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74-79-3 molecular structure
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(2S)-2-amino-5-carbamimidamidopentanoic acid

ChemBase ID: 11
Molecular Formular: C6H14N4O2
Molecular Mass: 174.20096
Monoisotopic Mass: 174.11167571
SMILES and InChIs

SMILES:
C(CCNC(=N)N)[C@@H](C(=O)O)N
Canonical SMILES:
NC(=N)NCCC[C@@H](C(=O)O)N
InChI:
InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m0/s1
InChIKey:
ODKSFYDXXFIFQN-BYPYZUCNSA-N

Cite this record

CBID:11 http://www.chembase.cn/molecule-11.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-amino-5-carbamimidamidopentanoic acid
IUPAC Traditional name
L-arginine
Brand Name
R-Gene 10 (Pharmacia Corp.)
Levargin
Minophagen A
Argivene
Argamine
Detoxargin
Synonyms
Arginine
(S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid
2-Amino-5-guanidinovaleric acid
L-(+)-Arginine
L-a-Amino-d-guanidinovaleric acid
L-Arg
L-Arginine
2-Amino-5-Guanidnovaleric Acid
(S)-2-Amino-5-guanidinopentanoic acid
Arg
R
L-ARGININE FREE BASE
2-Amino-5-guanidinopentanoic acid
Arginine
L-Arginine
L-2-Amino-5-guanidinopentanoic acid
H-Arg-OH
(S)-2-氨基-5-胍基戊酸
L-精氨酸
CAS Number
74-79-3
7200-25-1
EC Number
200-811-1
230-571-3
MDL Number
MFCD00002635
Beilstein Number
1725411, 1725412 R, 1725413 S
1725413
Merck Index
14780
PubChem SID
46507180
160963474
24890870
24891316
24278014
24846956
24901894
PubChem CID
232
6322
CHEBI ID
29016
ATC CODE
B05XB01
CHEMBL
212301
Chemspider ID
227
DrugBank ID
DB00125
FEMA ID
3819
Gmelin ID
364938 R
IUPHAR ligand ID
721
KEGG ID
C02385
MeSH Name
Arginine
Unique Ingredient Identifier
94ZLA3W45F
Wikipedia Title
Arginine
Flavis Number
17.003

