5-(N-(((2R,3S,4R,5R)-5-(3-bromobenzamido)-3,4,6-trihydroxytetrahydro-2H-pyran-2-yl)methyl)sulfamoyl)-2-methylfuran-3-carboxylic acid

ID: ALA3805205

Chembl Id: CHEMBL3805205

PubChem CID: 57411679

Max Phase: Preclinical

Molecular Formula: C19H21BrN2O10S

Molecular Weight: 549.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1oc(S(=O)(=O)NC[C@H]2OC(O)[C@H](NC(=O)c3cccc(Br)c3)[C@@H](O)[C@@H]2O)cc1C(=O)O

Standard InChI:  InChI=1S/C19H21BrN2O10S/c1-8-11(18(26)27)6-13(31-8)33(29,30)21-7-12-15(23)16(24)14(19(28)32-12)22-17(25)9-3-2-4-10(20)5-9/h2-6,12,14-16,19,21,23-24,28H,7H2,1H3,(H,22,25)(H,26,27)/t12-,14-,15-,16-,19?/m1/s1

Standard InChI Key:  GEVMYBPXLUPCSS-VGFLMNAYSA-N

Alternative Forms

1. Parent:

   

   ALA3805205

   5-[[(2R,3S,4R,5R)-5-[(3-bromobenzoyl)amino]-3,4,6-trihydroxyoxan-2-yl]methylsulfamoyl]-2-methylfuran-3-carboxylic acid

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: 549.35

Molecular Weight (Monoisotopic): 548.0100

AlogP: -0.44

#Rotatable Bonds: 7

Polar Surface Area: 195.63

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.09

CX Basic pKa: ┄

CX LogP: -0.19

CX LogD: -3.33

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.26

Np Likeness Score: -0.15

References

1. Lin H, Zeng J, Xie R, Schulz MJ, Tedesco R, Qu J, Erhard KF, Mack JF, Raha K, Rendina AR, Szewczuk LM, Kratz PM, Jurewicz AJ, Cecconie T, Martens S, McDevitt PJ, Martin JD, Chen SB, Jiang Y, Nickels L, Schwartz BJ, Smallwood A, Zhao B, Campobasso N, Qian Y, Briand J, Rominger CM, Oleykowski C, Hardwicke MA, Luengo JI..  (2016)  Discovery of a Novel 2,6-Disubstituted Glucosamine Series of Potent and Selective Hexokinase 2 Inhibitors.,  7  (3): [PMID:26985301] [10.1021/acsmedchemlett.5b00214]

Source

Source(1):

• Scientific Literature