(3R,8S,9R,10R,13R,14S,16R,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-16-hydroxy-4,4,9,13,14-pentamethyl-17-[(E,2R,3S)-2,3,6-trihydroxy-6-methylhept-4-en-2-yl]-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one

Details

• Internal ID: cd686d05-9496-4f33-be1d-78393a474c6e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (3R,8S,9R,10R,13R,14S,16R,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-16-hydroxy-4,4,9,13,14-pentamethyl-17-[(E,2R,3S)-2,3,6-trihydroxy-6-methylhept-4-en-2-yl]-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CCC4C(=CCC5C4(C(=O)CC6(C5(CC(C6C(C)(C(C=CC(C)(C)O)O)O)O)C)C)C)C3(C)C)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@@H]3CC[C@@H]4C(=CC[C@@H]5[C@]4(C(=O)C[C@]6([C@]5(C[C@H]([C@@H]6[C@](C)([C@H](/C=C/C(C)(C)O)O)O)O)C)C)C)C3(C)C)CO)O)O)O)O)O
• InChI: InChI=1S/C42H68O15/c1-19-28(47)30(49)32(51)35(54-19)57-33-31(50)29(48)23(18-43)55-36(33)56-27-13-11-21-20(38(27,4)5)10-12-24-39(6)16-22(44)34(40(39,7)17-26(46)41(21,24)8)42(9,53)25(45)14-15-37(2,3)52/h10,14-15,19,21-25,27-36,43-45,47-53H,11-13,16-18H2,1-9H3/b15-14+/t19-,21+,22+,23+,24-,25-,27+,28-,29+,30+,31-,32+,33+,34-,35-,36-,39-,40+,41-,42-/m0/s1
• InChI Key: JJNGJQDTXWNKKW-HQKPOTFKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₈O₁₅
• Molecular Weight: 813.00 g/mol
• Exact Mass: 812.45582146 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.22
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8800	88.00%
Caco-2	-	0.8764	87.64%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8515	85.15%
OATP2B1 inhibitior	-	0.8729	87.29%
OATP1B1 inhibitior	+	0.8368	83.68%
OATP1B3 inhibitior	-	0.3152	31.52%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	+	0.8515	85.15%
P-glycoprotein inhibitior	+	0.7559	75.59%
P-glycoprotein substrate	+	0.5463	54.63%
CYP3A4 substrate	+	0.7262	72.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8703	87.03%
CYP3A4 inhibition	-	0.9072	90.72%
CYP2C9 inhibition	-	0.8493	84.93%
CYP2C19 inhibition	-	0.9348	93.48%
CYP2D6 inhibition	-	0.9399	93.99%
CYP1A2 inhibition	-	0.9005	90.05%
CYP2C8 inhibition	+	0.6669	66.69%
CYP inhibitory promiscuity	-	0.9315	93.15%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6163	61.63%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9090	90.90%
Skin irritation	+	0.5341	53.41%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7297	72.97%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.7376	73.76%
skin sensitisation	-	0.9069	90.69%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.8151	81.51%
Acute Oral Toxicity (c)	III	0.6401	64.01%
Estrogen receptor binding	+	0.7718	77.18%
Androgen receptor binding	+	0.7413	74.13%
Thyroid receptor binding	-	0.4881	48.81%
Glucocorticoid receptor binding	+	0.7426	74.26%
Aromatase binding	+	0.6334	63.34%
PPAR gamma	+	0.7513	75.13%
Honey bee toxicity	-	0.6252	62.52%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9583	95.83%

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	99.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.01%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.44%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.25%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.17%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.08%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.21%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.17%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.28%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	88.36%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.56%	96.61%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.33%	93.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.01%	97.36%
CHEMBL1937	Q92769	Histone deacetylase 2	85.29%	94.75%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.08%	86.92%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.87%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.75%	100.00%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	84.67%	98.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.58%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.06%	96.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.21%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.44%	97.33%
CHEMBL226	P30542	Adenosine A1 receptor	80.34%	95.93%

Plants that contains it

• Ibervillea sonorae

Cross-Links

• PubChem: 163186510
• LOTUS: LTS0206399
• wikiData: Q105129752