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

Details

• Internal ID: 82c6094d-0083-48e0-bb5a-f6d032cd5364
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: (3aR,7R,8aR)-7-hydroxy-6-[(3S)-3-hydroxybutyl]-7-methyl-3-methylidene-3a,4,8,8a-tetrahydrocyclohepta[b]furan-2-one
• SMILES (Canonical): CC(CCC1=CCC2C(CC1(C)O)OC(=O)C2=C)O
• SMILES (Isomeric): C[C@@H](CCC1=CC[C@H]2[C@@H](C[C@@]1(C)O)OC(=O)C2=C)O
• InChI: InChI=1S/C15H22O4/c1-9(16)4-5-11-6-7-12-10(2)14(17)19-13(12)8-15(11,3)18/h6,9,12-13,16,18H,2,4-5,7-8H2,1,3H3/t9-,12+,13+,15+/m0/s1
• InChI Key: KXWQQQVNKKCKIP-XRFFLINXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.72
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9800	98.00%
Caco-2	+	0.6635	66.35%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5835	58.35%
OATP2B1 inhibitior	-	0.8546	85.46%
OATP1B1 inhibitior	+	0.8983	89.83%
OATP1B3 inhibitior	+	0.9313	93.13%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7320	73.20%
BSEP inhibitior	-	0.8823	88.23%
P-glycoprotein inhibitior	-	0.9386	93.86%
P-glycoprotein substrate	-	0.7432	74.32%
CYP3A4 substrate	+	0.6008	60.08%
CYP2C9 substrate	-	0.8111	81.11%
CYP2D6 substrate	-	0.8448	84.48%
CYP3A4 inhibition	-	0.6482	64.82%
CYP2C9 inhibition	-	0.8161	81.61%
CYP2C19 inhibition	-	0.7677	76.77%
CYP2D6 inhibition	-	0.9479	94.79%
CYP1A2 inhibition	+	0.5243	52.43%
CYP2C8 inhibition	-	0.8391	83.91%
CYP inhibitory promiscuity	-	0.9235	92.35%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5775	57.75%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.7187	71.87%
Skin irritation	+	0.5489	54.89%
Skin corrosion	-	0.9083	90.83%
Ames mutagenesis	-	0.7724	77.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.5103	51.03%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.8199	81.99%
skin sensitisation	-	0.7771	77.71%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.4718	47.18%
Acute Oral Toxicity (c)	II	0.3596	35.96%
Estrogen receptor binding	-	0.6430	64.30%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5732	57.32%
Glucocorticoid receptor binding	+	0.6614	66.14%
Aromatase binding	-	0.6059	60.59%
PPAR gamma	-	0.6956	69.56%
Honey bee toxicity	-	0.8610	86.10%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9876	98.76%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.09%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.32%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.10%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.57%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.82%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.69%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.71%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.43%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.13%	93.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.93%	93.40%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.59%	96.37%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.73%	97.14%

Plants that contains it

• Geigeria plumosa

Cross-Links

• PubChem: 163195040
• LOTUS: LTS0161853
• wikiData: Q105147566