Oleandrin

Details

• Internal ID: d9924092-d20c-4fb6-92a7-8a06810a161a
• 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)-14-hydroxy-3-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-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(CC(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CC(C5C6=CC(=O)OC6)OC(=O)C)O)C)C)OC)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H](C[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)OC)O
• InChI: InChI=1S/C32H48O9/c1-17-29(35)24(37-5)14-27(39-17)41-21-8-10-30(3)20(13-21)6-7-23-22(30)9-11-31(4)28(19-12-26(34)38-16-19)25(40-18(2)33)15-32(23,31)36/h12,17,20-25,27-29,35-36H,6-11,13-16H2,1-5H3/t17-,20+,21-,22-,23+,24-,25-,27-,28-,29-,30-,31+,32-/m0/s1
• InChI Key: JLPDBLFIVFSOCC-XYXFTTADSA-N
• Popularity: 182 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₈O₉
• Molecular Weight: 576.70 g/mol
• Exact Mass: 576.32983310 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.68
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 465-16-7
• Foliandrin
• Neriolin
• Folinerin
• Neriostene
• Oleandrina
• Oleandrine
• Neriol
• II95UDU7I4
• NSC-692219
• [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-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
• CHEBI:59030
• Card-20(22)-enolide, 16-(acetyloxy)-3-((2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)oxy)-14-hydroxy-, (3beta,5beta,16beta)-
• DTXSID40861950
• (3beta,5beta,16beta)-16-acetoxy-3-[(2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
• ((3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-((2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-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
• (3beta,5beta,16beta)-16-acetoxy-3-((2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)oxy)-14-hydroxycard-20(22)-enolide
• RefChem:44190
• DTXCID401474666
• (3 beta,16 beta)-16-(acetyloxy)-3-((2,6-dideoxy-3-O-methyl-L-arabino-hexopyranosyl)oxy)-14-hydroxy card-20(22)-enolide
• (1S,2S,5S,7R,10R,11S,13S,14R,15R)-11-hydroxy-5-((5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy)-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo(8.7.0.02,7.011,15)heptadecan-13-yl acetate
• 207-361-5
• Anvirzel
• Corrigen
• C32H48O9
• PBI 05204
• PBI-05204
• [(3S,8R,9S,10S,13R,14S,16S,17R)-14-Hydroxy-3-[(4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-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
• 1315607-79-4
• Oleandrina [Spanish]
• UNII-II95UDU7I4
• HSDB 3518
• EINECS 207-361-5
• Oleandrin (Standard)
• NSC 692219
• OLEANDRIN [MI]
• OLEANDRIN [WHO-DD]
• SCHEMBL25049
• Oleandrin (PBI-05204)
• orb1301315
• CHEMBL4285883
• Oleandrin, >=98% (HPLC)
• GTPL12618
• JLPDBLFIVFSOCC-XYXFTTADSA-N
• GLXC-10398
• PBI05204
• BDBM50465465
• HY-13719R
• MSK162607
• s6918
• STL565781
• AKOS032430539
• CS-5505
• DB12843
• MO26544
• 16beta-(Acetyloxy)-3beta-((2,6-dideoxy-3-O-methyl-L-arabino-hexopyranosyl)oxy)-14-hydroxycard-20-(22)-enolide
• 16beta-Acetoxy-3beta-(2,6-dideoxy-3-O-methyl-L-arabino-hexopyranosyloxy)-14-hydroxycard-20(22)-enolide
• DA-56415
• HY-13719
• MS-30375
• PBI-05204 (mixture of botanical compounds)
• C19987
• Q411532
• BRD-K98006098-001-01-6
• 5?\,20(22)-Cardenolide-3?, Corrigen, Foliandrin, Folinerin, Neriol, Neriolin, Neriostene
• (3?,5?,16?)-16-(Acetyloxy)-3-[(2,6-dideoxy-3-O-methyl-?-L-arabino-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide;Neriolin;Corrigen
• (3beta,16beta)-16-(Acetyloxy)-3-((2,6-dideoxy-3-O-methyl-L-arabino-hexopyranosyl)oxy)-14-hydroxy card-20(22)-enolide
• (3beta,5beta,16beta)-16-(acetyloxy)-3-[(2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
• [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-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
• CARD-20(22)-ENOLIDE, 16-(ACETYLOXY)-3-((2,6-DIDEOXY-3-O-METHYL-.ALPHA.-L-ARABINO-HEXOPYRANOSYL)OXY)-14-HYDROXY-, (3.BETA.,5.BETA.,16.BETA.)-
