(2R)-2-[(3R,8S,9R,10S,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-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-5-(2-hydroxypropan-2-yl)-2-methylfuran-3-one

Details

• Internal ID: 21c113d3-8654-40ab-84e2-8456d922e884
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R)-2-[(3R,8S,9R,10S,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-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-5-(2-hydroxypropan-2-yl)-2-methylfuran-3-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CCC4C(=CCC5C4(C(=O)CC6(C5(CC(C6C7(C(=O)C=C(O7)C(C)(C)O)C)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@@]7(C(=O)C=C(O7)C(C)(C)O)C)O)C)C)C)C3(C)C)CO)O)O)O)O)O
• InChI: InChI=1S/C42H64O15/c1-18-28(47)30(49)32(51)35(53-18)56-33-31(50)29(48)22(17-43)54-36(33)55-26-13-11-20-19(37(26,2)3)10-12-23-39(6)15-21(44)34(40(39,7)16-25(46)41(20,23)8)42(9)24(45)14-27(57-42)38(4,5)52/h10,14,18,20-23,26,28-36,43-44,47-52H,11-13,15-17H2,1-9H3/t18-,20-,21+,22+,23-,26+,28-,29+,30+,31-,32+,33+,34-,35-,36-,39-,40+,41-,42-/m0/s1
• InChI Key: FNNCXDZYMORRHA-KCXVRDEASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₄O₁₅
• Molecular Weight: 808.90 g/mol
• Exact Mass: 808.42452133 g/mol
• Topological Polar Surface Area (TPSA): 242.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.79
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9168	91.68%
Caco-2	-	0.8762	87.62%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.8881	88.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8300	83.00%
OATP1B3 inhibitior	+	0.8879	88.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5381	53.81%
P-glycoprotein inhibitior	+	0.7510	75.10%
P-glycoprotein substrate	+	0.5732	57.32%
CYP3A4 substrate	+	0.7344	73.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.6811	68.11%
CYP2C9 inhibition	-	0.8073	80.73%
CYP2C19 inhibition	-	0.9331	93.31%
CYP2D6 inhibition	-	0.9408	94.08%
CYP1A2 inhibition	-	0.9182	91.82%
CYP2C8 inhibition	+	0.6999	69.99%
CYP inhibitory promiscuity	-	0.9095	90.95%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4803	48.03%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9098	90.98%
Skin irritation	+	0.5206	52.06%
Skin corrosion	-	0.9353	93.53%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7257	72.57%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7153	71.53%
skin sensitisation	-	0.9137	91.37%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7857	78.57%
Acute Oral Toxicity (c)	I	0.6513	65.13%
Estrogen receptor binding	+	0.7439	74.39%
Androgen receptor binding	+	0.7598	75.98%
Thyroid receptor binding	-	0.5075	50.75%
Glucocorticoid receptor binding	+	0.7411	74.11%
Aromatase binding	+	0.6689	66.89%
PPAR gamma	+	0.7522	75.22%
Honey bee toxicity	-	0.6781	67.81%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9802	98.02%

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	98.80%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.46%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.49%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.64%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.83%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.26%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.72%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	90.68%	95.93%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.68%	97.36%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.44%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.78%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.47%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	89.12%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.84%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	86.59%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.48%	100.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.27%	97.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.09%	86.92%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.85%	97.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.62%	93.04%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	82.58%	98.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.25%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.97%	91.07%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.90%	92.94%
CHEMBL5255	O00206	Toll-like receptor 4	81.61%	92.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.56%	96.21%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.58%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.49%	93.56%
CHEMBL4208	P20618	Proteasome component C5	80.32%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.07%	99.23%

Plants that contains it

• Picria fel-terrae

Cross-Links

• PubChem: 101711553
• LOTUS: LTS0261571
• wikiData: Q104998386