(2R,3R,4R,5R)-2-[[(1S,3R,6S,8S,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]oxane-3,4,5-triol

Details

• Internal ID: 24c1db63-72ac-4970-8e17-90e92ae1708c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3R,4R,5R)-2-[[(1S,3R,6S,8S,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]oxane-3,4,5-triol
• SMILES (Canonical): CC1(C2CCC3C4(CC(C(C4(CCC35C2(C5)CCC1OC6C(C(C(CO6)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](CO7)O)O)O)CO)C)O
• InChI: InChI=1S/C35H58O9/c1-29(2)21-7-8-22-31(5)15-19(37)27(32(6)11-9-24(44-32)30(3,4)41)35(31,18-36)14-13-34(22)17-33(21,34)12-10-23(29)43-28-26(40)25(39)20(38)16-42-28/h19-28,36-41H,7-18H2,1-6H3/t19-,20+,21+,22-,23-,24+,25+,26+,27+,28+,31-,32-,33+,34-,35-/m0/s1
• InChI Key: KCAKQJIYVPOAJA-TYUXRNLQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₈O₉
• Molecular Weight: 622.80 g/mol
• Exact Mass: 622.40808342 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 5

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	-	0.8373	83.73%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6782	67.82%
OATP2B1 inhibitior	-	0.5791	57.91%
OATP1B1 inhibitior	+	0.8576	85.76%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.9103	91.03%
P-glycoprotein inhibitior	+	0.6991	69.91%
P-glycoprotein substrate	-	0.5388	53.88%
CYP3A4 substrate	+	0.7190	71.90%
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	+	0.6920	69.20%
CYP inhibitory promiscuity	-	0.9329	93.29%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6399	63.99%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9183	91.83%
Skin irritation	-	0.7237	72.37%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.6170	61.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7447	74.47%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6425	64.25%
skin sensitisation	-	0.9098	90.98%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8955	89.55%
Acute Oral Toxicity (c)	I	0.6658	66.58%
Estrogen receptor binding	-	0.4799	47.99%
Androgen receptor binding	+	0.7477	74.77%
Thyroid receptor binding	-	0.5484	54.84%
Glucocorticoid receptor binding	+	0.5793	57.93%
Aromatase binding	+	0.6723	67.23%
PPAR gamma	+	0.5945	59.45%
Honey bee toxicity	-	0.7146	71.46%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
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	98.88%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.65%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	97.11%	96.61%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	95.79%	83.57%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.78%	96.77%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	92.59%	92.88%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	92.52%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.33%	96.09%
CHEMBL204	P00734	Thrombin	92.09%	96.01%
CHEMBL226	P30542	Adenosine A1 receptor	90.66%	95.93%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	90.54%	97.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.10%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.40%	96.95%
CHEMBL259	P32245	Melanocortin receptor 4	86.50%	95.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.01%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.75%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.87%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.09%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.09%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.05%	97.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.83%	92.94%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.44%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.39%	94.45%
CHEMBL1977	P11473	Vitamin D receptor	83.39%	99.43%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.52%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.91%	86.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.29%	95.71%
CHEMBL2581	P07339	Cathepsin D	81.19%	98.95%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	81.02%	94.78%

Plants that contains it

• Beesia calthifolia

Cross-Links

• PubChem: 636999
• NPASS: NPC179487