(2R,3R,4S,5S,6R)-2-[[(1S,3R,6S,8R,11S,12S,14S,15R,16S)-14-hydroxy-16-(hydroxymethyl)-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: a8e70e0a-1a6b-4dcc-a19d-c445e19d2605
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(1S,3R,6S,8R,11S,12S,14S,15R,16S)-14-hydroxy-16-(hydroxymethyl)-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(C2CCC3C4(CC(C(C4(CCC35C2(C5)CCC1OC6C(C(C(C(O6)CO)O)O)O)CO)C7(CCC(O7)C(C)(C)O)C)O)C)C
• SMILES (Isomeric): C[C@]1(CC[C@@H](O1)C(C)(C)O)[C@H]2[C@H](C[C@@]3([C@@]2(CC[C@]45[C@H]3CC[C@@H]6[C@]4(C5)CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)CO)C)O
• InChI: InChI=1S/C36H60O10/c1-30(2)21-7-8-22-32(5)15-19(39)28(33(6)11-9-24(46-33)31(3,4)43)36(32,18-38)14-13-35(22)17-34(21,35)12-10-23(30)45-29-27(42)26(41)25(40)20(16-37)44-29/h19-29,37-43H,7-18H2,1-6H3/t19-,20+,21-,22-,23-,24+,25+,26-,27+,28+,29-,32-,33-,34+,35-,36-/m0/s1
• InChI Key: SINCDAOITNCHRQ-CEHVUTQISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₆₀O₁₀
• Molecular Weight: 652.90 g/mol
• Exact Mass: 652.41864811 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.26
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6581	65.81%
Caco-2	-	0.8497	84.97%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6782	67.82%
OATP2B1 inhibitior	-	0.5824	58.24%
OATP1B1 inhibitior	+	0.8415	84.15%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.9495	94.95%
P-glycoprotein inhibitior	+	0.7134	71.34%
P-glycoprotein substrate	-	0.6540	65.40%
CYP3A4 substrate	+	0.7160	71.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8361	83.61%
CYP3A4 inhibition	-	0.8783	87.83%
CYP2C9 inhibition	-	0.8009	80.09%
CYP2C19 inhibition	-	0.8368	83.68%
CYP2D6 inhibition	-	0.9401	94.01%
CYP1A2 inhibition	-	0.8971	89.71%
CYP2C8 inhibition	+	0.6627	66.27%
CYP inhibitory promiscuity	-	0.9329	93.29%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6399	63.99%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9148	91.48%
Skin irritation	-	0.7237	72.37%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.7370	73.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7473	74.73%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6963	69.63%
skin sensitisation	-	0.9098	90.98%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8294	82.94%
Acute Oral Toxicity (c)	I	0.6658	66.58%
Estrogen receptor binding	+	0.5318	53.18%
Androgen receptor binding	+	0.7580	75.80%
Thyroid receptor binding	-	0.5467	54.67%
Glucocorticoid receptor binding	+	0.5737	57.37%
Aromatase binding	+	0.6624	66.24%
PPAR gamma	+	0.6131	61.31%
Honey bee toxicity	-	0.6963	69.63%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8633	86.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.15%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.08%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	97.75%	96.61%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	95.05%	96.21%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	94.46%	83.57%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.62%	96.09%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	92.24%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.22%	97.09%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	89.89%	97.47%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.80%	96.95%
CHEMBL226	P30542	Adenosine A1 receptor	89.59%	95.93%
CHEMBL259	P32245	Melanocortin receptor 4	87.46%	95.38%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.34%	96.77%
CHEMBL2996	Q05655	Protein kinase C delta	87.23%	97.79%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.00%	92.88%
CHEMBL1977	P11473	Vitamin D receptor	86.95%	99.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.59%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.31%	95.50%
CHEMBL220	P22303	Acetylcholinesterase	85.82%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.16%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.62%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.95%	86.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.56%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.41%	100.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	83.32%	92.86%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.24%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.70%	97.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.73%	92.94%
CHEMBL2581	P07339	Cathepsin D	80.04%	98.95%

Plants that contains it

• Beesia calthifolia

Cross-Links

• PubChem: 162951532
• LOTUS: LTS0235352
• wikiData: Q105253866