Gelsemine

Details

• Internal ID: 9a11b4d3-5cd0-42d9-b97c-d3bc3c0e8ef6
• Taxonomy: Alkaloids and derivatives > Gelsemium alkaloids
• 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
• SMILES (Canonical): CN1CC2(C3CC4C5(C2C1C3CO4)C6=CC=CC=C6NC5=O)C=C
• SMILES (Isomeric): 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
• InChI: 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
• InChI Key: NFYYATWFXNPTRM-QJICHLCESA-N
• Popularity: 213 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂N₂O₂
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.168127949 g/mol
• Topological Polar Surface Area (TPSA): 41.60 Ų
• XlogP: 1.80

Synonyms

• 509-15-9
• Gelsemin
• 5Y13A78Z72
• NSC-21729
• UNII-5Y13A78Z72
• HSDB 3488
• gelsemine free base
• (+)-Gelsemine
• EINECS 208-095-2
• NSC 21729
• BRN 5406576
• GELSEMIN [HSDB]
• GELSEMINE [MI]
• GELSEMINE [WHO-DD]
• GELSEMINE, (+)-
• (3R-(3alpha,4abeta,5alpha,8alpha,8abeta,9S*,10S*))-5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methylspiro(3,5,8-ethanylylidene-1H-pyrano(3,4-c)pyridine-10,3'-(3H)indol)-2'(1',H)-one
• 4-27-00-07526 (Beilstein Handbook Reference)
• CHEMBL521561
• BDBM50459893
• MFCD00082347
• s9294
• CCG-267730
• AC-34231
• 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)-
• 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-(3alpha,4abeta,5alpha,8alpha,8abeta,9S*,10S*))-
• (3R-(3.ALPHA.,4A.BETA.,5.ALPHA.,8.ALPHA.,8A.BETA.,9S*,10S*))-5-ETHENYL-3,4,4A,5,6,7,8,8A-OCTAHYDRO-7-METHYLSPIRO(3,5,8-ETHANYLYLIDENE-1H-PYRANO(3,4-C)PYRIDINE-10,3'-(3H)INDOL)-2'(1'H)-ONE
• 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.ALPHA.,4A.BETA.,5.ALPHA.,8.ALPHA.,8.ABETA.,9S*,10S*))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	590 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.19%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	94.43%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.45%	96.09%
CHEMBL4208	P20618	Proteasome component C5	91.20%	90.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.96%	97.25%
CHEMBL2581	P07339	Cathepsin D	86.39%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.32%	91.11%
CHEMBL4530	P00488	Coagulation factor XIII	83.71%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.34%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.13%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.65%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.08%	97.09%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.84%	85.11%

Plants that contains it

• Gelsemium elegans

Cross-Links

• PubChem: 5390854
• LOTUS: LTS0038537
• wikiData: Q105178759