Livestock Metabolome Database: Showing metabocard for Creatine (LMDB00029)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:40:49 UTC

Update Date

2021-04-30 20:57:57 UTC

Lmdb

LMDB00029

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Creatine

Description

Creatine, also known as cosmocair C 100 or krebiozon, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Creatine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Creatine is a very strong basic compound (based on its pKa). Creatine exists in all living organisms, ranging from bacteria to humans. Within humans, creatine participates in a number of enzymatic reactions. In particular, S-adenosylhomocysteine and creatine can be biosynthesized from S-adenosylmethionine and guanidoacetic acid; which is mediated by the enzyme guanidinoacetate N-methyltransferase. In addition, creatine can be converted into phosphocreatine through the action of the enzyme creatine kinase b-type. In humans, creatine is involved in the metabolic disorder called hyperornithinemia with gyrate atrophy (hoga). Outside of the human body, Creatine is found, on average, in the highest concentration within milk (cow). Creatine has also been detected, but not quantified in, several different foods, such as mulberries, beans, rubus (blackberry, raspberry), highbush blueberries, and broccoli. This could make creatine a potential biomarker for the consumption of these foods. Creatine is a potentially toxic compound. A glycine derivative having methyl and amidino groups attached to the nitrogen.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
((Amino(imino)methyl)(methyl)amino)acetic acid	ChEBI
(alpha-Methylguanido)acetic acid	ChEBI
(N-Methylcarbamimidamido)acetic acid	ChEBI
alpha-Methylguanidino acetic acid	ChEBI
Creatin	ChEBI
Kreatin	ChEBI
Methylglycocyamine	ChEBI
N-(Aminoiminomethyl)-N-methylglycine	ChEBI
N-[(e)-AMINO(imino)methyl]-N-methylglycine	ChEBI
N-Amidinosarcosine	ChEBI
N-Carbamimidoyl-N-methylglycine	ChEBI
N-Methyl-N-guanylglycine	ChEBI
((Amino(imino)methyl)(methyl)amino)acetate	Generator
(a-Methylguanido)acetate	Generator
(a-Methylguanido)acetic acid	Generator
(alpha-Methylguanido)acetate	Generator
(Α-methylguanido)acetate	Generator
(Α-methylguanido)acetic acid	Generator
(N-Methylcarbamimidamido)acetate	Generator
a-Methylguanidino acetate	Generator
a-Methylguanidino acetic acid	Generator
alpha-Methylguanidino acetate	Generator
Α-methylguanidino acetate	Generator
Α-methylguanidino acetic acid	Generator
Cosmocair C 100	HMDB
Creatine hydrate	HMDB
Krebiozon	HMDB
Methylguanidoacetate	HMDB
Methylguanidoacetic acid	HMDB
N-(Aminoiminomethyl)-N-methyl-glycine	HMDB
Phosphagen	HMDB
[[Amino(imino)methyl](methyl)amino]acetate	HMDB
[[Amino(imino)methyl](methyl)amino]acetic acid	HMDB

Chemical Formula

C₄H₉N₃O₂

Average Molecular Weight

131.1332

Monoisotopic Molecular Weight

131.069476547

IUPAC Name

2-(N-methylcarbamimidamido)acetic acid

Traditional Name

creatine

CAS Registry Number

57-00-1

SMILES

CN(CC(O)=O)C(N)=N

InChI Identifier

InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)

InChI Key

CVSVTCORWBXHQV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Guanidine
Carboximidamide
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glycine derivative (CHEBI:16919 )
guanidines (CHEBI:16919 )

