(R,E)-(3-hydroxypropylidene)malic Acid

ID: ALA225714

PubChem CID: 24860313

Max Phase: Preclinical

Molecular Formula: C7H10O6

Molecular Weight: 190.15

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C7H10O6/c8-3-1-2-4(6(10)11)5(9)7(12)13/h2,5,8-9H,1,3H2,(H,10,11)(H,12,13)/b4-2+/t5-/m1/s1

Standard InChI Key:  JAWMCXNTMFJPQS-XWCPEMDWSA-N

Molfile:  

     RDKit          2D

 13 12  0  0  1  0  0  0  0  0999 V2000
   14.1831   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8976   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6153   -4.3410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9009   -3.1035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1835   -5.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4693   -5.5836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8982   -5.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9011   -6.4097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6149   -5.1719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4685   -3.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7542   -4.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0396   -3.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3252   -4.3424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  6
  2  4  2  0
  7  8  1  0
  7  9  2  0
  1  5  1  0
  1 10  2  0
  1  2  1  0
 10 11  1  0
  5  6  1  0
 11 12  1  0
  2  3  1  0
 12 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA225714

   (2R,3E)-2-hydroxy-3-(3-hydroxypropylidene)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: 190.15

Molecular Weight (Monoisotopic): 190.0477

AlogP: -1.17

#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: 3.22

CX Basic pKa: ┄

CX LogP: -1.27

CX LogD: -7.89

Aromatic Rings: ┄

Heavy Atoms: 13

QED Weighted: 0.41

Np Likeness Score: 2.17

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