Senecionine

Details

• Internal ID: af18a431-f6eb-4249-83bc-d55f4f987ddf
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (1R,4Z,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
• SMILES (Canonical): CC=C1CC(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)O)C
• SMILES (Isomeric): C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C
• InChI: InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-/t11-,14-,15-,18-/m1/s1
• InChI Key: HKODIGSRFALUTA-JTLQZVBZSA-N
• Popularity: 440 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.40 g/mol
• Exact Mass: 335.17327290 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 1.10

Synonyms

• Aureine
• Senecionin
• 130-01-8
• 12-Hydroxysenecionan-11,16-dione
• CCRIS 4340
• CHEBI:9107
• HSDB 3535
• Senecionan-11,16-dione, 12-hydroxy-
• UNII-BO6N1U5YG6
• BO6N1U5YG6
• NSC 89935
• BRN 0934445
• AI3-51771
• NSC-89935
• Intergerrimine
• [1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, (3Z,5R,6R,14aR,14bR)-
• C18H25NO5
• DTXSID40871615
• NSC89935
• (1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, (3Z,5R,6R,14aR,14bR)-
• Senecionine, analytical standard
• [1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione,3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-,(3Z,5R,6R,14aR,14bR)-
• SENECIONINE [MI]
• (-)-SENECIONINE
• SCHEMBL896098
• Senecionan-11, 12-hydroxy-
• CHEMBL362153
• DTXCID501474669
• Senecionine, >=95.0% (GC)
• HY-N2560
• BDBM50480301
• MFCD00221720
• AKOS037514834
• CCG-208634
• NCGC00163621-01
• (Z)-ethylidene-hydroxy-dimethyl-[?]dione
• AC-34604
• AS-79841
• LS-144941
• CS-0022892
• Senecionine 100 microg/mL in Methanol:Water
• C06176
• A905119
• J-005736
• Q2083871
• WLN: T55-12-1A Q EN IOVY OVO BUTJ KU2 M NQ N
• WLN: T55-12- 1A Q EN IOVY OVO BUTJ KU2 M1 NQ N1
• (1R,4Z,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
• (5R,6R,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-5,6-dimethyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione

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
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	28183.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.72%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	92.13%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.32%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.06%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.03%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.23%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.62%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.51%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.70%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.31%	95.89%
CHEMBL2581	P07339	Cathepsin D	82.56%	98.95%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	82.22%	82.38%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.74%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.28%	89.00%

Plants that contains it

• Ajuga parviflora
• Castilleja rhexifolia
• Crotalaria juncea
• Crotalaria micans
• Crotalaria naragutensis
• Crotalaria trichotoma
• Emilia sonchifolia
• Erechtites hieraciifolius
• Gynura elliptica
• Gynura japonica
• Gynura procumbens
• Jacobaea alpina subsp. samnitum
• Jacobaea aquatica
• Jacobaea arnautorum
• Jacobaea maritima subsp. maritima
• Jacobaea subalpina
• Jacobaea vulgaris
• Leucanthemum vulgare
• Liatris punctata
• Ligularia japonica
• Lotononis meyeri
• Melampyrum pratense
• Osyris alba
• Packera anonyma
• Packera aurea
• Packera candidissima
• Packera coahuilensis
• Packera glabella
• Packera multilobata
• Packera tomentosa
• Pericallis aurita
• Petasites hybridus
• Pittocaulon praecox
• Senecio albopurpureus
• Senecio brasiliensis
• Senecio flaccidus var. douglasii
• Senecio fremontii var. blitoides
• Senecio gallicus
• Senecio gilliesianus
• Senecio glaucus
• Senecio hualtaranensis
• Senecio hydrophilus
• Senecio ilicifolius
• Senecio inaequidens
• Senecio laricifolius
• Senecio leucanthemifolius
• Senecio magnificus
• Senecio mairetianus
• Senecio miser
• Senecio nemorensis
• Senecio nevadensis subsp. malacitanus
• Senecio ovatus subsp. stabianus
• Senecio patagonicus
• Senecio pleistocephalus
• Senecio pterophorus
• Senecio scandens
• Senecio selloi
• Senecio squalidus
• Senecio subulatus
• Senecio tenuifolius
• Senecio triangularis
• Senecio vernalis
• Senecio viscosus
• Senecio vulgaris
• Syneilesis palmata
• Tussilago farfara
• Werneria nubigena

Cross-Links

• PubChem: 5280906
• NPASS: NPC193471
• ChEMBL: CHEMBL362153
• LOTUS: LTS0172395
• wikiData: Q2083871