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	-1.6	ALOGPS
logP	-2.9	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.5	ChemAxon
pKa (Strongest Basic)	12.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.41 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.01 m³·mol⁻¹	ChemAxon
Polarizability	12.17 Å³	ChemAxon
Number of Rings	0	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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-7739f1c16da098ff4661	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-f89f340e776ae37776b3	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-7739f1c16da098ff4661	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-f89f340e776ae37776b3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-4697e8a17788c105f1aa	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9600000000-ef8c833ca7ddb4b1a500	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 (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 (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
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000x-9800000000-bc1387ab36f71e04b988	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-6c686da36a88d9fbdbcf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-13b7d28e8f5be1c5dada	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-cc4bd4c587dd80f63bcb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-3900000000-d35c7578ad50de8377b7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-a4d7fee14f74e1ed8b4b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-e5d62520dfcbf4bfe5c9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-06fbcf897ccce3fa90b7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-9a0b8275e74605a92681	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000f-9000000000-5f622f2c3de4f213a8ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-20ba65c7a2c9434fcf39	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-01qc-0965022201-53bb6f168e0934ae4a87	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-9000000000-638479794e8c3a6e0b61	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-39676937b1a3ad0dc0bc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0090000000-d53c75786742ecdb3c16	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001l-0945022201-2fc3f234454021c5e202	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-9000000000-40aa07f89dddb181e489	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-5aca4d0b8ed7d2500af2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0190000000-9a9685c32bf6c721a497	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-1900000000-c99f9492e0b84d5fae6b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0006-9300000000-8ab609e6dd62bd18841f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0006-9000000000-e04e407d5f06d21582c4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0006-9000000000-fd81d06317727fa740b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0006-9000000000-8428e2af90720afb4337	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-0900000000-3162b4c94e66796a643b	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9100000000-47f885347545055f546d	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
1D NMR	1H 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

Brain
Cerebrospinal Fluid (CSF)
Colostrum
Jejunum
Kidney
Liver
Lung
Meat
Milk
Plasma
Rumen
Serum
Synovial Fluid
Urine
Vitreous Humour
Whole blood

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Brain	Detected but not Quantified	Not Applicable	Not Available	Ovine	25959287	details
Cerebrospinal Fluid (CSF)	Detected but not Quantified	Not Applicable	Not Available	Ovine	17510975	details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Jejunum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21584308	details
Kidney	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Liver	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Lung	Detected and Quantified	0.29+/-0.01 umol/g	Not Available	Porcine	23412987	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	6.10+/-2.67 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	83.85+/-4.34 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	86.62+/-4.69 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	91.98+/-5.88 umol/g	Not Available	Bovine	S. F. Graham, T. ...	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 and Quantified	10147.92 +/- 171.42 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	7752.34 +/- 490.5 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	8768.14 +/- 196.21 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	8769.99 +/- 413.59 uM	Not Available	Bovine	20831251	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23182357	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	22370585	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	24937646	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24440255	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	22612070	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	22612070	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	21859467	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	23100586	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	19603403	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	24624922	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	22673149	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	21496096	details
Rumen	Detected but not Quantified	Not Applicable	Not Available	Bovine	Hanne Christine B...	details
Serum	Detected and Quantified	178.2479 +/- 50.6513 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	184.8214 +/- 52.4449 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	173.0701 +/- 41.7874 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	179.5023 +/- 51.5536 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	156.96 +/- 50.69 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	185.6088 +/- 60.6086 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	127.3101 +/- 55.7489 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	200.0242 +/- 68.8127 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	190.6252 +/- 54.27 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	150.8466 +/- 54.5158 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	177.1736 +/- 43.6642 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	136.0301 +/- 27.7711 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21942754	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	18989615	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21584308	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected and Quantified	204.1085 +/- 61.1679 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	146.7438 +/- 56.7632 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Serum	Detected and Quantified	158.8077 +/- 44.942 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	177.2965 +/- 49.0925 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21429726	details
Serum	Detected and Quantified	225.6261 +/- 78.887 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	137.1294 +/- 65.8906 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	203.6138 +/- 56.5862 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	157.1221 +/- 40.3271 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	189.0865 +/- 59.4725 uM	Normal	Ovine	Goldansaz et al.,...	details
Synovial Fluid	Detected but not Quantified	Not Applicable	Not Available	Ovine	25283885	details
Urine	Detected and Quantified	166 umol/mmol creatinine	Not Available	Porcine	23741447	details
Urine	Detected and Quantified	30 umol/mmol creatinine	Not Available	Porcine	23741447	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Vitreous Humour	Detected but not Quantified	Not Applicable	Not Available	Caprine	24845217	details
Whole blood	Detected and Quantified	189.883-542.197 uM	Not Available	Bovine	Arthur K. Anderso...	details