(1R,2S)-1-hydroxybutane-1,2,4-tricarboxylic acid

ID: ALA375897

PubChem CID: 5460287

Max Phase: Preclinical

Molecular Formula: C7H10O7

Molecular Weight: 206.15

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C7H10O7/c8-4(9)2-1-3(6(11)12)5(10)7(13)14/h3,5,10H,1-2H2,(H,8,9)(H,11,12)(H,13,14)/t3-,5+/m0/s1

Standard InChI Key:  OEJZZCGRGVFWHK-WVZVXSGGSA-N

Molfile:  

     RDKit          2D

 14 13  0  0  1  0  0  0  0  0999 V2000
   -3.9542    1.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2397    2.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252    1.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6686    2.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6695    3.0370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3840    1.7995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8108    2.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0930    1.8007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8075    3.0382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5248    0.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2391    0.5581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8101    0.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8072   -0.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934    0.9698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0
  7  8  1  0
  7  9  2  0
  3  2  1  6
  3 10  1  0
  4  5  1  0
 10 11  1  0
  4  6  2  0
 10 12  1  6
  1  2  1  0
  3  7  1  0
 12 13  1  0
 12 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA375897

   (1R,2S)-1-hydroxybutane-1,2,4-tricarboxylic 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: 206.15

Molecular Weight (Monoisotopic): 206.0427

AlogP: -1.00

#Rotatable Bonds: 6

Polar Surface Area: 132.13

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.12

CX Basic pKa: ┄

CX LogP: -1.00

CX LogD: -9.88

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.44

Np Likeness Score: 1.06

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