[(3aR,6R,7S,7aR)-6-ethenyl-7-(3-hydroxyprop-1-en-2-yl)-6-methyl-3-methylidene-2-oxo-4,5,7,7a-tetrahydro-3aH-1-benzofuran-4-yl] 2-(hydroxymethyl)prop-2-enoate

Details

• Internal ID: c267c0cd-c2a8-4b73-980f-db4901c394fd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(3aR,6R,7S,7aR)-6-ethenyl-7-(3-hydroxyprop-1-en-2-yl)-6-methyl-3-methylidene-2-oxo-4,5,7,7a-tetrahydro-3aH-1-benzofuran-4-yl] 2-(hydroxymethyl)prop-2-enoate
• SMILES (Canonical): CC1(CC(C2C(C1C(=C)CO)OC(=O)C2=C)OC(=O)C(=C)CO)C=C
• SMILES (Isomeric): C[C@@]1(CC([C@@H]2[C@@H]([C@@H]1C(=C)CO)OC(=O)C2=C)OC(=O)C(=C)CO)C=C
• InChI: InChI=1S/C19H24O6/c1-6-19(5)7-13(24-17(22)11(3)9-21)14-12(4)18(23)25-16(14)15(19)10(2)8-20/h6,13-16,20-21H,1-4,7-9H2,5H3/t13?,14-,15+,16+,19+/m1/s1
• InChI Key: NUWSDQMCCHNVBZ-BUIIFPGESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.15728848 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.31
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9594	95.94%
Caco-2	-	0.6484	64.84%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6846	68.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9082	90.82%
OATP1B3 inhibitior	+	0.9139	91.39%
MATE1 inhibitior	-	0.8212	82.12%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9080	90.80%
P-glycoprotein inhibitior	-	0.7770	77.70%
P-glycoprotein substrate	-	0.6718	67.18%
CYP3A4 substrate	+	0.6341	63.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8649	86.49%
CYP3A4 inhibition	-	0.8442	84.42%
CYP2C9 inhibition	-	0.8559	85.59%
CYP2C19 inhibition	-	0.8044	80.44%
CYP2D6 inhibition	-	0.9503	95.03%
CYP1A2 inhibition	-	0.7717	77.17%
CYP2C8 inhibition	-	0.7929	79.29%
CYP inhibitory promiscuity	-	0.8061	80.61%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.5373	53.73%
Eye corrosion	-	0.9768	97.68%
Eye irritation	-	0.8412	84.12%
Skin irritation	-	0.6709	67.09%
Skin corrosion	-	0.9284	92.84%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5587	55.87%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.7218	72.18%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.8001	80.01%
Acute Oral Toxicity (c)	III	0.6174	61.74%
Estrogen receptor binding	+	0.6088	60.88%
Androgen receptor binding	+	0.6435	64.35%
Thyroid receptor binding	+	0.5980	59.80%
Glucocorticoid receptor binding	+	0.6466	64.66%
Aromatase binding	+	0.5963	59.63%
PPAR gamma	+	0.5510	55.10%
Honey bee toxicity	-	0.6777	67.77%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9583	95.83%

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	96.79%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.17%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.66%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.93%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.31%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.49%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.61%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.02%	89.00%

Plants that contains it

• Cheirolophus intybaceus

Cross-Links

• PubChem: 162880468
• LOTUS: LTS0179946
• wikiData: Q105186055