(2R,3S)-3-(2-hydroxyethyl)malate

ID: ALA225985

PubChem CID: 44423271

Max Phase: Preclinical

Molecular Formula: C6H10O6

Molecular Weight: 178.14

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C6H10O6/c7-2-1-3(5(9)10)4(8)6(11)12/h3-4,7-8H,1-2H2,(H,9,10)(H,11,12)/t3-,4+/m0/s1

Standard InChI Key:  IBSXAXGEWZOBHE-IUYQGCFVSA-N

Molfile:  

     RDKit          2D

 12 11  0  0  1  0  0  0  0  0999 V2000
   12.6958   -4.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4103   -3.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1248   -4.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9814   -3.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8392   -3.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5570   -4.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8425   -2.8993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1252   -4.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4109   -5.3794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8399   -5.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8428   -6.2056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5566   -4.9677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  5  7  2  0
  1  4  1  0
  3  8  1  0
  8  9  1  0
  3  5  1  0
  8 10  1  6
  3  2  1  6
  1  2  1  0
 10 11  1  0
 10 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA225985

   (2R,3S)-2-hydroxy-3-(2-hydroxyethyl)butanedioic 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: 178.14

Molecular Weight (Monoisotopic): 178.0477

AlogP: -1.48

#Rotatable Bonds: 5

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: 3.39

CX Basic pKa: ┄

CX LogP: -1.56

CX LogD: -7.13

Aromatic Rings: ┄

Heavy Atoms: 12

QED Weighted: 0.41

Np Likeness Score: 1.29

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