[(3aR,4S,5R,6S,7R,7aR)-6-ethenyl-6-methyl-4-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-5-(3-oxoprop-1-en-2-yl)-4,5,7,7a-tetrahydro-3aH-1-benzofuran-7-yl] (2R)-2-methylbutanoate

Details

• Internal ID: 4bdc80fd-f921-43c5-9c5d-b05f4dddfed5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(3aR,4S,5R,6S,7R,7aR)-6-ethenyl-6-methyl-4-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-5-(3-oxoprop-1-en-2-yl)-4,5,7,7a-tetrahydro-3aH-1-benzofuran-7-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2C(C(C(C1(C)C=C)C(=C)C=O)OC(=O)C(=CC)C)C(=C)C(=O)O2
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1[C@H]2[C@@H]([C@H]([C@H]([C@]1(C)C=C)C(=C)C=O)OC(=O)/C(=C\C)/C)C(=C)C(=O)O2
• InChI: InChI=1S/C25H32O7/c1-9-13(4)22(27)30-19-17-16(7)24(29)31-20(17)21(32-23(28)14(5)10-2)25(8,11-3)18(19)15(6)12-26/h9,11-12,14,17-21H,3,6-7,10H2,1-2,4-5,8H3/b13-9-/t14-,17-,18-,19-,20-,21+,25+/m1/s1
• InChI Key: IUPREMZEHGJOAD-PGAPXWEDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₇
• Molecular Weight: 444.50 g/mol
• Exact Mass: 444.21480336 g/mol
• Topological Polar Surface Area (TPSA): 96.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 3.50
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9917	99.17%
Caco-2	-	0.6536	65.36%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4950	49.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7948	79.48%
OATP1B3 inhibitior	+	0.8973	89.73%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7736	77.36%
P-glycoprotein inhibitior	+	0.7795	77.95%
P-glycoprotein substrate	-	0.5828	58.28%
CYP3A4 substrate	+	0.6188	61.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9065	90.65%
CYP3A4 inhibition	+	0.5357	53.57%
CYP2C9 inhibition	-	0.8511	85.11%
CYP2C19 inhibition	-	0.7058	70.58%
CYP2D6 inhibition	-	0.9503	95.03%
CYP1A2 inhibition	-	0.6615	66.15%
CYP2C8 inhibition	-	0.6360	63.60%
CYP inhibitory promiscuity	+	0.5334	53.34%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9043	90.43%
Carcinogenicity (trinary)	Non-required	0.4638	46.38%
Eye corrosion	-	0.9489	94.89%
Eye irritation	-	0.9076	90.76%
Skin irritation	-	0.6394	63.94%
Skin corrosion	-	0.9362	93.62%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3910	39.10%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.6408	64.08%
skin sensitisation	+	0.4908	49.08%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.7758	77.58%
Acute Oral Toxicity (c)	III	0.5093	50.93%
Estrogen receptor binding	+	0.7772	77.72%
Androgen receptor binding	+	0.6589	65.89%
Thyroid receptor binding	+	0.6130	61.30%
Glucocorticoid receptor binding	+	0.6856	68.56%
Aromatase binding	-	0.5162	51.62%
PPAR gamma	+	0.6898	68.98%
Honey bee toxicity	-	0.6173	61.73%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9915	99.15%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.79%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.84%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.77%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.90%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	93.67%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.27%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	89.97%	89.34%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.27%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.33%	95.56%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	85.94%	80.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.11%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.24%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.93%	91.19%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.33%	96.47%
CHEMBL2996	Q05655	Protein kinase C delta	82.19%	97.79%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.13%	99.23%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.74%	89.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.57%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	80.09%	94.73%

Plants that contains it

• Zinnia peruviana

Cross-Links

• PubChem: 163019078
• LOTUS: LTS0058723
• wikiData: Q105120756