Milk Composition Database: Showing metabocard for L-Histidine (BMDB0000177)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:20:34 UTC

Update Date

2020-06-04 21:43:45 UTC

MCDB ID

BMDB0000177

Secondary Accession Numbers

BMDB00177

Metabolite Identification

Common Name

L-Histidine

Description

L-Histidine, also known as H, 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. L-Histidine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Histidine exists in all living species, ranging from bacteria to humans. L-Histidine participates in a number of enzymatic reactions, within cattle. In particular, beta-Alanine and L-histidine can be biosynthesized from carnosine; which is catalyzed by the enzyme Beta-ala-his dipeptidase. Furthermore, L-Histidine and beta-alanine can be converted into carnosine through the action of the enzyme carnosine synthase 1. Finally, beta-Alanine and L-histidine can be biosynthesized from carnosine through the action of the enzyme Beta-ala-his dipeptidase. In cattle, L-histidine is involved in a couple of metabolic pathways, which include the histidine metabolism pathway and the beta-alanine metabolism pathway. L-Histidine is a potentially toxic compound. L-Histidine has been found to be associated with several diseases known as autosomal dominant polycystic kidney disease, perillyl alcohol administration for cancer treatment, pyridoxamine 5-prime-phosphate oxidase deficiency, and epilepsy; also l-histidine has been linked to the inborn metabolic disorders including maple syrup urine disease.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-4-(2-Amino-2-carboxyethyl)imidazole	ChEBI
(S)-alpha-Amino-1H-imidazole-4-propanoic acid	ChEBI
(S)-alpha-Amino-1H-imidazole-4-propionic acid	ChEBI
H	ChEBI
His	ChEBI
HISTIDINE	ChEBI
L-(-)-Histidine	ChEBI
L-Histidin	ChEBI
(S)-a-Amino-1H-imidazole-4-propanoate	Generator
(S)-a-Amino-1H-imidazole-4-propanoic acid	Generator
(S)-alpha-Amino-1H-imidazole-4-propanoate	Generator
(S)-Α-amino-1H-imidazole-4-propanoate	Generator
(S)-Α-amino-1H-imidazole-4-propanoic acid	Generator
(S)-a-Amino-1H-imidazole-4-propionate	Generator
(S)-a-Amino-1H-imidazole-4-propionic acid	Generator
(S)-alpha-Amino-1H-imidazole-4-propionate	Generator
(S)-Α-amino-1H-imidazole-4-propionate	Generator
(S)-Α-amino-1H-imidazole-4-propionic acid	Generator
(S)-1H-Imidazole-4-alanine	HMDB
(S)-2-Amino-3-(4-imidazolyl)propionsaeure	HMDB
(S)-Histidine	HMDB
(S)1H-Imidazole-4-alanine	HMDB
3-(1H-Imidazol-4-yl)-L-alanine	HMDB
Amino-1H-imidazole-4-propanoate	HMDB
Amino-1H-imidazole-4-propanoic acid	HMDB
Amino-4-imidazoleproprionate	HMDB
Amino-4-imidazoleproprionic acid	HMDB
Glyoxaline-5-alanine	HMDB
Histidine, L isomer	HMDB
Histidine, L-isomer	HMDB
L-Isomer histidine	HMDB
L-Histidine	KEGG

Chemical Formula

C₆H₉N₃O₂

Average Molecular Weight

155.1546

Monoisotopic Molecular Weight

155.069476547

IUPAC Name

(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid

Traditional Name

L-histidine

CAS Registry Number

71-00-1

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 Key

HNDVDQJCIGZPNO-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.

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

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:15971 )
L-alpha-amino acid (CHEBI:15971 )
histidine (CHEBI:15971 )
Common amino acids (C00135 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	287 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	45.6 mg/mL	Not Available
LogP	-3.32	CHMELIK,J ET AL. (1991)

Predicted Properties

Property	Value	Source
logP	-2.7	ALOGPS
logP	-3.6	ChemAxon
logS	-0.34	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	9.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	38.06 m³·mol⁻¹	ChemAxon
Polarizability	14.67 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0udi-0940000000-43b9b035189af65e19cb	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0udi-0910000000-fc3ecec9d4ff3aa8cb09	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0udi-0910000000-8284a673a35f7ac2241f	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0fk9-8910000000-a3231b1a418b5798ecac	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0udi-1920000000-227e8116769731104e82	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0ufu-2942100000-31605fd50ecc1f5be0ed	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0940000000-43b9b035189af65e19cb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0910000000-fc3ecec9d4ff3aa8cb09	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0910000000-8284a673a35f7ac2241f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-0002-2901100000-ae0f3865934743de764c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fk9-8910000000-a3231b1a418b5798ecac	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-1920000000-227e8116769731104e82	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ufu-2942100000-31605fd50ecc1f5be0ed	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ue9-0900000000-75e38a3f347210c301b0	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0910000000-c54bd92cc112eec7e509	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9500000000-1d29684ccb6383687865	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-03di-6900000000-1dd400a16b8067f4daea	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-0900000000-21530fac9975dc1edc7c	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-053r-9300000000-a946c375931adb366aae	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-053r-9000000000-61a3602d80bc0d54c579	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0900000000-7d63b501889c2628f4f0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-d4ccd4e44ca818b4cb17	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0900000000-811aee5724fe0999c134	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-2900000000-052753eb699ae7cb4cb9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0900000000-3e145a05e6a71a0a2f56	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0900000000-143a4b9d88183bc5abe7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-0900000000-a8c213472da676a241f2	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-dfdf9562f155abb5fdeb	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0uk9-0879331100-8434b5b9e7e5700c2353	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0900000000-aaaaadcecd4cd7c94e1e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-90c4cbd09d7abc003013	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-1381708d18c24486773d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0w29-0696321100-eb62fc608270d1151707	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0900000000-3450566ff38e6506a70f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-01q9-7900000000-124509a66476629ce10a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-efa6a21b1be16fda0802	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-137840e69da48c6114e4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udu-3900000000-06d50e90c797793a72d7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9100000000-de7c9eb8068ef4f39f85	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00l6-9000000000-ebf778679d4c6d6a6057	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-014i-9000000000-08d0188684283d1b2372	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0a4i-0900000000-46c2f608d27f0381a039	2012-08-31	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9100000000-ae0a0b81669663b3b4a5	2018-05-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected and Quantified	3 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	2 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	4 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	4 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	2.0 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	3.1 +/- 0.2 uM	PMID: 30994344	details
Detected and Quantified	4.2 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	2.8 +/- 0.1 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0000177

DrugBank ID

DB00117

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

6274

PDB ID

Not Available

ChEBI ID

15971

References

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)

General References

Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for L-Histidine (BMDB0000177)

Structure for BMDB0000177 (L-Histidine)