2-[(1R,3R,6S,7S,8S,11S,12R,15S,16R)-6-[(2R,4S,5S,6S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-7-(hydroxymethyl)-7,12,16-trimethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-3-hydroxy-6-methylhept-5-enoic acid

Details

• Internal ID: 35b1c665-dae5-4979-a0e0-b10d4be17a72
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: 2-[(1R,3R,6S,7S,8S,11S,12R,15S,16R)-6-[(2R,4S,5S,6S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-7-(hydroxymethyl)-7,12,16-trimethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-3-hydroxy-6-methylhept-5-enoic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3CCC45CC46CCC7(C(CCC7(C6CCC5C3(C)CO)C)C(C(CC=C(C)C)O)C(=O)O)C)OC8C(C(C(C(O8)C)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2[C@H]([C@@H]([C@@H](O[C@H]2O[C@H]3CC[C@]45C[C@@]46CC[C@@]7([C@@H](CC[C@@]7([C@@H]6CC[C@@H]5[C@@]3(C)CO)C)C(C(CC=C(C)C)O)C(=O)O)C)CO[C@H]8C([C@@H]([C@H]([C@H](O8)C)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C48H78O18/c1-21(2)8-9-25(50)30(40(59)60)24-12-14-46(7)28-11-10-27-44(5,20-49)29(13-15-47(27)19-48(28,47)17-16-45(24,46)6)65-43-39(66-42-38(58)35(55)32(52)23(4)63-42)36(56)33(53)26(64-43)18-61-41-37(57)34(54)31(51)22(3)62-41/h8,22-39,41-43,49-58H,9-20H2,1-7H3,(H,59,60)/t22-,23+,24+,25?,26+,27-,28+,29+,30?,31+,32+,33-,34-,35-,36+,37?,38-,39?,41-,42+,43+,44-,45-,46-,47-,48-/m1/s1
• InChI Key: NNRUGCURQNHDND-YNDGQEERSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₈O₁₈
• Molecular Weight: 943.10 g/mol
• Exact Mass: 942.51881563 g/mol
• Topological Polar Surface Area (TPSA): 295.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 0.70
• H-Bond Acceptor: 17
• H-Bond Donor: 11
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7841	78.41%
Caco-2	-	0.8860	88.60%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7625	76.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8483	84.83%
OATP1B3 inhibitior	+	0.8420	84.20%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.8338	83.38%
P-glycoprotein inhibitior	+	0.7554	75.54%
P-glycoprotein substrate	+	0.5386	53.86%
CYP3A4 substrate	+	0.7177	71.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8730	87.30%
CYP3A4 inhibition	-	0.9401	94.01%
CYP2C9 inhibition	-	0.7158	71.58%
CYP2C19 inhibition	-	0.8694	86.94%
CYP2D6 inhibition	-	0.9337	93.37%
CYP1A2 inhibition	-	0.8753	87.53%
CYP2C8 inhibition	+	0.6635	66.35%
CYP inhibitory promiscuity	-	0.9421	94.21%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6712	67.12%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9063	90.63%
Skin irritation	-	0.6014	60.14%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	-	0.7008	70.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.7477	74.77%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6808	68.08%
skin sensitisation	-	0.8801	88.01%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8465	84.65%
Acute Oral Toxicity (c)	I	0.5180	51.80%
Estrogen receptor binding	+	0.7998	79.98%
Androgen receptor binding	+	0.7534	75.34%
Thyroid receptor binding	-	0.5456	54.56%
Glucocorticoid receptor binding	+	0.6868	68.68%
Aromatase binding	+	0.6457	64.57%
PPAR gamma	+	0.7760	77.60%
Honey bee toxicity	-	0.6532	65.32%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9481	94.81%

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	98.38%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.60%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.93%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.07%	98.95%
CHEMBL284	P27487	Dipeptidyl peptidase IV	90.67%	95.69%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.14%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.11%	86.33%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.82%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.65%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.41%	89.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	88.15%	97.47%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.45%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.15%	97.09%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	85.03%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.93%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.65%	96.61%
CHEMBL5255	O00206	Toll-like receptor 4	84.01%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.98%	99.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.63%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	82.45%	91.19%
CHEMBL5028	O14672	ADAM10	81.71%	97.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.55%	93.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.41%	91.24%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.16%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.01%	95.71%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.35%	93.04%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.33%	94.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101920420
• LOTUS: LTS0167873
• wikiData: Q105182285