(2R,3R,4S,5S,6R)-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2R,5S)-5-hydroxy-6-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-7,7,12,16-tetramethyl-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-9-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 6ca273a7-062b-442b-b42a-8c124f19fb46
• 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,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2R,5S)-5-hydroxy-6-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-7,7,12,16-tetramethyl-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-9-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(CCC(C(C)(C)OC1C(C(C(C(O1)CO)O)O)O)O)C2C(CC3(C2(CCC45C3CC(C6C4(C5)CCC(C6(C)C)OC7C(C(C(CO7)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C)O
• SMILES (Isomeric): C[C@H](CC[C@@H](C(C)(C)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)[C@H]2[C@H](C[C@@]3([C@@]2(CC[C@]45[C@H]3C[C@@H]([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)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)O
• InChI: InChI=1S/C47H80O19/c1-20(8-9-27(52)43(4,5)66-41-37(60)34(57)32(55)25(17-49)64-41)29-21(50)15-45(7)26-14-23(62-40-36(59)33(56)31(54)24(16-48)63-40)38-42(2,3)28(65-39-35(58)30(53)22(51)18-61-39)10-11-47(38)19-46(26,47)13-12-44(29,45)6/h20-41,48-60H,8-19H2,1-7H3/t20-,21+,22-,23+,24-,25-,26+,27+,28+,29+,30+,31-,32-,33+,34+,35-,36-,37-,38+,39+,40-,41+,44-,45+,46+,47-/m1/s1
• InChI Key: POTCIIJZZPWCOM-XANYYYLLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₈₀O₁₉
• Molecular Weight: 949.10 g/mol
• Exact Mass: 948.52938032 g/mol
• Topological Polar Surface Area (TPSA): 318.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -1.61
• H-Bond Acceptor: 19
• H-Bond Donor: 13
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4805	48.05%
Caco-2	-	0.8841	88.41%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5846	58.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8328	83.28%
OATP1B3 inhibitior	+	0.9122	91.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.6498	64.98%
P-glycoprotein inhibitior	+	0.7513	75.13%
P-glycoprotein substrate	+	0.5648	56.48%
CYP3A4 substrate	+	0.7275	72.75%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8164	81.64%
CYP3A4 inhibition	-	0.9472	94.72%
CYP2C9 inhibition	-	0.7996	79.96%
CYP2C19 inhibition	-	0.8391	83.91%
CYP2D6 inhibition	-	0.9505	95.05%
CYP1A2 inhibition	-	0.8918	89.18%
CYP2C8 inhibition	+	0.6595	65.95%
CYP inhibitory promiscuity	-	0.9671	96.71%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6868	68.68%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9037	90.37%
Skin irritation	-	0.7152	71.52%
Skin corrosion	-	0.9483	94.83%
Ames mutagenesis	-	0.6248	62.48%
Human Ether-a-go-go-Related Gene inhibition	+	0.7609	76.09%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6872	68.72%
skin sensitisation	-	0.9113	91.13%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8925	89.25%
Acute Oral Toxicity (c)	I	0.6066	60.66%
Estrogen receptor binding	+	0.7540	75.40%
Androgen receptor binding	+	0.7551	75.51%
Thyroid receptor binding	-	0.5520	55.20%
Glucocorticoid receptor binding	+	0.6485	64.85%
Aromatase binding	+	0.6524	65.24%
PPAR gamma	+	0.7582	75.82%
Honey bee toxicity	-	0.6124	61.24%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.8024	80.24%

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	99.44%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.87%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.62%	97.09%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	96.33%	95.58%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.93%	96.09%
CHEMBL220	P22303	Acetylcholinesterase	94.49%	94.45%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	94.11%	92.88%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.59%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.29%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.27%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	91.22%	95.93%
CHEMBL2996	Q05655	Protein kinase C delta	90.39%	97.79%
CHEMBL284	P27487	Dipeptidyl peptidase IV	89.73%	95.69%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.08%	91.24%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.85%	96.47%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	88.58%	99.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	88.56%	82.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.32%	96.21%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.30%	97.14%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	88.26%	100.00%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	87.08%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.59%	95.89%
CHEMBL2094135	Q96BI3	Gamma-secretase	86.11%	98.05%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.07%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.02%	91.07%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	86.00%	92.86%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	85.64%	92.50%
CHEMBL259	P32245	Melanocortin receptor 4	85.62%	95.38%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	85.50%	90.24%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.44%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.24%	89.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.13%	85.14%
CHEMBL1937	Q92769	Histone deacetylase 2	84.99%	94.75%
CHEMBL237	P41145	Kappa opioid receptor	84.90%	98.10%
CHEMBL4302	P08183	P-glycoprotein 1	84.71%	92.98%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.37%	100.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.67%	91.03%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.54%	96.77%
CHEMBL4581	P52732	Kinesin-like protein 1	83.52%	93.18%
CHEMBL4105786	P41182	B-cell lymphoma 6 protein	83.41%	92.86%
CHEMBL3589	P55263	Adenosine kinase	83.05%	98.05%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.30%	94.62%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.00%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.93%	92.94%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.86%	97.29%
CHEMBL206	P03372	Estrogen receptor alpha	81.85%	97.64%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.56%	95.71%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.49%	97.50%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	81.47%	92.78%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.14%	89.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.43%	95.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.39%	95.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.14%	86.33%

Plants that contains it

• Astragalus aureus
• Astragalus dissectus

Cross-Links

• PubChem: 101794561
• LOTUS: LTS0092402
• wikiData: Q105212644