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

Details

• Internal ID: feb1a224-1d4d-493c-8952-ec85f57462f0
• 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-(hydroxymethyl)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)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@@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)O)O)O
• InChI: InChI=1S/C36H56O12/c1-18-32(48-33-31(41)30(40)29(39)26(16-37)47-33)25(43-4)15-28(45-18)46-21-7-10-34(2)20(14-21)5-6-24-23(34)8-11-35(3)22(9-12-36(24,35)42)19-13-27(38)44-17-19/h13,18,20-26,28-33,37,39-42H,5-12,14-17H2,1-4H3/t18-,20-,21+,22-,23+,24-,25-,26-,28+,29-,30+,31-,32+,33+,34+,35-,36+/m1/s1
• InChI Key: BPGWSHOXZQEBEG-GNNLKLMMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₆O₁₂
• Molecular Weight: 680.80 g/mol
• Exact Mass: 680.37717722 g/mol
• Topological Polar Surface Area (TPSA): 174.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.96
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8177	81.77%
Caco-2	-	0.8740	87.40%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7900	79.00%
OATP2B1 inhibitior	-	0.7380	73.80%
OATP1B1 inhibitior	+	0.9232	92.32%
OATP1B3 inhibitior	+	0.9487	94.87%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7057	70.57%
P-glycoprotein inhibitior	+	0.7152	71.52%
P-glycoprotein substrate	+	0.7774	77.74%
CYP3A4 substrate	+	0.7192	71.92%
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	-	0.6884	68.84%
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	-	0.9304	93.04%
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	+	0.7660	76.60%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.9154	91.54%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.8480	84.80%
Acute Oral Toxicity (c)	I	0.7685	76.85%
Estrogen receptor binding	+	0.7652	76.52%
Androgen receptor binding	+	0.8365	83.65%
Thyroid receptor binding	-	0.7044	70.44%
Glucocorticoid receptor binding	+	0.6050	60.50%
Aromatase binding	+	0.6930	69.30%
PPAR gamma	+	0.6586	65.86%
Honey bee toxicity	-	0.6133	61.33%
Biodegradation	-	0.6750	67.50%
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	98.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.28%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.51%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.89%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.03%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.49%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.45%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.91%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.23%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.14%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.59%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.55%	92.94%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.80%	95.89%
CHEMBL2581	P07339	Cathepsin D	85.63%	98.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.29%	96.21%
CHEMBL1871	P10275	Androgen Receptor	84.70%	96.43%
CHEMBL5255	O00206	Toll-like receptor 4	83.90%	92.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.37%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.33%	94.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.37%	97.14%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.35%	97.33%

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: 101634824
• NPASS: NPC74221