Record Information
Version1.0
Created at2020-03-18 23:23:15 UTC
Updated at2020-12-07 19:07:02 UTC
CannabisDB IDCDB000059
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHistidine
DescriptionHistidine, or l-histidine, abbreviated His or H, an alpha-amino acid, is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3. Histidine is an essential amino acid that is not synthesized de novo in humans and must be obtained though ingestion of histidine. L-Histidine is a strong basic compound. It is an odorless white crystalline powder with a bitter taste. In humans, L-histidine is involved in methylhistidine metabolism. Histidine biosynthesis has been well studied in E. coli and involves eight gene products (His1, 2, 3, 4, 5, 6, 7, and 8, from a single gene) and occurs in ten steps. This is possible because a single gene product can catalyze more than one reaction (PMID:8852895 ). L-Histidine is found in high concentrations in beluga whales, caseins, and bearded seals and in lower concentration in prairie turnips, puddings, and black walnuts. L-Histidine has also been detected in climbing beans, sago palms, vanilla, pitanga (cherry) and allspices making histidine a potential biomarker for the consumption of these foods. Histidine is an amino acid found in cannabis plants (PMID: 6991645 ). It is a favouring ingredient and dietary supplement. Histidine was shown to have anti-hypertensive effects, decreasing blood pressure, by modulating the histamine H3 receptor (PMID: 19566844 ). Histidine is a precursor of histamine, an inflammatory product associated with allergies ( Ref:DOI ). Histidine can be post-translationally modified to 3-methylhistidine, which is excreted in urine and is a biomarker of skeletal muscle damage (PMID: 16079625 ).
Structure
Thumb
Synonyms
ValueSource
(S)-4-(2-Amino-2-carboxyethyl)imidazoleChEBI
(S)-alpha-Amino-1H-imidazole-4-propanoic acidChEBI
(S)-alpha-Amino-1H-imidazole-4-propionic acidChEBI
HChEBI
HisChEBI
HISTIDINEChEBI
L-(-)-HistidineChEBI
L-HistidinChEBI
(S)-a-Amino-1H-imidazole-4-propanoateGenerator
(S)-a-Amino-1H-imidazole-4-propanoic acidGenerator
(S)-alpha-Amino-1H-imidazole-4-propanoateGenerator
(S)-Α-amino-1H-imidazole-4-propanoateGenerator
(S)-Α-amino-1H-imidazole-4-propanoic acidGenerator
(S)-a-Amino-1H-imidazole-4-propionateGenerator
(S)-a-Amino-1H-imidazole-4-propionic acidGenerator
(S)-alpha-Amino-1H-imidazole-4-propionateGenerator
(S)-Α-amino-1H-imidazole-4-propionateGenerator
(S)-Α-amino-1H-imidazole-4-propionic acidGenerator
(S)-1H-Imidazole-4-alanineHMDB
(S)-2-Amino-3-(4-imidazolyl)propionsaeureHMDB
(S)-HistidineHMDB
(S)1H-Imidazole-4-alanineHMDB
3-(1H-Imidazol-4-yl)-L-alanineHMDB
Amino-1H-imidazole-4-propanoateHMDB
Amino-1H-imidazole-4-propanoic acidHMDB
Amino-4-imidazoleproprionateHMDB
Amino-4-imidazoleproprionic acidHMDB
Glyoxaline-5-alanineHMDB
Histidine, L isomerHMDB
Histidine, L-isomerHMDB
L-Isomer histidineHMDB
L-HistidineKEGG
Chemical FormulaC6H9N3O2
Average Molecular Weight155.15
Monoisotopic Molecular Weight155.0695
IUPAC Name(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid
Traditional NameL-histidine
CAS Registry Number30641-68-0
SMILES
N[C@@H](CC1=CN=CN1)C(O)=O
InChI Identifier
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
InChI KeyHNDVDQJCIGZPNO-YFKPBYRVSA-N
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point287 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility45.6 mg/mLNot Available
logP-3.32CHMELIK,J ET AL. (1991)
Predicted Properties
PropertyValueSource
logP-2.7ALOGPS
logP-3.6ChemAxon
logS-0.34ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-9100000000-ae0a0b81669663b3b4a5Spectrum
GC-MSHistidine, 3 TMS, GC-MS Spectrumsplash10-0udi-0940000000-43b9b035189af65e19cbSpectrum
GC-MSHistidine, 3 TMS, GC-MS Spectrumsplash10-0udi-0910000000-fc3ecec9d4ff3aa8cb09Spectrum
GC-MSHistidine, non-derivatized, GC-MS Spectrumsplash10-0udi-0910000000-8284a673a35f7ac2241fSpectrum
GC-MSHistidine, 3 TMS, GC-MS Spectrumsplash10-0fk9-8910000000-a3231b1a418b5798ecacSpectrum
GC-MSHistidine, 3 TMS, GC-MS Spectrumsplash10-0udi-1920000000-227e8116769731104e82Spectrum
GC-MSHistidine, 4 TMS, GC-MS Spectrumsplash10-0ufu-2942100000-31605fd50ecc1f5be0edSpectrum
GC-MSHistidine, non-derivatized, GC-MS Spectrumsplash10-0udi-0940000000-43b9b035189af65e19cbSpectrum
GC-MSHistidine, non-derivatized, GC-MS Spectrumsplash10-0udi-0910000000-fc3ecec9d4ff3aa8cb09Spectrum
GC-MSHistidine, non-derivatized, GC-MS Spectrumsplash10-0udi-0910000000-8284a673a35f7ac2241fSpectrum
GC-MSHistidine, non-derivatized, GC-MS Spectrumsplash10-0002-2901100000-ae0f3865934743de764cSpectrum
GC-MSHistidine, non-derivatized, GC-MS Spectrumsplash10-0fk9-8910000000-a3231b1a418b5798ecacSpectrum
GC-MSHistidine, non-derivatized, GC-MS Spectrumsplash10-0udi-1920000000-227e8116769731104e82Spectrum
GC-MSHistidine, non-derivatized, GC-MS Spectrumsplash10-0ufu-2942100000-31605fd50ecc1f5be0edSpectrum
GC-MSHistidine, non-derivatized, GC-MS Spectrumsplash10-0ue9-0900000000-75e38a3f347210c301b0Spectrum
GC-MSHistidine, non-derivatized, GC-MS Spectrumsplash10-0udi-0910000000-c54bd92cc112eec7e509Spectrum
Predicted GC-MSHistidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9500000000-1d29684ccb6383687865Spectrum
