(24S)-3beta-[2-O-(alpha-L-Arabinopyranosyl)-3-O-acetyl-alpha-L-arabinopyranosyloxy]-6alpha-(beta-D-glucopyranosyloxy)cycloartane-16beta,24,25-triol

Details

• Internal ID: 91a8fcc5-1ced-4e09-b695-c54ac1524c74
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(2S,3R,4S,5S)-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-14-hydroxy-7,7,12,16-tetramethyl-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-5-hydroxy-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-4-yl] acetate
• SMILES (Canonical): CC(CCC(C(C)(C)O)O)C1C(CC2(C1(CCC34C2CC(C5C3(C4)CCC(C5(C)C)OC6C(C(C(CO6)O)OC(=O)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)O)[C@H]1[C@H](C[C@@]2([C@@]1(CC[C@]34[C@H]2C[C@@H]([C@@H]5[C@]3(C4)CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)OC(=O)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/C48H80O19/c1-21(9-10-29(54)44(5,6)60)31-23(51)16-46(8)28-15-26(64-41-36(59)34(57)33(56)27(17-49)65-41)39-43(3,4)30(11-12-48(39)20-47(28,48)14-13-45(31,46)7)66-42-38(37(63-22(2)50)25(53)19-62-42)67-40-35(58)32(55)24(52)18-61-40/h21,23-42,49,51-60H,9-20H2,1-8H3/t21-,23+,24+,25+,26+,27-,28+,29+,30+,31+,32+,33-,34+,35-,36-,37+,38-,39+,40+,41-,42+,45-,46+,47+,48-/m1/s1
• InChI Key: PBHICKWSHXWPEQ-WAITYCARSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₀O₁₉
• Molecular Weight: 961.10 g/mol
• Exact Mass: 960.52938032 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.40
• H-Bond Acceptor: 19
• 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	+	0.6078	60.78%
Caco-2	-	0.8878	88.78%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6939	69.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8085	80.85%
OATP1B3 inhibitior	+	0.8998	89.98%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.7713	77.13%
P-glycoprotein inhibitior	+	0.7540	75.40%
P-glycoprotein substrate	+	0.6195	61.95%
CYP3A4 substrate	+	0.7425	74.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8804	88.04%
CYP3A4 inhibition	-	0.9251	92.51%
CYP2C9 inhibition	-	0.7950	79.50%
CYP2C19 inhibition	-	0.8502	85.02%
CYP2D6 inhibition	-	0.9519	95.19%
CYP1A2 inhibition	-	0.8924	89.24%
CYP2C8 inhibition	+	0.6876	68.76%
CYP inhibitory promiscuity	-	0.9717	97.17%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6989	69.89%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9063	90.63%
Skin irritation	-	0.6948	69.48%
Skin corrosion	-	0.9469	94.69%
Ames mutagenesis	-	0.5948	59.48%
Human Ether-a-go-go-Related Gene inhibition	+	0.7500	75.00%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6940	69.40%
skin sensitisation	-	0.9134	91.34%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.8244	82.44%
Acute Oral Toxicity (c)	I	0.5431	54.31%
Estrogen receptor binding	+	0.7803	78.03%
Androgen receptor binding	+	0.7392	73.92%
Thyroid receptor binding	-	0.5647	56.47%
Glucocorticoid receptor binding	+	0.6825	68.25%
Aromatase binding	+	0.6469	64.69%
PPAR gamma	+	0.7816	78.16%
Honey bee toxicity	-	0.5842	58.42%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8557	85.57%

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	99.52%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.77%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.56%	96.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	95.97%	91.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.71%	94.45%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	95.49%	95.58%
CHEMBL2581	P07339	Cathepsin D	94.59%	98.95%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	92.91%	92.88%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	92.66%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.23%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.27%	96.77%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	90.25%	82.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.07%	85.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.34%	96.61%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.12%	97.14%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.72%	98.75%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.55%	100.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	88.41%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	88.06%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.85%	89.00%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	87.80%	99.00%
CHEMBL226	P30542	Adenosine A1 receptor	87.75%	95.93%
CHEMBL284	P27487	Dipeptidyl peptidase IV	87.66%	95.69%
CHEMBL237	P41145	Kappa opioid receptor	87.59%	98.10%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	87.56%	95.71%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.14%	94.62%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	87.03%	97.29%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.29%	95.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.55%	91.07%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.27%	97.21%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.05%	100.00%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	84.80%	99.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.60%	94.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.16%	89.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.57%	96.95%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	83.52%	92.86%
CHEMBL1937	Q92769	Histone deacetylase 2	83.18%	94.75%
CHEMBL2996	Q05655	Protein kinase C delta	82.46%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.16%	95.89%
CHEMBL4105786	P41182	B-cell lymphoma 6 protein	82.15%	92.86%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	81.97%	92.78%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.95%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.89%	86.33%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.47%	90.24%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.46%	91.03%
CHEMBL2514	O95665	Neurotensin receptor 2	81.40%	100.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.32%	94.08%
CHEMBL259	P32245	Melanocortin receptor 4	81.26%	95.38%
CHEMBL5255	O00206	Toll-like receptor 4	81.19%	92.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.92%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.82%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.04%	92.62%
CHEMBL4581	P52732	Kinesin-like protein 1	80.03%	93.18%

Plants that contains it

• Astragalus icmadophilus

Cross-Links

• PubChem: 101514267
• LOTUS: LTS0048827
• wikiData: Q105205189