(2R,3S,4R,5R,6R)-2-(hydroxymethyl)-6-[[(3S,7R,8R,9S,10S,13R,14S,17R)-17-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-7-methoxy-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: d8c91195-5888-4162-ad02-f34f789b70d8
• 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-[[(3S,7R,8R,9S,10S,13R,14S,17R)-17-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-7-methoxy-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)O)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)O)[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/C37H62O8/c1-21(11-10-15-33(2,3)42)22-14-16-37(8)31-25(43-9)19-24-23(35(31,6)17-18-36(22,37)7)12-13-27(34(24,4)5)45-32-30(41)29(40)28(39)26(20-38)44-32/h10,15,19,21-23,25-32,38-42H,11-14,16-18,20H2,1-9H3/b15-10+/t21-,22-,23-,25-,26-,27+,28-,29-,30-,31-,32+,35+,36-,37+/m1/s1
• InChI Key: SQGCPGUUCGINMK-FTNJYLMYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₆₂O₈
• Molecular Weight: 634.90 g/mol
• Exact Mass: 634.44446893 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.75
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8161	81.61%
Caco-2	-	0.8361	83.61%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7889	78.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8060	80.60%
OATP1B3 inhibitior	+	0.8068	80.68%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.5190	51.90%
P-glycoprotein inhibitior	+	0.7592	75.92%
P-glycoprotein substrate	-	0.5881	58.81%
CYP3A4 substrate	+	0.7080	70.80%
CYP2C9 substrate	-	0.8020	80.20%
CYP2D6 substrate	-	0.8461	84.61%
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	+	0.5603	56.03%
CYP inhibitory promiscuity	-	0.8437	84.37%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6936	69.36%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9283	92.83%
Skin irritation	-	0.6297	62.97%
Skin corrosion	-	0.9460	94.60%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7208	72.08%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.7368	73.68%
skin sensitisation	-	0.8977	89.77%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8848	88.48%
Acute Oral Toxicity (c)	III	0.5925	59.25%
Estrogen receptor binding	+	0.6220	62.20%
Androgen receptor binding	+	0.7237	72.37%
Thyroid receptor binding	-	0.5396	53.96%
Glucocorticoid receptor binding	+	0.6880	68.80%
Aromatase binding	+	0.6866	68.66%
PPAR gamma	+	0.6459	64.59%
Honey bee toxicity	-	0.6885	68.85%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
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	98.51%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.37%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.40%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.30%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.77%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.62%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.48%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.22%	96.61%
CHEMBL1977	P11473	Vitamin D receptor	90.07%	99.43%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	88.82%	100.00%
CHEMBL2581	P07339	Cathepsin D	87.29%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.00%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.18%	86.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.45%	100.00%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	84.15%	97.88%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.57%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.50%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.18%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.12%	93.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.27%	92.62%
CHEMBL5028	O14672	ADAM10	81.02%	97.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.74%	97.28%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.45%	97.36%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.20%	91.03%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.18%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.09%	93.56%

Plants that contains it

• Momordica charantia

Cross-Links

• PubChem: 162932342
• LOTUS: LTS0033499
• wikiData: Q105257881