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 2.4118392  H Acceptors
H Donor LogD (pH = 5.5) -6.1142516 
LogD (pH = 7.4) -5.121845  Log P -3.1615653 
Molar Refractivity 53.9231 cm3 Polarizability 16.904032 Å3
Polar Surface Area 125.22 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -3.49  LOG S -1.88 
Solubility (Water) 2.28e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
182 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] expand Show data source
87.1 g L-1 (at 20 °C) in water expand Show data source
H2O: soluble100 mg/mL expand Show data source
H2O: soluble50 mg/mL expand Show data source
Apperance
powder expand Show data source
White crystals expand Show data source
white powder expand Show data source
Melting Point
222 °C (dec.)(lit.) expand Show data source
222-225°C expand Show data source
226°C dec. expand Show data source
259.85°C (533K) expand Show data source
Partition Coefficient
-1.652 expand Show data source
Optical Rotation
[α]20/D +27.0±0.5°, c = 5% in 5 M HCl expand Show data source
[α]20/D +27°, c = 8 in 6 M HCl expand Show data source
[α]24/D +26.1°, c = 1.6 in 6 M HCl expand Show data source
+26 (c=1.6 in 6N HCl) expand Show data source
Absorption Wavelength
λ: 280 nm Amax: ≤0.1 expand Show data source
Hydrophobicity(logP)
-3.6 expand Show data source
pKa
2.488 expand Show data source
pKb
11.509 expand Show data source
Odor
Odourless expand Show data source
Heat Capacity
232.8 J K-1 mol-1 (at 23.7 °C) expand Show data source
Std enthalpy of combustion
-3.7396–-3.7370 MJ mol-1 expand Show data source
Std enthalpy of formation
-624.9–-622.3 kJ mol-1 expand Show data source
Std molar entropy
250.6 J K-1 mol-1 expand Show data source
pH
10.5-12.0 (25 °C, 0.5 M in H2O) expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
Storage Warning
Air Sensitive expand Show data source
IRRITANT expand Show data source
RTECS
CF1934200 expand Show data source
CF1934200 S 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
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
Risk Statements
36 expand Show data source
R:36/37/38 expand Show data source
r36 expand Show data source
Safety Statements
26 expand Show data source
S:20-25-26-37/39 expand Show data source
s26 expand Show data source
TSCA Listed
false expand Show data source
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
GHS Hazard statements
319 expand Show data source
H319 expand Show data source
GHS Precautionary statements
305+351+338 expand Show data source
P280-P264-P305+P351+P338-P337+P313 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
20-25°C expand Show data source
Regulation Compliance
FCC expand Show data source
FDA 21 CFR (172.320) expand Show data source
Gene Information
human ... NOS1(4842), NOS2(4843) expand Show data source
human ... NOS1(4842), NOS2(4843)rat ... Ppm1a(24666) expand Show data source
Allergens
no known allergens expand Show data source
Purity
>98.5% expand Show data source
≥98% expand Show data source
≥98% (TLC) expand Show data source
≥98.0% expand Show data source
≥98.5% expand Show data source
≥99.5% (NT) expand Show data source
98% expand Show data source
98.5-101.0% expand Show data source
98+% expand Show data source
99% expand Show data source
Grade
EP expand Show data source
NI expand Show data source
PharmaGrade expand Show data source
reagent grade expand Show data source
SAJ special grade expand Show data source
USP expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
meets EP, USP testing specifications expand Show data source
suitable for cell culture expand Show data source
suitable for manufacturing use expand Show data source
Ignition Residue
≤0.05% (as SO4) expand Show data source
Impurities
≤0.3% foreign amino acids expand Show data source
endotoxin, tested expand Show data source
Cation Traces
Zn: ≤5 mg/kg expand Show data source
Antion Traces
sulfate (SO42-): ≤100 mg/kg expand Show data source
Biological Source
from non-animal source expand Show data source
Loss on Drying
≤0.1% loss on drying, 20 °C (HV) expand Show data source
Quality Level
GMP-COMPENDIA expand Show data source
λ
0.5 M in H2O expand Show data source
Linear Formula
H2NC(=NH)NH(CH2)3CH(NH2)CO2H expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich Wikipedia Wikipedia DrugBank DrugBank MP Biomedicals MP Biomedicals
Sigma Aldrich - A4474 external link
Biochem/physiol Actions
Substrate of nitric oxide synthase, which is converted to citrulline and nitric oxide (NO). Induces insulin release by a nitric oxide-dependent mechanism.
