3beta-[[4-O-(6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)-2,6-dideoxy-3-O-methyl-beta-D-galactopyranosyl]oxy]-14-hydroxy-5beta,14beta-card-20(22)-enolide

Details

• Internal ID: 132bd72d-e4df-44e0-a181-3b13c4113a47
• 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,17R)-14-hydroxy-3-[(2R,4R,5S,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-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(CCC5C6=CC(=O)OC6)O)C)C)OC)OC7C(C(C(C(O7)COC8C(C(C(C(O8)CO)O)O)O)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@@H]4[C@@H]3CC[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)C)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O
• InChI: InChI=1S/C42H66O17/c1-19-37(59-39-36(50)34(48)32(46)28(58-39)18-54-38-35(49)33(47)31(45)27(16-43)57-38)26(52-4)15-30(55-19)56-22-7-10-40(2)21(14-22)5-6-25-24(40)8-11-41(3)23(9-12-42(25,41)51)20-13-29(44)53-17-20/h13,19,21-28,30-39,43,45-51H,5-12,14-18H2,1-4H3/t19-,21-,22+,23-,24+,25-,26-,27-,28-,30+,31-,32-,33+,34+,35-,36-,37+,38-,39+,40+,41-,42+/m1/s1
• InChI Key: ITKDSJDYFJAVTJ-WQRBERDASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₆O₁₇
• Molecular Weight: 843.00 g/mol
• Exact Mass: 842.43000063 g/mol
• Topological Polar Surface Area (TPSA): 253.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.21
• H-Bond Acceptor: 17
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8177	81.77%
Caco-2	-	0.8998	89.98%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7900	79.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9115	91.15%
OATP1B3 inhibitior	+	0.9487	94.87%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8831	88.31%
P-glycoprotein inhibitior	+	0.7404	74.04%
P-glycoprotein substrate	+	0.7880	78.80%
CYP3A4 substrate	+	0.7268	72.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9002	90.02%
CYP3A4 inhibition	-	0.9358	93.58%
CYP2C9 inhibition	-	0.9140	91.40%
CYP2C19 inhibition	-	0.9183	91.83%
CYP2D6 inhibition	-	0.9397	93.97%
CYP1A2 inhibition	-	0.9208	92.08%
CYP2C8 inhibition	-	0.5846	58.46%
CYP inhibitory promiscuity	-	0.9347	93.47%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5835	58.35%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9279	92.79%
Skin irritation	-	0.5686	56.86%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	-	0.6624	66.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8459	84.59%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.9154	91.54%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.8206	82.06%
Acute Oral Toxicity (c)	I	0.7685	76.85%
Estrogen receptor binding	+	0.8495	84.95%
Androgen receptor binding	+	0.8109	81.09%
Thyroid receptor binding	-	0.6768	67.68%
Glucocorticoid receptor binding	+	0.6491	64.91%
Aromatase binding	+	0.7271	72.71%
PPAR gamma	+	0.7697	76.97%
Honey bee toxicity	-	0.6161	61.61%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9043	90.43%

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	98.94%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.43%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.51%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.12%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.82%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.50%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.78%	96.77%
CHEMBL1871	P10275	Androgen Receptor	90.98%	96.43%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.80%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.70%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.81%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	86.96%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.70%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	86.49%	92.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.46%	97.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.80%	95.89%
CHEMBL2581	P07339	Cathepsin D	85.41%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.78%	92.94%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.58%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.57%	94.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.91%	96.21%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.06%	97.14%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.32%	97.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.10%	99.23%

Plants that contains it

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

Cross-Links

• PubChem: 101634825
• NPASS: NPC259960
• LOTUS: LTS0085334
• wikiData: Q105120103