Encelin

Details

• Internal ID: 38e30f48-0ef2-4266-b58e-4b9542a801a4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,4aR,8aS,9aR)-8a-methyl-3,5-dimethylidene-4,4a,9,9a-tetrahydro-3aH-benzo[f][1]benzofuran-2,6-dione
• SMILES (Canonical): CC12CC3C(CC1C(=C)C(=O)C=C2)C(=C)C(=O)O3
• SMILES (Isomeric): C[C@@]12C[C@@H]3[C@H](C[C@H]1C(=C)C(=O)C=C2)C(=C)C(=O)O3
• InChI: InChI=1S/C15H16O3/c1-8-10-6-11-9(2)12(16)4-5-15(11,3)7-13(10)18-14(8)17/h4-5,10-11,13H,1-2,6-7H2,3H3/t10-,11+,13-,15-/m1/s1
• InChI Key: LXMUZMFQJGRVFW-NDPMZMCLSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₃
• Molecular Weight: 244.28 g/mol
• Exact Mass: 244.109944368 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.20
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Farinosin, dehydro-
• 15569-50-3
• CHEBI:4790
• CHEMBL512400
• NSC 311053
• (3aR,4aR,8aS,9aR)-8a-methyl-3,5-dimethylene-4,4a,9,9a-tetrahydro-3aH-benzo[f]benzofuran-2,6-dione
• AC1Q6AZN
• SCHEMBL6420856
• BDBM50269625
• (3aR,4aR,8aS,9aR)-8a-methyl-3,5-dimethylidene-4,4a,9,9a-tetrahydro-3aH-benzo[f][1]benzofuran-2,6-dione
• C09404
• Q27106481
• 8.beta-Hydroxy-3-oxo-eudesma-1,4(14),11(13)-trien-12-oic acid, .gamma.-lactone
• Eudesma-1,4(14),11(13)-trien-12-oic acid, 8.beta.-hydroxy-3-oxo-, .gamma.-lactone
• Eudesma-1,4(14),11(13)-trien-12-oic acid, 8beta-hydroxy-3-oxo-, gamma-lactone
• Naphtho(2,3-b)furan-2,6(3H,4H)-dione, 3a,4a,5,8a,9,9a-hexahydro-8a-methyl-3,5-bis(methylene)-, (3aR-(3aalpha,4aalpha,8abeta,9aalpha))-
• Naphtho[2,3-b]furan-2,6(3H,4H)-dione, 3a,4a,5,8a,9,9a-hexahydro-8a-methyl-3,5-bis(methylene)-, (3aR,4aR,8aS,9aR)-
• Naphtho[2,3-b]furan-2,6(3H,4H)-dione, 3a,4a,5,8a,9,9a-hexahydro-8a-methyl-3,5-bis(methylene)-, [3aR-(3a.alpha.,4a.alpha.,8a.beta.,9a.alpha.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.4919	49.19%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6211	62.11%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.9107	91.07%
OATP1B3 inhibitior	+	0.9357	93.57%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9457	94.57%
P-glycoprotein inhibitior	-	0.8661	86.61%
P-glycoprotein substrate	-	0.8547	85.47%
CYP3A4 substrate	+	0.5798	57.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8953	89.53%
CYP3A4 inhibition	-	0.6868	68.68%
CYP2C9 inhibition	-	0.9018	90.18%
CYP2C19 inhibition	-	0.6436	64.36%
CYP2D6 inhibition	-	0.9443	94.43%
CYP1A2 inhibition	-	0.5269	52.69%
CYP2C8 inhibition	-	0.8290	82.90%
CYP inhibitory promiscuity	-	0.7111	71.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4486	44.86%
Eye corrosion	-	0.9588	95.88%
Eye irritation	-	0.8463	84.63%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8459	84.59%
Ames mutagenesis	-	0.7224	72.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.4391	43.91%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.8711	87.11%
skin sensitisation	+	0.5438	54.38%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6775	67.75%
Acute Oral Toxicity (c)	III	0.6726	67.26%
Estrogen receptor binding	+	0.6979	69.79%
Androgen receptor binding	+	0.6041	60.41%
Thyroid receptor binding	-	0.7477	74.77%
Glucocorticoid receptor binding	-	0.5851	58.51%
Aromatase binding	-	0.7562	75.62%
PPAR gamma	-	0.5381	53.81%
Honey bee toxicity	-	0.7945	79.45%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9968	99.68%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL230	P35354	Cyclooxygenase-2	400 nM	IC50	PMID: 16038536

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.65%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.42%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.34%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.11%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.21%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.82%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.70%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.77%	100.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.71%	96.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.13%	97.25%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.51%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.18%	89.00%

Plants that contains it

• Achillea tuzsonii
• Asplenium septentrionale
• Brachylaena ramiflora
• Coespeletia moritziana
• Colliguaja salicifolia
• Encelia asperifolia
• Ferreyranthus fruticosus
• Kielmeyera albopunctata
• Montanoa speciosa
• Myroxylon balsamum
• Nuxia oppositifolia
• Orbivestus leopoldii
• Saussurea parviflora

Cross-Links

• PubChem: 72540
• NPASS: NPC73995
• ChEMBL: CHEMBL512400
• LOTUS: LTS0228461
• wikiData: Q27106481