(3S,4S,4aS,5'R,7S,8S,8aS)-5'-(furan-3-yl)-7,8-dihydroxy-3,8,8a-trimethylspiro[1,3,4a,5,6,7-hexahydronaphthalene-4,3'-oxolane]-2,2'-dione

Details

• Internal ID: fe9a8fee-1d93-492e-b0e3-c174b3893686
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (3S,4S,4aS,5'R,7S,8S,8aS)-5'-(furan-3-yl)-7,8-dihydroxy-3,8,8a-trimethylspiro[1,3,4a,5,6,7-hexahydronaphthalene-4,3'-oxolane]-2,2'-dione
• InChI: InChI=1S/C20H26O6/c1-11-13(21)8-18(2)15(4-5-16(22)19(18,3)24)20(11)9-14(26-17(20)23)12-6-7-25-10-12/h6-7,10-11,14-16,22,24H,4-5,8-9H2,1-3H3/t11-,14-,15+,16+,18+,19-,20-/m1/s1
• InChI Key: GWCNXMJAAJOWLR-LHCIFCQBSA-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): 97.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9572	95.72%
Caco-2	+	0.4890	48.90%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7806	78.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8048	80.48%
OATP1B3 inhibitior	-	0.2361	23.61%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8858	88.58%
BSEP inhibitior	-	0.5369	53.69%
P-glycoprotein inhibitior	-	0.8313	83.13%
P-glycoprotein substrate	-	0.6410	64.10%
CYP3A4 substrate	+	0.6647	66.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8224	82.24%
CYP3A4 inhibition	-	0.6038	60.38%
CYP2C9 inhibition	-	0.9009	90.09%
CYP2C19 inhibition	-	0.8752	87.52%
CYP2D6 inhibition	-	0.9671	96.71%
CYP1A2 inhibition	-	0.8417	84.17%
CYP2C8 inhibition	-	0.6574	65.74%
CYP inhibitory promiscuity	-	0.9833	98.33%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4557	45.57%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9722	97.22%
Skin irritation	-	0.5297	52.97%
Skin corrosion	-	0.8772	87.72%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6729	67.29%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.9040	90.40%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.5541	55.41%
Acute Oral Toxicity (c)	I	0.4511	45.11%
Estrogen receptor binding	+	0.8452	84.52%
Androgen receptor binding	+	0.6433	64.33%
Thyroid receptor binding	+	0.5683	56.83%
Glucocorticoid receptor binding	+	0.8174	81.74%
Aromatase binding	+	0.7118	71.18%
PPAR gamma	-	0.6857	68.57%
Honey bee toxicity	-	0.8985	89.85%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9900	99.00%

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	94.43%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.65%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.53%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	88.95%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.82%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.41%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.33%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.33%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.92%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.86%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.52%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.56%	96.77%

Plants that contains it

• Nardophyllum lanatum

Cross-Links

• PubChem: 14605598
• LOTUS: LTS0245627
• wikiData: Q105022192