[(1S,2S,3S,6E,10E,12R)-10-methyl-15-methylidene-5,14-dioxo-4,13-dioxatricyclo[10.3.0.03,6]pentadeca-6,10-dien-2-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: a00b4e50-a69e-4020-9d07-6dfd027cc573
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(1S,2S,3S,6E,10E,12R)-10-methyl-15-methylidene-5,14-dioxo-4,13-dioxatricyclo[10.3.0.03,6]pentadeca-6,10-dien-2-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2C(C=C(CCC=C3C1OC3=O)C)OC(=O)C2=C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@@H]2[C@@H](/C=C(/CC/C=C/3\[C@@H]1OC3=O)\C)OC(=O)C2=C
• InChI: InChI=1S/C20H22O6/c1-5-11(3)18(21)26-17-15-12(4)19(22)24-14(15)9-10(2)7-6-8-13-16(17)25-20(13)23/h5,8-9,14-17H,4,6-7H2,1-3H3/b10-9+,11-5-,13-8+/t14-,15+,16+,17+/m1/s1
• InChI Key: DGLVBWJFGXCXCG-PLPWPUAHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.40 g/mol
• Exact Mass: 358.14163842 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.55
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9849	98.49%
Caco-2	+	0.7252	72.52%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5815	58.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8912	89.12%
OATP1B3 inhibitior	+	0.8660	86.60%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6717	67.17%
P-glycoprotein inhibitior	+	0.6484	64.84%
P-glycoprotein substrate	-	0.8185	81.85%
CYP3A4 substrate	+	0.6143	61.43%
CYP2C9 substrate	-	0.6159	61.59%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	-	0.6988	69.88%
CYP2C9 inhibition	-	0.8182	81.82%
CYP2C19 inhibition	-	0.7608	76.08%
CYP2D6 inhibition	-	0.8919	89.19%
CYP1A2 inhibition	+	0.6047	60.47%
CYP2C8 inhibition	-	0.7274	72.74%
CYP inhibitory promiscuity	-	0.8666	86.66%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Danger	0.4064	40.64%
Eye corrosion	-	0.9415	94.15%
Eye irritation	-	0.8565	85.65%
Skin irritation	-	0.6218	62.18%
Skin corrosion	-	0.9024	90.24%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4124	41.24%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.5925	59.25%
skin sensitisation	-	0.7446	74.46%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6008	60.08%
Acute Oral Toxicity (c)	III	0.4556	45.56%
Estrogen receptor binding	+	0.6360	63.60%
Androgen receptor binding	-	0.5131	51.31%
Thyroid receptor binding	-	0.5471	54.71%
Glucocorticoid receptor binding	+	0.5956	59.56%
Aromatase binding	-	0.6230	62.30%
PPAR gamma	+	0.5958	59.58%
Honey bee toxicity	-	0.6641	66.41%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9802	98.02%

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	95.97%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.48%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.35%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.85%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.47%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	88.05%	83.82%
CHEMBL3401	O75469	Pregnane X receptor	85.30%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.01%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.78%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.22%	99.17%

Plants that contains it

• Grazielia intermedia

Cross-Links

• PubChem: 162997908
• LOTUS: LTS0207406
• wikiData: Q104978873