3-[(1S,3R,6R,7R,10R,11S,14S,16R)-14-[(2R,4R,5S,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-6-yl]-2H-furan-5-one

Details

• Internal ID: 19c77911-2b9e-4651-84ce-2c825856430c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(1S,3R,6R,7R,10R,11S,14S,16R)-14-[(2R,4R,5S,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-6-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C(C2)CCC45C3CCC6(C4(O5)CCC6C7=CC(=O)OC7)C)C)OC)OC8C(C(C(C(O8)CO)O)O)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@]45[C@@H]3CC[C@]6([C@]4(O5)CC[C@@H]6C7=CC(=O)OC7)C)C)OC)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O
• InChI: InChI=1S/C36H54O12/c1-18-31(47-32-30(41)29(40)28(39)24(16-37)46-32)23(42-4)15-27(44-18)45-21-6-9-33(2)20(14-21)5-11-35-25(33)8-10-34(3)22(7-12-36(34,35)48-35)19-13-26(38)43-17-19/h13,18,20-25,27-32,37,39-41H,5-12,14-17H2,1-4H3/t18-,20-,21+,22-,23-,24-,25-,27+,28-,29+,30-,31+,32+,33+,34-,35+,36-/m1/s1
• InChI Key: CIZSXZUKRRWNOP-NCCHFIKYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₄O₁₂
• Molecular Weight: 678.80 g/mol
• Exact Mass: 678.36152715 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.12
• H-Bond Acceptor: 12
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7913	79.13%
Caco-2	-	0.8686	86.86%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7600	76.00%
OATP2B1 inhibitior	-	0.8679	86.79%
OATP1B1 inhibitior	+	0.8837	88.37%
OATP1B3 inhibitior	+	0.9497	94.97%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7933	79.33%
P-glycoprotein inhibitior	+	0.7356	73.56%
P-glycoprotein substrate	+	0.6591	65.91%
CYP3A4 substrate	+	0.7256	72.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8875	88.75%
CYP3A4 inhibition	-	0.9188	91.88%
CYP2C9 inhibition	-	0.8145	81.45%
CYP2C19 inhibition	-	0.8323	83.23%
CYP2D6 inhibition	-	0.9291	92.91%
CYP1A2 inhibition	-	0.8522	85.22%
CYP2C8 inhibition	+	0.4458	44.58%
CYP inhibitory promiscuity	-	0.8866	88.66%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6355	63.55%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9266	92.66%
Skin irritation	-	0.6591	65.91%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7610	76.10%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8863	88.63%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7072	70.72%
Acute Oral Toxicity (c)	I	0.6868	68.68%
Estrogen receptor binding	+	0.7188	71.88%
Androgen receptor binding	+	0.7751	77.51%
Thyroid receptor binding	-	0.6603	66.03%
Glucocorticoid receptor binding	+	0.6321	63.21%
Aromatase binding	+	0.6939	69.39%
PPAR gamma	+	0.6838	68.38%
Honey bee toxicity	-	0.6247	62.47%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9428	94.28%

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	98.90%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.25%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.86%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.83%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.34%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.45%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.66%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.23%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.95%	94.00%
CHEMBL2581	P07339	Cathepsin D	87.34%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.88%	97.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.32%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.20%	97.14%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.81%	97.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.27%	85.14%
CHEMBL5255	O00206	Toll-like receptor 4	82.54%	92.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.04%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.75%	96.77%
CHEMBL226	P30542	Adenosine A1 receptor	81.07%	95.93%

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: 102484064
• NPASS: NPC219998