(2S,3S,4S,5R)-6-(3-(4-chlorophenyl)-1-(3,4-dichlorophenyl)ureido)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

ID: ALA3526638

PubChem CID: 118753093

Max Phase: Preclinical

Molecular Formula: C19H17Cl3N2O7

Molecular Weight: 491.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1OC(N(C(=O)Nc2ccc(Cl)cc2)c2ccc(Cl)c(Cl)c2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C19H17Cl3N2O7/c20-8-1-3-9(4-2-8)23-19(30)24(10-5-6-11(21)12(22)7-10)17-15(27)13(25)14(26)16(31-17)18(28)29/h1-7,13-17,25-27H,(H,23,30)(H,28,29)/t13-,14-,15+,16-,17?/m0/s1

Standard InChI Key:  IWDQKYQKASVMAH-CLYSKQOPSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   18.4754   -6.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4560   -5.2724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8696   -4.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6012   -6.4830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1391   -4.4451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8914   -6.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1775   -6.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1735   -5.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8756   -5.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5894   -5.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2972   -5.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0425   -5.5848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7746   -8.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7734   -8.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4815   -9.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1911   -8.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1883   -8.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4797   -7.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0667   -7.7263    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.0654   -9.3623    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.8945   -7.7199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6037   -8.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3099   -7.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6068   -8.9430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0191   -8.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0191   -8.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7275   -9.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4346   -8.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4289   -8.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7199   -7.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1444   -9.3360    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5 11  1  0
 10  4  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
  7  1  1  6
  8  2  1  1
  9  3  1  6
 11 12  2  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 13 19  1  0
 14 20  1  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
 21  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3526638

   ---

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: 491.71

Molecular Weight (Monoisotopic): 490.0101

AlogP: 2.58

#Rotatable Bonds: 4

Polar Surface Area: 139.56

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.30

CX Basic pKa: ┄

CX LogP: 2.70

CX LogD: -0.73

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: -0.50

References

1. Schebb NH, Franze B, Maul R, Ranganathan A, Hammock BD..  (2012)  In vitro glucuronidation of the antibacterial triclocarban and its oxidative metabolites.,  40  (1): [PMID:21953915] [10.1124/dmd.111.042283]

Source

Source(1):

• Scientific Literature