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Identification
YMDB IDYMDB00369
NameL-Histidine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionHistidine (abbreviated as His or H) is an alpha-amino acid. The L-isomer is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. It is classified as a charged, polar because of the hydrophilic nature of the imidazole side chain. L-Histidine is a positively charged (pKa 6.5) aromatic amino acid. Histidine residues are often found in enzyme active sites, where the chemistry of the imidazole ring of histidine makes it a nucleophile and a good acid/base catalyzer. Histidine is special in that its biosynthesis is inherently linked to the pathways of nucleotide formation. In the first step of histidine synthesis, PRPP (5-phosphoribosyl-alpha-pyrophosphate) condenses with ATP to form a purine, N1-5'-phosphoribosyl ATP, in a reaction that is driven by the subsequent hydrolysis of the pyrophosphate that condenses out. Glutamine plays a role as an amino group donor resulting in the formation of 5-aminoamidazole-4-carboximide ribonucleotide (ACAIR), which is an intermediate in purine biosynthesis. Hisitidne is catabolized by the enzyme histidine ammonia-lyase which converts histidine into ammonia and urocanic acid.
Structure
Thumb
Synonyms
  • (S)-1H-Imidazole-4-alanine
  • (S)-2-Amino-3-(4-imidazolyl)propionsaeure
  • (S)-4-(2-Amino-2-carboxyethyl)imidazole
  • (S)-a-Amino-1H-imidazole-4-propanoate
  • (S)-a-Amino-1H-imidazole-4-propanoic acid
  • (S)-alpha-Amino-1H-imidazole-4-propanoate
  • (S)-alpha-Amino-1H-imidazole-4-propanoic acid
  • (S)-alpha-Amino-1H-imidazole-4-propionate
  • (S)-alpha-Amino-1H-imidazole-4-propionic acid
  • (S)-Histidine
  • (S)1H-Imidazole-4-alanine
  • 3-(1H-imidazol-4-yl)-L-Alanine
  • amino-1H-imidazole-4-propanoate
  • amino-1H-imidazole-4-propanoic acid
  • amino-4-imidazoleproprionate
  • amino-4-imidazoleproprionic acid
  • Glyoxaline-5-alanine
  • His
  • Histidine
  • L-(-)-Histidine
  • H
  • L-Histidin
  • (S)-Α-amino-1H-imidazole-4-propanoate
  • (S)-Α-amino-1H-imidazole-4-propanoic acid
  • (S)-a-Amino-1H-imidazole-4-propionate
  • (S)-a-Amino-1H-imidazole-4-propionic acid
  • (S)-Α-amino-1H-imidazole-4-propionate
  • (S)-Α-amino-1H-imidazole-4-propionic acid
  • Histidine, L isomer
  • Histidine, L-isomer
  • L-Isomer histidine
  • L-Histidine
CAS number71-00-1
WeightAverage: 155.1546
Monoisotopic: 155.069476547
InChI KeyHNDVDQJCIGZPNO-YFKPBYRVSA-N
InChIInChI=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
IUPAC Name(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid
Traditional IUPAC NameL-histidine
Chemical FormulaC6H9N3O2
SMILES[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C1=C([H])N([H])C([H])=N1
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point287 °C
Experimental Properties
PropertyValueReference
Water Solubility45.6 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-3.32 [CHMELIK,J ET AL. (1991)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility62 g/LALOGPS
logP-3.1ALOGPS
logP-3.6ChemAxon
logS-0.4ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)9.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.06 m³·mol⁻¹ChemAxon
Polarizability14.67 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • vacuole
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
BitterFDB011856
OdorlessFDB011856
SMPDB Pathways
Histidine BiosynthesisPW002418 ThumbThumb?image type=greyscaleThumb?image type=simple
beta-Alanine metabolismPW002381 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Histidine metabolismec00340 Map00340
beta-Alanine metabolismec00410 Map00410
SMPDB Reactions
Histidinal + water + NADhydron + NADH + L-Histidine
KEGG Reactions
water + NAD + L-histidinolNADH + L-Histidine + hydron
Adenosine triphosphate + L-Histidine + tRNA(His) → Adenosine monophosphate + Pyrophosphate + His-tRNA(His)
L-Histidine + S-AdenosylmethionineS-Adenosylhomocysteine + N(pros)-methyl-L-histidine + hydron
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
8990 ± 180 µM YPD mediaaerobicBaker's yeastPMID: 7654310
8924 ± 178 µM YPG mediaaerobicBaker's yeastPMID: 7654310
4098 ± 82 µM SD mediaaerobicBaker's yeastPMID: 7654310
4098 ± 82 µM SG mediaaerobicBaker's yeastPMID: 7654310
5883 ± 118 µM M (molasses)aerobicBaker's yeastPMID: 7654310
6280 ± 126 µM MA (molasses)aerobicBaker's yeastPMID: 7654310
4694 ± 94 µM MB (molasses)aerobicBaker's yeastPMID: 7654310
4958 ± 99 µM MAB (molasses)aerobicBaker's yeastPMID: 7654310
767 ± 38 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
1970 ± 152 µM Synthetic medium with 20 g/L glucoseaerobicBaker's yeastPMID: 12584756
Conversion Details Here
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
367 ± 19 µM hops, malted barleyanaerobicBaker's yeastPMID: 16448171
Conversion Details Here
Spectra
Spectra
References
References:
  • Martinez-Force, E., Benitez, T. (1995). "Effects of varying media, temperature, and growth rates on the intracellular concentrations of yeast amino acids." Biotechnol Prog 11:386-392.7654310
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Vaseghi, S., Baumeister, A., Rizzi, M., Reuss, M. (1999). "In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae." Metab Eng 1:128-140.10935926
  • Almeida, C., Duarte, I. F., Barros, A., Rodrigues, J., Spraul, M., Gil, A. M. (2006). "Composition of beer by 1H NMR spectroscopy: effects of brewing site and date of production." J Agric Food Chem 54:700-706.16448171
  • Hans, M. A., Heinzle, E., Wittmann, C. (2003). "Free intracellular amino acid pools during autonomous oscillations in Saccharomyces cerevisiae." Biotechnol Bioeng 82:143-151.12584756
  • Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
  • Shimazu, M., Sekito, T., Akiyama, K., Ohsumi, Y., Kakinuma, Y. (2005). "A family of basic amino acid transporters of the vacuolar membrane from Saccharomyces cerevisiae." J Biol Chem 280:4851-4857.15572352
  • Gary, J. D., Lin, W. J., Yang, M. C., Herschman, H. R., Clarke, S. (1996). "The predominant protein-arginine methyltransferase from Saccharomyces cerevisiae." J Biol Chem 271:12585-12594.8647869
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
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.
External Links:
ResourceLink
CHEBI ID15971
HMDB IDHMDB00177
Pubchem Compound ID6274
Kegg IDC00135
ChemSpider ID6038
FOODB IDFDB011856
WikipediaHistidine
BioCyc IDHIS

