L-Histidine (ECMDB00177) (M2MDB000074)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 10:23:03 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:06 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | L-Histidine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Histidine is an amino acid. It is a precursor for histamine and carnosine biosynthesis. The enzyme histidine ammonia-lyase converts histidine into ammonia and urocanic acid. (Wikipedia) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C6H9N3O2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 155.1546 Monoisotopic: 155.069476547 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | HNDVDQJCIGZPNO-YFKPBYRVSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 71-00-1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | L-histidine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | N[C@@H](CC1=CN=CN1)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Carboxylic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Amino acids, peptides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Histidine and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
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| Molecular Framework | Aromatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 287 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Adenosine triphosphate + Water + L-Histidine > ADP + Hydrogen ion + L-Histidine + Phosphate Adenosine triphosphate + Water + L-Histidine > ADP + Hydrogen ion + L-Histidine + Phosphate Water + L-Histidinol + 2 NAD >3 Hydrogen ion + L-Histidine +2 NADH Adenosine triphosphate + L-Histidine + tRNA(His) + tRNA(His) <> Adenosine monophosphate + L-Histidyl-tRNA(His) + Pyrophosphate + L-Histidyl-tRNA(His) L-Histidinal + Water + NAD <> L-Histidine + NADH + Hydrogen ion Adenosine triphosphate + L-Histidine + tRNA(His) <> Adenosine monophosphate + Pyrophosphate + L-Histidyl-tRNA(His) Adenosine triphosphate + L-Histidine + Water > ADP + Phosphate + L-Histidine + Hydrogen ion Adenosine triphosphate + L-Histidine + Water > ADP + Phosphate + L-Histidine + Hydrogen ion histidinal + NAD + Water > Hydrogen ion + L-Histidine + NADH ala-his + Water > L-Alanine + L-Histidine L-Histidinol + Water + 2 NAD > L-Histidine +2 NADH Adenosine triphosphate + L-Histidine + tRNA(His) > Adenosine monophosphate + Pyrophosphate + L-histidyl-tRNA(His) L-Histidinol + 2 NAD + Water <> L-Histidine +2 NADH +3 Hydrogen ion L-Histidine + Adenosine triphosphate + Hydrogen ion + tRNA(His) + L-Histidine > Adenosine monophosphate + Pyrophosphate + L-histidyl-tRNA(His) Water + NAD + Histidinal >2 Hydrogen ion + NADH + L-Histidine + L-Histidine L-Histidine + Adenosine triphosphate + Water + L-Histidine > Adenosine diphosphate + Phosphate + Hydrogen ion + L-Histidine + ADP Adenosine triphosphate + L-Histidine + tRNA(His) <> Adenosine monophosphate + L-Histidyl-tRNA(His) + Pyrophosphate L-Histidinal + Water + NAD <> L-Histidine + NADH + Hydrogen ion Adenosine triphosphate + L-Histidine + tRNA(His) <> Adenosine monophosphate + L-Histidyl-tRNA(His) + Pyrophosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
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| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Aurelio Luigi; Brownlee Robert T C; Hughes Andrew B A novel synthesis of N-methyl asparagine, arginine, histidine, and tryptophan. Organic letters (2002), 4(21), 3767-9. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
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Enzymes
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Catalyzes the sequential NAD-dependent oxidations of L- histidinol to L-histidinaldehyde and then to L-histidine
- Gene Name:
- hisD
- Uniprot ID:
- P06988
- Molecular weight:
- 46110
Reactions
| L-histidinol + H(2)O + 2 NAD(+) = L-histidine + 2 NADH. |
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for histidine. Probably responsible for energy coupling to the transport system
- Gene Name:
- hisP
- Uniprot ID:
- P07109
- Molecular weight:
- 28653
- General function:
- Involved in nucleotide binding
- Specific function:
- ATP + L-histidine + tRNA(His) = AMP + diphosphate + L-histidyl-tRNA(His)
- Gene Name:
- hisS
- Uniprot ID:
- P60906
- Molecular weight:
- 47029
Reactions
| ATP + L-histidine + tRNA(His) = AMP + diphosphate + L-histidyl-tRNA(His). |
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- hisM
- Uniprot ID:
- P0AEU3
- Molecular weight:
- 26870
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- hisQ
- Uniprot ID:
- P52094
- Molecular weight:
- 24649
- General function:
- Involved in transporter activity
- Specific function:
- Component of the high-affinity histidine permease, a binding-protein-dependent transport system. The other components are proteins hisQ, hisM, and hisP
- Gene Name:
- hisJ
- Uniprot ID:
- P0AEU0
- Molecular weight:
- 28483
Transporters
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for histidine. Probably responsible for energy coupling to the transport system
- Gene Name:
- hisP
- Uniprot ID:
- P07109
- Molecular weight:
- 28653
- General function:
- Involved in nucleotide binding
- Specific function:
- Probably part of a binding-protein-dependent transport system yecCS for an amino acid. Probably responsible for energy coupling to the transport system
- Gene Name:
- yecC
- Uniprot ID:
- P37774
- Molecular weight:
- 27677
- General function:
- Involved in transporter activity
- Specific function:
- Probably part of the binding-protein-dependent transport system yecCS for an amino acid; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- yecS
- Uniprot ID:
- P0AFT2
- Molecular weight:
- 24801
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- hisM
- Uniprot ID:
- P0AEU3
- Molecular weight:
- 26870
- General function:
- Involved in transport
- Specific function:
- Permease that is involved in the transport across the cytoplasmic membrane of the aromatic amino acids (phenylalanine, tyrosine, and tryptophan)
- Gene Name:
- aroP
- Uniprot ID:
- P15993
- Molecular weight:
- 49690
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- hisQ
- Uniprot ID:
- P52094
- Molecular weight:
- 24649
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- Component of the high-affinity histidine permease, a binding-protein-dependent transport system. The other components are proteins hisQ, hisM, and hisP
- Gene Name:
- hisJ
- Uniprot ID:
- P0AEU0
- Molecular weight:
- 28483
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368