(S)-2-Amino-4-methylene-pentanedioic acid

ID: ALA38499

Chembl Id: CHEMBL38499

Cas Number: 16804-57-2

PubChem CID: 439282

Max Phase: Preclinical

Molecular Formula: C6H9NO4

Molecular Weight: 159.14

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C6H9NO4/c1-3(5(8)9)2-4(7)6(10)11/h4H,1-2,7H2,(H,8,9)(H,10,11)/t4-/m0/s1

Standard InChI Key:  RCCMXKJGURLWPB-BYPYZUCNSA-N

Alternative Forms

1. Parent:

   

   ALA38499

   4-Methylene-L-glutamic 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: 159.14

Molecular Weight (Monoisotopic): 159.0532

AlogP: -0.57

#Rotatable Bonds: 4

Polar Surface Area: 100.62

Molecular Species: ZWITTERION

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.93

CX Basic pKa: 9.48

CX LogP: -2.80

CX LogD: -5.78

Aromatic Rings: ┄

Heavy Atoms: 11

QED Weighted: 0.48

Np Likeness Score: 1.65

References

1. Jullian N, Brabet I, Pin JP, Acher FC..  (1999)  Agonist selectivity of mGluR1 and mGluR2 metabotropic receptors: a different environment but similar recognition of an extended glutamate conformation.,  42  (9): [PMID:10229625] [10.1021/jm980571q]

2. Baker SR, Bleakman D, Ezquerra J, Ballyk BA, Deverill M, Ho K, Kamboj RK, Collado I, Domínguez C, Escribano A, Mateo AI, Pedregal C, Rubio A..  (2000)  4-Alkylidenyl glutamic acids, potent and selective GluR5 agonists.,  10  (16): [PMID:10969973] [10.1016/s0960-894x(00)00346-2]

3. Carrigan CN, Bartlett RD, Esslinger CS, Cybulski KA, Tongcharoensirikul P, Bridges RJ, Thompson CM..  (2002)  Synthesis and in vitro pharmacology of substituted quinoline-2,4-dicarboxylic acids as inhibitors of vesicular glutamate transport.,  45  (11): [PMID:12014964] [10.1021/jm010261z]

4. Bräuner-Osborne H, Egebjerg J, Nielsen EO, Madsen U, Krogsgaard-Larsen P..  (2000)  Ligands for glutamate receptors: design and therapeutic prospects.,  43  (14): [PMID:10893301] [10.1021/jm000007r]

Source

Source(1):

• Scientific Literature