(2R,3R,4R,5S,6R)-2-[[(1S,4S,5S,9S,10R,13R,14R)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyl-5-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]methoxy]-6-(hydroxymethyl)-5-methoxyoxane-3,4-diol

Details

• Internal ID: 334a82bf-43bc-4178-bf78-8bfb8e5325a9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (2R,3R,4R,5S,6R)-2-[[(1S,4S,5S,9S,10R,13R,14R)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyl-5-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]methoxy]-6-(hydroxymethyl)-5-methoxyoxane-3,4-diol
• SMILES (Canonical): CC1(CCCC2(C1CCC34C2CCC(C3)C(C4)(CO)O)C)COC5C(C(C(C(O5)CO)OC)O)O
• SMILES (Isomeric): C[C@@]1(CCC[C@@]2([C@@H]1CC[C@]34[C@H]2CC[C@H](C3)[C@](C4)(CO)O)C)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)OC)O)O
• InChI: InChI=1S/C27H46O8/c1-24(15-34-23-21(31)20(30)22(33-3)17(12-28)35-23)8-4-9-25(2)18(24)7-10-26-11-16(5-6-19(25)26)27(32,13-26)14-29/h16-23,28-32H,4-15H2,1-3H3/t16-,17-,18-,19+,20-,21-,22-,23-,24-,25-,26+,27+/m1/s1
• InChI Key: VKJDYXCAVKUJHY-ZZXKXZKJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₆O₈
• Molecular Weight: 498.60 g/mol
• Exact Mass: 498.31926842 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.59
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6750	67.50%
Caco-2	-	0.7891	78.91%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5697	56.97%
OATP2B1 inhibitior	-	0.5780	57.80%
OATP1B1 inhibitior	+	0.8897	88.97%
OATP1B3 inhibitior	+	0.9142	91.42%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.7865	78.65%
P-glycoprotein inhibitior	-	0.5642	56.42%
P-glycoprotein substrate	-	0.6775	67.75%
CYP3A4 substrate	+	0.6987	69.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8385	83.85%
CYP3A4 inhibition	-	0.9156	91.56%
CYP2C9 inhibition	-	0.8543	85.43%
CYP2C19 inhibition	-	0.7905	79.05%
CYP2D6 inhibition	-	0.9640	96.40%
CYP1A2 inhibition	-	0.8211	82.11%
CYP2C8 inhibition	+	0.4930	49.30%
CYP inhibitory promiscuity	-	0.9736	97.36%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7082	70.82%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9338	93.38%
Skin irritation	-	0.7046	70.46%
Skin corrosion	-	0.9542	95.42%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7713	77.13%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.9283	92.83%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8268	82.68%
Acute Oral Toxicity (c)	I	0.4363	43.63%
Estrogen receptor binding	+	0.6388	63.88%
Androgen receptor binding	+	0.6463	64.63%
Thyroid receptor binding	-	0.5067	50.67%
Glucocorticoid receptor binding	+	0.6170	61.70%
Aromatase binding	+	0.6338	63.38%
PPAR gamma	-	0.5336	53.36%
Honey bee toxicity	-	0.7580	75.80%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.6716	67.16%

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	97.64%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.27%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.06%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.57%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.88%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	92.20%	95.93%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	91.29%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.61%	92.62%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	88.81%	100.00%
CHEMBL237	P41145	Kappa opioid receptor	88.23%	98.10%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.48%	96.21%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.67%	95.83%
CHEMBL5255	O00206	Toll-like receptor 4	85.09%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.19%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.66%	100.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.60%	89.05%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.55%	96.77%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	83.32%	92.86%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.03%	96.61%
CHEMBL259	P32245	Melanocortin receptor 4	83.03%	95.38%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.98%	92.94%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.53%	97.14%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.50%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	80.52%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.29%	86.33%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.13%	96.38%

Plants that contains it

• Microlepia marginata

Cross-Links

• PubChem: 101647903
• LOTUS: LTS0060032
• wikiData: Q104252381