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Showing NP-Card for Creatine (NP0001062)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-03 04:16:53 UTC
NP-MRD IDNP0001062
Natural Product DOIhttps://doi.org/10.57994/0846
Secondary Accession NumbersNone
Natural Product Identification
Common NameCreatine
DescriptionCreatine, is a naturally occurring non-protein compound. It 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 found in all vertebrates where it facilitates recycling of adenosine triphosphate (ATP). Its primary metabolic role is to combine with a phosphoryl group, via the enzyme creatine kinase, to generate phosphocreatine, which is used to regenerate ATP. Most of the human body's total creatine and phosphocreatine stores are found in skeletal muscle (95%), while the remainder is distributed in the blood, brain, testes, and other tissues. Creatine is not an essential nutrient as it is naturally produced in the human body from the amino acids glycine and arginine, with an additional requirement for methionine to catalyze the transformation of guanidinoacetate to creatine. In the first step of its biosynthesis glycine and arginine are combined by the enzyme arginine:Glycine amidinotransferase (AGAT) to form guanidinoacetate, which is then methylated by guanidinoacetate N-methyltransferase (GAMT), using S-adenosyl methionine as the methyl donor. Creatine can also be obtained through the diet at a rate of about 1 gram per day from an omnivorous diet. A cyclic form of creatine, called creatinine, exists in equilibrium with its tautomer and with creatine. Clinically, there are three distinct disorders of creatine metabolism. Deficiencies in the two synthesis enzymes (AGAT and GAMT) can cause L-arginine:Glycine amidinotransferase deficiency (caused by variants in AGAT) and guanidinoacetate methyltransferase deficiency (caused by variants in GAMT). Both disorders are inherited in an autosomal recessive manner. A third defect, creatine transporter defect, is caused by mutations in SLC6A8 and inherited in a X-linked manner. Creatine is widely used as a supplement by athletes. Its use can increase maximum power and performance in high-intensity anaerobic repetitive work (periods of work and rest) by 5 to 15% (PMID: 24688272 ). Creatine has no significant effect on aerobic endurance, although it will increase power during short sessions of high-intensity aerobic exercise (PMID: 9662683 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001062 (Creatine)


  Mrv1652303182019232D          

  9  8  0  0  0  0            999 V2000
 9987.5558 9987.6828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9988.2695 9988.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9847 9987.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.6999 9988.0946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9847 9986.8578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9986.8414 9988.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.8414 9988.9190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9986.1269 9987.6828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9987.5558 9986.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
Download

3D MOL for NP0001062 (Creatine)

HMDB0000064
     RDKit          3D
Creatine
 18 17  0  0  0  0  0  0  0  0999 V2000
    0.4532   -1.6037    0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1264   -0.3892   -0.2502 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6349    0.4458   -1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7874    1.0856   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5760    1.8634   -1.0264 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0183    0.8280    0.9116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294   -0.0257    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4102   -0.6434   -0.4454 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7031    0.9766    1.1117 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2785   -2.2086    0.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7556   -2.2388   -0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3040   -1.4132    0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9889   -0.2124   -1.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0541    1.2780   -1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2471    1.0039    1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775   -1.3781   -1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    0.8383    2.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713    1.7935    0.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  3
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  6 15  1  0
  8 16  1  0
  9 17  1  0
  9 18  1  0
M  END
Download

3D SDF for NP0001062 (Creatine)


  Mrv1652303182019232D          

  9  8  0  0  0  0            999 V2000
 9987.5558 9987.6828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9988.2695 9988.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9847 9987.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.6999 9988.0946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9847 9986.8578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9986.8414 9988.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.8414 9988.9190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9986.1269 9987.6828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9987.5558 9986.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001062

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C4H9N3O2

> <MOLECULAR_WEIGHT>
131.1332

> <EXACT_MASS>
131.069476547

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.170880209535248

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(N-methylcarbamimidamido)acetic acid

> <ALOGPS_LOGP>
-1.59

> <JCHEM_LOGP>
-2.8642238844128185

> <ALOGPS_LOGS>
-1.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.501029063602651

> <JCHEM_PKA_STRONGEST_BASIC>
12.429771248504041

> <JCHEM_POLAR_SURFACE_AREA>
90.41

> <JCHEM_REFRACTIVITY>
42.0127

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
creatine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001062 (Creatine)

HMDB0000064
     RDKit          3D
Creatine
 18 17  0  0  0  0  0  0  0  0999 V2000
    0.4532   -1.6037    0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1264   -0.3892   -0.2502 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6349    0.4458   -1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7874    1.0856   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5760    1.8634   -1.0264 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0183    0.8280    0.9116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294   -0.0257    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4102   -0.6434   -0.4454 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7031    0.9766    1.1117 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2785   -2.2086    0.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7556   -2.2388   -0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3040   -1.4132    0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9889   -0.2124   -1.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0541    1.2780   -1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2471    1.0039    1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775   -1.3781   -1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    0.8383    2.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713    1.7935    0.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  3
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  6 15  1  0
  8 16  1  0
  9 17  1  0
  9 18  1  0
M  END
Download

PDB for NP0001062 (Creatine)

