CID 101633451

Details

• Internal ID: 1aa7d69e-72aa-431b-bed4-e9429c7c343e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14,16-dihydroxy-3-[(2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-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(CC(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CC(C5C6=CC(=O)OC6)O)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)O)O)C)C)OC)O
• InChI: InChI=1S/C30H46O8/c1-16-27(33)23(35-4)13-25(37-16)38-19-7-9-28(2)18(12-19)5-6-21-20(28)8-10-29(3)26(17-11-24(32)36-15-17)22(31)14-30(21,29)34/h11,16,18-23,25-27,31,33-34H,5-10,12-15H2,1-4H3/t16-,18-,19+,20+,21-,22+,23-,25+,26+,27+,28+,29-,30+/m1/s1
• InChI Key: ROKXRURUBUVHBD-GYSSGZLQSA-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: 2.30
• Atomic LogP (AlogP): 3.11
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• DTXSID201025124
• 3-[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14,16-Dihydroxy-3-[(2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-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
• 3beta-[(3-O-Methyl-2,6-dideoxy-beta-D-lyxo-hexopyranosyl)oxy]-14,16beta-dihydroxy-5beta-carda-20(22)-enolide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9583	95.83%
Caco-2	-	0.7955	79.55%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7896	78.96%
OATP2B1 inhibitior	-	0.5839	58.39%
OATP1B1 inhibitior	+	0.9343	93.43%
OATP1B3 inhibitior	+	0.9683	96.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7501	75.01%
P-glycoprotein inhibitior	-	0.4341	43.41%
P-glycoprotein substrate	+	0.8290	82.90%
CYP3A4 substrate	+	0.7216	72.16%
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	-	0.7703	77.03%
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	-	0.9357	93.57%
Skin irritation	-	0.5363	53.63%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.5493	54.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.6749	67.49%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.7192	71.92%
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	-	0.7742	77.42%
Acute Oral Toxicity (c)	I	0.7811	78.11%
Estrogen receptor binding	+	0.7539	75.39%
Androgen receptor binding	+	0.8207	82.07%
Thyroid receptor binding	-	0.6125	61.25%
Glucocorticoid receptor binding	+	0.7606	76.06%
Aromatase binding	+	0.7335	73.35%
PPAR gamma	+	0.5281	52.81%
Honey bee toxicity	-	0.6409	64.09%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9474	94.74%

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	97.57%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.29%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.90%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.19%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.05%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.63%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.96%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.92%	85.14%
CHEMBL1871	P10275	Androgen Receptor	89.49%	96.43%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.07%	96.77%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.95%	92.94%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.89%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.07%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.09%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.32%	94.00%
CHEMBL2581	P07339	Cathepsin D	84.81%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.81%	97.14%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.57%	97.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.70%	82.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.36%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.70%	91.07%

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: 101633451
• NPASS: NPC235842
• LOTUS: LTS0128360
• wikiData: Q105242286