source(1):

• Scientific Literature