[3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl] 10-hydroxy-5,9-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate

Details

• Internal ID: 23c1f2b0-4eb8-4a45-9458-5a353df9e7ce
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides > Steviol glycosides
• IUPAC Name: [3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 10-hydroxy-5,9-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• SMILES (Canonical): CC1(CCCC2(C1CCC34C2(CCC(C3)C(=C)C4=O)O)C)C(=O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): CC1(CCCC2(C1CCC34C2(CCC(C3)C(=C)C4=O)O)C)C(=O)OC5C(C(C(C(O5)CO)O)O)O
• InChI: InChI=1S/C26H38O9/c1-13-14-5-10-26(33)24(3)8-4-7-23(2,16(24)6-9-25(26,11-14)20(13)31)22(32)35-21-19(30)18(29)17(28)15(12-27)34-21/h14-19,21,27-30,33H,1,4-12H2,2-3H3
• InChI Key: PKAGWWDWHSCPAS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₈O₉
• Molecular Weight: 494.60 g/mol
• Exact Mass: 494.25158279 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.59
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9R,10R,13R)-10-hydroxy-5,9-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0^{1,10.0^{4,9]hexadecane-5-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7851	78.51%
Caco-2	-	0.7750	77.50%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7603	76.03%
OATP2B1 inhibitior	-	0.7157	71.57%
OATP1B1 inhibitior	+	0.8311	83.11%
OATP1B3 inhibitior	+	0.9427	94.27%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6975	69.75%
BSEP inhibitior	-	0.7831	78.31%
P-glycoprotein inhibitior	-	0.5887	58.87%
P-glycoprotein substrate	-	0.7095	70.95%
CYP3A4 substrate	+	0.7025	70.25%
CYP2C9 substrate	-	0.8049	80.49%
CYP2D6 substrate	-	0.8626	86.26%
CYP3A4 inhibition	-	0.7856	78.56%
CYP2C9 inhibition	-	0.8060	80.60%
CYP2C19 inhibition	-	0.8707	87.07%
CYP2D6 inhibition	-	0.9386	93.86%
CYP1A2 inhibition	-	0.8353	83.53%
CYP2C8 inhibition	-	0.6720	67.20%
CYP inhibitory promiscuity	-	0.9434	94.34%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7556	75.56%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9414	94.14%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9377	93.77%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3795	37.95%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6539	65.39%
skin sensitisation	-	0.9109	91.09%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.5733	57.33%
Acute Oral Toxicity (c)	III	0.3955	39.55%
Estrogen receptor binding	+	0.7374	73.74%
Androgen receptor binding	+	0.7184	71.84%
Thyroid receptor binding	+	0.5276	52.76%
Glucocorticoid receptor binding	+	0.7019	70.19%
Aromatase binding	+	0.6831	68.31%
PPAR gamma	+	0.5516	55.16%
Honey bee toxicity	-	0.8351	83.51%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.9835	98.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.60%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.58%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.81%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.45%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.08%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.90%	85.14%
CHEMBL5255	O00206	Toll-like receptor 4	89.35%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.25%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.24%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.11%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.76%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.23%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.17%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	83.91%	95.93%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.05%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.20%	86.33%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.56%	93.04%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.53%	91.24%
CHEMBL259	P32245	Melanocortin receptor 4	80.40%	95.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.24%	92.62%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.00%	97.33%

Plants that contains it

• Pteris semipinnata

Cross-Links

• PubChem: 124222349
• LOTUS: LTS0261699
• wikiData: Q105210267