(1R,3R,5S,6R,7S,9R)-7-methyl-12-methylidene-5-(2-oxopropyl)-4,10-dioxatricyclo[7.3.0.03,6]dodecan-11-one

Details

• Internal ID: f1bc4f3c-2d52-4542-8463-2b59d81a2241
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: (1R,3R,5S,6R,7S,9R)-7-methyl-12-methylidene-5-(2-oxopropyl)-4,10-dioxatricyclo[7.3.0.03,6]dodecan-11-one
• SMILES (Canonical): CC1CC2C(CC3C1C(O3)CC(=O)C)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@H]1C[C@@H]2[C@H](C[C@@H]3[C@@H]1[C@@H](O3)CC(=O)C)C(=C)C(=O)O2
• InChI: InChI=1S/C15H20O4/c1-7-4-11-10(9(3)15(17)19-11)6-13-14(7)12(18-13)5-8(2)16/h7,10-14H,3-6H2,1-2H3/t7-,10+,11+,12-,13+,14-/m0/s1
• InChI Key: AYISIGODMBIKBM-ZJUCDMOJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.88
• H-Bond Acceptor: 4
• 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	+	0.9804	98.04%
Caco-2	+	0.7270	72.70%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5913	59.13%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8623	86.23%
OATP1B3 inhibitior	+	0.9040	90.40%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8968	89.68%
P-glycoprotein inhibitior	-	0.8257	82.57%
P-glycoprotein substrate	-	0.8373	83.73%
CYP3A4 substrate	+	0.5521	55.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8778	87.78%
CYP3A4 inhibition	-	0.7173	71.73%
CYP2C9 inhibition	-	0.8104	81.04%
CYP2C19 inhibition	-	0.7723	77.23%
CYP2D6 inhibition	-	0.9308	93.08%
CYP1A2 inhibition	-	0.6461	64.61%
CYP2C8 inhibition	-	0.8796	87.96%
CYP inhibitory promiscuity	-	0.8886	88.86%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8543	85.43%
Carcinogenicity (trinary)	Non-required	0.4754	47.54%
Eye corrosion	-	0.9491	94.91%
Eye irritation	+	0.5505	55.05%
Skin irritation	-	0.6221	62.21%
Skin corrosion	-	0.9084	90.84%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5878	58.78%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.7859	78.59%
skin sensitisation	-	0.6914	69.14%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5658	56.58%
Acute Oral Toxicity (c)	III	0.4705	47.05%
Estrogen receptor binding	-	0.5167	51.67%
Androgen receptor binding	-	0.5730	57.30%
Thyroid receptor binding	-	0.5203	52.03%
Glucocorticoid receptor binding	+	0.7774	77.74%
Aromatase binding	-	0.4896	48.96%
PPAR gamma	-	0.6076	60.76%
Honey bee toxicity	-	0.8367	83.67%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9921	99.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.35%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.28%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.84%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.73%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.01%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.94%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.25%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.96%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.51%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.34%	86.33%

Plants that contains it

• Dittrichia graveolens

Cross-Links

• PubChem: 162875180
• LOTUS: LTS0074237
• wikiData: Q104921141