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  N   UNK     0    8643.4378643.675   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0    8644.7708644.443   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8646.1058643.675   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8647.4408644.443   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8646.1058642.135   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8642.1048644.443   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8642.1048645.982   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0    8640.7708643.675   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0    8643.4378642.135   0.000  0.00  0.00           C+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
Download

3D PDB for NP0001062 (Creatine)

COMPND    HMDB0000064
HETATM    1  C1  UNL     1       0.453  -1.604   0.252  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.126  -0.389  -0.250  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.635   0.446  -1.132  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.787   1.086  -0.438  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.576   1.863  -1.026  1.00  0.00           O  
HETATM    6  O2  UNL     1       2.018   0.828   0.912  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.429  -0.026   0.134  1.00  0.00           C  
HETATM    8  N2  UNL     1      -2.410  -0.643  -0.445  1.00  0.00           N  
HETATM    9  N3  UNL     1      -1.703   0.977   1.112  1.00  0.00           N  
HETATM   10  H1  UNL     1      -0.278  -2.209   0.848  1.00  0.00           H  
HETATM   11  H2  UNL     1       0.756  -2.239  -0.605  1.00  0.00           H  
HETATM   12  H3  UNL     1       1.304  -1.413   0.945  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.989  -0.212  -1.970  1.00  0.00           H  
HETATM   14  H5  UNL     1       0.054   1.278  -1.580  1.00  0.00           H  
HETATM   15  H6  UNL     1       1.247   1.004   1.544  1.00  0.00           H  
HETATM   16  H7  UNL     1      -2.277  -1.378  -1.163  1.00  0.00           H  
HETATM   17  H8  UNL     1      -1.323   0.838   2.063  1.00  0.00           H  
HETATM   18  H9  UNL     1      -2.271   1.793   0.801  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    7
CONECT    3    4   13   14
CONECT    4    5    5    6
CONECT    6   15
CONECT    7    8    8    9
CONECT    8   16
CONECT    9   17   18
END
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SMILES for NP0001062 (Creatine)

CN(CC(O)=O)C(N)=N
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INCHI for NP0001062 (Creatine)

InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)
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View in JSmol
Synonyms
ValueSource
((Amino(imino)methyl)(methyl)amino)acetic acidChEBI
(alpha-Methylguanido)acetic acidChEBI
(N-Methylcarbamimidamido)acetic acidChEBI
alpha-Methylguanidino acetic acidChEBI
CreatinChEBI
KreatinChEBI
MethylglycocyamineChEBI
N-(Aminoiminomethyl)-N-methylglycineChEBI
N-[(e)-AMINO(imino)methyl]-N-methylglycineChEBI
N-AmidinosarcosineChEBI
N-Carbamimidoyl-N-methylglycineChEBI
N-Methyl-N-guanylglycineChEBI
((Amino(imino)methyl)(methyl)amino)acetateGenerator
(a-Methylguanido)acetateGenerator
(a-Methylguanido)acetic acidGenerator
(alpha-Methylguanido)acetateGenerator
(Α-methylguanido)acetateGenerator
(Α-methylguanido)acetic acidGenerator
(N-Methylcarbamimidamido)acetateGenerator
a-Methylguanidino acetateGenerator
a-Methylguanidino acetic acidGenerator
alpha-Methylguanidino acetateGenerator
Α-methylguanidino acetateGenerator
Α-methylguanidino acetic acidGenerator
Cosmocair C 100HMDB
Creatine hydrateHMDB
KrebiozonHMDB
MethylguanidoacetateHMDB
Methylguanidoacetic acidHMDB
N-(Aminoiminomethyl)-N-methyl-glycineHMDB
PhosphagenHMDB
[[Amino(imino)methyl](methyl)amino]acetateHMDB
[[Amino(imino)methyl](methyl)amino]acetic acidHMDB
Chemical FormulaC4H9N3O2
Average Mass131.1332 Da
Monoisotopic Mass131.06948 Da
IUPAC Name2-(N-methylcarbamimidamido)acetic acid
Traditional Namecreatine
CAS Registry Number57-00-1
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 KeyCVSVTCORWBXHQV-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-19View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
Carcharhinus obscurusLOTUS Database
Carica papayaKNApSAcK Database
Carica papaya L.Plant
CervidaeFooDB
Cervus canadensisFooDB
Citrus natsudaidaiLOTUS Database
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Eriobotrya japonicaFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
Lates calcariferLOTUS Database
LeporidaeFooDB
Lepus timidusFooDB
Litoria verreauxiiLOTUS Database
Lucilia sericataLOTUS Database
Malus pumilaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Thalassiosira pseudonanaLOTUS Database
Trypanosoma bruceiLOTUS Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point303 °CNot Available
Boiling Point536.92 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility13.3 mg/mL at 18 °CNot Available
LogP10.982 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility4.11 g/LALOGPS
logP-1.6ALOGPS
logP-2.9ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.5ChemAxon
pKa (Strongest Basic)12.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.41 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.01 m³·mol⁻¹ChemAxon
Polarizability12.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000064
DrugBank IDDB00148
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005403
KNApSAcK IDC00052250
Chemspider ID566
KEGG Compound IDC00300
BioCyc IDCREATINE
BiGG ID34543
Wikipedia LinkCreatine
METLIN ID7
PubChem Compound586
PDB IDNot Available
ChEBI ID16919
Good Scents IDrw1364761
References
General References
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