(2R,3S)-2-hydroxy-3-vinylsuccinic acid

ID: ALA225713

Cas Number: 246233-05-6

PubChem CID: 10654516

Max Phase: Preclinical

Molecular Formula: C6H8O5

Molecular Weight: 160.12

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C6H8O5/c1-2-3(5(8)9)4(7)6(10)11/h2-4,7H,1H2,(H,8,9)(H,10,11)/t3-,4+/m0/s1

Standard InChI Key:  CCYHZXJMZCTPIG-IUYQGCFVSA-N

Molfile:  

     RDKit          2D

 11 10  0  0  1  0  0  0  0  0999 V2000
   -2.1544   -3.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4399   -3.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7222   -3.5827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4366   -2.3452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1540   -4.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8682   -4.8252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4393   -4.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4364   -5.6514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226   -4.4135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8690   -3.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8692   -2.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  2  3  1  0
  5  7  1  6
  2  4  2  0
  7  8  1  0
  7  9  2  0
  1  5  1  0
  1 10  1  6
  1  2  1  0
 10 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA225713

   (2S,3R)-2-ethenyl-3-hydroxybutanedioic 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: 160.12

Molecular Weight (Monoisotopic): 160.0372

AlogP: -0.68

#Rotatable Bonds: 4

Polar Surface Area: 94.83

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.46

CX Basic pKa: ┄

CX LogP: -0.43

CX LogD: -5.94

Aromatic Rings: ┄

Heavy Atoms: 11

QED Weighted: 0.47

Np Likeness Score: 0.97

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]

Source

Source(1):

• Scientific Literature