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

Details

• Internal ID: e2809188-205c-4787-81aa-a99235baa8d6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(3aR,4S,6R,7R,7aR)-6-(acetyloxymethyl)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-4,5,7,7a-tetrahydro-3aH-1-benzofuran-4-yl] 2-(hydroxymethyl)prop-2-enoate
• InChI: InChI=1S/C21H24O8/c1-6-21(10-27-14(5)24)7-15(28-19(25)12(3)9-23)16-13(4)20(26)29-18(16)17(21)11(2)8-22/h6,8,15-18,23H,1-4,7,9-10H2,5H3/t15-,16+,17+,18-,21+/m0/s1
• InChI Key: GYESMJFGTLPHOY-NPGRCNIMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₈
• Molecular Weight: 404.40 g/mol
• Exact Mass: 404.14711772 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.05
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9811	98.11%
Caco-2	-	0.7993	79.93%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6715	67.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8773	87.73%
OATP1B3 inhibitior	+	0.9358	93.58%
MATE1 inhibitior	-	0.8612	86.12%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6049	60.49%
P-glycoprotein inhibitior	-	0.4795	47.95%
P-glycoprotein substrate	-	0.5786	57.86%
CYP3A4 substrate	+	0.6455	64.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8897	88.97%
CYP3A4 inhibition	-	0.8814	88.14%
CYP2C9 inhibition	-	0.8845	88.45%
CYP2C19 inhibition	-	0.8064	80.64%
CYP2D6 inhibition	-	0.9488	94.88%
CYP1A2 inhibition	-	0.7378	73.78%
CYP2C8 inhibition	-	0.6024	60.24%
CYP inhibitory promiscuity	-	0.8061	80.61%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5797	57.97%
Eye corrosion	-	0.9600	96.00%
Eye irritation	-	0.8385	83.85%
Skin irritation	-	0.6168	61.68%
Skin corrosion	-	0.8905	89.05%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6666	66.66%
Micronuclear	-	0.6741	67.41%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.6308	63.08%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.8522	85.22%
Acute Oral Toxicity (c)	III	0.5810	58.10%
Estrogen receptor binding	+	0.7253	72.53%
Androgen receptor binding	+	0.6795	67.95%
Thyroid receptor binding	+	0.6157	61.57%
Glucocorticoid receptor binding	+	0.6415	64.15%
Aromatase binding	+	0.5458	54.58%
PPAR gamma	+	0.6516	65.16%
Honey bee toxicity	-	0.6624	66.24%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9158	91.58%

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	97.31%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.67%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.38%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.96%	95.56%
CHEMBL299	P17252	Protein kinase C alpha	86.22%	98.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.76%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.24%	95.50%
CHEMBL5028	O14672	ADAM10	82.28%	97.50%
CHEMBL2996	Q05655	Protein kinase C delta	81.98%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.95%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.83%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.63%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.48%	97.09%

Plants that contains it

• Distephanus angulifolius

Cross-Links

• PubChem: 42646679
• LOTUS: LTS0098848
• wikiData: Q105023657