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

ID: ALA1093142

Max Phase: Preclinical

Molecular Formula: C28H31NO8S

Molecular Weight: 541.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(CCCCC(=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/C28H31NO8S/c1-15-17(25(34)22-18(24(15)33)11-7-12-19(22)31)10-5-6-13-21(32)29-23-27(36)26(35)20(14-30)37-28(23)38-16-8-3-2-4-9-16/h2-4,7-9,11-12,20,23,26-28,30-31,35-36H,5-6,10,13-14H2,1H3,(H,29,32)/t20-,23-,26-,27-,28-/m1/s1

Standard InChI Key:  HXNLIDZRYOFVCO-JKFDDXDISA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA1093142

   ---

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: 541.62

Molecular Weight (Monoisotopic): 541.1770

AlogP: 2.36

#Rotatable Bonds: 9

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: 2.82

CX LogD: 2.77

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.30

Np Likeness Score: 0.97

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