Bovine Metabolome Database: Showing metabocard for Carnosine (BMDB0000033)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:18:44 UTC

Update Date

2020-06-04 21:54:05 UTC

BMDB ID

BMDB0000033

Secondary Accession Numbers

BMDB00033

Metabolite Identification

Common Name

Carnosine

Description

Carnosine, also known as b-alanylhistidine or ignotine, belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. Carnosine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Carnosine exists in all living species, ranging from bacteria to humans. Carnosine is a potentially toxic compound. Carnosine has been found to be associated with several diseases known as eosinophilic esophagitis, crohn's disease, ulcerative colitis, and alzheimer's disease; also carnosine has been linked to the inborn metabolic disorders including carnosinuria.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Nalpha-(beta-alanyl)-L-histidine	ChEBI
Nalpha-(b-alanyl)-L-histidine	Generator
Nalpha-(β-alanyl)-L-histidine	Generator
b-Alanyl-L-histidine	HMDB
b-Alanylhistidine	HMDB
beta-Alanyl-L-histidine	HMDB
beta-Alanylhistidine	HMDB
Ignotine	HMDB
Karnozin	HMDB
Karnozzn	HMDB
L-Carnosine	HMDB
N-(3-Aminopropanoyl)histidine	HMDB
N-(b-Alanyl)-L-histidine	HMDB
N-b-Alanyl-L-histidine	HMDB
N-beta-Alanyl-L-histidine	HMDB
Sevitin	HMDB
Carnosine, (D-his)-isomer	HMDB
Hydrochloride, carnosine	HMDB
L Carnosine	HMDB
Carnosine hydrochloride	HMDB
beta Alanylhistidine	HMDB

Chemical Formula

C₉H₁₄N₄O₃

Average Molecular Weight

226.2325

Monoisotopic Molecular Weight

226.106590334

IUPAC Name

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

Traditional Name

β-alanyl-L-histidine

CAS Registry Number

305-84-0

SMILES

NCCC(=O)N[C@@H](CC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1

InChI Key

CQOVPNPJLQNMDC-ZETCQYMHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
Histidine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Beta amino acid or derivatives
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Azole
Heteroaromatic compound
Imidazole
Amino acid
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Primary aliphatic amine
Organic nitrogen compound
Amine
Organonitrogen compound
Organooxygen compound
Carbonyl group
Primary amine
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:15727 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	253 - 256 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	384 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3	ALOGPS
logP	-4.5	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.1 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	55.56 m³·mol⁻¹	ChemAxon
Polarizability	22.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9200000000-e1b627f2d6087f1a4f3e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-9110000000-a23fcd512ed705116d19	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a6r-0590000000-3facdeb7a9f1b833cadf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03di-1900000000-a39c1a1f1db8549d69fe	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-03e9-9500000000-0a9e5951251391cb0caa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03fr-0930000000-037f91ca363dacbc0112	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0900000000-d75632020730d38db12a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0900000000-eae5a77f232972048ea2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-08fr-0390000000-61159b9b20f5afda0d0c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03fs-0930000000-2164b41d8882cd740337	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4j-0900000000-d36823b00135c9d452c9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-2d556024df911bfcf1f0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-0390000000-7a7d8e991b46e87abc36	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0490200000-e7a68540cb7eb6b88020	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-9000000000-0ea0b380dcef3109e0dc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-d329921f45fac5494381	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0090000000-bf47d3f6eac10e087754	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0392411100-6efd739ab2e55ac98d81	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-22bfeae9981523b0cbc3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0090000000-35810c1e1756541bd16a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0190000000-a4df7b97ef1090978371	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0090000000-8eb3d9ac409912a61228	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0w4i-0930000000-4568b16b1f6ed9a27f0a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-03di-1900000000-7771effc7ceb4499f395	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-03di-6900000000-2a23069b75992b4bfcac	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-01q9-9200000000-702c77c424d21cbeb2c0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-004i-0190000000-441d34f3fa359acb868e	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Brain
Colostrum
Fibroblasts
Intestine
Kidney
Liver
Longissimus Thoracis Muscle
Milk
Muscle
Neuron
Placenta
Ruminal Fluid
Semimembranosus Muscle
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
beta-Alanine Metabolism		Not Available
Histidine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	30 +/- 12 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Blood	Detected and Quantified	15-20 uM	Not Specified	Not Specified	Normal	PMID: 28036059	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Colostrum	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected and Quantified	393 +/- 130 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Longissimus Thoracis Muscle	Detected and Quantified	22085 +/- 4859 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Milk	Detected and Quantified	0.48 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.50 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.46 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.46 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23438684	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Muscle	Detected and Quantified	1802.96 +/- 87.68 uM	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected and Quantified	2187.41 +/- 125.15 uM	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected and Quantified	89360 +/- 4060 nmol/g of tissue	Not Specified	Not Specified	Normal	S. F. Graham, T. ...	details
Muscle	Detected and Quantified	4730 +/- 480 nmol/g of tissue	Not Specified	Not Specified	Normal	S. F. Graham, T. ...	details
Muscle	Detected and Quantified	2492.74 +/- 320.38 uM	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected and Quantified	3960 +/- 640 nmol/g of tissue	Not Specified	Not Specified	Normal	S. F. Graham, T. ...	details
Muscle	Detected and Quantified	4460 +/- 430 nmol/g of tissue	Not Specified	Not Specified	Normal	S. F. Graham, T. ...	details
Muscle	Detected and Quantified	3447.54 +/- 171.14 uM	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected and Quantified	1715-3619 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected and Quantified	9900 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 26437054	details
Muscle	Detected and Quantified	433-701 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 28465593	details
Muscle	Detected and Quantified	9690-13658 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 30744349	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	0.47 +/- 0.24 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.47 +/- 0.24 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Semimembranosus Muscle	Detected and Quantified	21958 +/- 3048 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	12 +/- 3 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Colostrum	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Fed pasture vs barley-based concentrate	PMID: 22436164	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Fed pasture vs barley-based concentrate	PMID: 22436164	details

External Links

HMDB ID

HMDB0000033

DrugBank ID

DB11695

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012937

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

439224

PDB ID

Not Available

ChEBI ID

15727

References

Synthesis Reference

Vezenkov, L.; Yanachkov, O. Synthesis of carnosine by trimethylsilyl protection. Dokladi na Bulgarskata Akademiya na Naukite (1991), 44(8), 53-6

Material Safety Data Sheet (MSDS)

Not Available

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
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.

Enzymes

Enzyme Details

1. Cytosolic non-specific dipeptidase

General function:: Amino acid transport and metabolism
Specific function:: Hydrolyzes a variety of dipeptides including L-carnosine but has a strong preference for Cys-Gly. Catalyzes the production of N-lactoyl-amino acids from lactate and amino acids by reverse proteolysis.
Gene Name:: CNDP2
Uniprot ID:: Q3ZC84
Molecular weight:: 52655.0

Reactions

Carnosine + Water → Beta-Alanine + L-Histidine	details

Enzyme Details

2. ATP-grasp domain-containing protein

General function:: Not Available
Specific function:: Not Available
Gene Name:: Not Available
Uniprot ID:: A5PJL9
Molecular weight:: 54461.0

Reactions

Adenosine triphosphate + L-Histidine + Beta-Alanine → ADP + Hydrogen phosphate + Carnosine	details

Showing metabocard for Carnosine (BMDB0000033)

Structure for BMDB0000033 (Carnosine)

Enzymes

Reactions

Reactions