(2R,3S,4R,5R,6R)-2-(hydroxymethyl)-6-[[(1S,4S,5S,8R,9R,12R,13S,16S)-8-[(E,2R)-6-methoxy-6-methylhept-4-en-2-yl]-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.01,13.04,12.05,9]nonadec-2-en-16-yl]oxy]oxane-3,4,5-triol

Details

• Internal ID: bd18e39c-b7eb-4797-97e5-b1e43811ac48
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3S,4R,5R,6R)-2-(hydroxymethyl)-6-[[(1S,4S,5S,8R,9R,12R,13S,16S)-8-[(E,2R)-6-methoxy-6-methylhept-4-en-2-yl]-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.01,13.04,12.05,9]nonadec-2-en-16-yl]oxy]oxane-3,4,5-triol
• SMILES (Canonical): CC(CC=CC(C)(C)OC)C1CCC2(C1(CCC34C2C=CC5(C3CCC(C5(C)C)OC6C(C(C(C(O6)CO)O)O)O)OC4)C)C
• SMILES (Isomeric): C[C@H](C/C=C/C(C)(C)OC)[C@H]1CC[C@@]2([C@@]1(CC[C@@]34[C@H]2C=C[C@@]5([C@H]3CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@@H]([C@@H]([C@H](O6)CO)O)O)O)OC4)C)C
• InChI: InChI=1S/C37H60O8/c1-22(10-9-15-32(2,3)42-8)23-13-16-35(7)25-14-17-37-26(36(25,21-43-37)19-18-34(23,35)6)11-12-27(33(37,4)5)45-31-30(41)29(40)28(39)24(20-38)44-31/h9,14-15,17,22-31,38-41H,10-13,16,18-21H2,1-8H3/b15-9+/t22-,23-,24-,25+,26+,27+,28-,29-,30-,31+,34-,35+,36-,37+/m1/s1
• InChI Key: MQGABSJZVJOSCX-IZSXVOFISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₆₀O₈
• Molecular Weight: 632.90 g/mol
• Exact Mass: 632.42881887 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.77
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5592	55.92%
Caco-2	-	0.8426	84.26%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6975	69.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8379	83.79%
OATP1B3 inhibitior	+	0.9081	90.81%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.7319	73.19%
P-glycoprotein inhibitior	+	0.7600	76.00%
P-glycoprotein substrate	+	0.5499	54.99%
CYP3A4 substrate	+	0.7118	71.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8287	82.87%
CYP3A4 inhibition	-	0.9613	96.13%
CYP2C9 inhibition	-	0.8448	84.48%
CYP2C19 inhibition	-	0.8310	83.10%
CYP2D6 inhibition	-	0.9434	94.34%
CYP1A2 inhibition	-	0.8983	89.83%
CYP2C8 inhibition	+	0.6129	61.29%
CYP inhibitory promiscuity	-	0.9212	92.12%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6230	62.30%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9230	92.30%
Skin irritation	-	0.7304	73.04%
Skin corrosion	-	0.9460	94.60%
Ames mutagenesis	-	0.6040	60.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.7976	79.76%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.9077	90.77%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7402	74.02%
Acute Oral Toxicity (c)	I	0.5512	55.12%
Estrogen receptor binding	+	0.6538	65.38%
Androgen receptor binding	+	0.7509	75.09%
Thyroid receptor binding	-	0.4926	49.26%
Glucocorticoid receptor binding	+	0.7076	70.76%
Aromatase binding	+	0.6762	67.62%
PPAR gamma	+	0.6612	66.12%
Honey bee toxicity	-	0.6391	63.91%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.8932	89.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.05%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.70%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.49%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.25%	97.25%
CHEMBL2581	P07339	Cathepsin D	96.46%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	94.72%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.10%	97.09%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	92.06%	97.47%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	90.89%	91.03%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	88.53%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.37%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.20%	91.24%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.20%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	87.40%	97.28%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.39%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.06%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.78%	89.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	85.44%	92.86%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.10%	96.61%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.79%	92.62%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.60%	93.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	84.59%	92.88%
CHEMBL2243	O00519	Anandamide amidohydrolase	84.43%	97.53%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.12%	98.75%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	83.65%	97.88%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.20%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.40%	96.77%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.36%	97.36%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.18%	89.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.89%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.79%	91.07%

Plants that contains it

• Momordica charantia

Cross-Links

• PubChem: 159640132
• LOTUS: LTS0250460
• wikiData: Q105169983