| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:32:51 UTC |
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| Update Date | 2020-06-04 21:06:09 UTC |
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| BMDB ID | BMDB0000562 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Creatinine |
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| Description | Creatinine, also known as krebiozen, 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. Creatinine exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Creatinine exists in all living organisms, ranging from bacteria to humans. Creatinine is a potentially toxic compound. Creatinine has been found to be associated with several diseases known as partial lipodystrophy, crohn's disease, long-chain fatty acids, defect in transport of, and chronic renal failure; also creatinine has been linked to the inborn metabolic disorders including hyperoxalemia. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 1-Methylglycocyamidine | ChEBI | | 1-Methylhydantoin-2-imide | ChEBI | | 2-Amino-1,5-dihydro-1-methyl-4H-imidazol-4-one | ChEBI | | 2-Amino-1-methylimidazolin-4-one | ChEBI | | Creatine anhydride | ChEBI | | Creatinina | ChEBI | | Kreatinin | ChEBI | | 2-Amino-1-methyl-1,5-dihydroimidazol-4-one | HMDB | | Krebiozen | HMDB | | Sulfate salt, creatinine | HMDB | | Creatinine sulfate salt | HMDB | | Salt, creatinine sulfate | HMDB |
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| Chemical Formula | C4H7N3O |
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| Average Molecular Weight | 113.1179 |
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| Monoisotopic Molecular Weight | 113.058911861 |
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| IUPAC Name | 2-imino-1-methylimidazolidin-4-one |
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| Traditional Name | creatinina |
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| CAS Registry Number | 60-27-5 |
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| SMILES | CN1CC(=O)NC1=N |
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| InChI Identifier | InChI=1S/C4H7N3O/c1-7-2-3(8)6-4(7)5/h2H2,1H3,(H2,5,6,8) |
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| InChI Key | DDRJAANPRJIHGJ-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | Alpha amino acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Alpha-amino acid or derivatives
- Imidazolinone
- 2-imidazoline
- Guanidine
- N-acylimine
- Carboximidamide
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Organoheterocyclic compound
- Azacycle
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Organic nitrogen compound
- Carbonyl group
- Organic oxygen compound
- Organopnictogen compound
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 303 °C (decomposes) | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 80.1 mg/mL at 16 °C | Not Available | | LogP | -1.76 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | |
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| Biospecimen Locations | - Adipose Tissue
- Bladder
- Blood
- Colostrum
- Fibroblasts
- Kidney
- Liver
- Longissimus Thoracis Muscle
- Milk
- Muscle
- Neuron
- Pancreas
- Placenta
- Platelet
- Prostate Tissue
- Semimembranosus Muscle
- Spleen
- Testis
- Thyroid Gland
- Urine
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| Pathways | |
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| Normal Concentrations |
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| Adipose Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Bladder | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 97.9 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 105.200-171.502 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 109-140 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 113 +/- 17 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 143-179 uM | Not Specified | Not Specified | Normal | | details | | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 58 +/- 12 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 313 +/- 48 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 50.69 +/- 7.42 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 53.0420 - 106.0839 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 80 - 176 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 80 - 167 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 81 - 125 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 81 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 87 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 83 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 68 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 66 +/- 7 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 70 +/- 6 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 71 +/- 4 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 66 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 53.41 +/- 9.12 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 45.12 +/- 8.40 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 138.25 +/- 10.52 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 189.32 +/- 12.46 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 242.65 +/- 27.29 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 128-429 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 413.08 +/- 15.73 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 1200 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 469-1050 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Pancreas | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Platelet | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 315 +/- 47 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Spleen | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 123 +/- 26 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Thyroid Gland | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Treated with growth-promoting hormones | | details | | Blood | Detected and Quantified | 85.5 uM | Not Specified | Not Specified | Treated with bovine somatotropin | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Fed pasture vs barley-based concentrate | | details |
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| External Links |
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| HMDB ID | HMDB0000562 |
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| DrugBank ID | DB11846 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB021814 |
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| KNApSAcK ID | C00052251 |
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| Chemspider ID | 568 |
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| KEGG Compound ID | C00791 |
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| BioCyc ID | CREATININE |
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| BiGG ID | 36009 |
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| Wikipedia Link | Creatinine |
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| METLIN ID | 8 |
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| PubChem Compound | 588 |
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| PDB ID | Not Available |
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| ChEBI ID | 16737 |
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| References |
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| Synthesis Reference | Reddick, Rebecca E.; Kenyon, George L. Syntheses and NMR studies of specifically labeled [2-15N]phosphocreatine, [2-15N]creatinine, and related 15N-labeled compounds. Journal of the American Chemical Society (1987), 109(14), 4380-7. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Indyk HE, Woollard DC: Determination of orotic acid, uric acid, and creatinine in milk by liquid chromatography. J AOAC Int. 2004 Jan-Feb;87(1):116-22. [PubMed:15084094 ]
- Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
- Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
- Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
- Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
- Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
- O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
- 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.
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