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

Details

• Internal ID: dde6bd8a-dc85-4b29-9533-54f5482e4157
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (3S,8S,9R,10R,13R,14R,16R,17R)-16-hydroxy-4,4,9,13,14-pentamethyl-17-[(2R,3S)-2,3,6-trihydroxy-6-methylheptan-2-yl]-3-[(2R,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]oxy-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
• SMILES (Canonical): CC1(C(CCC2C1=CCC3C2(C(=O)CC4(C3(CC(C4C(C)(C(CCC(C)(C)O)O)O)O)C)C)C)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O)C
• SMILES (Isomeric): C[C@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3CC[C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)O)C)C)[C@](C)([C@H](CCC(C)(C)O)O)O)O
• InChI: InChI=1S/C42H70O16/c1-37(2,53)14-13-25(45)42(8,54)34-21(44)15-39(5)24-11-9-19-20(41(24,7)26(46)16-40(34,39)6)10-12-27(38(19,3)4)58-36-33(52)31(50)29(48)23(57-36)18-55-35-32(51)30(49)28(47)22(17-43)56-35/h9,20-25,27-36,43-45,47-54H,10-18H2,1-8H3/t20-,21-,22-,23-,24+,25+,27+,28-,29-,30+,31+,32-,33-,34+,35-,36+,39-,40-,41+,42+/m1/s1
• InChI Key: RLSXWJUYUFUJLU-DMFFLCDUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₇₀O₁₆
• Molecular Weight: 831.00 g/mol
• Exact Mass: 830.46638614 g/mol
• Topological Polar Surface Area (TPSA): 277.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.59
• H-Bond Acceptor: 16
• H-Bond Donor: 11
• 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	-	0.8856	88.56%
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	+	0.8536	85.36%
OATP1B3 inhibitior	-	0.3515	35.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	+	0.7523	75.23%
P-glycoprotein inhibitior	+	0.7454	74.54%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7165	71.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8687	86.87%
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	+	0.5869	58.69%
CYP inhibitory promiscuity	-	0.9524	95.24%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6051	60.51%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9083	90.83%
Skin irritation	-	0.5396	53.96%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.7478	74.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7170	71.70%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6501	65.01%
skin sensitisation	-	0.9029	90.29%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.6614	66.14%
Acute Oral Toxicity (c)	III	0.6642	66.42%
Estrogen receptor binding	+	0.8103	81.03%
Androgen receptor binding	+	0.7362	73.62%
Thyroid receptor binding	-	0.5418	54.18%
Glucocorticoid receptor binding	+	0.6959	69.59%
Aromatase binding	+	0.6418	64.18%
PPAR gamma	+	0.7614	76.14%
Honey bee toxicity	-	0.6981	69.81%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.01%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.31%	97.09%
CHEMBL2581	P07339	Cathepsin D	96.76%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.74%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.30%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.01%	96.61%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.34%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.47%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.52%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	86.51%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	86.48%	92.50%
CHEMBL2996	Q05655	Protein kinase C delta	86.29%	97.79%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.76%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.51%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.04%	97.14%
CHEMBL4581	P52732	Kinesin-like protein 1	84.72%	93.18%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.70%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.68%	86.92%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.51%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.32%	93.04%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.14%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.62%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.56%	94.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.35%	93.56%
CHEMBL226	P30542	Adenosine A1 receptor	82.96%	95.93%
CHEMBL1871	P10275	Androgen Receptor	80.68%	96.43%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.49%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.13%	99.23%

Plants that contains it

• Cyclanthera pedata

Cross-Links

• PubChem: 162940414
• LOTUS: LTS0182053
• wikiData: Q105240502