(1R,4R,5R)-1,4,5-Trihydroxy-cyclohex-2-enecarboxylic acid

ID: ALA190265

PubChem CID: 445905

Max Phase: Preclinical

Molecular Formula: C7H10O5

Molecular Weight: 174.15

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2,3-Anhydroquinic Acid | 2,3-anhydroquinic acid|2,3 -ANHYDRO-QUINIC ACID|CHEMBL190265|(1R,4R,5R)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid|FA1|2,3-Anhydro-quinic acid|1gu1|1h0r|2c57|BDBM50170812|DB02801|PD059979|NS00070060|(1R,4R,5R)-1,4,5-Trihydroxy-cyclohex-2-enecarboxylic acid|2-Cyclohexene-1-carboxylic acid, 1,4,5-trihydroxy-, (1R,4R,5R)-

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

Standard InChI:  InChI=1S/C7H10O5/c8-4-1-2-7(12,6(10)11)3-5(4)9/h1-2,4-5,8-9,12H,3H2,(H,10,11)/t4-,5-,7+/m1/s1

Standard InChI Key:  VTEDVYGIJPLVFF-XAHCXIQSSA-N

Molfile:  

     RDKit          2D

 12 12  0  0  0  0  0  0  0  0999 V2000
    0.4866    0.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4866   -0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2010   -1.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279   -1.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279   -2.0224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9424   -0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9424    0.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594    1.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2778    1.8807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6152    1.1810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9839    1.2098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279    0.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
 12  1  1  0
  2  3  1  1
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  2  0
 12  7  1  0
  8  9  1  0
  8 11  2  0
 12  8  1  1
 12 10  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA190265

   2,3-Anhydro-quinic 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: 174.15

Molecular Weight (Monoisotopic): 174.0528

AlogP: -1.52

#Rotatable Bonds: 1

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: 3.49

CX Basic pKa: ┄

CX LogP: -1.60

CX LogD: -4.98

Aromatic Rings: ┄

Heavy Atoms: 12

QED Weighted: 0.36

Np Likeness Score: 2.36

References

1. Sánchez-Sixto C, Prazeres VF, Castedo L, Lamb H, Hawkins AR, González-Bello C..  (2005)  Structure-based design, synthesis, and biological evaluation of inhibitors of Mycobacterium tuberculosis type II dehydroquinase.,  48  (15): [PMID:16033267] [10.1021/jm0501836]

2. Robinson DA, Stewart KA, Price NC, Chalk PA, Coggins JR, Lapthorn AJ..  (2006)  Crystal structures of Helicobacter pylori type II dehydroquinase inhibitor complexes: new directions for inhibitor design.,  49  (4): [PMID:16480265] [10.1021/jm0505361]

Source

Source(1):

• Scientific Literature