(2E,4E,6R)-6-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-7,7,12,16-tetramethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-N-[(3S,4R,5R)-4,5-dimethyl-2-oxooxolan-3-yl]-2-methylhepta-2,4-dienamide

Details

• Internal ID: 659a1920-1c43-48ee-9d17-2056110e1bc8
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2E,4E,6R)-6-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-7,7,12,16-tetramethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-N-[(3S,4R,5R)-4,5-dimethyl-2-oxooxolan-3-yl]-2-methylhepta-2,4-dienamide
• SMILES (Canonical): CC1C(OC(=O)C1NC(=O)C(=CC=CC(C)C2CCC3(C2(CCC45C3CCC6C4(C5)CCC(C6(C)C)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C)C)C
• SMILES (Isomeric): C[C@H]1[C@H](OC(=O)[C@H]1NC(=O)/C(=C/C=C/[C@@H](C)[C@H]2CC[C@@]3([C@@]2(CC[C@]45[C@H]3CC[C@@H]6[C@]4(C5)CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)/C)C
• InChI: InChI=1S/C48H75NO14/c1-23(10-9-11-24(2)40(57)49-33-25(3)26(4)59-41(33)58)27-14-16-46(8)31-13-12-30-44(5,6)32(15-17-47(30)22-48(31,47)19-18-45(27,46)7)62-43-39(37(55)35(53)29(21-51)61-43)63-42-38(56)36(54)34(52)28(20-50)60-42/h9-11,23,25-39,42-43,50-56H,12-22H2,1-8H3,(H,49,57)/b10-9+,24-11+/t23-,25+,26-,27-,28-,29-,30+,31+,32+,33+,34-,35-,36+,37+,38-,39-,42+,43+,45-,46+,47-,48+/m1/s1
• InChI Key: SMLUUCVJPGLTPV-WMRYDCPASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₅NO₁₄
• Molecular Weight: 890.10 g/mol
• Exact Mass: 889.51875607 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 2.64
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4775	47.75%
Caco-2	-	0.8695	86.95%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6884	68.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7769	77.69%
OATP1B3 inhibitior	+	0.9203	92.03%
MATE1 inhibitior	-	0.9646	96.46%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8902	89.02%
P-glycoprotein inhibitior	+	0.7532	75.32%
P-glycoprotein substrate	+	0.6070	60.70%
CYP3A4 substrate	+	0.7328	73.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8822	88.22%
CYP3A4 inhibition	-	0.9151	91.51%
CYP2C9 inhibition	-	0.8140	81.40%
CYP2C19 inhibition	-	0.8376	83.76%
CYP2D6 inhibition	-	0.9341	93.41%
CYP1A2 inhibition	-	0.8705	87.05%
CYP2C8 inhibition	+	0.6598	65.98%
CYP inhibitory promiscuity	-	0.7125	71.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5370	53.70%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.9044	90.44%
Skin irritation	-	0.7255	72.55%
Skin corrosion	-	0.9236	92.36%
Ames mutagenesis	-	0.7054	70.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8284	82.84%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.6975	69.75%
skin sensitisation	-	0.8464	84.64%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.4684	46.84%
Acute Oral Toxicity (c)	III	0.6293	62.93%
Estrogen receptor binding	+	0.7810	78.10%
Androgen receptor binding	+	0.7516	75.16%
Thyroid receptor binding	+	0.5347	53.47%
Glucocorticoid receptor binding	+	0.7603	76.03%
Aromatase binding	+	0.6499	64.99%
PPAR gamma	+	0.7921	79.21%
Honey bee toxicity	-	0.6021	60.21%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9580	95.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.73%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.05%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.62%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	94.00%	96.21%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	93.98%	95.58%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	92.58%	98.75%
CHEMBL2581	P07339	Cathepsin D	91.18%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.82%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.48%	96.61%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.99%	92.88%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.61%	97.14%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.34%	94.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.57%	99.17%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	86.28%	97.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.60%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.55%	96.77%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.46%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.43%	96.47%
CHEMBL5255	O00206	Toll-like receptor 4	85.19%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.73%	91.24%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.68%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.67%	95.56%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.60%	95.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.49%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.25%	93.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.93%	89.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.75%	93.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.49%	96.38%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.27%	89.34%
CHEMBL340	P08684	Cytochrome P450 3A4	80.86%	91.19%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.51%	92.86%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.50%	95.71%

Plants that contains it

• Mussaenda pubescens

Cross-Links

• PubChem: 162981236
• LOTUS: LTS0275381
• wikiData: Q105256010