Cardenolide B-3

Details

• Internal ID: f869cfda-6c97-4be0-a596-36a157504c47
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(1R,3S,5S,7S,10S,11R,14R,15R,18R)-18-hydroxy-7-[(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-10,14-dimethyl-2-oxapentacyclo[9.7.0.01,3.05,10.014,18]octadecan-15-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C4CCC5(C(CCC5(C46C(O6)CC3C2)O)C7=CC(=O)OC7)C)C)OC)OC8C(C(C(C(O8)COC9C(C(C(C(O9)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]4CC[C@@]5([C@H](CC[C@@]5([C@]46[C@@H](O6)C[C@@H]3C2)O)C7=CC(=O)OC7)C)C)OC)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O)O
• InChI: InChI=1S/C42H64O18/c1-18-36(59-38-35(50)33(48)31(46)25(58-38)17-54-37-34(49)32(47)30(45)24(15-43)57-37)23(52-4)14-29(55-18)56-21-5-8-39(2)20(12-21)13-27-42(60-27)26(39)7-9-40(3)22(6-10-41(40,42)51)19-11-28(44)53-16-19/h11,18,20-27,29-38,43,45-51H,5-10,12-17H2,1-4H3/t18-,20+,21+,22-,23-,24-,25-,26-,27+,29+,30-,31-,32+,33+,34-,35-,36+,37-,38+,39+,40-,41-,42-/m1/s1
• InChI Key: CDDZQSPMZJIHKC-PIIDMWCDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₄O₁₈
• Molecular Weight: 856.90 g/mol
• Exact Mass: 856.40926519 g/mol
• Topological Polar Surface Area (TPSA): 265.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.08
• H-Bond Acceptor: 18
• 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	+	0.8225	82.25%
Caco-2	-	0.8951	89.51%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7203	72.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8759	87.59%
OATP1B3 inhibitior	+	0.9589	95.89%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9032	90.32%
P-glycoprotein inhibitior	+	0.7423	74.23%
P-glycoprotein substrate	+	0.7444	74.44%
CYP3A4 substrate	+	0.7388	73.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8901	89.01%
CYP3A4 inhibition	-	0.8737	87.37%
CYP2C9 inhibition	-	0.8101	81.01%
CYP2C19 inhibition	-	0.8481	84.81%
CYP2D6 inhibition	-	0.9268	92.68%
CYP1A2 inhibition	-	0.8719	87.19%
CYP2C8 inhibition	+	0.5399	53.99%
CYP inhibitory promiscuity	-	0.9327	93.27%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6227	62.27%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9222	92.22%
Skin irritation	-	0.6276	62.76%
Skin corrosion	-	0.9358	93.58%
Ames mutagenesis	-	0.6279	62.79%
Human Ether-a-go-go-Related Gene inhibition	+	0.8503	85.03%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.5873	58.73%
skin sensitisation	-	0.8850	88.50%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6570	65.70%
Acute Oral Toxicity (c)	I	0.6944	69.44%
Estrogen receptor binding	+	0.8369	83.69%
Androgen receptor binding	+	0.7681	76.81%
Thyroid receptor binding	-	0.6219	62.19%
Glucocorticoid receptor binding	+	0.6700	67.00%
Aromatase binding	+	0.7096	70.96%
PPAR gamma	+	0.7878	78.78%
Honey bee toxicity	-	0.6328	63.28%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9165	91.65%

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	97.39%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.55%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.66%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.45%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.38%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.18%	85.14%
CHEMBL2581	P07339	Cathepsin D	92.24%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.53%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.13%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.88%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.60%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.20%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.18%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	87.08%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.91%	95.89%
CHEMBL1871	P10275	Androgen Receptor	84.86%	96.43%
CHEMBL5255	O00206	Toll-like receptor 4	84.85%	92.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.28%	96.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.16%	94.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.04%	89.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.63%	97.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.09%	97.14%

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: 101482497
• NPASS: NPC209357
• LOTUS: LTS0044054
• wikiData: Q104954271