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

ID: ALA3526639

PubChem CID: 118753094

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)c(Cl)c2)c2ccc(Cl)cc2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C19H17Cl3N2O7/c20-8-1-4-10(5-2-8)24(19(30)23-9-3-6-11(21)12(22)7-9)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:  LYTMAQKRWKXIFV-CLYSKQOPSA-N

Molfile:  

     RDKit          2D

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   28.0049   -7.0369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9855   -5.3950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3991   -4.5664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1307   -6.6056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6687   -4.5677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4209   -7.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7071   -6.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7030   -5.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4051   -5.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1190   -5.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8268   -5.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5721   -5.7074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8887   -8.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8875   -9.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5956   -9.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3052   -9.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3024   -8.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5938   -7.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1809   -7.8542    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.1795   -9.4902    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   28.0086   -7.8478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7178   -8.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4240   -7.8425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7209   -9.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1332   -8.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1332   -9.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8416   -9.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5488   -9.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5430   -8.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8341   -7.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2586   -9.4640    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5 11  1  0
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  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
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 17 18  2  0
 18 13  1  0
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 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
 23  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3526639

   ---

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: 3.26

CX Basic pKa: ┄

CX LogP: 2.70

CX LogD: -0.73

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: -0.56

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