(1R,4R,5R)-1,4,5-Trihydroxy-3-(2-hydroxy)ethylcyclohex-2-ene-1-carboxylic Acid

ID: ALA3233397

PubChem CID: 73441656

Max Phase: Preclinical

Molecular Formula: C9H14O6

Molecular Weight: 218.21

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C9H14O6/c10-2-1-5-3-9(15,8(13)14)4-6(11)7(5)12/h3,6-7,10-12,15H,1-2,4H2,(H,13,14)/t6-,7-,9+/m1/s1

Standard InChI Key:  HVNZLWXJZRWNGG-BHNWBGBOSA-N

Molfile:  

     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
    7.1896   -2.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1896   -3.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8949   -3.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6002   -3.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6002   -2.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8949   -1.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3093   -1.3909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5817   -1.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3089   -1.9011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5412   -0.7113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8949   -4.4244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3073   -3.6124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4825   -3.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4837   -4.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7766   -4.8392    0.0000 O   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  0
 14 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3233397

   (1r,4r,5r)-1,4,5-Trihydroxy-3-(2-Hydroxy)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: 218.21

Molecular Weight (Monoisotopic): 218.0790

AlogP: -1.76

#Rotatable Bonds: 3

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: 3.56

CX Basic pKa: ┄

CX LogP: -2.35

CX LogD: -5.70

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.36

Np Likeness Score: 1.99

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