(1R,4R,5R)-1,4,5-Trihydroxy-3-hydroxymethylcyclohex-2-en-1-carboxylic Acid

ID: ALA3233396

PubChem CID: 73441655

Max Phase: Preclinical

Molecular Formula: C8H12O6

Molecular Weight: 204.18

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C8H12O6/c9-3-4-1-8(14,7(12)13)2-5(10)6(4)11/h1,5-6,9-11,14H,2-3H2,(H,12,13)/t5-,6-,8+/m1/s1

Standard InChI Key:  QZOLOUIVSUKSKM-JKMUOGBPSA-N

Molfile:  

     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
    1.8903   -2.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903   -3.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -3.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008   -3.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008   -2.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -2.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0100   -1.6715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2824   -1.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0096   -2.1817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2418   -0.9920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -4.7050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0079   -3.8930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1832   -3.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4749   -3.4854    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
M  END

Alternative Forms

1. Parent:

   

   ALA3233396

   (1r,4r,5r)-1,4,5-Trihydroxy-3-Hydroxymethylcyclohex-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: 204.18

Molecular Weight (Monoisotopic): 204.0634

AlogP: -2.15

#Rotatable Bonds: 2

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: 3.46

CX Basic pKa: ┄

CX LogP: -2.64

CX LogD: -6.02

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.33

Np Likeness Score: 2.13

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