[(1R,6S,8R,11S,12S,15S)-3,15-dimethyl-4,13-dioxo-5,14-dioxatetracyclo[6.6.1.02,6.012,15]pentadec-2-en-11-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: c4e36d30-0ac3-4367-8107-08061c212693
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: [(1R,6S,8R,11S,12S,15S)-3,15-dimethyl-4,13-dioxo-5,14-dioxatetracyclo[6.6.1.02,6.012,15]pentadec-2-en-11-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCC2CC3C(=C(C(=O)O3)C)C4C2(C1C(=O)O4)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1CC[C@@H]2C[C@H]3C(=C(C(=O)O3)C)[C@H]4[C@@]2([C@@H]1C(=O)O4)C
• InChI: InChI=1S/C20H24O6/c1-5-9(2)17(21)24-12-7-6-11-8-13-14(10(3)18(22)25-13)16-20(11,4)15(12)19(23)26-16/h5,11-13,15-16H,6-8H2,1-4H3/b9-5-/t11-,12+,13+,15+,16+,20+/m1/s1
• InChI Key: OWACIDNMPZLRTG-LBHLHHGYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.40 g/mol
• Exact Mass: 360.15728848 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.47
• 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	+	0.9935	99.35%
Caco-2	+	0.6730	67.30%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7911	79.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8587	85.87%
OATP1B3 inhibitior	+	0.8911	89.11%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5812	58.12%
P-glycoprotein inhibitior	-	0.4875	48.75%
P-glycoprotein substrate	-	0.5853	58.53%
CYP3A4 substrate	+	0.6762	67.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9122	91.22%
CYP3A4 inhibition	-	0.6027	60.27%
CYP2C9 inhibition	-	0.8740	87.40%
CYP2C19 inhibition	-	0.9135	91.35%
CYP2D6 inhibition	-	0.9502	95.02%
CYP1A2 inhibition	-	0.6029	60.29%
CYP2C8 inhibition	-	0.6800	68.00%
CYP inhibitory promiscuity	-	0.7681	76.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Danger	0.4030	40.30%
Eye corrosion	-	0.9800	98.00%
Eye irritation	-	0.8852	88.52%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.7777	77.77%
Ames mutagenesis	-	0.6364	63.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7929	79.29%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.6158	61.58%
skin sensitisation	-	0.7689	76.89%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.7945	79.45%
Acute Oral Toxicity (c)	III	0.6357	63.57%
Estrogen receptor binding	+	0.9108	91.08%
Androgen receptor binding	+	0.6279	62.79%
Thyroid receptor binding	+	0.5838	58.38%
Glucocorticoid receptor binding	+	0.8326	83.26%
Aromatase binding	-	0.5376	53.76%
PPAR gamma	+	0.6424	64.24%
Honey bee toxicity	-	0.7032	70.32%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9856	98.56%

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	96.98%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.95%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.59%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.13%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	87.41%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.19%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.67%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.66%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.29%	93.03%

Plants that contains it

• Ligularia atroviolacea

Cross-Links

• PubChem: 162951728
• LOTUS: LTS0253920
• wikiData: Q105201813