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57-00-1 molecular structure
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2-(1-methylcarbamimidamido)acetic acid

ChemBase ID: 34
Molecular Formular: C4H9N3O2
Molecular Mass: 131.13316
Monoisotopic Mass: 131.06947654
SMILES and InChIs

SMILES:
OC(=O)CN(C)C(=N)N
Canonical SMILES:
OC(=O)CN(C(=N)N)C
InChI:
InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)
InChIKey:
CVSVTCORWBXHQV-UHFFFAOYSA-N

Cite this record

CBID:34 http://www.chembase.cn/molecule-34.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-(1-methylcarbamimidamido)acetic acid
IUPAC Traditional name
creatine
Brand Name
Cosmocair C 100
Creatin
Kreatin
Krebiozon
Phosphagen
Pyrolysate
Synonyms
(alpha-Methylguanido)acetic acid
Creatine, hydrate
N-Methyl-N-guanylglycine
N-Amidinosarcosine
Methylguanidoacetic acid
Creatine (8CI)
Creatine
2-(1-methylguanidino)acetic acid
2-(Methylguanidino)ethanoic acid
Creatine
(α-Methylguanido)acetic acid
Creatine, anhydrous
N-胺肉胺酸
α-甲胍乙酸
肌酸
无水肌酸
CAS Number
57-00-1
EC Number
200-306-6
MDL Number
MFCD00004282
Beilstein Number
907175
Merck Index
142568
PubChem SID
24857517
160963497
46504868
24892273
PubChem CID
586
CHEBI ID
16919
ATC CODE
C01EB06
CHEMBL
283800
Chemspider ID
566
DrugBank ID
DB00148
Gmelin ID
240513
KEGG ID
C00300
MeSH Name
Creatine
Unique Ingredient Identifier
MU72812GK0
Wikipedia Title
Creatine

