(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(3S,7S,8R,9S,10S,13R,14S,17R)-7-methoxy-17-[(E,2R)-6-methoxy-6-methylhept-4-en-2-yl]-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-3,4,5-triol

Details

• Internal ID: bb82a855-b327-4650-9380-e6e3f8558166
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(3S,7S,8R,9S,10S,13R,14S,17R)-7-methoxy-17-[(E,2R)-6-methoxy-6-methylhept-4-en-2-yl]-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-3,4,5-triol
• SMILES (Canonical): CC(CC=CC(C)(C)OC)C1CCC2(C1(CCC3(C2C(C=C4C3CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)O)OC)C)C)C
• SMILES (Isomeric): C[C@H](C/C=C/C(C)(C)OC)[C@H]1CC[C@@]2([C@@]1(CC[C@@]3([C@H]2[C@H](C=C4[C@H]3CC[C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)OC)C)C)C
• InChI: InChI=1S/C38H64O8/c1-22(12-11-16-34(2,3)44-10)23-15-17-38(8)32-26(43-9)20-25-24(36(32,6)18-19-37(23,38)7)13-14-28(35(25,4)5)46-33-31(42)30(41)29(40)27(21-39)45-33/h11,16,20,22-24,26-33,39-42H,12-15,17-19,21H2,1-10H3/b16-11+/t22-,23-,24-,26+,27-,28+,29-,30+,31-,32-,33+,36+,37-,38+/m1/s1
• InChI Key: YCUBHAWXGLKZIA-IMIQUVAFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₄O₈
• Molecular Weight: 648.90 g/mol
• Exact Mass: 648.46011900 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 5.41
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8161	81.61%
Caco-2	-	0.8428	84.28%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7889	78.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7975	79.75%
OATP1B3 inhibitior	+	0.8068	80.68%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.4885	48.85%
P-glycoprotein inhibitior	+	0.7688	76.88%
P-glycoprotein substrate	-	0.5463	54.63%
CYP3A4 substrate	+	0.7082	70.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8347	83.47%
CYP3A4 inhibition	-	0.9070	90.70%
CYP2C9 inhibition	-	0.7992	79.92%
CYP2C19 inhibition	-	0.8519	85.19%
CYP2D6 inhibition	-	0.9306	93.06%
CYP1A2 inhibition	-	0.7930	79.30%
CYP2C8 inhibition	+	0.5389	53.89%
CYP inhibitory promiscuity	-	0.8437	84.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6936	69.36%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9255	92.55%
Skin irritation	-	0.6297	62.97%
Skin corrosion	-	0.9460	94.60%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6848	68.48%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.6868	68.68%
skin sensitisation	-	0.8977	89.77%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8786	87.86%
Acute Oral Toxicity (c)	III	0.5925	59.25%
Estrogen receptor binding	+	0.6417	64.17%
Androgen receptor binding	+	0.7298	72.98%
Thyroid receptor binding	-	0.5419	54.19%
Glucocorticoid receptor binding	+	0.7212	72.12%
Aromatase binding	+	0.6930	69.30%
PPAR gamma	+	0.6593	65.93%
Honey bee toxicity	-	0.6806	68.06%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9361	93.61%

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	98.33%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.47%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.42%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.94%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.14%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.09%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.91%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.58%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.45%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.33%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.94%	91.07%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.50%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.23%	97.36%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.94%	97.14%
CHEMBL1977	P11473	Vitamin D receptor	84.49%	99.43%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.16%	100.00%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	83.62%	97.88%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.52%	97.28%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.21%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.08%	89.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.31%	91.03%
CHEMBL5028	O14672	ADAM10	81.02%	97.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.57%	92.62%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.19%	93.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.18%	95.89%

Plants that contains it

• Momordica charantia

Cross-Links

• PubChem: 16093690
• LOTUS: LTS0109636
• wikiData: Q105346497