Cyclofoetoside B

Details

• Internal ID: f9c4c5fe-613d-488f-86f9-5b06d5f1bb9c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6R)-6-[[(1S,3R,6S,7S,8R,11S,12S,14S,16R)-15-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-7-(hydroxymethyl)-7,12,16-trimethyl-6-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-14-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3CC4(C5CCC6C(C(CCC67C5(C7)CCC4(C3C(C)CCC(C(C)(C)O)O)C)OC8C(C(C(CO8)O)O)O)(C)CO)C)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@H]3C[C@]4([C@@H]5CC[C@H]6[C@@]([C@H](CC[C@]67[C@]5(C7)CC[C@@]4(C3[C@H](C)CC[C@@H](C(C)(C)O)O)C)O[C@H]8[C@@H]([C@H]([C@H](CO8)O)O)O)(C)CO)C)O)O)O)O)O)O
• InChI: InChI=1S/C47H80O18/c1-21(8-11-28(50)42(3,4)59)30-24(63-41-38(58)35(55)33(53)25(64-41)18-61-39-37(57)34(54)31(51)22(2)62-39)16-45(7)27-10-9-26-43(5,20-48)29(65-40-36(56)32(52)23(49)17-60-40)12-13-46(26)19-47(27,46)15-14-44(30,45)6/h21-41,48-59H,8-20H2,1-7H3/t21-,22+,23+,24+,25-,26+,27+,28+,29+,30?,31+,32+,33-,34-,35+,36-,37-,38-,39-,40+,41-,43-,44-,45+,46-,47+/m1/s1
• InChI Key: JDYWIMCSAUNOHC-OOLFRTMQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₈₀O₁₈
• Molecular Weight: 933.10 g/mol
• Exact Mass: 932.53446570 g/mol
• Topological Polar Surface Area (TPSA): 298.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.58
• H-Bond Acceptor: 18
• H-Bond Donor: 12
• Rotatable Bonds: 13

Synonyms

• 108333-83-1
• (2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6R)-6-[[(1S,3R,6S,7S,8R,11S,12S,14S,16R)-15-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-7-(hydroxymethyl)-7,12,16-trimethyl-6-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-14-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol
• C08939
• CHEBI:4002
• DTXSID40331668
• Q27106285

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4805	48.05%
Caco-2	-	0.8853	88.53%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5846	58.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8580	85.80%
OATP1B3 inhibitior	+	0.9122	91.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.5853	58.53%
P-glycoprotein inhibitior	+	0.7521	75.21%
P-glycoprotein substrate	+	0.6662	66.62%
CYP3A4 substrate	+	0.7312	73.12%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.8301	83.01%
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	+	0.6977	69.77%
CYP inhibitory promiscuity	-	0.9671	96.71%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6868	68.68%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9060	90.60%
Skin irritation	-	0.7152	71.52%
Skin corrosion	-	0.9483	94.83%
Ames mutagenesis	-	0.5932	59.32%
Human Ether-a-go-go-Related Gene inhibition	+	0.7855	78.55%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6747	67.47%
skin sensitisation	-	0.9113	91.13%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.9310	93.10%
Acute Oral Toxicity (c)	I	0.6066	60.66%
Estrogen receptor binding	+	0.7252	72.52%
Androgen receptor binding	+	0.7454	74.54%
Thyroid receptor binding	-	0.5698	56.98%
Glucocorticoid receptor binding	+	0.6579	65.79%
Aromatase binding	+	0.6491	64.91%
PPAR gamma	+	0.7524	75.24%
Honey bee toxicity	-	0.6455	64.55%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
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	99.60%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.26%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	97.42%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.94%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.87%	98.95%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	93.81%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	93.78%	94.75%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	92.98%	92.88%
CHEMBL284	P27487	Dipeptidyl peptidase IV	92.22%	95.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.20%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.69%	89.00%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	91.19%	95.58%
CHEMBL226	P30542	Adenosine A1 receptor	91.01%	95.93%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	90.69%	92.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.94%	96.77%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	88.04%	92.78%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	87.88%	99.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	87.33%	97.31%
CHEMBL4302	P08183	P-glycoprotein 1	87.32%	92.98%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.12%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.93%	97.36%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.83%	100.00%
CHEMBL204	P00734	Thrombin	86.55%	96.01%
CHEMBL4105786	P41182	B-cell lymphoma 6 protein	86.37%	92.86%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.34%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	86.12%	91.49%
CHEMBL1741186	P51449	Nuclear receptor ROR-gamma	85.80%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.57%	92.94%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	85.05%	92.86%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.95%	94.45%
CHEMBL4482	O96013	Serine/threonine-protein kinase PAK 4	84.60%	95.42%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.44%	100.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	84.21%	82.50%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	84.19%	97.47%
CHEMBL203	P00533	Epidermal growth factor receptor erbB1	83.86%	97.34%
CHEMBL259	P32245	Melanocortin receptor 4	83.86%	95.38%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.80%	97.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.68%	95.83%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.45%	92.62%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.45%	96.90%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	83.22%	97.29%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	83.08%	95.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.06%	98.75%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.55%	95.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.35%	96.47%
CHEMBL1977	P11473	Vitamin D receptor	82.02%	99.43%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.62%	89.62%
CHEMBL206	P03372	Estrogen receptor alpha	81.60%	97.64%
CHEMBL5747	Q92793	CREB-binding protein	81.21%	95.12%
CHEMBL1871	P10275	Androgen Receptor	80.81%	96.43%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.61%	86.92%

Plants that contains it

• Thalictrum foetidum

Cross-Links

• PubChem: 441917
• LOTUS: LTS0105465
• wikiData: Q27106285