Naphtho[1,2-b]furan-2,8(3H,4H)-dione, 6-(I(2)-D-glucopyranosyloxy)octahydro-3,5a,9-trimethyl-, [3S-(3I+/-,3aI+/-,5aI(2),6I(2),9I+/-,9aI+/-,9bI(2))]-

Details

• Internal ID: 28cf69de-fcac-438a-8144-4ce230b92a52
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aS,5aR,6R,9S,9aS,9bS)-3,5a,9-trimethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6,7,9,9a,9b-octahydro-3H-benzo[g][1]benzofuran-2,8-dione
• InChI: InChI=1S/C21H32O9/c1-8-10-4-5-21(3)13(6-11(23)9(2)14(21)18(10)30-19(8)27)29-20-17(26)16(25)15(24)12(7-22)28-20/h8-10,12-18,20,22,24-26H,4-7H2,1-3H3/t8-,9+,10-,12+,13+,14+,15+,16-,17+,18-,20-,21-/m0/s1
• InChI Key: ZNBJBJUEJZNPLD-LZGJUQLXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₉
• Molecular Weight: 428.50 g/mol
• Exact Mass: 428.20463259 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.63
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 75911-12-5
• Naphtho[1,2-b]furan-2,8(3H,4H)-dione, 6-(beta-D-glucopyranosyloxy)octahydro-3,5a,9-trimethyl-, [3S-(3alpha,3aalpha,5abeta,6beta,9alpha,9aalpha,9bbeta)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5439	54.39%
Caco-2	-	0.7763	77.63%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8316	83.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8633	86.33%
OATP1B3 inhibitior	+	0.9352	93.52%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.6405	64.05%
P-glycoprotein inhibitior	-	0.7171	71.71%
P-glycoprotein substrate	-	0.8203	82.03%
CYP3A4 substrate	+	0.6747	67.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8866	88.66%
CYP3A4 inhibition	-	0.8852	88.52%
CYP2C9 inhibition	-	0.9073	90.73%
CYP2C19 inhibition	-	0.9226	92.26%
CYP2D6 inhibition	-	0.9651	96.51%
CYP1A2 inhibition	-	0.9050	90.50%
CYP2C8 inhibition	-	0.7839	78.39%
CYP inhibitory promiscuity	-	0.9518	95.18%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6580	65.80%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9714	97.14%
Skin irritation	-	0.6200	62.00%
Skin corrosion	-	0.9381	93.81%
Ames mutagenesis	-	0.7124	71.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5855	58.55%
skin sensitisation	-	0.9512	95.12%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6426	64.26%
Acute Oral Toxicity (c)	I	0.5992	59.92%
Estrogen receptor binding	+	0.7916	79.16%
Androgen receptor binding	+	0.6145	61.45%
Thyroid receptor binding	-	0.5282	52.82%
Glucocorticoid receptor binding	+	0.5494	54.94%
Aromatase binding	+	0.5697	56.97%
PPAR gamma	+	0.5334	53.34%
Honey bee toxicity	-	0.7260	72.60%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5650	56.50%
Fish aquatic toxicity	+	0.9258	92.58%

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	96.76%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	95.33%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.31%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.90%	97.09%
CHEMBL2581	P07339	Cathepsin D	89.73%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.75%	85.14%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.69%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.08%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.28%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.25%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.14%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.66%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.65%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.51%	86.92%
CHEMBL5255	O00206	Toll-like receptor 4	81.63%	92.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.15%	94.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.67%	93.04%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.39%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.08%	96.77%

Plants that contains it

• Taraxacum officinale

Cross-Links

• PubChem: 162985653
• LOTUS: LTS0047585
• wikiData: Q105379923