[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4S,5R,8S,9S,10R,13R,14R)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyl-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate

Details

• Internal ID: 1e01daf7-a3c0-4e64-bf73-3ccb2bbd02c7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4S,5R,8S,9S,10R,13R,14R)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyl-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• SMILES (Canonical): CC1(CCC(C2(C1CCC34C2CCC(C3)C(C4)(CO)O)C)OC5C(C(C(C(O5)CO)O)O)O)C(=O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C[C@]1(CC[C@@H]([C@@]2([C@@H]1CC[C@]34[C@H]2CC[C@H](C3)[C@](C4)(CO)O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C32H52O15/c1-29(28(42)47-27-25(41)23(39)21(37)16(11-34)45-27)7-6-19(46-26-24(40)22(38)20(36)15(10-33)44-26)30(2)17(29)5-8-31-9-14(3-4-18(30)31)32(43,12-31)13-35/h14-27,33-41,43H,3-13H2,1-2H3/t14-,15-,16-,17-,18+,19+,20-,21-,22+,23+,24-,25-,26+,27+,29-,30-,31+,32+/m1/s1
• InChI Key: WFMUUUXXUIVMAH-LBAVWMHWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₅₂O₁₅
• Molecular Weight: 676.70 g/mol
• Exact Mass: 676.33062095 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -2.74
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.8755	87.55%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6736	67.36%
OATP2B1 inhibitior	-	0.5851	58.51%
OATP1B1 inhibitior	+	0.8887	88.87%
OATP1B3 inhibitior	+	0.9356	93.56%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7034	70.34%
BSEP inhibitior	-	0.7456	74.56%
P-glycoprotein inhibitior	-	0.4345	43.45%
P-glycoprotein substrate	-	0.7303	73.03%
CYP3A4 substrate	+	0.7075	70.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8574	85.74%
CYP3A4 inhibition	-	0.9487	94.87%
CYP2C9 inhibition	-	0.9128	91.28%
CYP2C19 inhibition	-	0.8622	86.22%
CYP2D6 inhibition	-	0.9553	95.53%
CYP1A2 inhibition	-	0.9028	90.28%
CYP2C8 inhibition	+	0.4718	47.18%
CYP inhibitory promiscuity	-	0.9783	97.83%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7141	71.41%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9235	92.35%
Skin irritation	-	0.6853	68.53%
Skin corrosion	-	0.9499	94.99%
Ames mutagenesis	-	0.6628	66.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.6889	68.89%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.7865	78.65%
skin sensitisation	-	0.9375	93.75%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.7580	75.80%
Acute Oral Toxicity (c)	I	0.5844	58.44%
Estrogen receptor binding	+	0.7191	71.91%
Androgen receptor binding	+	0.6836	68.36%
Thyroid receptor binding	-	0.5735	57.35%
Glucocorticoid receptor binding	+	0.5446	54.46%
Aromatase binding	+	0.6240	62.40%
PPAR gamma	+	0.6307	63.07%
Honey bee toxicity	-	0.7215	72.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.8119	81.19%

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	97.28%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.00%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.24%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.08%	97.09%
CHEMBL2581	P07339	Cathepsin D	92.42%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.10%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.64%	96.21%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	87.96%	100.00%
CHEMBL4302	P08183	P-glycoprotein 1	87.19%	92.98%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	86.90%	92.86%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.51%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.51%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.47%	96.61%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.19%	96.77%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.00%	91.24%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.92%	92.62%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.20%	92.88%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	84.90%	97.86%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.42%	99.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.34%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	83.73%	92.50%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	83.68%	92.78%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.61%	94.33%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	82.53%	92.32%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.26%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.62%	91.19%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.81%	82.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.62%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.53%	95.83%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.50%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.18%	86.92%

Plants that contains it

• Diplospora dubia

Cross-Links

• PubChem: 50993567
• LOTUS: LTS0259810
• wikiData: Q105304071