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71-00-1 molecular structure
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(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid

ChemBase ID: 4
Molecular Formular: C6H9N3O2
Molecular Mass: 155.15456
Monoisotopic Mass: 155.06947654
SMILES and InChIs

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

Cite this record

CBID:4 http://www.chembase.cn/molecule-4.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid
(2S)-2-amino-3-(1H-imidazol-4-yl)propanoic acid
IUPAC Traditional name
L-histidine
L-histidin
N-tele-L-histidino
Synonyms
(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-Amino-3-(4-imidazolyl)propionic acid
L-HISTIDINE FREE BASE
2-Amino-3-(1H-imidazol-4-yl)propanoic acid
Histidine
L-Histidine
(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
H-His-OH
l-2-amino-3-(4-imidazolyl)propionic acid
(S)-2-氨基-3-(4-咪唑基)丙酸
L-组氨酸
CAS Number
71-00-1
EC Number
200-745-3
MDL Number
MFCD00064315
Beilstein Number
84088
4673585
Merck Index
144720
PubChem SID
24895605
46507001
160963467
24895816
24895728
24877543
PubChem CID
6274
773
CHEBI ID
57595
CHEMBL
17962
Chemspider ID
6038
DrugBank ID
DB00117
KEGG ID
D00032
Unique Ingredient Identifier
4QD397987E
Wikipedia Title
Histidine

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 1.8547646  H Acceptors
H Donor LogD (pH = 5.5) -3.85503 
LogD (pH = 7.4) -3.2925096  Log P -3.293445 
Molar Refractivity 37.4933 cm3 Polarizability 14.774462 Å3
Polar Surface Area 92.0 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -3.09  LOG S -0.4 
Solubility (Water) 6.20e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
4.19g/100g @ 25 °C in water expand Show data source
H2O: soluble0.1 M at 20 °C, clear, colorless expand Show data source
H2O: soluble50 mg/mL expand Show data source
Not AvailableSoluble expand Show data source
Apperance
powder expand Show data source
Melting Point
~285 °C (dec.) expand Show data source
282 °C (dec.)(lit.) expand Show data source
282°C expand Show data source
ca 281°C dec. expand Show data source
Optical Rotation
[α]20/D -39±1°, c = 2% in H2O expand Show data source
[α]23/D -38.4°, c = 3 in H2O expand Show data source
-39 (c=5 in water) expand Show data source
Absorption Wavelength
λ: 260 nm Amax: 0.05 expand Show data source
λ: 280 nm Amax: 0.05 expand Show data source
Hydrophobicity(logP)
-3.4 expand Show data source
pH
7.0-8.0 (25 °C, 0.1 M in H2O) expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
RTECS
MS3070000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
20-25°C expand Show data source
Gene Information
human ... CA1(759), CA2(760) expand Show data source
Purity
≥98.5% expand Show data source
≥99% expand Show data source
≥98.5% expand Show data source
≥99% (TLC) expand Show data source
≥99.0% (NT) expand Show data source
≥99.5% (NT) expand Show data source
98% expand Show data source
98+% expand Show data source
Grade
certified reference material expand Show data source
EP expand Show data source
PharmaGrade expand Show data source
ReagentPlus® expand Show data source
SAJ special grade expand Show data source
TraceCERT® expand Show data source
USP expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
cell culture tested expand Show data source
meets EP, USP testing specifications expand Show data source
suitable for cell culture expand Show data source
suitable for manufacturing use expand Show data source
Ignition Residue
≤0.1% (as SO4) expand Show data source
Impurities
≤0.5% foreign amino acids expand Show data source
endotoxin, tested expand Show data source
insoluble matter, passes filter test expand Show data source
Cation Traces
Al: ≤5 mg/kg expand Show data source
As: ≤0.1 mg/kg expand Show data source
Ba: ≤5 mg/kg expand Show data source
Bi: ≤5 mg/kg expand Show data source
Ca: ≤10 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Li: ≤5 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Mo: ≤5 mg/kg expand Show data source
Na: ≤50 mg/kg expand Show data source
NH4+: ≤500 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Sr: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Antion Traces
chloride (Cl-): ≤100 mg/kg expand Show data source
sulfate (SO42-): ≤100 mg/kg expand Show data source
Biological Source
from non-animal source expand Show data source
Loss on Drying
≤0.5% loss on drying, 110 °C expand Show data source
Quality Level
GMP-COMPENDIA expand Show data source
λ
0.1 M in H2O expand Show data source
Product Line
BioUltra expand Show data source
Empirical Formula (Hill Notation)
C6H9N3O2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich Wikipedia Wikipedia TRC TRC
DrugBank - DB00117 external link
Item Information
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
MP Biomedicals - 02194684 external link
Cell Culture Reagent
Free Base
Purity: 98.5+%
MP Biomedicals - 02101954 external link
Free Base
Crystalline
Purity: 98.5+%
MP Biomedicals - 05212554 external link
MP Biomedicals Rare Chemical collection
Sigma Aldrich - H6034 external link
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 - 53319 external link
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 - H3911 external link
Biochem/physiol Actions
Precursor of histamine by action of histidine decarboxylase.
Packaging
Manufactured and Packaged under cGMP
Sigma Aldrich - 53320 external link
Biochem/physiol Actions
Precursor of histamine by action of histidine decarboxylase.
Sigma Aldrich - 151688 external link
Biochem/physiol Actions
Precursor of histamine by action of histidine decarboxylase.
Sigma Aldrich - 13-1160 external link
Biochem/physiol Actions
Precursor of histamine by action of histidine decarboxylase.
Sigma Aldrich - H8000 external link
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 - 73767 external link
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
Toronto Research Chemicals - H456010 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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