Phenyl-2-deoxy-2-[3'-(8''-hydroxy-3''-methyl-1'',4''-dioxo-1'',4''-dihydronaphthalen-2''-yl)propanamido]-1-thio-alpha-D-glucopyranoside

ID: ALA1089085

Max Phase: Preclinical

Molecular Formula: C26H27NO8S

Molecular Weight: 513.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(CCC(=O)N[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]2Sc2ccccc2)C(=O)c2c(O)cccc2C1=O

Standard InChI:  InChI=1S/C26H27NO8S/c1-13-15(23(32)20-16(22(13)31)8-5-9-17(20)29)10-11-19(30)27-21-25(34)24(33)18(12-28)35-26(21)36-14-6-3-2-4-7-14/h2-9,18,21,24-26,28-29,33-34H,10-12H2,1H3,(H,27,30)/t18-,21-,24-,25-,26-/m1/s1

Standard InChI Key:  PTRHLXSWTVRMIU-PBDOEIEUSA-N

Molfile:  

     RDKit          2D

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  4  7  1  6
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M  END

Alternative Forms

1. Parent:

   

   ALA1089085

   ---

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: 513.57

Molecular Weight (Monoisotopic): 513.1457

AlogP: 1.58

#Rotatable Bonds: 7

Polar Surface Area: 153.39

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.26

CX Basic pKa: ┄

CX LogP: 1.94

CX LogD: 1.88

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.37

Np Likeness Score: 0.91

References

1. Gammon DW, Steenkamp DJ, Mavumengwana V, Marakalala MJ, Mudzunga TT, Hunter R, Munyololo M..  (2010)  Conjugates of plumbagin and phenyl-2-amino-1-thioglucoside inhibit MshB, a deacetylase involved in the biosynthesis of mycothiol.,  18  (7): [PMID:20304659] [10.1016/j.bmc.2010.02.049]

Source

Source(1):

• Scientific Literature