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.501029  H Acceptors
H Donor LogD (pH = 5.5) -2.8677905 
LogD (pH = 7.4) -2.8642461  Log P -2.864224 
Molar Refractivity 42.0127 cm3 Polarizability 11.747328 Å3
Polar Surface Area 90.41 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -1.59  LOG S -1.5 
Solubility (Water) 4.11e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
13.3 g L-1 (at 18 °C) in water expand Show data source
13.3 mg/mL at 18 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] expand Show data source
Apperance
White crystals expand Show data source
Melting Point
~295 °C (dec.) expand Show data source
255°C expand Show data source
ca 290°C dec. expand Show data source
Density
1.33 expand Show data source
Partition Coefficient
-1.258 expand Show data source
Hydrophobicity(logP)
-0.2 expand Show data source
pKa
3.429 expand Show data source
pKb
10.568 expand Show data source
Isoelectric Point
8.47 expand Show data source
Odor
Odourless expand Show data source
Heat Capacity
171.1 J K-1 mol-1 (at 23.2 °C) expand Show data source
Std enthalpy of combustion
-2.3239–-2.3223 MJ mol-1 expand Show data source
Std enthalpy of formation
-538.06–-536.30 kJ mol-1 expand Show data source
Std molar entropy
189.5 J K-1 mol-1 expand Show data source
RTECS
MB7706000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
r36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
26-37 expand Show data source
s26, s36 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS exclamation mark expand Show data source
GHS07 expand Show data source
GHS Signal Word
WARNING expand Show data source
Warning expand Show data source
GHS Hazard statements
315, 319, 335 expand Show data source
H315-H319-H335 expand Show data source
GHS Precautionary statements
261, 305+351+338 expand Show data source
P261-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Half Life
3 hours expand Show data source
Purity
≥99.0% (NT) expand Show data source
95+% expand Show data source
98% expand Show data source
Grade
anhydrous expand Show data source
Impurities
≤0.5% water expand Show data source
Linear Formula
H2NC(=NH)N(CH3)CH2CO2H expand Show data source
Classification
Genuine Natural Compounds expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
DrugBank - DB00148 external link
Item Information
Drug Groups approved; nutraceutical
Description An amino acid that occurs in vertebrate tissues and in urine. In muscle tissue, creatine generally occurs as phosphocreatine. Creatine is excreted as creatinine in the urine. [PubChem]
Indication For nutritional supplementation, also for treating dietary shortage or imbalance
Pharmacology Creatine is a essential, non-proteinaceous amino acid found in all animals and, in some plants. Creatine is synthesized in the kidney, liver and pancreas from L-arginine, glycine and L-methionine. Following its biosynthesis, creatine is transported to the skeletal muscle, heart, brain and other tissues. Most of the creatine is metabolized in these tissues to phosphocreatine (creatine phosphate). Phosphocreatine is a major energy storage form in the body. Supplemental creatine may have an energy-generating action during anaerobic exercise and may also have neuroprotective and cardioprotective actions.
Affected Organisms
Humans and other mammals
Half Life 3 hours
References
Burke DG, Chilibeck PD, Parise G, Tarnopolsky MA, Candow DG: Effect of alpha-lipoic acid combined with creatine monohydrate on human skeletal muscle creatine and phosphagen concentration. Int J Sport Nutr Exerc Metab. 2003 Sep;13(3):294-302. [Pubmed]
Dangott B, Schultz E, Mozdziak PE: Dietary creatine monohydrate supplementation increases satellite cell mitotic activity during compensatory hypertrophy. Int J Sports Med. 2000 Jan;21(1):13-6. [Pubmed]
Hespel P, Op't Eijnde B, Van Leemputte M, Urso B, Greenhaff PL, Labarque V, Dymarkowski S, Van Hecke P, Richter EA: Oral creatine supplementation facilitates the rehabilitation of disuse atrophy and alters the expression of muscle myogenic factors in humans. J Physiol. 2001 Oct 15;536(Pt 2):625-33. [Pubmed]
Hultman E, Soderlund K, Timmons JA, Cederblad G, Greenhaff PL: Muscle creatine loading in men. J Appl Physiol. 1996 Jul;81(1):232-7. [Pubmed]
Juhn M: Popular sports supplements and ergogenic aids. Sports Med. 2003;33(12):921-39. [Pubmed]
External Links
Wikipedia
PDRhealth
Drugs.com
Sigma Aldrich - 27890 external link
Other Notes
Identification of creatine as a cofactor of thiamine-diphosphate kinase1
Biochem/physiol Actions
Creatine is a nitrogenous compound that acts as a high-energy reservoir for the rapid regeneration of ATP. Approximately 95% of creatine is found in skeletal muscle, primarily as phosphocreatine. Creatine can be acquired through dietary consumption or formed from L-arginine, glycine, and L-methionine in a multi-step reaction that occurs in the kidneys and liver. Creatine is then transported to muscle tissue. Creatine supplementation is used for the enhancement of sports performance, primarily by increasing muscle mass. Creatine is also being investigated as a treatment of neuromuscular diseases, where it may aid in neuroprotection and by improving the cellular bioenergetic state.
Sigma Aldrich - 291196 external link
Packaging
5 g in glass bottle
Biochem/physiol Actions
Creatine is a nitrogenous compound that acts as a high-energy reservoir for the rapid regeneration of ATP. Approximately 95% of creatine is found in skeletal muscle, primarily as phosphocreatine. Creatine can be acquired through dietary consumption or formed from L-arginine, glycine, and L-methionine in a multi-step reaction that occurs in the kidneys and liver. Creatine is then transported to muscle tissue. Creatine supplementation is used for the enhancement of sports performance, primarily by increasing muscle mass. Creatine is also being investigated as a treatment of neuromuscular diseases, where it may aid in neuroprotection and by improving the cellular bioenergetic state.
Sigma Aldrich - C0780 external link
包装
10 mg in autosmp vl
50, 100, 500 g in poly bottle
Biochem/physiol Actions
Creatine is a nitrogenous compound that acts as a high-energy reservoir for the rapid regeneration of ATP. Approximately 95% of creatine is found in skeletal muscle, primarily as phosphocreatine. Creatine can be acquired through dietary consumption or formed from L-arginine, glycine, and L-methionine in a multi-step reaction that occurs in the kidneys and liver. Creatine is then transported to muscle tissue. Creatine supplementation is used for the enhancement of sports performance, primarily by increasing muscle mass. Creatine is also being investigated as a treatment of neuromuscular diseases, where it may aid in neuroprotection and by improving the cellular bioenergetic state.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Burke DG, Chilibeck PD, Parise G, Tarnopolsky MA, Candow DG: Effect of alpha-lipoic acid combined with creatine monohydrate on human skeletal muscle creatine and phosphagen concentration. Int J Sport Nutr Exerc Metab. 2003 Sep;13(3):294-302. Pubmed
  • • Dangott B, Schultz E, Mozdziak PE: Dietary creatine monohydrate supplementation increases satellite cell mitotic activity during compensatory hypertrophy. Int J Sports Med. 2000 Jan;21(1):13-6. Pubmed
  • • Hespel P, Op't Eijnde B, Van Leemputte M, Urso B, Greenhaff PL, Labarque V, Dymarkowski S, Van Hecke P, Richter EA: Oral creatine supplementation facilitates the rehabilitation of disuse atrophy and alters the expression of muscle myogenic factors in humans. J Physiol. 2001 Oct 15;536(Pt 2):625-33. Pubmed
  • • Hultman E, Soderlund K, Timmons JA, Cederblad G, Greenhaff PL: Muscle creatine loading in men. J Appl Physiol. 1996 Jul;81(1):232-7. Pubmed
  • • Juhn M: Popular sports supplements and ergogenic aids. Sports Med. 2003;33(12):921-39. Pubmed
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PATENTS

PATENTS

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