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

ID: ALA226523

PubChem CID: 44423275

Max Phase: Preclinical

Molecular Formula: C9H16O5

Molecular Weight: 204.22

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C9H16O5/c1-2-3-4-5-6(8(11)12)7(10)9(13)14/h6-7,10H,2-5H2,1H3,(H,11,12)(H,13,14)/t6-,7+/m0/s1

Standard InChI Key:  QRXKEYMWUCJOKS-NKWVEPMBSA-N

Molfile:  

     RDKit          2D

 14 13  0  0  1  0  0  0  0  0999 V2000
    7.3423  -21.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0527  -21.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7663  -21.7811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0560  -20.5392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3428  -22.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6326  -23.0321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0534  -23.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0563  -23.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7659  -22.6162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6318  -21.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9174  -21.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1975  -21.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4841  -21.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7642  -21.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  2  0
  7  8  1  0
  7  9  2  0
  1  5  1  0
  1 10  1  6
  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
 13 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA226523

   (2R,3S)-2-hydroxy-3-pentylbutanedioic 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: 204.22

Molecular Weight (Monoisotopic): 204.0998

AlogP: 0.71

#Rotatable Bonds: 7

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: 3.88

CX Basic pKa: ┄

CX LogP: 1.21

CX LogD: -3.71

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.53

Np Likeness Score: 1.28

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