Nudifloside B

Details

• Internal ID: 613ae30a-1023-45fd-be92-0093f42734d2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (4S,5E,6S)-5-ethylidene-4-[2-[[(5R,6S,7S,9S,10R,15S,16E,17S)-16-ethylidene-5,9-dimethyl-2,13-dioxo-17-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,12,18-trioxatricyclo[13.4.0.06,10]nonadec-1(19)-en-7-yl]oxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• SMILES (Canonical): CC=C1C2CC(=O)OCC3C(CC(C3C(COC(=O)C2=COC1OC4C(C(C(C(O4)CO)O)O)O)C)OC(=O)CC5C(=COC(C5=CC)OC6C(C(C(C(O6)CO)O)O)O)C(=O)OC)C
• SMILES (Isomeric): C/C=C/1\[C@@H]2CC(=O)OC[C@@H]3[C@H](C[C@@H]([C@H]3[C@H](COC(=O)C2=CO[C@H]1O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C)OC(=O)C[C@@H]\5C(=CO[C@H](/C5=C/C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C(=O)OC)C
• InChI: InChI=1S/C43H60O22/c1-6-19-21-9-29(46)57-14-23-17(3)8-26(31(23)18(4)13-58-39(55)25(21)16-60-40(19)64-42-36(52)34(50)32(48)27(11-44)62-42)61-30(47)10-22-20(7-2)41(59-15-24(22)38(54)56-5)65-43-37(53)35(51)33(49)28(12-45)63-43/h6-7,15-18,21-23,26-28,31-37,40-45,48-53H,8-14H2,1-5H3/b19-6+,20-7+/t17-,18-,21-,22-,23+,26-,27+,28+,31-,32+,33+,34-,35-,36+,37+,40-,41-,42-,43-/m0/s1
• InChI Key: MTAJKOPZPBBTGY-GKGRVPSRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₀O₂₂
• Molecular Weight: 928.90 g/mol
• Exact Mass: 928.35762354 g/mol
• Topological Polar Surface Area (TPSA): 322.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.90
• H-Bond Acceptor: 22
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

• Nudifloside B
• Methyl (4S,5E,6S)-5-ethylidene-4-[2-[[(5R,6S,7S,9S,10R,15S,16E,17S)-16-ethylidene-5,9-dimethyl-2,13-dioxo-17-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,12,18-trioxatricyclo[13.4.0.06,10]nonadec-1(19)-en-7-yl]oxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• NudiflosideB
• AKOS040762126

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7074	70.74%
Caco-2	-	0.8673	86.73%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7639	76.39%
OATP2B1 inhibitior	-	0.8641	86.41%
OATP1B1 inhibitior	+	0.7631	76.31%
OATP1B3 inhibitior	+	0.9182	91.82%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9155	91.55%
P-glycoprotein inhibitior	+	0.7406	74.06%
P-glycoprotein substrate	+	0.7162	71.62%
CYP3A4 substrate	+	0.7237	72.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8905	89.05%
CYP3A4 inhibition	-	0.8445	84.45%
CYP2C9 inhibition	-	0.9220	92.20%
CYP2C19 inhibition	-	0.8992	89.92%
CYP2D6 inhibition	-	0.9365	93.65%
CYP1A2 inhibition	-	0.8717	87.17%
CYP2C8 inhibition	+	0.7480	74.80%
CYP inhibitory promiscuity	-	0.9365	93.65%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6541	65.41%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9050	90.50%
Skin irritation	-	0.6980	69.80%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.5232	52.32%
Human Ether-a-go-go-Related Gene inhibition	+	0.6525	65.25%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9033	90.33%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.4675	46.75%
Acute Oral Toxicity (c)	III	0.4985	49.85%
Estrogen receptor binding	+	0.8045	80.45%
Androgen receptor binding	+	0.7035	70.35%
Thyroid receptor binding	+	0.5395	53.95%
Glucocorticoid receptor binding	+	0.7745	77.45%
Aromatase binding	+	0.6025	60.25%
PPAR gamma	+	0.7535	75.35%
Honey bee toxicity	-	0.6260	62.60%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9561	95.61%

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	98.06%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.46%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.39%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.41%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.37%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.58%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.92%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.23%	86.92%
CHEMBL299	P17252	Protein kinase C alpha	88.39%	98.03%
CHEMBL2996	Q05655	Protein kinase C delta	87.89%	97.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.16%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.95%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.24%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	85.09%	92.50%
CHEMBL220	P22303	Acetylcholinesterase	84.91%	94.45%
CHEMBL5028	O14672	ADAM10	83.89%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.83%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.60%	95.83%
CHEMBL221	P23219	Cyclooxygenase-1	81.78%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.13%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.75%	91.24%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.31%	94.00%

Plants that contains it

• Euonymus japonicus
• Jasminum nudiflorum

Cross-Links

• PubChem: 11803920
• NPASS: NPC237501
• LOTUS: LTS0228679
• wikiData: Q105171576