(3aR,7R,8aR)-7-hydroxy-7-methyl-3-methylidene-6-(3-oxobutyl)-3a,4,8,8a-tetrahydrocyclohepta[b]furan-2-one

Details

• Internal ID: 2111b1e1-b1f4-45c2-a8a0-5d289eaef96c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: (3aR,7R,8aR)-7-hydroxy-7-methyl-3-methylidene-6-(3-oxobutyl)-3a,4,8,8a-tetrahydrocyclohepta[b]furan-2-one
• SMILES (Canonical): CC(=O)CCC1=CCC2C(CC1(C)O)OC(=O)C2=C
• SMILES (Isomeric): CC(=O)CCC1=CC[C@H]2[C@@H](C[C@@]1(C)O)OC(=O)C2=C
• InChI: InChI=1S/C15H20O4/c1-9(16)4-5-11-6-7-12-10(2)14(17)19-13(12)8-15(11,3)18/h6,12-13,18H,2,4-5,7-8H2,1,3H3/t12-,13-,15-/m1/s1
• InChI Key: JQUVVIZBCRFHAO-UMVBOHGHSA-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): 63.60 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.92
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9798	97.98%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6591	65.91%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.8911	89.11%
OATP1B3 inhibitior	+	0.9093	90.93%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6592	65.92%
BSEP inhibitior	-	0.8082	80.82%
P-glycoprotein inhibitior	-	0.8887	88.87%
P-glycoprotein substrate	-	0.7863	78.63%
CYP3A4 substrate	+	0.5838	58.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8879	88.79%
CYP3A4 inhibition	-	0.6535	65.35%
CYP2C9 inhibition	-	0.8130	81.30%
CYP2C19 inhibition	-	0.8125	81.25%
CYP2D6 inhibition	-	0.9549	95.49%
CYP1A2 inhibition	-	0.5473	54.73%
CYP2C8 inhibition	-	0.7250	72.50%
CYP inhibitory promiscuity	-	0.9603	96.03%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6117	61.17%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.6333	63.33%
Skin irritation	+	0.5685	56.85%
Skin corrosion	-	0.8826	88.26%
Ames mutagenesis	-	0.5970	59.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4283	42.83%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.8505	85.05%
skin sensitisation	-	0.7931	79.31%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.6200	62.00%
Acute Oral Toxicity (c)	II	0.4494	44.94%
Estrogen receptor binding	-	0.5068	50.68%
Androgen receptor binding	-	0.5537	55.37%
Thyroid receptor binding	-	0.6009	60.09%
Glucocorticoid receptor binding	+	0.6384	63.84%
Aromatase binding	-	0.6458	64.58%
PPAR gamma	-	0.7712	77.12%
Honey bee toxicity	-	0.8591	85.91%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9910	99.10%

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	98.10%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.68%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.02%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.59%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.54%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.41%	99.23%
CHEMBL255	P29275	Adenosine A2b receptor	83.66%	98.59%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.65%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.13%	95.56%
CHEMBL2581	P07339	Cathepsin D	81.25%	98.95%

Plants that contains it

• Geigeria plumosa

Cross-Links

• PubChem: 14414318
• LOTUS: LTS0197721
• wikiData: Q105133699