(1R,4R,5R)-1,4,5-Trihydroxy-3-[(1S)-1-chloro-2-phenyl]-ethylcyclohex-2-en-1-carboxylic Acid

ID: ALA3233399

PubChem CID: 90670057

Max Phase: Preclinical

Molecular Formula: C15H17ClO5

Molecular Weight: 312.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C([C@@H](Cl)Cc2ccccc2)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C15H17ClO5/c16-11(6-9-4-2-1-3-5-9)10-7-15(21,14(19)20)8-12(17)13(10)18/h1-5,7,11-13,17-18,21H,6,8H2,(H,19,20)/t11-,12+,13+,15-/m0/s1

Standard InChI Key:  QMQNCCFRKZZYHM-JLNYLFASSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   28.7258   -1.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7258   -2.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4379   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1499   -2.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1499   -1.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4379   -1.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8467   -0.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1313   -1.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8654   -1.4818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0904   -0.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4379   -4.0293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8638   -3.2095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0119   -3.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0132   -4.0345    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.2969   -2.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5830   -3.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8704   -2.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1570   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1577   -4.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8779   -4.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5883   -4.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  8 10  2  0
  3 11  1  6
  4 12  1  1
  2 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3233399

   (1R,4R,5R)-3-[(1S)-1-chloro-2-phenylethyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid

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: 312.75

Molecular Weight (Monoisotopic): 312.0765

AlogP: 0.70

#Rotatable Bonds: 4

Polar Surface Area: 97.99

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.81

CX Basic pKa: ┄

CX LogP: 0.79

CX LogD: -2.46

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.48

Np Likeness Score: 1.01

References

1. Blanco B, Sedes A, Peón A, Otero JM, van Raaij MJ, Thompson P, Hawkins AR, González-Bello C..  (2014)  Exploring the water-binding pocket of the type II dehydroquinase enzyme in the structure-based design of inhibitors.,  57  (8): [PMID:24689821] [10.1021/jm500175z]

Source

Source(1):

• Scientific Literature