CAS 71-00-1|Histidine|Glyoxaline-5-alanine|(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid|(S)-4-(2-Amino-2-carboxyethyl)imidazole|L-(-)-Histidine|L-histidine|(S)-a-Amino-1H-imidazole-4-propanoic ac...

General Information

Structure

Molecular Formula

C₆H₉N₃O₂

Molecular Mass

155.15456

Exact Mass

155.06947654

Charge

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

Canonic Smiles

N[C@H](C(=O)O)Cc1cnc[nH]1

Isomeric Smiles

OC(=O)[C@@H](N)Cc1[nH]cnc1

Calculated Properties

JChem

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

Polarizability

14.774462

Polar Surface Area

92.0

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

-3.09

LOG S

-0.4

Solubility (Water)

6.20e+01 g/l

Data Source

Names and Identifiers

Synonyms

HistidineGlyoxaline-5-alanine(S)-4-(2-Amino-2-carboxyethyl)imidazoleL-(-)-Histidine(S)-a-Amino-1H-imidazole-4-propanoic acid(S)-alpha-Amino-1H-imidazole-4-propionic acidL-HISTIDINE FREE BASEL-Histidine(S)-Histidine(S)-2-Amino-3-(4-imidazolyl)propionic acid2-Amino-3-(1H-imidazol-4-yl)propanoic acidHistidine(S)-2-氨基-3-(4-咪唑基)丙酸L-HistidineL-组氨酸NSC 1377731448: PN: WO2009077864 SEQID: (S)-1H-Imidazole-4-alanine1448: PN: EP2071334 SEQID: 1532 claimed protein(S)-α-Amino-1H-imidazole-4-propanoic AcidPN: WO2009046220 SEQID: 343 claimed sequence3-(1H-Imidazol-4-yl)-L-alanine(2S)-2-Amino-3-(1H-imidazol-4-yl)propanoic AcidH-His-OH l-2-amino-3-(4-imidazolyl)propionic acid

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

Names and Identifiers

Registration numbers

EC Number

200-745-3

Beilstein Number

840884673585

CAS Number

71-00-1

PubChem SID

2487754346507001248958162489572824895605160963467

MDL Number

PubChem CID

Merck Index

Chemspider ID

DrugBank ID

Wikipedia Title

KEGG ID

Unique Ingredient Identifier

4QD397987E

CHEMBL

17962

CHEBI ID

57595

Registration numbers

Properties

Pharmacology Properties

Gene Information

human ... CA1(759), CA2(760)

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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]

MP Biomedicals

02101954

Free Base
Crystalline
Purity: 98.5+%

02194684

Cell Culture Reagent
Free Base
Purity: 98.5+%

05212554

MP Biomedicals Rare Chemical collection

Wikipedia

Histidine

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

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

151688

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

53320

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

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

13-1160

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

H3911

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

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.

TRC

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.

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

• Kopple, J.D. et al.: J. Clin. Invest., 55, 881 (1975)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

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

Registration numbers

EC Number

200-745-3

Beilstein Number

840884673585

CAS Number

71-00-1

PubChem SID

2487754346507001248958162489572824895605160963467

MDL Number

PubChem CID

Merck Index

Chemspider ID

DrugBank ID

Wikipedia Title

KEGG ID

Unique Ingredient Identifier

CHEMBL

CHEBI ID

Molecule Details

DB00117

Drug Groups

approved; nutraceutical

Description

An essential amino acid that is required for the production of histamine. [PubChem]

Indication

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

02101954

Free Base
Crystalline
Purity: 98.5+%