Cycloaraloside F

Details

• Internal ID: 3935c201-804f-4aa5-9942-8b45036c4974
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[2-[(2S,5R)-5-[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-6-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,14-dihydroxy-7,7,12,16-tetramethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-5-methyloxolan-2-yl]propan-2-yloxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(C(CCC23C1C(CC4C2(C3)CCC5(C4(CC(C5C6(CCC(O6)C(C)(C)OC7C(C(C(C(O7)CO)O)O)O)C)O)C)C)O)OC8C(C(C(C(O8)CO)O)O)OC9C(C(CO9)(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@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)O)C)O)(C)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O[C@H]9[C@@H]([C@](CO9)(CO)O)O
• InChI: InChI=1S/C47H78O19/c1-40(2)26(63-38-33(31(56)29(54)24(17-49)62-38)64-39-36(58)47(59,19-50)20-60-39)9-11-46-18-45(46)13-12-42(5)35(22(52)15-43(42,6)25(45)14-21(51)34(40)46)44(7)10-8-27(65-44)41(3,4)66-37-32(57)30(55)28(53)23(16-48)61-37/h21-39,48-59H,8-20H2,1-7H3/t21-,22-,23+,24+,25-,26-,27-,28+,29+,30-,31-,32+,33+,34-,35-,36-,37-,38-,39-,42+,43-,44+,45-,46+,47+/m0/s1
• InChI Key: YRRJXVAUNQTHBA-AHHXIVGRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₈O₁₉
• Molecular Weight: 947.10 g/mol
• Exact Mass: 946.51373025 g/mol
• Topological Polar Surface Area (TPSA): 307.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.45
• H-Bond Acceptor: 19
• H-Bond Donor: 12
• Rotatable Bonds: 11

Synonyms

• C17792

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6581	65.81%
Caco-2	-	0.8835	88.35%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6782	67.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8306	83.06%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.4670	46.70%
P-glycoprotein inhibitior	+	0.7485	74.85%
P-glycoprotein substrate	+	0.5669	56.69%
CYP3A4 substrate	+	0.7390	73.90%
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	+	0.7256	72.56%
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	-	0.9033	90.33%
Skin irritation	-	0.7237	72.37%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7698	76.98%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.5217	52.17%
skin sensitisation	-	0.9098	90.98%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8257	82.57%
Acute Oral Toxicity (c)	I	0.6658	66.58%
Estrogen receptor binding	+	0.7492	74.92%
Androgen receptor binding	+	0.7680	76.80%
Thyroid receptor binding	-	0.5210	52.10%
Glucocorticoid receptor binding	+	0.6805	68.05%
Aromatase binding	+	0.6362	63.62%
PPAR gamma	+	0.7603	76.03%
Honey bee toxicity	-	0.6394	63.94%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
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	98.89%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	97.84%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.30%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.61%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.43%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.32%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.19%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.05%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.81%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.33%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.25%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.20%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.81%	95.89%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	87.50%	83.57%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	87.36%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.20%	92.94%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.03%	97.36%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	86.98%	91.03%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	86.29%	92.86%
CHEMBL240	Q12809	HERG	86.23%	89.76%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.93%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.88%	94.45%
CHEMBL220	P22303	Acetylcholinesterase	84.61%	94.45%
CHEMBL259	P32245	Melanocortin receptor 4	84.16%	95.38%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.73%	96.95%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.06%	92.88%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.04%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.94%	96.90%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.25%	96.00%

Plants that contains it

• Astragalus amarus

Cross-Links

• PubChem: 21626649
• LOTUS: LTS0272150
• wikiData: Q104398902