(2S,3R)-2,3-dihydroxysuccinic acid

ID: ALA225983

Cas Number: 147-73-9

PubChem CID: 447315

Max Phase: Preclinical

Molecular Formula: C4H6O6

Molecular Weight: 150.09

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (2S,3R)-2,3-Dihydroxysuccinic Acid | Meso-Tartrate | mesotartaric acid|meso-tartaric acid|147-73-9|erythraric acid|i-Tartaric acid|(2R,3S)-2,3-dihydroxybutanedioic acid|(r,s)-tartaric acid|Mesoweinsaeure|(2R,3S)-2,3-dihydroxysuccinic acid|Mesotartaricacid|m-tartaric acid|(2R,3S)-tartaric acid|S,R MESO-TARTARIC ACID|(R*,S*)-2,3-Dihydroxybutanedioic acid|unresolvable tartaric acid|Butanedioic acid, 2,3-dihydroxy-, (2R,3S)-rel-|JQO211TF1A|CHEMBL225983|(2R,3S)-rel-2,3-dihydroxybutanedioic acid|CHEBIShow More⌵

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

Standard InChI:  InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2+

Standard InChI Key:  FEWJPZIEWOKRBE-XIXRPRMCSA-N

Molfile:  

     RDKit          2D

 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.7862   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0
  3  2  2  0
  3  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  2  0
  8 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA225983

   Mesotartaric acid

Molecule Features

Natural Product: Yes

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: 150.09

Molecular Weight (Monoisotopic): 150.0164

AlogP: -2.12

#Rotatable Bonds: 3

Polar Surface Area: 115.06

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.72

CX Basic pKa: ┄

CX LogP: -1.83

CX LogD: -7.89

Aromatic Rings: ┄

Heavy Atoms: 10

QED Weighted: 0.37

Np Likeness Score: 0.66

References

1. Yamamoto T, Miyazaki K, Eguchi T..  (2007)  Substrate specificity analysis and inhibitor design of homoisocitrate dehydrogenase.,  15  (3): [PMID:17116397] [10.1016/j.bmc.2006.11.008]

2. Katane M, Osaka N, Matsuda S, Maeda K, Kawata T, Saitoh Y, Sekine M, Furuchi T, Doi I, Hirono S, Homma H..  (2013)  Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.,  56  (5): [PMID:23391306] [10.1021/jm3017865]

Source

Source(1):

• Scientific Literature