(R,E)-(3-carboxypropylidene)malic acid

ID: ALA388631

PubChem CID: 24860315

Max Phase: Preclinical

Molecular Formula: C8H10O7

Molecular Weight: 218.16

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C8H10O7/c9-5(10)3-1-2-4(7(12)13)6(11)8(14)15/h2,6,11H,1,3H2,(H,9,10)(H,12,13)(H,14,15)/b4-2+/t6-/m1/s1

Standard InChI Key:  QDXKDNNEMCNNFM-QMVXTRQFSA-N

Molfile:  

     RDKit          2D

 15 14  0  0  1  0  0  0  0  0999 V2000
    7.3623  -10.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0767  -10.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7945  -10.5327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0800   -9.2952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3627  -11.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6484  -11.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0774  -11.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803  -12.6014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7941  -11.3635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6477  -10.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9333  -10.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2188  -10.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5044  -10.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7892  -10.1245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5040  -11.3618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  5  7  1  6
  2  4  2  0
 13 14  1  0
 13 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA388631

   (1R,2E)-1-hydroxypent-2-ene-1,2,5-tricarboxylic 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: 218.16

Molecular Weight (Monoisotopic): 218.0427

AlogP: -0.69

#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: 3.00

CX Basic pKa: ┄

CX LogP: -0.71

CX LogD: -10.56

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.43

Np Likeness Score: 1.92

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