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372-75-8 molecular structure
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(2S)-2-amino-5-(carbamoylamino)pentanoic acid

ChemBase ID: 41
Molecular Formular: C6H13N3O3
Molecular Mass: 175.18572
Monoisotopic Mass: 175.09569129
SMILES and InChIs

SMILES:
OC(=O)[C@@H](N)CCCNC(=O)N
Canonical SMILES:
NC(=O)NCCC[C@@H](C(=O)O)N
InChI:
InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1
InChIKey:
RHGKLRLOHDJJDR-BYPYZUCNSA-N

Cite this record

CBID:41 http://www.chembase.cn/molecule-41.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-amino-5-(carbamoylamino)pentanoic acid
IUPAC Traditional name
L-citrulline
Synonyms
2-Amino-5-uredovaleric acid
Sitrulline
Citrulline
delta-Ureidonorvaline
N5-carbamylornithine
N5-carbamoylornithine
N5-(Aminocarbonyl)ornithine
N5-Carbamoyl-L-ornithine
L-2-Amino-5-ureidovaleric acid
(S)-2-Amino-5-ureidopentanoic acid
L-Citrulline
N5-(Aminocarbonyl)-L-ornithine
NSC 27425
Nδ-Carbamylornithine
α-Amino-δ-ureidovaleric Acid
L-(+)-2-Amino-5-ureidovaleric acid
L-Citrulline
δ-Ureidonorvaline
(S)-2-氨基-5-脲戊酸
L-2-氨基-5-脲戊酸
L-瓜氨酸
CAS Number
372-75-8
EC Number
206-759-6
MDL Number
MFCD00064397
Beilstein Number
1725416
6055157
Merck Index
142331
PubChem SID
24892975
160963504
46506583
PubChem CID
9750

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 2.2682476  H Acceptors
H Donor LogD (pH = 5.5) -3.9319353 
LogD (pH = 7.4) -3.9377463  Log P -3.9319577 
Molar Refractivity 41.329 cm3 Polarizability 16.298895 Å3
Polar Surface Area 118.44 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -3.27  LOG S -0.9 
Solubility (Water) 2.18e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
200 g/L (at 20 oC) expand Show data source
Water expand Show data source
Apperance
White Solid expand Show data source
Melting Point
207-209°C (dec.) expand Show data source
212-214°C dec. expand Show data source
220-221 °C expand Show data source
Optical Rotation
[α]20/D +22.0±1°, c = 2% in 1 M HCl expand Show data source
+22 (c=2 in 1N HCl) expand Show data source
Hydrophobicity(logP)
-3.9 expand Show data source
Storage Condition
2-8°C expand Show data source
Refrigerator 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
German water hazard class
3 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥98% (TLC) expand Show data source
≥99.0% (NT) expand Show data source
98% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
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Ignition Residue
≤0.05% expand Show data source
Cation Traces
Ca: ≤20 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Li: ≤5 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Mo: ≤5 mg/kg expand Show data source
Na: ≤50 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Antion Traces
chloride (Cl-): ≤500 mg/kg expand Show data source
sulfate (SO42-): ≤50 mg/kg expand Show data source
Empirical Formula (Hill Notation)
C6H13N3O3 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals TRC TRC DrugBank DrugBank Sigma Aldrich Sigma Aldrich
MP Biomedicals - 05211125 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02101397 external link
Crystalline
Toronto Research Chemicals - C535700 external link
An amino acid, first isolated from the juice of watermelon, Citrullus vulgaris Schrad., Cucurbitaceae. Used in the treatment of asthenia.
DrugBank - DB00155 external link
Item Information
Drug Groups approved; nutraceutical
Description Citrulline is an amino acid. It is made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family. Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolated.
Indication Used for nutritional supplementation, also for treating dietary shortage or imbalance.
Pharmacology A non-essential amino acid and a precursor of arginine. Citrulline supplements have been claimed to promote energy levels, stimulate the immune system and help detoxify ammonia (a cell toxin). L-citrulline is made from L-ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from L-arginine as a by-product of the reaction catalyzed by the enzyme NO synthase. L-citrulline, while being an amino acid, is not involved in protein synthesis and is not one of the amino acids coded for by DNA. Although citrulline cannot be incorporated in proteins during protein synthesis, several proteins are known to contain citrulline as an amino acid. These citrulline residues are generated by a family of enzymes called peptidylarginine deiminases (PADs), which convert the amino acid arginine into citrulline. Proteins that contain citrulline residues include myelin basic protein (MBP), fillagrin and several histone proteins.
Affected Organisms
Humans and other mammals
Sigma Aldrich - C7629 external link
Biochem/physiol Actions
Intermediate in the production of nitric oxide from L-arginine by NO synthetase.
包装
10 mg in autosmp vl
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7629.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7629.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Sigma Aldrich - 27510 external link
Other Notes
Substrate for the assay of argininosuccinate synthetase, EC 6.3.4.51

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Kurtz, et al.: J. Biol. Chem., 122, 477 (1938)
  • • Rajantie, J., et al.: J. Pediatr., 97, 927 (1938)
  • • Carpenter, T.O., et al.: N. Engl. J. Med., 312, 290 (1938)
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PATENTS

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