• Card-20(22)-enolide, 16-(acetyloxy)-3-((2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)oxy)-14-hydroxy-, (3-beta,5-beta,16-beta)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9759	97.59%
Caco-2	-	0.8135	81.35%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8454	84.54%
OATP2B1 inhibitior	-	0.5765	57.65%
OATP1B1 inhibitior	+	0.9293	92.93%
OATP1B3 inhibitior	+	0.9726	97.26%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8364	83.64%
BSEP inhibitior	+	0.7261	72.61%
P-glycoprotein inhibitior	+	0.6932	69.32%
P-glycoprotein substrate	+	0.8234	82.34%
CYP3A4 substrate	+	0.7305	73.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9043	90.43%
CYP2C19 inhibition	-	0.9471	94.71%
CYP2D6 inhibition	-	0.9540	95.40%
CYP1A2 inhibition	-	0.9087	90.87%
CYP2C8 inhibition	-	0.6203	62.03%
CYP inhibitory promiscuity	-	0.9394	93.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4628	46.28%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9349	93.49%
Skin irritation	+	0.4943	49.43%
Skin corrosion	-	0.9372	93.72%
Ames mutagenesis	-	0.5593	55.93%
Human Ether-a-go-go-Related Gene inhibition	-	0.3887	38.87%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7342	73.42%
skin sensitisation	-	0.9150	91.50%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7210	72.10%
Acute Oral Toxicity (c)	I	0.8422	84.22%
Estrogen receptor binding	+	0.7191	71.91%
Androgen receptor binding	+	0.8096	80.96%
Thyroid receptor binding	-	0.6394	63.94%
Glucocorticoid receptor binding	+	0.7300	73.00%
Aromatase binding	+	0.6765	67.65%
PPAR gamma	+	0.6159	61.59%
Honey bee toxicity	-	0.6083	60.83%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9692	96.92%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.18%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.35%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.02%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.64%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.44%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.46%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.66%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.46%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.38%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.23%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.95%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.91%	91.07%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.88%	82.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.33%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.15%	94.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.29%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.86%	92.50%
CHEMBL4208	P20618	Proteasome component C5	82.59%	90.00%
CHEMBL5028	O14672	ADAM10	81.72%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.53%	91.19%
CHEMBL1871	P10275	Androgen Receptor	81.47%	96.43%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.33%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.29%	97.33%

Plants that contains it

• Aconitum brevicalcaratum
• Cirsium dipsacolepis
• Crinum kirkii
• Cryptotaenia japonica
• Cytisus scoparius
• Heliomeris longifolia var. annua
• Hypericum triquetrifolium
• Isodon japonicus
• Knightia deplanchei
• Mallotus rhamnifolius
• Malva sylvestris
• Mesembryanthemum emarcidum
• Nephroia diversifolia
• Nerium oleander
• Plantago lanceolata
• Plumeria obtusa
• Ptilidium ciliare
• Rhododendron farrerae
• Scutellaria seleriana
• Solanum pimpinellifolium
• Sophora conollyi
• Teucrium pestalozzae
• Toxicodendron succedaneum
• Trichotosia subsessilis
• Trifolium apertum
• Tripodanthus acutifolius
• Veronica pectinata

Cross-Links

• PubChem: 11541511
• NPASS: NPC103534
• LOTUS: LTS0102960
• wikiData: Q411532