Enzymes

General function:
Involved in nucleotide binding
Specific function:
ATP + L-histidine + tRNA(His) = AMP + diphosphate + L-histidyl-tRNA(His)
Gene Name:
HTS1
Uniprot ID:
P07263
Molecular weight:
59952.0
Reactions
ATP + L-histidine + tRNA(His) → AMP + diphosphate + L-histidyl-tRNA(His).
General function:
Involved in oxidoreductase activity
Specific function:
1-(5-phosphoribosyl)-AMP + H(2)O = 1-(5- phosphoribosyl)-5-((5- phosphoribosylamino)methylideneamino)imidazole-4-carboxamide
Gene Name:
HIS4
Uniprot ID:
P00815
Molecular weight:
87720.5
Reactions
1-(5-phosphoribosyl)-AMP + H(2)O → 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide.
1-(5-phosphoribosyl)-ATP + H(2)O → 1-(5-phosphoribosyl)-AMP + diphosphate.
L-histidinol + H(2)O + 2 NAD(+) → L-histidine + 2 NADH.
General function:
Involved in protein methyltransferase activity
Specific function:
Methylates arginines in a variety of RNA-binding proteins. Methylates NOP3. Can catalyze both the mono- and asymmetric dimethylation
Gene Name:
HMT1
Uniprot ID:
P38074
Molecular weight:
39785.80078
Reactions

Transporters

General function:
Involved in transport
Specific function:
Permease for various amino acids as well as for GABA. Can also transport L-cysteine and beta-alanine
Gene Name:
GAP1
Uniprot ID:
P19145
Molecular weight:
65654.89844
General function:
Involved in transport
Specific function:
High-affinity transport of valine and tyrosine. Low- affinity transport of tryptophan. Can also transport L-cysteine
Gene Name:
TAT1
Uniprot ID:
P38085
Molecular weight:
68756.89844
General function:
Involved in transport
Specific function:
Broad substrate range permease which transports asparagine and glutamine with intermediate specificity. Also transports Ala, Cys, Gly, Ile, Leu, Met, Phe, Ser, Thr, Tyr and Val. Important for the utilization of amino acids as a nitrogen source
Gene Name:
AGP1
Uniprot ID:
P25376
Molecular weight:
69670.70313
General function:
Involved in transmembrane transport
Specific function:
Transporter required for vacuolar uptake of at least histidine and lysine
Gene Name:
VBA1
Uniprot ID:
Q04301
Molecular weight:
62638.80078
General function:
Involved in transmembrane transport
Specific function:
Transporter required for vacuolar uptake of histidine and lysine
Gene Name:
VBA3
Uniprot ID:
P25594
Molecular weight:
50224.89844
General function:
Involved in transmembrane transport
Specific function:
Transporter required for vacuolar uptake of histidine, arginine and lysine and to a lesser extent tyrosine
Gene Name:
VBA2
Uniprot ID:
P38358
Molecular weight:
51676.39844
General function:
Involved in transport
Specific function:
High-affinity permease for histidine
Gene Name:
HIP1
Uniprot ID:
P06775
Molecular weight:
66005.60156