[(2R,3R,4R,5R,6R)-3,4,5-triacetyloxy-6-[[(1R,4S,5S,8R,9R,12S,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]oxan-2-yl]methyl acetate

Details

• Internal ID: b31eb224-46f9-41e8-98e0-86a2f0638ecc
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(2R,3R,4R,5R,6R)-3,4,5-triacetyloxy-6-[[(1R,4S,5S,8R,9R,12S,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]oxan-2-yl]methyl acetate
• SMILES (Canonical): CC(CC=CC(C)(C)OC)C1CCC2(C1(CCC34C2C=CC5(C3CCC(C5(C)C)OC6C(C(C(C(O6)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)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)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC4)C)C
• InChI: InChI=1S/C45H68O12/c1-26(14-13-19-40(6,7)50-12)31-17-20-43(11)33-18-21-45-34(44(33,25-52-45)23-22-42(31,43)10)15-16-35(41(45,8)9)57-39-38(55-30(5)49)37(54-29(4)48)36(53-28(3)47)32(56-39)24-51-27(2)46/h13,18-19,21,26,31-39H,14-17,20,22-25H2,1-12H3/b19-13+/t26-,31-,32-,33+,34+,35+,36-,37-,38-,39+,42-,43+,44+,45-/m1/s1
• InChI Key: OMGGPLTZARDXEH-SFFZUTDPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₆₈O₁₂
• Molecular Weight: 801.00 g/mol
• Exact Mass: 800.47107760 g/mol
• Topological Polar Surface Area (TPSA): 142.00 Ų
• XlogP: 6.90
• Atomic LogP (AlogP): 7.06
• H-Bond Acceptor: 12
• H-Bond Donor: 0
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9553	95.53%
Caco-2	-	0.8494	84.94%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7934	79.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8141	81.41%
OATP1B3 inhibitior	+	0.9261	92.61%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9953	99.53%
P-glycoprotein inhibitior	+	0.7989	79.89%
P-glycoprotein substrate	+	0.5790	57.90%
CYP3A4 substrate	+	0.7321	73.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8782	87.82%
CYP3A4 inhibition	-	0.9130	91.30%
CYP2C9 inhibition	-	0.8929	89.29%
CYP2C19 inhibition	-	0.8158	81.58%
CYP2D6 inhibition	-	0.9428	94.28%
CYP1A2 inhibition	-	0.9165	91.65%
CYP2C8 inhibition	+	0.6696	66.96%
CYP inhibitory promiscuity	-	0.9131	91.31%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5614	56.14%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9055	90.55%
Skin irritation	-	0.7518	75.18%
Skin corrosion	-	0.9292	92.92%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7004	70.04%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8684	86.84%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.7395	73.95%
Acute Oral Toxicity (c)	I	0.4612	46.12%
Estrogen receptor binding	+	0.7753	77.53%
Androgen receptor binding	+	0.7486	74.86%
Thyroid receptor binding	+	0.5364	53.64%
Glucocorticoid receptor binding	+	0.7897	78.97%
Aromatase binding	+	0.6657	66.57%
PPAR gamma	+	0.7713	77.13%
Honey bee toxicity	-	0.6489	64.89%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9746	97.46%

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	99.45%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.12%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.73%	97.25%
CHEMBL2581	P07339	Cathepsin D	96.17%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.72%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.25%	95.89%
CHEMBL3922	P50579	Methionine aminopeptidase 2	91.50%	97.28%
CHEMBL4227	P25090	Lipoxin A4 receptor	90.47%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.77%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.57%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.38%	93.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.86%	86.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.09%	89.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.07%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.18%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	87.12%	92.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.08%	92.62%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.18%	96.47%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.84%	91.07%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.56%	98.75%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.61%	91.03%
CHEMBL5028	O14672	ADAM10	84.19%	97.50%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.69%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.17%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.25%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.10%	94.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.21%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.98%	91.24%
CHEMBL340	P08684	Cytochrome P450 3A4	80.81%	91.19%
CHEMBL3474	P14555	Phospholipase A2 group IIA	80.67%	94.05%

Plants that contains it

• Momordica charantia

Cross-Links

• PubChem: 162915460
• LOTUS: LTS0234310
• wikiData: Q105194326