(4aR)-3,4,4abeta,5,6,7,8,8a-Octahydro-8abeta-vinyl-5beta-hydroxy-7beta-[(2-hydroxymethyl-1-oxo-2-propenyl)oxy]-alpha,4-bis(methylene)-3-oxo-1H-2-benzopyran-6alpha-acetic acid methyl ester

Details

• Internal ID: f641e445-316b-4da4-9dfc-babf844fc75c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-1,4a,5,6,7,8-hexahydroisochromen-7-yl] 2-(hydroxymethyl)prop-2-enoate
• SMILES (Canonical): COC(=O)C(=C)C1C(CC2(COC(=O)C(=C)C2C1O)C=C)OC(=O)C(=C)CO
• SMILES (Isomeric): COC(=O)C(=C)C1C(CC2(COC(=O)C(=C)C2C1O)C=C)OC(=O)C(=C)CO
• InChI: InChI=1S/C20H24O8/c1-6-20-7-13(28-17(23)10(2)8-21)14(11(3)18(24)26-5)16(22)15(20)12(4)19(25)27-9-20/h6,13-16,21-22H,1-4,7-9H2,5H3
• InChI Key: FZALQGCQQJLGKE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₈
• Molecular Weight: 392.40 g/mol
• Exact Mass: 392.14711772 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.46
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 65388-17-2
• [(4aR,5R,6S,7S,8aR)-8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-1,4a,5,6,7,8-hexahydroisochromen-7-yl] 2-(hydroxymethyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8088	80.88%
Caco-2	-	0.7841	78.41%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7461	74.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9027	90.27%
OATP1B3 inhibitior	+	0.9537	95.37%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8060	80.60%
P-glycoprotein inhibitior	-	0.6414	64.14%
P-glycoprotein substrate	+	0.5117	51.17%
CYP3A4 substrate	+	0.6688	66.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8315	83.15%
CYP3A4 inhibition	-	0.7506	75.06%
CYP2C9 inhibition	-	0.8075	80.75%
CYP2C19 inhibition	-	0.6844	68.44%
CYP2D6 inhibition	-	0.9162	91.62%
CYP1A2 inhibition	-	0.8158	81.58%
CYP2C8 inhibition	-	0.6128	61.28%
CYP inhibitory promiscuity	-	0.6481	64.81%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9413	94.13%
Carcinogenicity (trinary)	Non-required	0.6013	60.13%
Eye corrosion	-	0.9748	97.48%
Eye irritation	-	0.8804	88.04%
Skin irritation	-	0.7406	74.06%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5729	57.29%
Micronuclear	-	0.5241	52.41%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.7677	76.77%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.7675	76.75%
Acute Oral Toxicity (c)	III	0.5190	51.90%
Estrogen receptor binding	+	0.6979	69.79%
Androgen receptor binding	+	0.5867	58.67%
Thyroid receptor binding	+	0.5622	56.22%
Glucocorticoid receptor binding	+	0.7044	70.44%
Aromatase binding	-	0.5159	51.59%
PPAR gamma	+	0.5733	57.33%
Honey bee toxicity	-	0.6896	68.96%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.7082	70.82%

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	99.42%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.37%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.30%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	92.69%	95.93%
CHEMBL340	P08684	Cytochrome P450 3A4	90.13%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.44%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.12%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.11%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.28%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.72%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.56%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.51%	97.14%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.80%	89.67%
CHEMBL4530	P00488	Coagulation factor XIII	82.84%	96.00%
CHEMBL5028	O14672	ADAM10	82.24%	97.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.99%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.58%	100.00%

Plants that contains it

• Baccharoides anthelmintica
• Baccharoides lasiopus
• Distephanus angulifolius
• Gymnanthemum amygdalinum

Cross-Links

• PubChem: 3493164
• NPASS: NPC184853
• LOTUS: LTS0140018
• wikiData: Q105004840