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

ID: ALA1093143

Max Phase: Preclinical

Molecular Formula: C29H33NO8S

Molecular Weight: 555.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(CCCCCC(=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/C29H33NO8S/c1-16-18(26(35)23-19(25(16)34)12-8-13-20(23)32)11-6-3-7-14-22(33)30-24-28(37)27(36)21(15-31)38-29(24)39-17-9-4-2-5-10-17/h2,4-5,8-10,12-13,21,24,27-29,31-32,36-37H,3,6-7,11,14-15H2,1H3,(H,30,33)/t21-,24-,27-,28-,29-/m1/s1

Standard InChI Key:  RZUKWCGTIQBYBZ-WQCIBWCFSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA1093143

   ---

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: 555.65

Molecular Weight (Monoisotopic): 555.1927

AlogP: 2.75

#Rotatable Bonds: 10

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: 3.27

CX LogD: 3.21

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.28

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