Neriifoside

Details

• Internal ID: fcef7c9e-110b-4dd4-ad81-f713a9664f2f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5S,8R,9S,10S,13R,14S,17R)-3-[(2R,3R,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)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(CC[C@@H]5C6=CC(=O)OC6)O)C)C)O)OC)O
• InChI: InChI=1S/C30H46O8/c1-16-24(32)26(35-4)25(33)27(37-16)38-19-7-10-28(2)18(14-19)5-6-22-21(28)8-11-29(3)20(9-12-30(22,29)34)17-13-23(31)36-15-17/h13,16,18-22,24-27,32-34H,5-12,14-15H2,1-4H3/t16-,18-,19-,20+,21-,22+,24-,25+,26+,27-,28-,29+,30-/m0/s1
• InChI Key: VPUNMTHWNSJUOG-QJGGEYRBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆O₈
• Molecular Weight: 534.70 g/mol
• Exact Mass: 534.31926842 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 3.11
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9583	95.83%
Caco-2	-	0.8001	80.01%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7896	78.96%
OATP2B1 inhibitior	-	0.5896	58.96%
OATP1B1 inhibitior	+	0.9427	94.27%
OATP1B3 inhibitior	+	0.9683	96.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.4534	45.34%
P-glycoprotein inhibitior	-	0.4422	44.22%
P-glycoprotein substrate	+	0.7776	77.76%
CYP3A4 substrate	+	0.7025	70.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9037	90.37%
CYP3A4 inhibition	-	0.8949	89.49%
CYP2C9 inhibition	-	0.9092	90.92%
CYP2C19 inhibition	-	0.9351	93.51%
CYP2D6 inhibition	-	0.9376	93.76%
CYP1A2 inhibition	-	0.9214	92.14%
CYP2C8 inhibition	-	0.7762	77.62%
CYP inhibitory promiscuity	-	0.8900	89.00%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5406	54.06%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9407	94.07%
Skin irritation	-	0.5363	53.63%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.6624	66.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7657	76.57%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.7926	79.26%
skin sensitisation	-	0.9064	90.64%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8134	81.34%
Acute Oral Toxicity (c)	I	0.7811	78.11%
Estrogen receptor binding	+	0.7185	71.85%
Androgen receptor binding	+	0.8181	81.81%
Thyroid receptor binding	-	0.5933	59.33%
Glucocorticoid receptor binding	+	0.6930	69.30%
Aromatase binding	+	0.6728	67.28%
PPAR gamma	+	0.5476	54.76%
Honey bee toxicity	-	0.6655	66.55%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9474	94.74%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	31.6 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	70.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.36%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.17%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.56%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.17%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.41%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.66%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.50%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.70%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.78%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.73%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.66%	82.69%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.06%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.38%	94.00%
CHEMBL1871	P10275	Androgen Receptor	86.74%	96.43%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	86.54%	81.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.46%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.16%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.35%	99.23%
CHEMBL3038469	P24941	CDK2/Cyclin A	82.23%	91.38%
CHEMBL2581	P07339	Cathepsin D	82.05%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.49%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	81.42%	92.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.25%	97.25%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.96%	97.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.64%	90.71%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.04%	93.04%

Plants that contains it

• Cascabela thevetia
• Nerium oleander

Cross-Links

• PubChem: 101634641
• NPASS: NPC253568
• LOTUS: LTS0173549
• wikiData: Q105291019