Neritaloside

Details

• Internal ID: c63dec86-97b5-41f3-8bdc-2726e781574c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-3-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CC(C5C6=CC(=O)OC6)OC(=O)C)O)C)C)O)OC)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(C[C@@H]([C@@H]5C6=CC(=O)OC6)OC(=O)C)O)C)C)O)OC)O
• InChI: InChI=1S/C32H48O10/c1-16-26(35)28(38-5)27(36)29(40-16)42-20-8-10-30(3)19(13-20)6-7-22-21(30)9-11-31(4)25(18-12-24(34)39-15-18)23(41-17(2)33)14-32(22,31)37/h12,16,19-23,25-29,35-37H,6-11,13-15H2,1-5H3/t16-,19-,20+,21+,22-,23+,25+,26+,27-,28+,29+,30+,31-,32+/m1/s1
• InChI Key: UZQOZJNEDXAJEZ-VZJXLKLWSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₈O₁₀
• Molecular Weight: 592.70 g/mol
• Exact Mass: 592.32474772 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.65
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 465-13-4
• 16-Acetylstrospeside
• Strospeside, 16-acetate
• C32H48O10
• Card-20(22)-enolide, 16-(acetyloxy)-3-((6-deoxy-3-O-methyl-beta-D-galactopyranosyl)oxy)-14-hydroxy-, (3-beta,5-beta,16-beta)-
• CHEMBL510771
• DTXSID401318018
• HY-N3193
• AKOS040744771
• CS-0023547
• Strospeside, 16-acetate (6CI,7CI,8CI); (3,5,16)-16-(Acetyloxy)-3-[(6-deoxy-3-O-methyl--D-galactopyranosyl)oxy]-14-hydroxycard-20(22)-enolide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9507	95.07%
Caco-2	-	0.8435	84.35%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7993	79.93%
OATP2B1 inhibitior	-	0.5849	58.49%
OATP1B1 inhibitior	+	0.9243	92.43%
OATP1B3 inhibitior	+	0.9765	97.65%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8614	86.14%
BSEP inhibitior	-	0.4790	47.90%
P-glycoprotein inhibitior	+	0.6633	66.33%
P-glycoprotein substrate	+	0.7714	77.14%
CYP3A4 substrate	+	0.7334	73.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	-	0.8667	86.67%
CYP2C9 inhibition	-	0.9068	90.68%
CYP2C19 inhibition	-	0.9471	94.71%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.9330	93.30%
CYP2C8 inhibition	+	0.4628	46.28%
CYP inhibitory promiscuity	-	0.9265	92.65%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5140	51.40%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9331	93.31%
Skin irritation	-	0.5328	53.28%
Skin corrosion	-	0.9349	93.49%
Ames mutagenesis	-	0.6393	63.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.6959	69.59%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7092	70.92%
skin sensitisation	-	0.9124	91.24%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7445	74.45%
Acute Oral Toxicity (c)	I	0.8350	83.50%
Estrogen receptor binding	+	0.7143	71.43%
Androgen receptor binding	+	0.7912	79.12%
Thyroid receptor binding	-	0.6627	66.27%
Glucocorticoid receptor binding	+	0.6902	69.02%
Aromatase binding	+	0.6870	68.70%
PPAR gamma	+	0.6287	62.87%
Honey bee toxicity	-	0.6184	61.84%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9625	96.25%

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	98.31%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.02%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.33%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.18%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.02%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.95%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.94%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.12%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.64%	92.94%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	90.13%	81.11%
CHEMBL204	P00734	Thrombin	88.93%	96.01%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.25%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.96%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	85.15%	92.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.55%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.19%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.19%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.61%	97.36%
CHEMBL340	P08684	Cytochrome P450 3A4	83.43%	91.19%
CHEMBL4208	P20618	Proteasome component C5	83.13%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.81%	99.23%
CHEMBL5028	O14672	ADAM10	81.56%	97.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.52%	82.69%
CHEMBL1871	P10275	Androgen Receptor	81.20%	96.43%
CHEMBL2581	P07339	Cathepsin D	80.90%	98.95%

Plants that contains it

• Aconitum brevicalcaratum
• Ammodendron conollyi
• Cirsium dipsacolepis
• Cocculus diversifolius
• Crinum kirkii
• Cytisus scoparius
• Heliomeris longifolia var. annua
• Hypericum triquetrifolium
• Isodon japonicus
• Knightia deplanchei
• Mallotus rhamnifolius
• Malva sylvestris
• Mesembryanthemum emarcidum
• Nerium oleander
• Plantago lanceolata
• Ptilidium ciliare
• Scutellaria seleriana
• Solanum pimpinellifolium
• Teucrium pestalozzae
• Trichotosia subsessilis
• Trifolium apertum
• Tripodanthus acutifolius
• Veronica pectinata

Cross-Links

• PubChem: 44566654
• NPASS: NPC5883