Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110219
Identification
Name: creatinine
Description:A lactam obtained by formal cyclocondensation of creatine. It is a metabolite of creatine.
Structure
Thumb
Synonyms:
  • krebiozen
  • 2-imino-1-methyl-4-imidazolidinone
  • 1-methyl-2-amino-imidazol-4-one
Chemical Formula: C4H7N3O
Average Molecular Weight: 113.12
Monoisotopic Molecular Weight: 113.0589118624
InChI Key: DDRJAANPRJIHGJ-UHFFFAOYSA-N
InChI: InChI=1S/C4H7N3O/c1-7-2-3(8)6-4(7)5/h2H2,1H3,(H2,5,6,8)
CAS number: 60-27-5
IUPAC Name:2-imino-1-methylimidazolidin-4-one
Traditional IUPAC Name: creatinina
SMILES:CN1(CC(=O)NC(=N)1)
Chemical Taxonomy
Taxonomy DescriptionThis compound 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 ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Alpha amino acids and derivatives
Alternative Parents
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
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 303 °C (decomposes)
Experimental Properties:
PropertyValueReference
Melting Point303 °C (decomposes)Not Available
Boiling PointNot AvailableNot Available
Water Solubility80.1 mg/mL at 16 °CNot Available
LogP-1.76HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility9.92 mg/mLALOGPS
logP-1.6ALOGPS
logP-1.1ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)13.19ChemAxon
pKa (Strongest Basic)2.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area56.19 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.81 m3·mol-1ChemAxon
Polarizability10.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014i-0900000000-434db9fb715c467d6e22View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0l05-3930000000-0efef64758a717fd8a7bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-0901000000-bd882951c92733ecbc9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-5900000000-9a1d9dadbe33ae2d1306View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-e79b269b74d9c6e99118View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-bfa35af1a437cbc8b5ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-57f60152c562a170b9fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-1900000000-ef69e2d63505f5b30467View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-01ox-9500000000-88d102c7e4686e30b719View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-f87b49f5a20f18c9f6f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-1498f1dfaa82105e4414View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-0900000000-87b686020b9ef983648cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03di-5900000000-5ac55d9993e2227ed724View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9000000000-ed919da9ef2eaa0e3b24View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-e0fbc3bd29181697fb8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-445863d7d688052704e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-0900000000-844659480059fd60d69fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-41e3cbcd832bbcfa8cd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-6900000000-557a2affe27acf1b78f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-daa2222b345889ef7eceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3900000000-233fc8a5c8c5754cc3f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-11990e8b9bad7fdbeb0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-c4791b13b30e29c01832View in MoNA
MSMass Spectrum (Electron Ionization)splash10-01ox-9400000000-fc8e70dbbe2575dc0957View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
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  • Salek RM, Maguire ML, Bentley E, Rubtsov DV, Hough T, Cheeseman M, Nunez D, Sweatman BC, Haselden JN, Cox RD, Connor SC, Griffin JL (2007)A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human. Physiological genomics 29, Pubmed: 17190852
  • Ning WB, Hu J, Tao LJ, Liu CY, Sun J, Xiao Y, Jia AJ (2007)[Effect of losartan on the expressions of TGF-beta1, p-Smad2/3, and Smad7 in the remnant renal tissues of 5/6 nephrectomized rats]. Zhong nan da xue xue bao. Yi xue ban = Journal of Central South University. Medical sciences 32, Pubmed: 18182718
