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

Details

• Internal ID: c15f1295-b74e-47ec-bc78-da5385a2d023
• 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-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2R,5R)-5-hydroxy-6-methyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-7,7,12,16-tetramethyl-14-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-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]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)OC9C(C(C(C(O9)CO)O)O)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[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O
• InChI: InChI=1S/C53H90O24/c1-21(8-9-29(58)49(4,5)77-47-42(69)38(65)35(62)27(18-56)75-47)31-24(72-46-41(68)37(64)34(61)26(17-55)74-46)15-51(7)28-14-23(71-45-40(67)36(63)33(60)25(16-54)73-45)43-48(2,3)30(76-44-39(66)32(59)22(57)19-70-44)10-11-53(43)20-52(28,53)13-12-50(31,51)6/h21-47,54-69H,8-20H2,1-7H3/t21-,22-,23+,24+,25-,26-,27-,28+,29-,30+,31+,32+,33-,34-,35-,36+,37+,38+,39-,40-,41-,42-,43+,44+,45-,46-,47+,50-,51+,52+,53-/m1/s1
• InChI Key: AFYCRSVRZJCGCA-KPYBXWLUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₉₀O₂₄
• Molecular Weight: 1111.30 g/mol
• Exact Mass: 1110.58220373 g/mol
• Topological Polar Surface Area (TPSA): 398.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -3.79
• H-Bond Acceptor: 24
• H-Bond Donor: 16
• Rotatable Bonds: 16

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	-	0.8810	88.10%
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	+	0.8353	83.53%
OATP1B3 inhibitior	+	0.9122	91.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.5992	59.92%
P-glycoprotein inhibitior	+	0.7502	75.02%
P-glycoprotein substrate	+	0.5860	58.60%
CYP3A4 substrate	+	0.7293	72.93%
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	+	0.6659	66.59%
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	-	0.9015	90.15%
Skin irritation	-	0.7152	71.52%
Skin corrosion	-	0.9483	94.83%
Ames mutagenesis	-	0.6378	63.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7520	75.20%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6747	67.47%
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	-	0.9027	90.27%
Acute Oral Toxicity (c)	I	0.6066	60.66%
Estrogen receptor binding	+	0.7504	75.04%
Androgen receptor binding	+	0.7573	75.73%
Thyroid receptor binding	-	0.5263	52.63%
Glucocorticoid receptor binding	+	0.6735	67.35%
Aromatase binding	+	0.6446	64.46%
PPAR gamma	+	0.7630	76.30%
Honey bee toxicity	-	0.6044	60.44%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
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	98.92%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.72%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.75%	97.09%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	95.83%	95.58%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.62%	96.09%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	92.90%	92.88%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.54%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	92.43%	97.79%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.27%	96.21%
CHEMBL2581	P07339	Cathepsin D	91.18%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.43%	96.61%
CHEMBL206	P03372	Estrogen receptor alpha	89.95%	97.64%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	89.61%	92.50%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.98%	89.62%
CHEMBL4302	P08183	P-glycoprotein 1	88.86%	92.98%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.98%	96.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.68%	95.89%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	87.38%	82.50%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	87.21%	99.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.19%	97.14%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	87.10%	100.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	86.60%	97.29%
CHEMBL226	P30542	Adenosine A1 receptor	86.59%	95.93%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.34%	100.00%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	86.26%	99.17%
CHEMBL259	P32245	Melanocortin receptor 4	86.25%	95.38%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	85.86%	92.86%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	85.85%	92.78%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.77%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.98%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.79%	85.14%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	84.62%	90.24%
CHEMBL4105786	P41182	B-cell lymphoma 6 protein	84.23%	92.86%
CHEMBL1937	Q92769	Histone deacetylase 2	83.87%	94.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.86%	96.77%
CHEMBL240	Q12809	HERG	83.46%	89.76%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.23%	92.62%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.76%	98.75%
CHEMBL2094135	Q96BI3	Gamma-secretase	82.47%	98.05%
CHEMBL4581	P52732	Kinesin-like protein 1	82.40%	93.18%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.38%	89.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.37%	91.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.26%	95.83%
CHEMBL284	P27487	Dipeptidyl peptidase IV	82.08%	95.69%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.77%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.71%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.43%	91.07%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.30%	94.62%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	81.20%	95.00%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.14%	97.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.99%	95.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.88%	95.17%

Plants that contains it

• Astragalus pterocephalus

Cross-Links

• PubChem: 162942913
• LOTUS: LTS0258754
• wikiData: Q104911627