Packaging
Manufactured and Packaged under cGMP.
Sigma Aldrich - A8094 external link
Biochem/physiol Actions
一氧化氮合成酶的底物,可转化为瓜氨酸和一氧化氮 (NO)。通过与一氧化氮相关的机理诱导胰岛素释放。
包装
10 mg in autosmp vl
Sigma Aldrich - 01-6430 external link
Biochem/physiol Actions
Substrate of nitric oxide synthase, which is converted to citrulline and nitric oxide (NO). Induces insulin release by a nitric oxide-dependent mechanism.
Sigma Aldrich - W381918 external link
Biochem/physiol Actions
Substrate of nitric oxide synthase, which is converted to citrulline and nitric oxide (NO). Induces insulin release by a nitric oxide-dependent mechanism.
Packaging
1 kg in poly bottle
1 sample in glass bottle
5, 10 kg in poly drum
Sigma Aldrich - A5006 external link
Biochem/physiol Actions
一氧化氮合成酶的底物,可转化为瓜氨酸和一氧化氮 (NO)。通过与一氧化氮相关的机理诱导胰岛素释放。
包装
1 kg in poly bottle
100, 500 g in poly bottle
Sigma Aldrich - A92406 external link
Biochem/physiol Actions
Substrate of nitric oxide synthase, which is converted to citrulline and nitric oxide (NO). Induces insulin release by a nitric oxide-dependent mechanism.
Sigma Aldrich - 11009 external link
Biochem/physiol Actions
Substrate of nitric oxide synthase, which is converted to citrulline and nitric oxide (NO). Induces insulin release by a nitric oxide-dependent mechanism.
Other Notes
Exhibits stabilizing effects on plant protoplasts1; pH drift correction in IEF of proteins2; Growth requirement of various microorganisms3.
DrugBank - DB00125 external link
Item Information
Drug Groups approved; nutraceutical
Description An essential amino acid that is physiologically active in the L-form. [PubChem]
Indication Used for nutritional supplementation, also for treating dietary shortage or imbalance.
Pharmacology Studies have shown that is has improved immune responses to bacteria, viruses and tumor cells; promotes wound healing and regeneration of the liver; causes the release of growth hormones; considered crucial for optimal muscle growth and tissue repair.
Toxicity Oral supplementation with L-arginine at doses up to 15 grams daily are generally well tolerated. The most common adverse reactions of higher doses from 15 to 30 grams daily are nausea, abdominal cramps and diarrhea. Some may experience these symptoms at lower doses.
Affected Organisms
Humans and other mammals
Biotransformation Some metabolism of L-arginine takes place in the enterocytes. L-arginine not metabolized in the enterocytes enters the portal circulation from whence it is transported to the liver, where again some portion of the amino acid is metabolized.
Absorption Absorbed from the lumen of the small intestine into the enterocytes. Absorption is efficient and occurs by an active transport mechanism.
References
Morris SM Jr: Enzymes of arginine metabolism. J Nutr. 2004 Oct;134(10 Suppl):2743S-2747S; discussion 2765S-2767S. [Pubmed]
Schulman SP, Becker LC, Kass DA, Champion HC, Terrin ML, Forman S, Ernst KV, Kelemen MD, Townsend SN, Capriotti A, Hare JM, Gerstenblith G: L-arginine therapy in acute myocardial infarction: the Vascular Interaction With Age in Myocardial Infarction (VINTAGE MI) randomized clinical trial. JAMA. 2006 Jan 4;295(1):58-64. [Pubmed]
Alba-Roth J, Muller OA, Schopohl J, von Werder K: Arginine stimulates growth hormone secretion by suppressing endogenous somatostatin secretion. J Clin Endocrinol Metab. 1988 Dec;67(6):1186-9. [Pubmed]
External Links
Wikipedia
PDRhealth
Drugs.com
MP Biomedicals - 02194626 external link
Cell Culture Reagent
Free Base
Purity: 99%
MP Biomedicals - 05201612 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02100736 external link
Crystalline
Purity: 99%

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Morris SM Jr: Enzymes of arginine metabolism. J Nutr. 2004 Oct;134(10 Suppl):2743S-2747S; discussion 2765S-2767S. Pubmed
  • • Schulman SP, Becker LC, Kass DA, Champion HC, Terrin ML, Forman S, Ernst KV, Kelemen MD, Townsend SN, Capriotti A, Hare JM, Gerstenblith G: L-arginine therapy in acute myocardial infarction: the Vascular Interaction With Age in Myocardial Infarction (VINTAGE MI) randomized clinical trial. JAMA. 2006 Jan 4;295(1):58-64. Pubmed
  • • Alba-Roth J, Muller OA, Schopohl J, von Werder K: Arginine stimulates growth hormone secretion by suppressing endogenous somatostatin secretion. J Clin Endocrinol Metab. 1988 Dec;67(6):1186-9. Pubmed
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PATENTS

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