5'-(furan-3-yl)-1,2,7-trihydroxy-8a-(hydroxymethyl)-3-methyl-8-methylidenespiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-4,3'-oxolane]-2'-one

Details

• Internal ID: 0254a16b-751d-4551-8731-197efbc484b2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 5'-(furan-3-yl)-1,2,7-trihydroxy-8a-(hydroxymethyl)-3-methyl-8-methylidenespiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-4,3'-oxolane]-2'-one
• SMILES (Canonical): CC1C(C(C2(C(C13CC(OC3=O)C4=COC=C4)CCC(C2=C)O)CO)O)O
• SMILES (Isomeric): CC1C(C(C2(C(C13CC(OC3=O)C4=COC=C4)CCC(C2=C)O)CO)O)O
• InChI: InChI=1S/C20H26O7/c1-10-13(22)3-4-15-19(11(2)16(23)17(24)20(10,15)9-21)7-14(27-18(19)25)12-5-6-26-8-12/h5-6,8,11,13-17,21-24H,1,3-4,7,9H2,2H3
• InChI Key: OKOVUKLUFCRNMX-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₇
• Molecular Weight: 378.40 g/mol
• Exact Mass: 378.16785316 g/mol
• Topological Polar Surface Area (TPSA): 120.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.93
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9388	93.88%
Caco-2	-	0.7840	78.40%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7900	79.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7983	79.83%
OATP1B3 inhibitior	+	0.9486	94.86%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9501	95.01%
P-glycoprotein inhibitior	-	0.8658	86.58%
P-glycoprotein substrate	-	0.6253	62.53%
CYP3A4 substrate	+	0.6138	61.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7888	78.88%
CYP3A4 inhibition	-	0.8892	88.92%
CYP2C9 inhibition	-	0.8710	87.10%
CYP2C19 inhibition	-	0.8512	85.12%
CYP2D6 inhibition	-	0.9181	91.81%
CYP1A2 inhibition	-	0.8703	87.03%
CYP2C8 inhibition	-	0.6453	64.53%
CYP inhibitory promiscuity	-	0.8967	89.67%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5294	52.94%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9609	96.09%
Skin irritation	-	0.5810	58.10%
Skin corrosion	-	0.9372	93.72%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6729	67.29%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.8638	86.38%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	I	0.3748	37.48%
Estrogen receptor binding	+	0.7921	79.21%
Androgen receptor binding	+	0.6278	62.78%
Thyroid receptor binding	+	0.5143	51.43%
Glucocorticoid receptor binding	+	0.7472	74.72%
Aromatase binding	+	0.6662	66.62%
PPAR gamma	-	0.5998	59.98%
Honey bee toxicity	-	0.8510	85.10%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9864	98.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	92.56%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.43%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.77%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.13%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.90%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.84%	94.00%
CHEMBL221	P23219	Cyclooxygenase-1	85.15%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.64%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.79%	95.89%
CHEMBL2581	P07339	Cathepsin D	82.29%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.49%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.21%	94.80%

Plants that contains it

• Teucrium polium

Cross-Links

• PubChem: 162864482
• LOTUS: LTS0042969
• wikiData: Q105193670