(2R)-2-amino-3-(1H-imidazol-4-yl)propanoic acid

• ChemBase ID: 103306
• Molecular Formular: C6H9N3O2
• Molecular Mass: 155.15456
• Monoisotopic Mass: 155.06947654
• SMILES: N[C@H](Cc1c[nH]cn1)C(=O)O
• Canonical SMILES: N[C@@H](C(=O)O)Cc1c[nH]cn1
• InChI: InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m1/s1
• InChIKey: HNDVDQJCIGZPNO-RXMQYKEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-(1H-imidazol-4-yl)propanoic acid
• IUPAC Traditional name: D-histidine
• Synonyms: (R)-2-Amino-3-(4-imidazolyl)propionic acid; D-α-Amino-β-(4-imidazolyl)propionic acid; D-HISTIDINE; D-α-Amino-β-(4-imidazolyl)propionic acid; D-Histidine; (R)-2-Amino-3-(1H-imidazol-4-yl)propanoic acid; H-D-His-OH; D-2-氨基-3-(4-咪唑基)丙酸; D-组氨酸

Database IDs

• CAS Number: 351-50-8
• EC Number: 206-513-8
• MDL Number: MFCD00065963
• Beilstein Number: 84089
• PubChem SID: 24877545; 24895591; 162090357
• PubChem CID: 71083

CALCULATED PROPERTIES

• Acid pKa: 1.8547646
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.85503
• LogD (pH = 7.4): -3.2925096
• Log P: -3.293445
• Molar Refractivity: 37.4933 cm^3
• Polarizability: 14.774462 Å^3
• Polar Surface Area: 92.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 280-290 °C (dec.); ca 285°C dec.
• Optical Rotation: [α]20/D +39±1°, c = 5% in H2O; +39 (c=5 in water)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• German water hazard class: 1
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... CA1(759), CA2(760)

Product Information

• Purity: ≥98% (TLC); ≥99.0% (T); 98%; 99%
• Grade: puriss.
• Empirical Formula (Hill Notation): C6H9N3O2

DETAILS

MP Biomedicals - 02151263

Free Base
Crystalline

Sigma Aldrich - H3751

Other Notes
Inactive isomer
Biochem/physiol Actions
D-Histidine may be used in the design of peptide drugs, cationic peptides, such as analogues of carnosine. D-Histidine may also be used as a heavy metal sequestration agent.

Sigma Aldrich - 53321

Other Notes
Inactive isomer