(2S)-2-aminopent-4-enoic acid

• ChemBase ID: 77381
• Molecular Formular: C5H9NO2
• Molecular Mass: 115.13046
• Monoisotopic Mass: 115.06332853
• SMILES: N[C@@H](CC=C)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)CC=C
• InChI: InChI=1S/C5H9NO2/c1-2-3-4(6)5(7)8/h2,4H,1,3,6H2,(H,7,8)/t4-/m0/s1
• InChIKey: WNNNWFKQCKFSDK-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-aminopent-4-enoic acid
• IUPAC Traditional name: (2S)-2-aminopent-4-enoic acid
• Synonyms: (2S)-2-Aminopent-4-enoic acid; 2-Allyl-L-glycine; L-Allylglycine; L-2-Amino-4-pentenoic acid; L-Allylglycine; (S)-(-)-2-Amino-4-pentenoic acid; (S)-(-)-2-Amino-4-pentenoic acid; 2-Allyl-L-glycine; (S)-(-)-2-氨基-4-戊烯酸; L-2-氨基-4-戊烯酸; L-烯丙基甘氨酸; L-烯丙基甘氨酸; (S)-(-)-2-氨基-4-戊烯酸; 2-烯丙基-L-氨基乙酸

Database IDs

• CAS Number: 195316-72-4; 16338-48-0
• MDL Number: MFCD00002627
• Beilstein Number: 1721512
• PubChem SID: 24845889; 162042254; 24278237; 24856862
• PubChem CID: 167529

CALCULATED PROPERTIES

• Acid pKa: 2.6015377
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.1777115
• LogD (pH = 7.4): -2.180603
• Log P: -2.1774926
• Molar Refractivity: 29.6664 cm^3
• Polarizability: 11.756323 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble100 mg/mL
• Apperance: white powder
• Melting Point: ~283 °C (dec.); 283 °C (dec.)(lit.); 283(dec.)°C
• Optical Rotation: [α]20/D -36°, c = 4 in H2O; [α]20/D -38±2°, c = 4% in H2O; [α]25/D -37.1°, c = 4 in H2O(lit.)

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C; room temp

Pharmacology Properties

• Gene Information: human ... GAD1(2571), GAD2(2572)

Product Information

• Purity: ≥99% (TLC); ≥99.0% (TLC); 95%; 98%
• Linear Formula: H2C=CHCH2CH(NH2)CO2H
• Empirical Formula (Hill Notation): C5H9NO2

DETAILS

Sigma Aldrich - A7762

Biochem/physiol Actions
Glutamic acid decarboxylase inhibitor.

Sigma Aldrich - 285013

Packaging
1 g in glass bottle

Sigma Aldrich - 05958

Biochem/physiol Actions
Glutamic acid decarboxylase inhibitor.
Other Notes
Inhibitor: of glutamate decarboxylases, of uptake of methionine and of proline 1; Protected derivatives are used as chiral building blocks, e.g. as masked derivatives of L-aspartate β-aldehyde 2,3