(1R,4R,5R)-1,4,5-Trihydroxy-3-[(1R)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic Acid

ID: ALA3233398

PubChem CID: 73441658

Max Phase: Preclinical

Molecular Formula: C15H18O6

Molecular Weight: 294.30

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H18O6/c16-11(6-9-4-2-1-3-5-9)10-7-15(21,14(19)20)8-12(17)13(10)18/h1-5,7,11-13,16-18,21H,6,8H2,(H,19,20)/t11-,12-,13-,15+/m1/s1

Standard InChI Key:  TUXIFONUTATTJM-BHPKHCPMSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   28.7276   -1.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7276   -2.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4397   -3.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1518   -2.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1518   -1.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4397   -1.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8485   -0.9668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1332   -1.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8673   -1.4819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0923   -0.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4397   -4.0296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8657   -3.2097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0136   -3.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0149   -4.0348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2986   -2.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5847   -3.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8720   -2.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1586   -3.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1593   -4.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8795   -4.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5900   -4.0348    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  6
 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:

   

   ALA3233398

   (1r,4r,5r)-1,4,5-Trihydroxy-3-[(1r)-1-Hydroxy-2-Phenyl]ethylcyclohex-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: 294.30

Molecular Weight (Monoisotopic): 294.1103

AlogP: -0.54

#Rotatable Bonds: 4

Polar Surface Area: 118.22

Molecular Species: ACID

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.69

CX Basic pKa: ┄

CX LogP: -0.56

CX LogD: -3.87

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.48

Np Likeness Score: 1.17

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