[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-6-methyl-5-methylene-, (3Z,6R,14aR,14bR)-

Details

• Internal ID: 2ea4787d-de8a-4831-ae18-72774c2079eb
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: 4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
• SMILES (Canonical): CC=C1CC(=C)C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)O
• SMILES (Isomeric): CC=C1CC(=C)C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)O
• InChI: InChI=1S/C18H23NO5/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/h4-5,14-15,22H,2,6-10H2,1,3H3
• InChI Key: FCEVNJIUIMLVML-UHFFFAOYSA-N
• Popularity: 27 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.40 g/mol
• Exact Mass: 333.15762283 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.11
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• CHEBI:181715
• [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-6-methyl-5-methylene-, (3Z,6R,14aR,14bR)-
• FT-0775678
• 12-hydroxy-13,19-didehydrosenecionan-11,16-dione
• (1R,4Z,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17]heptadec-11-ene-3,8-dione
• 4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8984	89.84%
Caco-2	+	0.5596	55.96%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6198	61.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9023	90.23%
OATP1B3 inhibitior	+	0.9370	93.70%
MATE1 inhibitior	-	0.8809	88.09%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.7022	70.22%
P-glycoprotein inhibitior	-	0.8412	84.12%
P-glycoprotein substrate	-	0.6452	64.52%
CYP3A4 substrate	+	0.6200	62.00%
CYP2C9 substrate	-	0.8019	80.19%
CYP2D6 substrate	-	0.7791	77.91%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.8392	83.92%
CYP inhibitory promiscuity	-	0.9849	98.49%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Danger	0.6682	66.82%
Eye corrosion	-	0.9798	97.98%
Eye irritation	-	0.9702	97.02%
Skin irritation	-	0.7252	72.52%
Skin corrosion	-	0.8967	89.67%
Ames mutagenesis	+	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4895	48.95%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	1.0000	100.00%
skin sensitisation	-	0.8172	81.72%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7926	79.26%
Acute Oral Toxicity (c)	II	0.7302	73.02%
Estrogen receptor binding	-	0.7420	74.20%
Androgen receptor binding	+	0.5637	56.37%
Thyroid receptor binding	-	0.6084	60.84%
Glucocorticoid receptor binding	+	0.6935	69.35%
Aromatase binding	-	0.5656	56.56%
PPAR gamma	-	0.6173	61.73%
Honey bee toxicity	-	0.8292	82.92%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8374	83.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.39%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.43%	95.56%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.80%	83.57%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.96%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.76%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.57%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.65%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.72%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.32%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.98%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.13%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.85%	85.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.84%	82.69%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.84%	93.40%
CHEMBL5805	Q9NR97	Toll-like receptor 8	80.61%	96.25%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.34%	82.38%

Plants that contains it

• Caucasalia macrophylla
• Crotalaria juncea
• Jacobaea arnautorum
• Jacobaea erucifolia subsp. argunensis
• Jacobaea persoonii
• Jacobaea subalpina
• Jacobaea vulgaris
• Senecio ampullaceus
• Senecio bollei
• Senecio brasiliensis
• Senecio fremontii var. blitoides
• Senecio laricifolius
• Senecio pterophorus
• Senecio sarracenicus
• Senecio spartioides
• Senecio vernalis
• Senecio vulgaris

Cross-Links

• PubChem: 521227
• LOTUS: LTS0191483
• wikiData: Q104993112