(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(1S,3R,6S,8R,11S,12S,14S,15R,16S)-14-hydroxy-16-(hydroxymethyl)-15-[(2R,5S)-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]oxan-2-yl]methoxy]oxane-3,4,5-triol

Details

• Internal ID: f1a17d0b-d012-4516-96fa-9167afbb9b77
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(1S,3R,6S,8R,11S,12S,14S,15R,16S)-14-hydroxy-16-(hydroxymethyl)-15-[(2R,5S)-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]oxan-2-yl]methoxy]oxane-3,4,5-triol
• SMILES (Canonical): CC1(C2CCC3C4(CC(C(C4(CCC35C2(C5)CCC1OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)O)CO)C8(CCC(O8)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[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O)CO)C)O
• InChI: InChI=1S/C42H70O15/c1-36(2)23-7-8-24-38(5)15-20(45)33(39(6)11-9-26(57-39)37(3,4)52)42(38,19-44)14-13-41(24)18-40(23,41)12-10-25(36)56-35-32(51)30(49)28(47)22(55-35)17-53-34-31(50)29(48)27(46)21(16-43)54-34/h20-35,43-52H,7-19H2,1-6H3/t20-,21+,22+,23-,24-,25-,26-,27+,28+,29-,30-,31+,32+,33+,34+,35-,38-,39+,40+,41-,42-/m0/s1
• InChI Key: CPPPESTUUSAHJH-MYRJBNPQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₇₀O₁₅
• Molecular Weight: 815.00 g/mol
• Exact Mass: 814.47147152 g/mol
• Topological Polar Surface Area (TPSA): 248.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.09
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 9

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	-	0.8818	88.18%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6782	67.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8416	84.16%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.7058	70.58%
P-glycoprotein inhibitior	+	0.7370	73.70%
P-glycoprotein substrate	-	0.5659	56.59%
CYP3A4 substrate	+	0.7241	72.41%
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	+	0.7054	70.54%
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	-	0.9086	90.86%
Skin irritation	-	0.7237	72.37%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.7454	74.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7773	77.73%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6463	64.63%
skin sensitisation	-	0.9098	90.98%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7984	79.84%
Acute Oral Toxicity (c)	I	0.6658	66.58%
Estrogen receptor binding	+	0.7081	70.81%
Androgen receptor binding	+	0.7536	75.36%
Thyroid receptor binding	-	0.5983	59.83%
Glucocorticoid receptor binding	+	0.5915	59.15%
Aromatase binding	+	0.6448	64.48%
PPAR gamma	+	0.7215	72.15%
Honey bee toxicity	-	0.6881	68.81%
Biodegradation	-	0.8000	80.00%
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	98.85%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.45%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	98.30%	96.61%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	95.91%	83.57%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	94.14%	96.21%
CHEMBL226	P30542	Adenosine A1 receptor	93.62%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.43%	97.09%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	93.15%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.00%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.94%	96.95%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	90.19%	97.47%
CHEMBL2996	Q05655	Protein kinase C delta	89.59%	97.79%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.11%	95.50%
CHEMBL259	P32245	Melanocortin receptor 4	88.65%	95.38%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.81%	96.77%
CHEMBL1977	P11473	Vitamin D receptor	87.06%	99.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.12%	95.89%
CHEMBL220	P22303	Acetylcholinesterase	86.00%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.98%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.92%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.38%	94.45%
CHEMBL1871	P10275	Androgen Receptor	84.93%	96.43%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.57%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.48%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.41%	100.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.34%	92.88%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.62%	92.86%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.40%	97.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.55%	93.04%

Plants that contains it

• Beesia calthifolia

Cross-Links

• PubChem: 162969066
• LOTUS: LTS0185053
• wikiData: Q104967692