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

• ChemBase ID: 4
• Molecular Formular: C6H9N3O2
• Molecular Mass: 155.15456
• Monoisotopic Mass: 155.06947654
• SMILES: OC(=O)[C@@H](N)Cc1[nH]cnc1
• Canonical SMILES: N[C@H](C(=O)O)Cc1cnc[nH]1
• 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-/m0/s1
• InChIKey: HNDVDQJCIGZPNO-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(1H-imidazol-4-yl)propanoic acid; (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid
• IUPAC Traditional name: N-tele-L-histidino; L-histidin; L-histidine
• Synonyms: (S)-2-Amino-3-(4-imidazolyl)propionic acid; L-HISTIDINE FREE BASE; H-His-OH; (2S)-2-Amino-3-(1H-imidazol-4-yl)propanoic Acid; (S)-α-Amino-1H-imidazole-4-propanoic Acid; 1448: PN: EP2071334 SEQID: 1532 claimed protein; NSC 137773; 1448: PN: WO2009077864 SEQID: (S)-1H-Imidazole-4-alanine; PN: WO2009046220 SEQID: 343 claimed sequence; 3-(1H-Imidazol-4-yl)-L-alanine; l-2-amino-3-(4-imidazolyl)propionic acid; L-Histidine; 2-Amino-3-(1H-imidazol-4-yl)propanoic acid; Histidine; (S)-4-(2-Amino-2-carboxyethyl)imidazole; (S)-a-Amino-1H-imidazole-4-propanoic acid; (S)-alpha-Amino-1H-imidazole-4-propionic acid; (S)-Histidine; Glyoxaline-5-alanine; Histidine; L-(-)-Histidine; L-Histidine; (S)-2-氨基-3-(4-咪唑基)丙酸; L-组氨酸

Database IDs

• CAS Number: 71-00-1
• EC Number: 200-745-3
• MDL Number: MFCD00064315
• Beilstein Number: 4673585; 84088
• Merck Index: 144720
• PubChem SID: 46507001; 160963467; 24877543; 24895605; 24895816; 24895728
• PubChem CID: 773; 6274
• CHEBI ID: 57595
• CHEMBL: 17962
• Chemspider ID: 6038
• DrugBank ID: DB00117
• KEGG ID: D00032
• Unique Ingredient Identifier: 4QD397987E
• Wikipedia Title: Histidine

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -3.09
• LOG S: -0.4
• Solubility (Water): 6.20e+01 g/l

PROPERTIES

Physical Property

• Solubility: 4.19g/100g @ 25 °C in water; H2O: soluble0.1 M at 20 °C, clear, colorless; H2O: soluble50 mg/mL; Not AvailableSoluble
• Apperance: powder
• Melting Point: ~285 °C (dec.); 282 °C (dec.)(lit.); 282°C; ca 281°C dec.
• Optical Rotation: [α]20/D -39±1°, c = 2% in H2O; [α]23/D -38.4°, c = 3 in H2O; -39 (c=5 in water)
• Absorption Wavelength: λ: 260 nm Amax: 0.05; λ: 280 nm Amax: 0.05
• Hydrophobicity(logP): -3.4
• pH: 7.0-8.0 (25 °C, 0.1 M in H2O)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: MS3070000
• German water hazard class: 1
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 20-25°C

Pharmacology Properties

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

Product Information

• Purity: ≥98.5%; ≥99%; ≥98.5%; ≥99% (TLC); ≥99.0% (NT); ≥99.5% (NT); 98%; 98+%
• Grade: certified reference material; EP; PharmaGrade; ReagentPlus®; SAJ special grade; TraceCERT®; USP
• Suitability: cell culture tested; meets EP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• Ignition Residue: ≤0.1% (as SO4)
• Impurities: ≤0.5% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test
• Cation Traces: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; NH4+: ≤500 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤100 mg/kg; sulfate (SO42-): ≤100 mg/kg
• Biological Source: from non-animal source
• Loss on Drying: ≤0.5% loss on drying, 110 °C
• Quality Level: GMP-COMPENDIA
• λ: 0.1 M in H2O
• Product Line: BioUltra
• Empirical Formula (Hill Notation): C6H9N3O2

DETAILS

MP Biomedicals - 02101954

Free Base
Crystalline
Purity: 98.5+%

MP Biomedicals - 02194684

Cell Culture Reagent
Free Base
Purity: 98.5+%

MP Biomedicals - 05212554

MP Biomedicals Rare Chemical collection

DrugBank - DB00117

• Drug Groups: approved; nutraceutical
• Description: An essential amino acid that is required for the production of histamine. [PubChem]
• Indication: The actions of supplemental L-histidine are entirely unclear. It may have some immunomodulatory as well as antioxidant activity. L-histidine may be indicated for use in some with rheumatoid arthritis. It is not indicated for treatment of anemia or uremia or for lowering serum cholesterol.
• Pharmacology: Is found abundantly in hemoglobin; has been used in the treatment of rheumatoid arthritis, allergic diseases, ulcers and anemia. A deficiency can cause poor hearing.
• Toxicity: ORL-RAT LD₅₀ > 15000 mg/kg, IPR-RAT LD₅₀ > 8000 mg/kg, ORL-MUS LD₅₀ > 15000 mg/kg, IVN-MUS LD₅₀ > 2000 mg/kg; Mild gastrointestinal side effects.
• Affected Organisms: Humans and other mammals
• Absorption: Absorbed from the small intestine via an active transport mechanism requiring the presence of sodium.
• External Links: Wikipedia; PDRhealth

Sigma Aldrich - H3911

Biochem/physiol Actions
Precursor of histamine by action of histidine decarboxylase.
Packaging
Manufactured and Packaged under cGMP

Sigma Aldrich - 53319

Biochem/physiol Actions
Precursor of histamine by action of histidine decarboxylase.
Other Notes
Amino acid spacing in isotachophoresis on polyacrylamide gels - a critical evaluation1; Prevents circular DNA strand cleavage in a xanthine-xanthine oxidase system2; Growth requirement of various microorganisms3.

Sigma Aldrich - H6034

Biochem/physiol Actions
组胺的前体,经组氨酸脱羧酶作用可生成组胺。
包装
10 mg in autosmp vl

Sigma Aldrich - 151688

Biochem/physiol Actions
Precursor of histamine by action of histidine decarboxylase.

Sigma Aldrich - 73767

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
Biochem/physiol Actions
Precursor of histamine by action of histidine decarboxylase.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 53320

Biochem/physiol Actions
Precursor of histamine by action of histidine decarboxylase.

Sigma Aldrich - H8000

Biochem/physiol Actions
组胺的前体,经组氨酸脱羧酶作用可生成组胺。
包装
1 kg in poly bottle
5 kg in poly drum
5, 10, 25, 100, 500 g in poly bottle
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 13-1160

Biochem/physiol Actions
Precursor of histamine by action of histidine decarboxylase.

Toronto Research Chemicals - H456010

L-Histidine is an essential amino acid for human development which the body cannot produce on its own. L-Histidine is one of the 22 proteinogenic amino acids. L-Histidine precursor to histamine (H436500) and a component of carnosine.

REFERENCES

• Kopple, J.D. et al.: J. Clin. Invest., 55, 881 (1975)
• Sachs, D.H., et al.: J. Biol. Chem., 246, 6576 (1975)
• Mercer, L.P., et al.: Nutrition, 6, 273 (1975)
• Morgan, W.T., et al.: J. Biol. Chem., 268, 6256 (1975)