(1R,3R,4R,4aS,5'S,8R,8aR)-5'-(furan-3-yl)-1-hydroxy-8,8a-bis(hydroxymethyl)-3-methylspiro[1,2,3,4a,7,8-hexahydronaphthalene-4,3'-oxolane]-2'-one

Details

• Internal ID: 8ba9f402-866e-4f5f-a0c6-17cad6793de1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1R,3R,4R,4aS,5'S,8R,8aR)-5'-(furan-3-yl)-1-hydroxy-8,8a-bis(hydroxymethyl)-3-methylspiro[1,2,3,4a,7,8-hexahydronaphthalene-4,3'-oxolane]-2'-one
• InChI: InChI=1S/C20H26O6/c1-12-7-17(23)20(11-22)14(9-21)3-2-4-16(20)19(12)8-15(26-18(19)24)13-5-6-25-10-13/h2,4-6,10,12,14-17,21-23H,3,7-9,11H2,1H3/t12-,14+,15+,16-,17-,19-,20+/m1/s1
• InChI Key: XQOCZQJNHOAGKY-XPBRLJOJSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.17293854 g/mol
• Topological Polar Surface Area (TPSA): 100.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9706	97.06%
Caco-2	-	0.7715	77.15%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6985	69.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8226	82.26%
OATP1B3 inhibitior	+	0.9566	95.66%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7087	70.87%
P-glycoprotein inhibitior	-	0.8633	86.33%
P-glycoprotein substrate	-	0.5721	57.21%
CYP3A4 substrate	+	0.6317	63.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7821	78.21%
CYP3A4 inhibition	-	0.9284	92.84%
CYP2C9 inhibition	-	0.8887	88.87%
CYP2C19 inhibition	-	0.8376	83.76%
CYP2D6 inhibition	-	0.9307	93.07%
CYP1A2 inhibition	-	0.9222	92.22%
CYP2C8 inhibition	-	0.6441	64.41%
CYP inhibitory promiscuity	-	0.8202	82.02%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5216	52.16%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9844	98.44%
Skin irritation	-	0.7315	73.15%
Skin corrosion	-	0.9511	95.11%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7286	72.86%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.7254	72.54%
skin sensitisation	-	0.8840	88.40%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5690	56.90%
Acute Oral Toxicity (c)	III	0.3992	39.92%
Estrogen receptor binding	+	0.7923	79.23%
Androgen receptor binding	+	0.5680	56.80%
Thyroid receptor binding	-	0.5354	53.54%
Glucocorticoid receptor binding	+	0.7261	72.61%
Aromatase binding	+	0.6572	65.72%
PPAR gamma	-	0.6378	63.78%
Honey bee toxicity	-	0.7732	77.32%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9860	98.60%

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	96.88%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.31%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.05%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.08%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.14%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	87.94%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.31%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.54%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.48%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.14%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.86%	94.00%
CHEMBL4208	P20618	Proteasome component C5	82.21%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.18%	95.56%

Plants that contains it

• Teucrium polium

Cross-Links

• PubChem: 54598289
• LOTUS: LTS0248462
• wikiData: Q105339922