cycloorbicoside G

Details

• Internal ID: 141fdc78-6b77-472b-b0a8-7ff518b0d1e5
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-[(1R,3S,4S,5S,7R,9S,12R,14S,17R,18R,19R,21R,22S)-5-hydroxy-3,8,8,17,19-pentamethyl-9-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-22-yl]propan-2-yloxy]oxane-3,4,5-triol
• SMILES (Canonical): CC1CC2C(OC3(C1C4(CCC56CC57CCC(C(C7CC(C6C4(C3)C)O)(C)C)OC8C(C(C(CO8)O)O)O)C)O2)C(C)(C)OC9C(C(C(C(O9)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1C[C@@H]2[C@H](O[C@]3([C@H]1[C@]4(CC[C@@]56C[C@@]57CC[C@@H](C([C@@H]7C[C@@H]([C@H]6[C@@]4(C3)C)O)(C)C)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)C)O2)C(C)(C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O
• InChI: InChI=1S/C41H66O14/c1-18-12-21-32(36(4,5)55-34-29(49)27(47)26(46)22(14-42)51-34)54-41(53-21)16-38(7)31-19(43)13-23-35(2,3)24(52-33-28(48)25(45)20(44)15-50-33)8-9-39(23)17-40(31,39)11-10-37(38,6)30(18)41/h18-34,42-49H,8-17H2,1-7H3/t18-,19+,20-,21-,22-,23+,24+,25+,26-,27+,28-,29-,30-,31+,32+,33+,34+,37-,38+,39-,40+,41-/m1/s1
• InChI Key: KTINGOVWVPSKNN-RQRKGEPUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₆O₁₄
• Molecular Weight: 783.00 g/mol
• Exact Mass: 782.44525677 g/mol
• Topological Polar Surface Area (TPSA): 217.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 0.95
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

• CHEMBL372097
• 114317-53-2
• (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-[(1R,3S,4S,5S,7R,9S,12R,14S,17R,18R,19R,21R,22S)-5-hydroxy-3,8,8,17,19-pentamethyl-9-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-22-yl]propan-2-yloxy]oxane-3,4,5-triol
• [(3beta,7beta,23R,24S)-16beta,23:16alpha,24-Diepoxy-7-hydroxy-3-(beta-D-xylopyranosyloxy)-9,19-cyclolanostan-25-yl]beta
• BDBM50176696

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5750	57.50%
Caco-2	-	0.8773	87.73%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6150	61.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8093	80.93%
OATP1B3 inhibitior	+	0.9371	93.71%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.7614	76.14%
P-glycoprotein inhibitior	+	0.7475	74.75%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7282	72.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8205	82.05%
CYP3A4 inhibition	-	0.9241	92.41%
CYP2C9 inhibition	-	0.8017	80.17%
CYP2C19 inhibition	-	0.8330	83.30%
CYP2D6 inhibition	-	0.9431	94.31%
CYP1A2 inhibition	-	0.8946	89.46%
CYP2C8 inhibition	+	0.7190	71.90%
CYP inhibitory promiscuity	-	0.9524	95.24%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6376	63.76%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9066	90.66%
Skin irritation	-	0.7097	70.97%
Skin corrosion	-	0.9446	94.46%
Ames mutagenesis	-	0.5724	57.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7094	70.94%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.5999	59.99%
skin sensitisation	-	0.9091	90.91%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8219	82.19%
Acute Oral Toxicity (c)	I	0.6862	68.62%
Estrogen receptor binding	+	0.6304	63.04%
Androgen receptor binding	+	0.7629	76.29%
Thyroid receptor binding	-	0.5869	58.69%
Glucocorticoid receptor binding	+	0.5868	58.68%
Aromatase binding	+	0.6747	67.47%
PPAR gamma	+	0.7038	70.38%
Honey bee toxicity	-	0.6662	66.62%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8309	83.09%

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	99.35%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.19%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.88%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.13%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.06%	96.61%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	91.03%	92.88%
CHEMBL259	P32245	Melanocortin receptor 4	89.65%	95.38%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	89.30%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.13%	96.77%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.34%	97.14%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.40%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.87%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.32%	92.94%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.04%	91.03%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.09%	96.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.87%	89.62%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.15%	91.24%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.05%	98.75%
CHEMBL2581	P07339	Cathepsin D	82.59%	98.95%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	82.54%	97.31%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.39%	96.21%
CHEMBL2996	Q05655	Protein kinase C delta	82.02%	97.79%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.93%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.76%	91.07%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	80.69%	98.99%
CHEMBL5255	O00206	Toll-like receptor 4	80.48%	92.50%

Plants that contains it

• Astragalus orbiculatus

Cross-Links

• PubChem: 13943263
• LOTUS: LTS0197153
• wikiData: Q105145802