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

ID: ALA226414

Cas Number: 152204-30-3

PubChem CID: 440892

Max Phase: Preclinical

Molecular Formula: C5H8O5

Molecular Weight: 148.11

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C5H8O5/c1-2(4(7)8)3(6)5(9)10/h2-3,6H,1H3,(H,7,8)(H,9,10)/t2-,3+/m0/s1

Standard InChI Key:  NPYQJIHHTGFBLN-STHAYSLISA-N

Molfile:  

     RDKit          2D

 10  9  0  0  1  0  0  0  0  0999 V2000
   -2.5002  -15.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7858  -14.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0680  -15.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7825  -14.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998  -16.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2141  -16.5919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851  -16.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822  -17.4181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684  -16.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2148  -14.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA226414

   (2R,3S)-2-hydroxy-3-methylbutanedioic 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: 148.11

Molecular Weight (Monoisotopic): 148.0372

AlogP: -0.85

#Rotatable Bonds: 3

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: 3.39

CX Basic pKa: ┄

CX LogP: -0.57

CX LogD: -6.10

Aromatic Rings: ┄

Heavy Atoms: 10

QED Weighted: 0.48

Np Likeness Score: 0.93

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