Livestock Metabolome Database: Showing metabocard for Carnosine (LMDB00010)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:40:23 UTC

Update Date

2021-04-30 20:57:41 UTC

Lmdb

LMDB00010

Secondary Accession Numbers

None

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 is a very strong basic compound (based on its pKa). Carnosine exists in all living species, ranging from bacteria to humans. carnosine can be converted into β-alanine and L-histidine; which is mediated by the enzyme Beta-ala-his dipeptidase. In humans, carnosine is involved in beta-alanine metabolism. It is highly concentrated in muscle and brain tissues. Carnosine is a potentially toxic compound. Carnosine is a biomarker for the consumption of meat. Carnosine, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, eosinophilic esophagitis, crohn's disease, and alzheimer's disease; carnosine has also been linked to the inborn metabolic disorder carnosinuria. Some autistic patients take it as a dietary supplement and attribute an improvement in their condition to it. This may explain the "hyperactivity" seen in autistic subjects at higher doses. Carnosine also exhibits some antioxidant effects. Carnosine (beta-alanyl-L-histidine) is found exclusively in animal tissues. The antioxidant mechanism of carnosine is attributed to its chelating effect against metal ions, superoxide dismutase (SOD)-like activity, and ROS and free radicals scavenging ability (PMID: 16406688 ). Carnosine has the potential to suppress many of the biochemical changes that accompany ageing (e.g. protein oxidation, glycation, AGE formation, and cross-linking) and associated pathologies (PMID: 16804013 ). It is a dipeptide of the amino acids beta-alanine and histidine. SupplementaCarnosine may increase corticosterone levels.

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

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9200000000-e1b627f2d6087f1a4f3e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-9110000000-a23fcd512ed705116d19	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a6r-0590000000-3facdeb7a9f1b833cadf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03di-1900000000-a39c1a1f1db8549d69fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-03e9-9500000000-0a9e5951251391cb0caa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03fr-0930000000-037f91ca363dacbc0112	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0900000000-d75632020730d38db12a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0900000000-eae5a77f232972048ea2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-08fr-0390000000-61159b9b20f5afda0d0c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03fs-0930000000-2164b41d8882cd740337	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4j-0900000000-d36823b00135c9d452c9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-2d556024df911bfcf1f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-0390000000-7a7d8e991b46e87abc36	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0490200000-e7a68540cb7eb6b88020	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-9000000000-0ea0b380dcef3109e0dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-d329921f45fac5494381	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0090000000-bf47d3f6eac10e087754	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0392411100-6efd739ab2e55ac98d81	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-22bfeae9981523b0cbc3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0090000000-35810c1e1756541bd16a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0190000000-a4df7b97ef1090978371	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0090000000-8eb3d9ac409912a61228	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0w4i-0930000000-4568b16b1f6ed9a27f0a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-03di-1900000000-7771effc7ceb4499f395	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-03di-6900000000-2a23069b75992b4bfcac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-01q9-9200000000-702c77c424d21cbeb2c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-004i-0190000000-441d34f3fa359acb868e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Colostrum
Follicular Fluid
Meat
Milk
Plasma
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	22436164	details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Follicular Fluid	Detected and Quantified	68 +/- 4-100+/-2 uM	Not Available	Porcine	183842	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	22436164	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Porcine	24200563	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	3.96+/-0.64 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	4.46+/-0.43 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	4.73+/-0.48 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	89.36+/-4.06 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	1802.96 +/- 87.68 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	2187.41 +/- 125.15 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	2492.74 +/- 320.38 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	3447.54 +/- 171.14 uM	Not Available	Bovine	20831251	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Plasma	Detected and Quantified	15.03 uM	Not Available	Porcine	25820777	details
Plasma	Detected and Quantified	17.96 uM	Not Available	Porcine	25820777	details
Plasma	Detected and Quantified	21.64 uM	Not Available	Porcine	25820777	details
Plasma	Detected and Quantified	38.02 uM	Not Available	Porcine	25820777	details
Plasma	Detected and Quantified	29 +/- 3-31+/-7 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	33 +/- 5-26+/-3 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	38 +/- 6-46+/-8 uM	Not Available	Porcine	22513987	details
Ruminal Fluid	Detected and Quantified	0.47 +/- 0.24 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	33.6556 +/- 10.1197 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	33.788 +/- 13.0833 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.0775 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	1.503 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	1.635 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	2.696 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	30.0833 +/- 7.3492 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	42.1 +/- 17.16 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	34.8 +/- 7.5827 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	32.256 +/- 11.5134 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	32.744 +/- 6.9201 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	27.2346 +/- 7.6542 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	110 +/- 20 uM	Not Available	Porcine	183842	details
Serum	Detected and Quantified	28.6385 +/- 5.2338 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	29.163 +/- 7.3541 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	19 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	24.9 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	27.4 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	31 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	26.8346 +/- 5.4067 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	32.2212 +/- 13.4457 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	29.952 +/- 7.0459 uM	Normal	Ovine	Goldansaz et al.,...	details

External Links

DrugBank ID

DB11695

HMDB ID

HMDB0000033

FooDB ID

FDB012937

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

1800369

BioCyc ID

CARNOSINE

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Hipkiss AR: Would carnosine or a carnivorous diet help suppress aging and associated pathologies? Ann N Y Acad Sci. 2006 May;1067:369-74. [16804013 ]
Guney Y, Turkcu UO, Hicsonmez A, Andrieu MN, Guney HZ, Bilgihan A, Kurtman C: Carnosine may reduce lung injury caused by radiation therapy. Med Hypotheses. 2006;66(5):957-9. Epub 2006 Jan 10. [16406688 ]

Showing metabocard for Carnosine (LMDB00010)

Structure for LMDB00010 (Carnosine)