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

Details

• Internal ID: bcbd7c01-4d98-4299-a615-83a229e5d836
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3R,4R,5S,6R)-2-[(4S,5S,6S)-5-hydroxy-6-[(1R,4S,5S,8R,9R,12S,13S,16S)-16-hydroxy-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.01,13.04,12.05,9]nonadec-2-en-8-yl]-2-methylhept-2-en-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(C1CCC2(C1(CCC34C2C=CC5(C3CCC(C5(C)C)O)OC4)C)C)C(C(C=C(C)C)OC6C(C(C(C(O6)CO)O)O)O)O
• SMILES (Isomeric): C[C@@H]([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)OC4)C)C)[C@@H]([C@H](C=C(C)C)O[C@H]6[C@@H]([C@@H]([C@@H]([C@H](O6)CO)O)O)O)O
• InChI: InChI=1S/C36H58O9/c1-19(2)16-22(44-31-30(42)29(41)28(40)23(17-37)45-31)27(39)20(3)21-10-12-34(7)24-11-13-36-25(8-9-26(38)32(36,4)5)35(24,18-43-36)15-14-33(21,34)6/h11,13,16,20-31,37-42H,8-10,12,14-15,17-18H2,1-7H3/t20-,21+,22-,23+,24-,25-,26-,27-,28+,29+,30+,31+,33+,34-,35-,36+/m0/s1
• InChI Key: KQDRBMHUHNJNGK-OJWHYBJPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₈O₉
• Molecular Weight: 634.80 g/mol
• Exact Mass: 634.40808342 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.09
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7413	74.13%
Caco-2	-	0.8499	84.99%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7037	70.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8452	84.52%
OATP1B3 inhibitior	+	0.9043	90.43%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.5801	58.01%
P-glycoprotein inhibitior	+	0.7197	71.97%
P-glycoprotein substrate	+	0.5241	52.41%
CYP3A4 substrate	+	0.6966	69.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8287	82.87%
CYP3A4 inhibition	-	0.9289	92.89%
CYP2C9 inhibition	-	0.8037	80.37%
CYP2C19 inhibition	-	0.8690	86.90%
CYP2D6 inhibition	-	0.9287	92.87%
CYP1A2 inhibition	-	0.8837	88.37%
CYP2C8 inhibition	+	0.6367	63.67%
CYP inhibitory promiscuity	-	0.9253	92.53%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5990	59.90%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9206	92.06%
Skin irritation	-	0.6011	60.11%
Skin corrosion	-	0.9420	94.20%
Ames mutagenesis	-	0.5670	56.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8199	81.99%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8915	89.15%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7816	78.16%
Acute Oral Toxicity (c)	I	0.6110	61.10%
Estrogen receptor binding	+	0.7100	71.00%
Androgen receptor binding	+	0.7518	75.18%
Thyroid receptor binding	-	0.5315	53.15%
Glucocorticoid receptor binding	+	0.6848	68.48%
Aromatase binding	+	0.7132	71.32%
PPAR gamma	+	0.6801	68.01%
Honey bee toxicity	-	0.6555	65.55%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9382	93.82%

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	99.39%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.56%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.60%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.53%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.55%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.12%	95.89%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	91.78%	92.86%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	90.90%	85.00%
CHEMBL1951	P21397	Monoamine oxidase A	90.54%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.47%	97.09%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.62%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.04%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.73%	96.77%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.92%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.88%	91.24%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.93%	95.50%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	82.67%	95.58%
CHEMBL226	P30542	Adenosine A1 receptor	82.58%	95.93%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.24%	89.05%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.07%	95.83%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.40%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.05%	89.00%
CHEMBL268	P43235	Cathepsin K	80.83%	96.85%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	80.75%	97.29%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	80.74%	95.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.59%	89.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.10%	86.33%
CHEMBL5555	O00767	Acyl-CoA desaturase	80.08%	97.50%

Plants that contains it

• Momordica charantia

Cross-Links

• PubChem: 162969443
• LOTUS: LTS0041181
• wikiData: Q105144493