[(2R)-4-[(3aR,7R,8aR)-7-hydroxy-7-methyl-3-methylidene-2-oxo-3a,4,8,8a-tetrahydrocyclohepta[b]furan-6-yl]butan-2-yl] acetate

Details

• Internal ID: 70fa1728-b85c-40c1-a629-5007845929d9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: [(2R)-4-[(3aR,7R,8aR)-7-hydroxy-7-methyl-3-methylidene-2-oxo-3a,4,8,8a-tetrahydrocyclohepta[b]furan-6-yl]butan-2-yl] acetate
• SMILES (Canonical): CC(CCC1=CCC2C(CC1(C)O)OC(=O)C2=C)OC(=O)C
• SMILES (Isomeric): C[C@H](CCC1=CC[C@H]2[C@@H](C[C@@]1(C)O)OC(=O)C2=C)OC(=O)C
• InChI: InChI=1S/C17H24O5/c1-10(21-12(3)18)5-6-13-7-8-14-11(2)16(19)22-15(14)9-17(13,4)20/h7,10,14-15,20H,2,5-6,8-9H2,1,3-4H3/t10-,14-,15-,17-/m1/s1
• InChI Key: BRNRZUWILJEQSZ-GWBBYGMBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.40 g/mol
• Exact Mass: 308.16237386 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.29
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9813	98.13%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6341	63.41%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8904	89.04%
OATP1B3 inhibitior	+	0.8390	83.90%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7271	72.71%
BSEP inhibitior	-	0.7992	79.92%
P-glycoprotein inhibitior	-	0.7857	78.57%
P-glycoprotein substrate	-	0.6807	68.07%
CYP3A4 substrate	+	0.6525	65.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8958	89.58%
CYP3A4 inhibition	+	0.5407	54.07%
CYP2C9 inhibition	-	0.5854	58.54%
CYP2C19 inhibition	-	0.6456	64.56%
CYP2D6 inhibition	-	0.9546	95.46%
CYP1A2 inhibition	+	0.6178	61.78%
CYP2C8 inhibition	-	0.7343	73.43%
CYP inhibitory promiscuity	-	0.9260	92.60%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6380	63.80%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.8240	82.40%
Skin irritation	+	0.5626	56.26%
Skin corrosion	-	0.9153	91.53%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3659	36.59%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.8140	81.40%
skin sensitisation	-	0.8271	82.71%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.7002	70.02%
Acute Oral Toxicity (c)	II	0.4730	47.30%
Estrogen receptor binding	+	0.6724	67.24%
Androgen receptor binding	+	0.5201	52.01%
Thyroid receptor binding	+	0.6112	61.12%
Glucocorticoid receptor binding	+	0.7046	70.46%
Aromatase binding	+	0.5579	55.79%
PPAR gamma	-	0.6556	65.56%
Honey bee toxicity	-	0.7851	78.51%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.9918	99.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.80%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.74%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.58%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.65%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.40%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.87%	98.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.74%	93.56%
CHEMBL255	P29275	Adenosine A2b receptor	85.07%	98.59%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.83%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.19%	95.56%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.12%	95.71%

Plants that contains it

• Geigeria burkei

Cross-Links

• PubChem: 162901420
• LOTUS: LTS0225765
• wikiData: Q104944933