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

ID: ALA225712

PubChem CID: 44423278

Max Phase: Preclinical

Molecular Formula: C10H10O5

Molecular Weight: 210.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H](O)[C@@H](C(=O)O)c1ccccc1

Standard InChI:  InChI=1S/C10H10O5/c11-8(10(14)15)7(9(12)13)6-4-2-1-3-5-6/h1-5,7-8,11H,(H,12,13)(H,14,15)/t7-,8+/m0/s1

Standard InChI Key:  JHERUGSFPODGRD-JGVFFNPUSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  1  0  0  0  0  0999 V2000
    7.5184    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2362    1.6507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5217    2.8882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8044    0.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0901    0.4081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5191    0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5219   -0.4181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2358    0.8198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0894    2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0938    2.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3801    3.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6647    2.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6676    2.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3819    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8039    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  6  8  2  0
 15  4  1  0
 15  9  1  0
 15  1  1  0
  9 10  2  0
  4  5  1  0
 10 11  1  0
  1  2  1  0
 11 12  2  0
  4  6  1  6
 12 13  1  0
  1  3  2  0
 13 14  2  0
 14  9  1  0
 15 16  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA225712

   (2R,3S)-2-hydroxy-3-phenylbutanedioic 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: 210.19

Molecular Weight (Monoisotopic): 210.0528

AlogP: 0.30

#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: 3.58

CX Basic pKa: ┄

CX LogP: 0.56

CX LogD: -4.84

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.66

Np Likeness Score: 0.20

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