Predicted GC-MSHistidine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-6900000000-1dd400a16b8067f4daeaSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0900000000-21530fac9975dc1edc7cSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-053r-9300000000-a946c375931adb366aaeSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-053r-9000000000-61a3602d80bc0d54c579Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-7d63b501889c2628f4f0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-d4ccd4e44ca818b4cb17Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-811aee5724fe0999c134Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-052753eb699ae7cb4cb9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-3e145a05e6a71a0a2f56Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-143a4b9d88183bc5abe7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0900000000-a8c213472da676a241f2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-dfdf9562f155abb5fdebSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0uk9-0879331100-8434b5b9e7e5700c2353Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0900000000-aaaaadcecd4cd7c94e1eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-90c4cbd09d7abc003013Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-1381708d18c24486773dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0w29-0696321100-eb62fc608270d1151707Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0900000000-3450566ff38e6506a70fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-01q9-7900000000-124509a66476629ce10aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-efa6a21b1be16fda0802Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-137840e69da48c6114e4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udu-3900000000-06d50e90c797793a72d7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9100000000-de7c9eb8068ef4f39f85Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00l6-9000000000-ebf778679d4c6d6a6057Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-9000000000-08d0188684283d1b2372Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0900000000-46c2f608d27f0381a039Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Aromatic-L-amino-acid decarboxylaseDDC7p12.2P20711 details
Beta-Ala-His dipeptidaseCNDP118q22.3Q96KN2 details
Protein arginine N-methyltransferase 3PRMT311p15.1O60678 details
Probable histidine--tRNA ligase, mitochondrialHARS25q31.3P49590 details
Histidine--tRNA ligase, cytoplasmicHARS5q31.3P12081 details
Histidine ammonia-lyaseHAL12q22-q24.1P42357 details
Histidine decarboxylaseHDC15q21-q22P19113 details
Carnosine synthase 1CARNS111q13.2A5YM72 details
HemK methyltransferase family member 1HEMK1Q9Y5R4 details
Methyltransferase-like protein 2BMETTL2BQ6P1Q9 details
Methyltransferase-like protein 6METTL6Q8TCB7 details
Uncharacterized methyltransferase WBSCR22WBSCR22O43709 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Sodium-coupled neutral amino acid transporter 3SLC38A33p21.3Q99624 details
Monocarboxylate transporter 10SLC16A106q21-q22Q8TF71 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Protein arginine N-methyltransferase 3PRMT311p15.1O60678 details
Carnosine synthase 1CARNS111q13.2A5YM72 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Histamine H3 receptorHRH320q13.33Q9Y5N1 details
Taste receptor type 2 member 10TAS2R1012p13Q9NYW0 details
Taste receptor type 2 member 16TAS2R167q31.1-q31.3|7q31Q9NYV7 details
Taste receptor type 2 member 40TAS2R407q34P59535 details
Taste receptor type 2 member 3TAS2R37q31.3-q32Q9NYW6 details
Taste receptor type 2 member 4TAS2R47q31.3-q32Q9NYW5 details
Taste receptor type 2 member 7TAS2R712p13Q9NYW3 details
Taste receptor type 2 member 9TAS2R912p13Q9NYW1 details
Taste receptor type 2 member 50TAS2R5012p13.2P59544 details
Taste receptor type 2 member 38TAS2R387q34P59533 details
Taste receptor type 2 member 31TAS2R3112p13.2P59538 details
Taste receptor type 2 member 1TAS2R15p15.31Q9NYW7 details
Taste receptor type 2 member 20TAS2R2012p13.2P59543 details
Taste receptor type 2 member 39TAS2R397q34P59534 details
Taste receptor type 2 member 19TAS2R1912p13.2P59542 details
Taste receptor type 2 member 45TAS2R45P59539 details
Taste receptor type 2 member 30TAS2R3012p13.2P59541 details
Taste receptor type 2 member 42TAS2R42Q7RTR8 details
Taste receptor type 2 member 41TAS2R417q35P59536 details
Taste receptor type 2 member 43TAS2R4312p13.2P59537 details
Taste receptor type 2 member 5TAS2R57q34Q9NYW4 details
Taste receptor type 2 member 46TAS2R4612p13.2P59540 details
Taste receptor type 2 member 13TAS2R1312p13.2Q9NYV9 details
Taste receptor type 2 member 60TAS2R607q35P59551 details
Taste receptor type 2 member 8TAS2R812p13.2Q9NYW2 details
Taste receptor type 2 member 14TAS2R1412p13.2Q9NYV8 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified4.34 mg/g dry wt
    • Jiamin Zheng, Yil...
details
GabriolaDetected and Quantified5.64 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Island HoneyDetected and Quantified6.57 mg/g dry wt
    • Jiamin Zheng, Yil...
details
QuadraDetected and Quantified2.46 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Sensi StarDetected and Quantified3.39 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Tangerine DreamDetected and Quantified1.93 mg/g dry wt
    • Jiamin Zheng, Yil...
details
HMDB IDHMDB0000177
DrugBank IDDB00117
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011856
KNApSAcK IDC00001363
Chemspider ID6038
KEGG Compound IDC00135
BioCyc IDHIS
BiGG ID33985
Wikipedia LinkL-histidine
METLIN ID21
PubChem Compound6274
PDB IDNot Available
ChEBI ID15971
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Alifano P, Fani R, Lio P, Lazcano A, Bazzicalupo M, Carlomagno MS, Bruni CB: Histidine biosynthetic pathway and genes: structure, regulation, and evolution. Microbiol Rev. 1996 Mar;60(1):44-69. [PubMed:8852895 ]
  3. Toba H, Nakamori A, Tanaka Y, Yukiya R, Tatsuoka K, Narutaki M, Tokitaka M, Hariu H, Kobara M, Nakata T: Oral L-histidine exerts antihypertensive effects via central histamine H3 receptors and decreases nitric oxide content in the rostral ventrolateral medulla in spontaneously hypertensive rats. Clin Exp Pharmacol Physiol. 2010 Jan;37(1):62-8. doi: 10.1111/j.1440-1681.2009.05227.x. [PubMed:19566844 ]
  4. Chinkes DL: Methods for measuring tissue protein breakdown rate in vivo. Curr Opin Clin Nutr Metab Care. 2005 Sep;8(5):534-7. doi: 10.1097/01.mco.0000170754.25372.37. [PubMed:16079625 ]

