5-[1-(Acetyloxy)-3-methoxy-3-oxopropyl]-2-[(furan-3-yl)({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid

Details

• Internal ID: e40e5fb9-b572-47f5-a49b-6cd8a4265d05
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: 8-(1-acetyloxy-3-methoxy-3-oxopropyl)-3-[furan-3-yl-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-7-(2-hydroxypropan-2-yl)-3,4a,8-trimethyl-5-oxospiro[2,6,7,8a-tetrahydro-1H-naphthalene-4,3'-oxirane]-2'-carboxylic acid
• InChI: InChI=1S/C35H50O16/c1-16(37)48-22(13-23(39)46-7)33(5)19-8-10-32(4,35(28(51-35)29(43)44)34(19,6)21(38)12-20(33)31(2,3)45)27(17-9-11-47-15-17)50-30-26(42)25(41)24(40)18(14-36)49-30/h9,11,15,18-20,22,24-28,30,36,40-42,45H,8,10,12-14H2,1-7H3,(H,43,44)
• InChI Key: UWQVYSUHQUNHFN-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₀O₁₆
• Molecular Weight: 726.80 g/mol
• Exact Mass: 726.30988550 g/mol
• Topological Polar Surface Area (TPSA): 252.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 0.64
• H-Bond Acceptor: 15
• H-Bond Donor: 6
• Rotatable Bonds: 11

Synonyms

• CHEBI:185333
• 5-[1-(Acetyloxy)-3-methoxy-3-oxopropyl]-2-[(furan-3-yl)({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid
• 8-(1-acetyloxy-3-methoxy-3-oxopropyl)-3-[uran-3-yl-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-7-(2-hydroxypropan-2-yl)-3,4a,8-trimethyl-5-oxospiro[2,6,7,8a-tetrahydro-1H-naphthalene-4,3'-oxirane]-2'-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6620	66.20%
Caco-2	-	0.8648	86.48%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7664	76.64%
OATP2B1 inhibitior	-	0.8645	86.45%
OATP1B1 inhibitior	+	0.7902	79.02%
OATP1B3 inhibitior	+	0.9198	91.98%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.5547	55.47%
P-glycoprotein inhibitior	+	0.7384	73.84%
P-glycoprotein substrate	+	0.7053	70.53%
CYP3A4 substrate	+	0.7232	72.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8698	86.98%
CYP3A4 inhibition	-	0.5733	57.33%
CYP2C9 inhibition	-	0.7521	75.21%
CYP2C19 inhibition	-	0.8455	84.55%
CYP2D6 inhibition	-	0.9328	93.28%
CYP1A2 inhibition	-	0.8457	84.57%
CYP2C8 inhibition	+	0.6956	69.56%
CYP inhibitory promiscuity	-	0.9161	91.61%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6302	63.02%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9052	90.52%
Skin irritation	-	0.7400	74.00%
Skin corrosion	-	0.9316	93.16%
Ames mutagenesis	-	0.6707	67.07%
Human Ether-a-go-go-Related Gene inhibition	+	0.7316	73.16%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8968	89.68%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6057	60.57%
Acute Oral Toxicity (c)	I	0.3973	39.73%
Estrogen receptor binding	+	0.7722	77.22%
Androgen receptor binding	+	0.7798	77.98%
Thyroid receptor binding	-	0.4901	49.01%
Glucocorticoid receptor binding	+	0.7379	73.79%
Aromatase binding	+	0.6790	67.90%
PPAR gamma	+	0.7630	76.30%
Honey bee toxicity	-	0.7059	70.59%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9013	90.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.46%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.32%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.40%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.97%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.44%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.95%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	89.33%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.16%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.00%	95.89%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	87.63%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.92%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.85%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.46%	97.25%
CHEMBL5028	O14672	ADAM10	85.96%	97.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.66%	93.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	85.52%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.13%	95.83%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.07%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.92%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.81%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.01%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.57%	93.04%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.87%	92.62%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.48%	94.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.31%	96.90%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 85262693
• LOTUS: LTS0008495
• wikiData: Q105280507