Catharanthine - analytical standard, ≥98% , CAS No.2468-21-5

CAS: 2468-21-5 Cat. No.: V107317 Molecular Weight: 336.43 EC Number: 219-586-6 PubChem CID: 5458190

GRADE & PURITY Analytical standard, ≥98%

Synonyms

7-Ethyl-9,10,12,13-tetrahydro-6,9-methano-5H-pyrido[1',2':1,2]azepino[4,5-b]indole-6(6aH)-carboxylic acid methyl ester | (+)-3,4-Didehydrocoronaridine

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

7-Ethyl-9, 10, 12, 13-tetrahydro-6, 9-methano-5H-pyrido[1', 2':1, 2]azepino[4, 5-b]indole-6(6aH)-carboxylic acid methyl ester | (+)-3, 4-Didehydrocoronaridine

Specifications & Purity

analytical standard, ≥98%

Biochemical and Physiological Mechanisms

Catharanthine is a precursor of the anti-tumor drugs vinblastine and vincristine, formed by dimerization of catharanthine with vindoline. Catharanthine itself is an inhibitor of tubulin self-assembly into microtubules, although not so potent as vinblastin

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

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

Grade

Analytical standard

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCC1=CC2CC3(C1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC
• IUPAC Name: methyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate
• InChIKey: CMKFQVZJOWHHDV-NQZBTDCJSA-N
• INCHI: 1S/C21H24N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13-,19+,21-/m0/s1
• Isomeric SMILES: CCC1=C[C@H]2C[C@]3([C@@H]1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC
• WGK Germany: 3
• PubChem CID: 5458190
• Molecular Weight: 336.43

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Ibogan-type alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Ibogan-type alkaloids
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Ibogan-type alkaloids
• Alternative Parents: 3-alkylindoles Pyrroloazepines Piperidinecarboxylic acids Aralkylamines Azepines Benzenoids Methyl esters Heteroaromatic compounds Pyrroles Amino acids and derivatives Trialkylamines Monocarboxylic acids and derivatives Azacyclic compounds Hydrocarbon derivatives Carbonyl compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Ibogan skeleton - Catharanthine skeleton - Pyrroloazepine - 3-alkylindole - Indole - Indole or derivatives - Piperidinecarboxylic acid - Azepine - Aralkylamine - Piperidine - Benzenoid - Pyrrole - Methyl ester - Heteroaromatic compound - Tertiary aliphatic amine - Tertiary amine - Amino acid or derivatives - Carboxylic acid ester - Organoheterocyclic compound - Carboxylic acid derivative - Azacycle - Monocarboxylic acid or derivatives - Organic oxide - Organic oxygen compound - Amine - Carbonyl group - Hydrocarbon derivative - Organooxygen compound - Organic nitrogen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond.
• External Descriptors: Not available

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)

TRPA1 Tclin Transient receptor potential cation channel subfamily A member 1 (1 Activities)

Discover Target: TRPA1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

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

CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 Activities)

Discover Target: CACNA1C

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

TRPV1 Tclin Vanilloid receptor (8273 Activities)

Discover Target: TRPV1

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

BCHE Tclin Butyrylcholinesterase (7174 Activities)

Discover Target: BCHE

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

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)

Discover Target: Trpa1

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

Trpm8 Transient receptor potential cation channel subfamily M member 8 (889 Activities)

Discover Target: Trpm8

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

BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive；Air sensitive
• Molecular Weight: 336.400 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 336.184 Da
• Monoisotopic Mass: 336.184 Da
• Topological Polar Surface Area: 45.300 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 603.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• 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. Chuxin Liang, Chang Chen, Pengfei Zhou, Lv Xu, Jianhua Zhu, Jincai Liang, Jiachen Zi, Rongmin Yu.  (2018)  Effect of Aspergillus flavus Fungal Elicitor on the Production of Terpenoid Indole Alkaloids in Catharanthus roseus Cambial Meristematic Cells.  MOLECULES,  23  (12): (3276).  [PMID:30544939] [10.3390/molecules23123276]

2. Jianhua Zhu, Shuijie He, Pengfei Zhou, Jiachen Zi, Jincai Liang, Liyan Song, Rongmin Yu.  (2018)  Eliciting Effect of Catharanthine on the Biosynthesis of Vallesiachotamine and Isovallesiachotamine in Catharanthus roseus Cambial Meristematic Cells.  Natural Product Communications,      [PMID:] [10.1177/1934578X1801300508]

3. Zhi Liu, Hai-Long Wu, Yong Li, Hui-Wen Gu, Xiao-Li Yin, Li-Xia Xie, Ru-Qin Yu.  (2015)  Rapid and simultaneous determination of five vinca alkaloids in Catharanthus roseus and human serum using trilinear component modeling of liquid chromatography–diode array detection data.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,      [PMID:26321366] [10.1016/j.jchromb.2015.08.008]