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

ID: ALA1091142

PubChem CID: 46871789

Max Phase: Preclinical

Molecular Formula: C27H29NO8S

Molecular Weight: 527.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(CCCC(=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/C27H29NO8S/c1-14-16(24(33)21-17(23(14)32)10-5-11-18(21)30)9-6-12-20(31)28-22-26(35)25(34)19(13-29)36-27(22)37-15-7-3-2-4-8-15/h2-5,7-8,10-11,19,22,25-27,29-30,34-35H,6,9,12-13H2,1H3,(H,28,31)/t19-,22-,25-,26-,27-/m1/s1

Standard InChI Key:  BEKQIAVEBGPSSJ-PYZIYVKRSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   -3.9629   -5.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9629   -6.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2508   -6.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5387   -6.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5387   -5.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2508   -5.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8248   -6.8975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2508   -7.7174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6768   -6.8975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6786   -5.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3919   -5.6630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8230   -5.2484    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8206   -4.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041   -4.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1013   -3.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152   -2.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5333   -3.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5325   -4.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096   -6.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3957   -6.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1084   -5.6609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3194   -6.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0334   -6.9016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486   -6.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4589   -6.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4636   -5.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7444   -5.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1774   -5.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686   -6.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8775   -6.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5956   -6.5116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6005   -5.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911   -5.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0301   -5.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4676   -4.4329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4554   -7.7322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8696   -7.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 18 13  1  0
  2  9  1  6
  7 19  1  0
  2  3  1  0
 19 20  1  0
  1 10  1  1
 19 21  2  0
  3  4  1  0
 20 22  1  0
 10 11  1  0
 22 23  1  0
  4  5  1  0
 23 24  1  0
 24 25  1  0
  5 12  1  6
  5  6  1  0
 12 13  1  0
 24 27  2  0
 25 29  1  0
 28 26  1  0
 26 27  1  0
 13 14  2  0
 28 29  2  0
  4  7  1  6
 29 30  1  0
 14 15  1  0
 30 31  2  0
  1  2  1  0
 31 32  1  0
 15 16  2  0
 32 33  2  0
 33 28  1  0
  3  8  1  1
 27 34  1  0
 16 17  1  0
 26 35  2  0
  1  6  1  0
 25 36  2  0
 17 18  2  0
 30 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091142

   N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylsulfanyloxan-3-yl]-4-(8-hydroxy-3-methyl-1,4-dioxonaphthalen-2-yl)butanamide

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: 527.60

Molecular Weight (Monoisotopic): 527.1614

AlogP: 1.97

#Rotatable Bonds: 8

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: 2.38

CX LogD: 2.32

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.35

Np Likeness Score: 0.93

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