(3S,8S,9R,10R,13R,14S,17R)-17-[(2R,5R)-5-hydroxy-6-methyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-4,4,9,13,14-pentamethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one

Details

• Internal ID: c97e0cba-43c8-493b-b599-336e49837276
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (3S,8S,9R,10R,13R,14S,17R)-17-[(2R,5R)-5-hydroxy-6-methyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-4,4,9,13,14-pentamethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
• SMILES (Canonical): CC(CCC(C(C)(C)OC1C(C(C(C(O1)CO)O)O)O)O)C2CCC3(C2(CC(=O)C4(C3CC=C5C4CCC(C5(C)C)OC6C(C(C(C(O6)CO)O)O)O)C)C)C
• SMILES (Isomeric): C[C@H](CC[C@H](C(C)(C)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)[C@H]2CC[C@@]3([C@@]2(CC(=O)[C@@]4([C@H]3CC=C5[C@H]4CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)C
• InChI: InChI=1S/C42H70O14/c1-20(9-13-27(45)39(4,5)56-37-35(52)33(50)31(48)25(19-44)54-37)21-15-16-40(6)26-12-10-22-23(42(26,8)28(46)17-41(21,40)7)11-14-29(38(22,2)3)55-36-34(51)32(49)30(47)24(18-43)53-36/h10,20-21,23-27,29-37,43-45,47-52H,9,11-19H2,1-8H3/t20-,21-,23-,24-,25-,26+,27-,29+,30-,31-,32+,33+,34-,35-,36+,37+,40+,41-,42+/m1/s1
• InChI Key: QIGZAMBHIPKALQ-OWGIULRUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₇₀O₁₄
• Molecular Weight: 799.00 g/mol
• Exact Mass: 798.47655690 g/mol
• Topological Polar Surface Area (TPSA): 236.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8258	82.58%
Caco-2	-	0.8780	87.80%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8432	84.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8368	83.68%
OATP1B3 inhibitior	-	0.3515	35.15%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	-	0.6545	65.45%
P-glycoprotein inhibitior	+	0.7553	75.53%
P-glycoprotein substrate	-	0.5536	55.36%
CYP3A4 substrate	+	0.7240	72.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8581	85.81%
CYP3A4 inhibition	-	0.9446	94.46%
CYP2C9 inhibition	-	0.8769	87.69%
CYP2C19 inhibition	-	0.9253	92.53%
CYP2D6 inhibition	-	0.9396	93.96%
CYP1A2 inhibition	-	0.9147	91.47%
CYP2C8 inhibition	+	0.5601	56.01%
CYP inhibitory promiscuity	-	0.9524	95.24%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6051	60.51%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9109	91.09%
Skin irritation	-	0.5396	53.96%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7595	75.95%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5933	59.33%
skin sensitisation	-	0.9029	90.29%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.6524	65.24%
Acute Oral Toxicity (c)	III	0.6642	66.42%
Estrogen receptor binding	+	0.7823	78.23%
Androgen receptor binding	+	0.7599	75.99%
Thyroid receptor binding	-	0.5754	57.54%
Glucocorticoid receptor binding	+	0.7161	71.61%
Aromatase binding	+	0.6761	67.61%
PPAR gamma	+	0.7380	73.80%
Honey bee toxicity	-	0.7152	71.52%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9477	94.77%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.01%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.28%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.69%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.92%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.48%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.40%	96.21%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.81%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.18%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.91%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	87.97%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.21%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	86.62%	97.79%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.37%	93.04%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.11%	93.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.02%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.52%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.20%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.78%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.14%	100.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.03%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.61%	100.00%
CHEMBL4581	P52732	Kinesin-like protein 1	82.52%	93.18%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.38%	92.62%
CHEMBL4208	P20618	Proteasome component C5	81.98%	90.00%
CHEMBL1937	Q92769	Histone deacetylase 2	81.67%	94.75%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.21%	93.00%

Plants that contains it

• Bryonia cretica

Cross-Links

• PubChem: 15143903
• LOTUS: LTS0121737
• wikiData: Q104393327