L-Canavanine - ≥98%, from Canavalia ensiformis , CAS No.543-38-4

CAS: 543-38-4 Cat. No.: L329592 Molecular Weight: 176.17 EC Number: 624-714-2

GRADE & PURITY ≥98%, from Canavalia ensiformis

Synonyms

CANAVANINE [HSDB] | EN300-16717 | BDBM50370459 | O-((Aminoiminomethyl)amino)homoserine | KBio3_002092 | SPECTRUM1500833 | GGB | L-alpha-Amino-gamma-(guanidinooxy)-n-butyric acid | L-CAV | O-carbamimidamido-L-homoserine | SMP1_000062 | L-2-AMINO-4-(GUANIDI

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

L-Canavanine is a selective inhibitor of NOS2 (iNOS). Overproduction of NO by NOS2 plays a crucial role in the pathophysiology of septic shock and chronic inflammation. L-Canavanine is a naturally occurring L-amino acid that interferes with L-arginine-utilizing enzymes due to its structural similarity.

Specifications

Synonyms

CANAVANINE [HSDB] | EN300-16717 | BDBM50370459 | O-((Aminoiminomethyl)amino)homoserine | KBio3_002092 | SPECTRUM1500833 | GGB | L-alpha-Amino-gamma-(guanidinooxy)-n-butyric acid | L-CAV | O-carbamimidamido-L-homoserine | SMP1_000062 | L-2-AMINO-4-(GUANIDI

Specifications & Purity

≥98%, from Canavalia ensiformis

Biochemical and Physiological Mechanisms

Canavanine is a naturally occurring L-amino acid that interferes with L-arginine-utilizing enzymes due to its structural similarity. It is a selective inhibitor of inducible nitric oxide synthase (iNOS). Excessive NO production by iNOS plays a crucial rol

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Product Properties

• pKa: pKₐ: 2.16 (Predicted), pKₐ: 9.49 (Predicted)
• Ki Data: NOS2: Ki= 0.22 mM (human)

Names and Identifiers

• Pubchem Sid: 504758690
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504758690
• Canonical Smiles: C(CON=C(N)N)C(C(=O)O)N
• IUPAC Name: (2S)-2-amino-4-(diaminomethylideneamino)oxybutanoic acid
• InChIKey: FSBIGDSBMBYOPN-VKHMYHEASA-N
• INCHI: 1S/C5H12N4O3/c6-3(4(10)11)1-2-12-9-5(7)8/h3H,1-2,6H2,(H,10,11)(H4,7,8,9)/t3-/m0/s1
• Isomeric SMILES: C(CON=C(N)N)[C@@H](C(=O)O)N
• WGK Germany: 3
• RTECS: ES7002000
• Molecular Weight: 176.17
• Reaxy-Rn: 5735733
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5735733&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alpha amino acids
              • Level8 L-alpha-amino acids

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids
• Direct Parent: L-alpha-amino acids
• Alternative Parents: Fatty acids and conjugates Guanidines Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: L-alpha-amino acid - Fatty acid - Guanidine - Amino acid - Monocarboxylic acid or derivatives - Carboxylic acid - Amine - Hydrocarbon derivative - Organic oxygen compound - Organic nitrogen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Carbonyl group - Organic oxide - Organopnictogen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
• External Descriptors: non-proteinogenic L-alpha-amino acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

Discover Target: TSHR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

Discover Target: ALOX15

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

Discover Target: CYP1A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

Discover Target: CYP2C19

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SH-SY5Y (11521 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HEK293 (82097 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ATXN2 Tbio Ataxin-2 (54410 Activities)

Discover Target: ATXN2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

Discover Target: USP1

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

Discover Target: MEN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Nos2 Nitric oxide synthase, inducible (3573 Activities)

Discover Target: Nos2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

Discover Target: Txnrd1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (<100 mg/ml).
• Refractive Index: n20D1.60 (Predicted)
• Boil Point(°C): ~365.8° C at 760 mmHg (Predicted)
• Melt Point(°C): ~295.1° C (Predicted)
• Molecular Weight: 176.170 g/mol
• XLogP3: -4.800
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 176.091 Da
• Monoisotopic Mass: 176.091 Da
• Topological Polar Surface Area: 137.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 178.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Wang Ying, Li ZhiRong, Chen RongXiang.  (2022)  Simultaneous Determination of Metabolites Related to Arginine Metabolism in Rat plasma by Hydrophilic Interaction Chromatography–Tandem Mass Spectrometry.  JOURNAL OF CHROMATOGRAPHIC SCIENCE,  61  (3): (203-210).  [PMID:35704851] [10.1093/chromsci/bmac047]