Only showing the first 10 proteins. There are 42 proteins in total.

Enzymes

General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
General function:
Involved in metallopeptidase activity
Specific function:
Preferential hydrolysis of the beta-Ala-|-His dipeptide (carnosine), and also anserine, Xaa-|-His dipeptides and other dipeptides including homocarnosine
Gene Name:
CNDP1
Uniprot ID:
Q96KN2
Molecular weight:
56691.6
General function:
Involved in protein methyltransferase activity
Specific function:
Methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues in some proteins
Gene Name:
PRMT3
Uniprot ID:
O60678
Molecular weight:
59902.7
General function:
Involved in nucleotide binding
Specific function:
Not Available
Gene Name:
HARS2
Uniprot ID:
P49590
Molecular weight:
56887.865
General function:
Involved in nucleotide binding
Specific function:
Not Available
Gene Name:
HARS
Uniprot ID:
P12081
Molecular weight:
52719.54
General function:
Involved in histidine ammonia-lyase activity
Specific function:
Not Available
Gene Name:
HAL
Uniprot ID:
P42357
Molecular weight:
49122.09
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the biosynthesis of histamine from histidine.
Gene Name:
HDC
Uniprot ID:
P19113
Molecular weight:
74139.825
General function:
Involved in catalytic activity
Specific function:
Catalyzes the synthesis of carnosine and homocarnosine. Carnosine is synthesized more efficiently than homocarnosine.
Gene Name:
CARNS1
Uniprot ID:
A5YM72
Molecular weight:
101318.725
General function:
Not Available
Specific function:
N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:
HEMK1
Uniprot ID:
Q9Y5R4
Molecular weight:
Not Available
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL2B
Uniprot ID:
Q6P1Q9
Molecular weight:
Not Available

Transporters

General function:
Amino acid transport and metabolism
Specific function:
Sodium-dependent amino acid/proton antiporter. Mediates electrogenic cotransport of glutamine and sodium ions in exchange for protons. Also recognizes histidine, asparagine and alanine. May mediate amino acid transport in either direction under physiological conditions. May play a role in nitrogen metabolism and synaptic transmission
Gene Name:
SLC38A3
Uniprot ID:
Q99624
Molecular weight:
55772.4
General function:
Involved in transmembrane transport
Specific function:
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71
Molecular weight:
55492.1

Only showing the first 10 proteins. There are 42 proteins in total.