(2E,4E,6R)-6-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-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: 0c966429-e7bf-4281-b0f0-9fa3f9417884
• 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)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-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)OC8C(C(C(C(O8)C)O)O)O)O)OC9C(C(C(C(O9)COC1C(C(C(C(O1)CO)O)O)O)O)O)OC1C(C(C(C(O1)C)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[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)C)C)/C)C
• InChI: InChI=1S/C66H105NO27/c1-26(12-11-13-27(2)55(82)67-39-28(3)29(4)85-56(39)83)32-16-18-64(10)37-15-14-36-62(7,8)38(17-19-65(36)25-66(37,65)21-20-63(32,64)9)91-60-54(51(81)52(34(23-69)89-60)92-58-49(79)44(74)40(70)30(5)86-58)94-61-53(93-59-50(80)45(75)41(71)31(6)87-59)47(77)43(73)35(90-61)24-84-57-48(78)46(76)42(72)33(22-68)88-57/h11-13,26,28-54,57-61,68-81H,14-25H2,1-10H3,(H,67,82)/b12-11+,27-13+/t26-,28+,29-,30+,31+,32-,33-,34-,35-,36+,37+,38+,39+,40+,41+,42-,43-,44-,45-,46+,47+,48-,49-,50-,51+,52-,53-,54-,57-,58+,59+,60+,61+,63-,64+,65-,66+/m1/s1
• InChI Key: NJMKFBJXWPURTF-JPNQMDOFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₆₆H₁₀₅NO₂₇
• Molecular Weight: 1344.50 g/mol
• Exact Mass: 1343.68739707 g/mol
• Topological Polar Surface Area (TPSA): 431.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -1.83
• H-Bond Acceptor: 27
• H-Bond Donor: 15
• Rotatable Bonds: 18

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	-	0.8619	86.19%
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	+	0.7921	79.21%
OATP1B3 inhibitior	+	0.9203	92.03%
MATE1 inhibitior	-	0.9646	96.46%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9464	94.64%
P-glycoprotein inhibitior	+	0.7437	74.37%
P-glycoprotein substrate	+	0.6959	69.59%
CYP3A4 substrate	+	0.7428	74.28%
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	+	0.7476	74.76%
CYP inhibitory promiscuity	-	0.7125	71.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5370	53.70%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.8972	89.72%
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	+	0.7759	77.59%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.6850	68.50%
skin sensitisation	-	0.8464	84.64%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6161	61.61%
Acute Oral Toxicity (c)	III	0.6293	62.93%
Estrogen receptor binding	+	0.7233	72.33%
Androgen receptor binding	+	0.7531	75.31%
Thyroid receptor binding	+	0.6478	64.78%
Glucocorticoid receptor binding	+	0.7811	78.11%
Aromatase binding	+	0.7108	71.08%
PPAR gamma	+	0.8170	81.70%
Honey bee toxicity	-	0.5941	59.41%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
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	99.26%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.88%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.73%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.74%	96.61%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	92.09%	98.75%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	92.04%	95.58%
CHEMBL2581	P07339	Cathepsin D	91.90%	98.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.34%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.27%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.56%	94.45%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	86.77%	95.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.59%	97.09%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	85.62%	97.47%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.56%	92.88%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.33%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	85.15%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.03%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.69%	96.77%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.64%	93.04%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.62%	99.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.62%	94.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.50%	95.71%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.26%	97.14%
CHEMBL1937	Q92769	Histone deacetylase 2	84.07%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.92%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.13%	96.38%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.90%	96.47%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.81%	89.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.69%	91.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.33%	95.83%
CHEMBL340	P08684	Cytochrome P450 3A4	82.10%	91.19%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.95%	100.00%
CHEMBL5957	P21589	5'-nucleotidase	81.68%	97.78%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.27%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	81.00%	90.17%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.75%	92.86%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.57%	93.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.57%	95.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.24%	93.00%

Plants that contains it

• Mussaenda pubescens

Cross-Links

• PubChem: 163019684
• LOTUS: LTS0105496
• wikiData: Q105180201