Cycloaraloside C

Details

• Internal ID: 5c1d9619-d71d-45ca-810d-f6f1104a65e9
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3S,4S,5R,6R)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-9,14-dihydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-2-(hydroxymethyl)oxane-3,4-diol
• SMILES (Canonical): CC1(C(CCC23C1C(CC4C2(C3)CCC5(C4(CC(C5C6(CCC(O6)C(C)(C)O)C)O)C)C)O)OC7C(C(C(C(O7)CO)O)O)OC8C(C(CO8)(CO)O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@]34C[C@@]35CC[C@@H](C([C@@H]5[C@H](C[C@H]4[C@@]1(C[C@@H]([C@@H]2[C@]6(CC[C@H](O6)C(C)(C)O)C)O)C)O)(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O[C@H]8[C@@H]([C@](CO8)(CO)O)O
• InChI: InChI=1S/C41H68O14/c1-34(2)24(53-32-28(27(47)26(46)22(16-42)52-32)54-33-31(48)41(50,18-43)19-51-33)9-11-40-17-39(40)13-12-36(5)30(38(7)10-8-25(55-38)35(3,4)49)21(45)15-37(36,6)23(39)14-20(44)29(34)40/h20-33,42-50H,8-19H2,1-7H3/t20-,21-,22+,23-,24-,25-,26+,27-,28+,29-,30-,31-,32-,33-,36+,37-,38+,39-,40+,41+/m0/s1
• InChI Key: DMAOFWOOOIHKPU-NNGAJOSASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₈O₁₄
• Molecular Weight: 785.00 g/mol
• Exact Mass: 784.46090684 g/mol
• Topological Polar Surface Area (TPSA): 228.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 0.73
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

• C17791

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6581	65.81%
Caco-2	-	0.8755	87.55%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6782	67.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8276	82.76%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8303	83.03%
P-glycoprotein inhibitior	+	0.7504	75.04%
P-glycoprotein substrate	+	0.5491	54.91%
CYP3A4 substrate	+	0.7367	73.67%
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	+	0.6941	69.41%
CYP inhibitory promiscuity	-	0.9329	93.29%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6399	63.99%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9115	91.15%
Skin irritation	-	0.7237	72.37%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7002	70.02%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5874	58.74%
skin sensitisation	-	0.9098	90.98%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8365	83.65%
Acute Oral Toxicity (c)	I	0.6658	66.58%
Estrogen receptor binding	+	0.6490	64.90%
Androgen receptor binding	+	0.7591	75.91%
Thyroid receptor binding	-	0.5859	58.59%
Glucocorticoid receptor binding	+	0.6318	63.18%
Aromatase binding	+	0.6681	66.81%
PPAR gamma	+	0.7041	70.41%
Honey bee toxicity	-	0.6449	64.49%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.99%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	98.25%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.28%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.68%	97.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	94.04%	83.57%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.75%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.88%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.78%	89.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	89.69%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.46%	100.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	89.10%	92.88%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.06%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.79%	96.61%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.30%	96.95%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	87.94%	95.58%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.88%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.56%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.20%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.78%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.50%	97.14%
CHEMBL220	P22303	Acetylcholinesterase	85.12%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.68%	97.36%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.55%	92.86%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.06%	91.03%
CHEMBL1871	P10275	Androgen Receptor	82.05%	96.43%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.04%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.84%	95.71%
CHEMBL2996	Q05655	Protein kinase C delta	81.78%	97.79%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.09%	96.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.81%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.53%	94.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.53%	96.90%

Plants that contains it

• Astragalus amarus
• Astragalus iliensis
• Astragalus villosissimus

Cross-Links

• PubChem: 21626650
• LOTUS: LTS0230282
• wikiData: Q104398903