Gelsemine - analytical standard , CAS No.509-15-9

CAS: 509-15-9 Cat. No.: G343887 Formule: C₂₀H₂₂N₂O₂ Poids moléculaire: 322.4 Numéro CE: 208-095-2

QUALITÉ & PURETÉ Analytical standard

Synonyms

s9294 | GELSEMINE [MI] | NSC 21729 | Spiro(3,5,8-ethanylylidene-1H-pyrano(3,4-c)pyridine-10,3'-(3H)indol)-2'(1'H)-one, 5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methyl-, (3R,3'S,4aR,5S,8S,8aS,9S)- | Gelsemin | 4-27-00-07526 (Beilstein Handbook Reference) |

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Vue d’ensemble

Gelsemine is a CNS stimulant derived from the roots and rhizome of Gelsemium sempervirens.

Spécifications

Synonymes

s9294 | GELSEMINE [MI] | NSC 21729 | Spiro(3,5,8-ethanylylidene-1H-pyrano(3,4-c)pyridine-10,3'-(3H)indol)-2'(1'H)-one, 5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methyl-, (3R,3'S,4aR,5S,8S,8aS,9S)- | Gelsemin | 4-27-00-07526 (Beilstein Handbook Reference) |

Spécifications et pureté

analytical standard

Conditions de stockage de stockage

Store at -20°C

Expédié en

Ice chest + Ice pads

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Grade

Analytical standard

Noms et identifiants

Pubchem Sid

528776114

Sourires canoniques

CN1CC2(C3CC4C5(C2C1C3CO4)C6=CC=CC=C6NC5=O)C=C

IUPAC Name

(1'R,2'S,3S,5'S,6'S,8'R,11'S)-2'-ethenyl-4'-methylspiro[1H-indole-3,7'-9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane]-2-one

InChIKey

NFYYATWFXNPTRM-QJICHLCESA-N

INCHI

1S/C20H22N2O2/c1-3-19-10-22(2)16-11-9-24-15(8-13(11)19)20(17(16)19)12-6-4-5-7-14(12)21-18(20)23/h3-7,11,13,15-17H,1,8-10H2,2H3,(H,21,23)/t11-,13+,15+,16+,17-,19-,20-/m0/s1

Isomères SMILES

CN1C[C@]2([C@@H]3C[C@@H]4[C@]5([C@H]2[C@H]1[C@H]3CO4)C6=CC=CC=C6NC5=O)C=C

Poids moléculaire

322.4

Reaxy-Rn

102312

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=102312&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Classe Gelsemium alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Classe: Gelsemium alkaloids
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Gelsemium alkaloids
• Alternative Parents: Indolines Isoindolines Aralkylamines Oxepanes Benzenoids Piperidines Oxanes N-alkylpyrrolidines Amino acids and derivatives Trialkylamines Secondary carboxylic acid amides Lactams Dialkyl ethers Oxacyclic compounds Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Gelsemium skeleton - Indole or derivatives - Dihydroindole - Isoindoline - Isoindole or derivatives - Aralkylamine - Oxepane - Benzenoid - N-alkylpyrrolidine - Piperidine - Oxane - Pyrrolidine - Carboxamide group - Amino acid or derivatives - Lactam - Tertiary aliphatic amine - Tertiary amine - Secondary carboxylic acid amide - Oxacycle - Azacycle - Carboxylic acid derivative - Dialkyl ether - Ether - Organoheterocyclic compound - Amine - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Carbonyl group - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as gelsemium alkaloids. These are alkaloids with a structure that is based on the tetracyclic gelsemium skeleton. These alkaloids contain an oxindole function and a cage-like, hydroaromatic residue which is believed to arise from an intermediate related to anhydrovobasinediol by formation of a 6,20 bond and rearrangement to an oxindole. The major alkaloids in this group are related to Gelsemine; however, a smaller group, characterized by Gelsedine, lack the 6,20 bond, and have also lost C-21.
• External Descriptors: Indole alkaloids

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

Cibles associées (humaines)

GLRA1 Tclin Glycine receptor subunit alpha-1 (1 Activities)

Discover Target: GLRA1

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

A-431 (6446 Activities)

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KB (17409 Activities)

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GLRA1 Tclin Glycine receptor (alpha-1/beta) (119 Activities)

Discover Target: GLRA1

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

GLRA3 Tchem Glycine receptor alpha-3/beta (286 Activities)

Discover Target: GLRA3

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

GLRA2 Tchem Glycine receptor subunit alpha-2/beta (1 Activities)

Discover Target: GLRA2

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

Cibles associées (non humaines)

Glra1 Glycine receptor subunit alpha-1 (65 Activities)

Discover Target: Glra1

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

P388 (20296 Activities)

Explore this target

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Mécanismes d'action

Propriétés chimiques et physiques

• Point de fusion (°C): 180-181° C
• Poids moléculaire: 322.400 g/mol
• XLogP3: 1.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 322.168 Da
• Monoisotopic Mass: 322.168 Da
• Topological Polar Surface Area: 41.600 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 635.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 7
• 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