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  • Chang YS, Ko TH, Hsu TJ, Syu MJ (2009)Synthesis of an imprinted hybrid organic-inorganic polymeric sol-gel matrix toward the specific binding and isotherm kinetics investigation of creatinine. Analytical chemistry 81, Pubmed: 19236048
  • Chen CH, Lin MS (2012)A novel structural specific creatinine sensing scheme for the determination of the urine creatinine. Biosensors & bioelectronics 31, Pubmed: 22047975
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  • Grubb A, Nyman U, Björk J (2012)Improved estimation of glomerular filtration rate (GFR) by comparison of eGFRcystatin C and eGFRcreatinine. Scandinavian journal of clinical and laboratory investigation 72, Pubmed: 22121923
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  • Walther CP, Carter CW, Low CL, Williams P, Rifkin DE, Steiner RW, Ix JH (2012)Interdialytic creatinine change versus predialysis creatinine as indicators of nutritional status in maintenance hemodialysis. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 27, Pubmed: 21775764
  • Slort PR, Ozden N, Pape L, Offner G, Tromp WF, Wilhelm AJ, Bokenkamp A (2012)Comparing cystatin C and creatinine in the diagnosis of pediatric acute renal allograft dysfunction. Pediatric nephrology (Berlin, Germany) 27, Pubmed: 22207347
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  • Ciarimboli G, Lancaster CS, Schlatter E, Franke RM, Sprowl JA, Pavenstädt H, Massmann V, Guckel D, Mathijssen RH, Yang W, Pui CH, Relling MV, Herrmann E, Sparreboom A (2012)Proximal tubular secretion of creatinine by organic cation transporter OCT2 in cancer patients. Clinical cancer research : an official journal of the American Association for Cancer Research 18, Pubmed: 22223530
  • Vallon V, Eraly SA, Rao SR, Gerasimova M, Rose M, Nagle M, Anzai N, Smith T, Sharma K, Nigam SK, Rieg T (2012)A role for the organic anion transporter OAT3 in renal creatinine secretion in mice. American journal of physiology. Renal physiology 302, Pubmed: 22338083
  • Darby D, So J, Russell J, Monaghan PJ (2012)Spuriously raised serum creatinine associated with an excipient present in an intravenous dexamethasone formulation. Annals of clinical biochemistry 49, Pubmed: 22349552
  • Nelson WK, Formica RN, Cooper DL, Schwartz PE, Rutherford TJ (2012)An analysis of measured and estimated creatinine clearance rates in normal weight, overweight, and obese patients with gynecologic cancers. Journal of oncology pharmacy practice : official publication of the International Society of Oncology Pharmacy Practitioners 18, Pubmed: 22331238
  • Shimazaki Y, Kushiyama M, Murakami M, Yamashita Y (2013)Relationship between normal serum creatinine concentration and periodontal disease in Japanese middle-aged males. Journal of periodontology 84, Pubmed: 22390548
  • Haginaka J, Miura C, Funaya N, Matsunaga H (2012)Monodispersed molecularly imprinted polymer for creatinine by modified precipitation polymerization. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 28, Pubmed: 22498455
  • Zinchenko OA, Marchenko SV, Sergeyeva TA, Kukla AL, Pavlyuchenko AS, Krasyuk EK, Soldatkin AP, El'skaya AV (2012)Application of creatinine-sensitive biosensor for hemodialysis control. Biosensors & bioelectronics 35, Pubmed: 22459582
  • Solorzano GT, Silva MV, Moreira SR, Nishida SK, Kirsztajn GM (2012)Urinary protein/creatinine ratio versus 24-hour proteinuria in the evaluation of lupus nephritis. Jornal brasileiro de nefrologia : 'orgao oficial de Sociedades Brasileira e Latino-Americana de Nefrologia 34, Pubmed: 22441184
  • Mychaleckyj JC, Craven T, Nayak U, Buse J, Crouse JR, Elam M, Kirchner K, Lorber D, Marcovina S, Sivitz W, Sperl-Hillen J, Bonds DE, Ginsberg HN (2012)Reversibility of fenofibrate therapy-induced renal function impairment in ACCORD type 2 diabetic participants. Diabetes care 35, Pubmed: 22432114
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.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS60-27-5
ChEBI16737
ChemSpider568
HMDBHMDB00562
KEGGC00791
MetaboLightsMTBLC16737
PubChem588