(3S,8S,9R,10R,13R,14S,17R)-17-[(2R,5R)-5-hydroxy-6-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]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: f938aa9c-ec18-4025-8347-3866868928ca
• 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-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]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)COC2C(C(C(C(O2)CO)O)O)O)O)O)O)O)C3CCC4(C3(CC(=O)C5(C4CC=C6C5CCC(C6(C)C)OC7C(C(C(C(O7)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[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)O)O)[C@H]3CC[C@@]4([C@@]3(CC(=O)[C@@]5([C@H]4CC=C6[C@H]5CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)C)C
• InChI: InChI=1S/C48H80O19/c1-21(9-13-29(51)45(4,5)67-43-40(61)37(58)34(55)27(65-43)20-62-41-38(59)35(56)32(53)25(18-49)63-41)22-15-16-46(6)28-12-10-23-24(48(28,8)30(52)17-47(22,46)7)11-14-31(44(23,2)3)66-42-39(60)36(57)33(54)26(19-50)64-42/h10,21-22,24-29,31-43,49-51,53-61H,9,11-20H2,1-8H3/t21-,22-,24-,25-,26-,27-,28+,29-,31+,32-,33-,34-,35+,36+,37+,38-,39-,40-,41-,42+,43+,46+,47-,48+/m1/s1
• InChI Key: IJNWRPOFXBROQB-GDOAMJOQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₀O₁₉
• Molecular Weight: 961.10 g/mol
• Exact Mass: 960.52938032 g/mol
• Topological Polar Surface Area (TPSA): 315.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.85
• H-Bond Acceptor: 19
• H-Bond Donor: 12
• Rotatable Bonds: 14

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	-	0.8832	88.32%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8432	84.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8362	83.62%
OATP1B3 inhibitior	-	0.3515	35.15%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	+	0.7964	79.64%
P-glycoprotein inhibitior	+	0.7510	75.10%
P-glycoprotein substrate	+	0.5127	51.27%
CYP3A4 substrate	+	0.7291	72.91%
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	+	0.6175	61.75%
CYP inhibitory promiscuity	-	0.9524	95.24%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6051	60.51%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9042	90.42%
Skin irritation	-	0.5396	53.96%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7827	78.27%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5933	59.33%
skin sensitisation	-	0.9029	90.29%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.6099	60.99%
Acute Oral Toxicity (c)	III	0.6642	66.42%
Estrogen receptor binding	+	0.8255	82.55%
Androgen receptor binding	+	0.7645	76.45%
Thyroid receptor binding	+	0.5157	51.57%
Glucocorticoid receptor binding	+	0.7548	75.48%
Aromatase binding	+	0.6789	67.89%
PPAR gamma	+	0.8023	80.23%
Honey bee toxicity	-	0.7057	70.57%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
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	97.97%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.81%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.80%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.19%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.64%	97.09%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	91.12%	93.04%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.81%	96.61%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.15%	96.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.75%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	89.08%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.28%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.10%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	87.48%	94.45%
CHEMBL4581	P52732	Kinesin-like protein 1	86.91%	93.18%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.83%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	84.69%	94.75%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.66%	93.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.64%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.25%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.67%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.66%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.46%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.14%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.94%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.46%	100.00%
CHEMBL4208	P20618	Proteasome component C5	81.19%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	80.20%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.05%	99.23%

Plants that contains it

• Bryonia cretica

Cross-Links

• PubChem: 15143904
• LOTUS: LTS0150951
• wikiData: Q104393323