Dendronobiloside A

Details

• Internal ID: 30ae6fcb-3ab7-4f4b-858b-5e92eda4edd3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(1S,3aR,4R,5R,7aS)-7a-methyl-5-propan-2-yl-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(C)C1CCC2(C(CCC2C1COC3C(C(C(C(O3)CO)O)O)O)COC4C(C(C(C(O4)CO)O)O)O)C
• SMILES (Isomeric): CC(C)[C@H]1CC[C@@]2([C@H](CC[C@@H]2[C@@H]1CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C
• InChI: InChI=1S/C27H48O12/c1-12(2)14-6-7-27(3)13(10-36-25-23(34)21(32)19(30)17(8-28)38-25)4-5-16(27)15(14)11-37-26-24(35)22(33)20(31)18(9-29)39-26/h12-26,28-35H,4-11H2,1-3H3/t13-,14-,15-,16-,17-,18-,19-,20-,21+,22+,23-,24-,25-,26-,27-/m1/s1
• InChI Key: BZZQPBIRQSCVAL-QSTLOTDISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₈O₁₂
• Molecular Weight: 564.70 g/mol
• Exact Mass: 564.31457696 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): -1.67
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

• CHEMBL463632
• (2R,3R,4S,5S,6R)-2-[[(1S,3aR,4R,5R,7aS)-7a-methyl-5-propan-2-yl-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5810	58.10%
Caco-2	-	0.8759	87.59%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7203	72.03%
OATP2B1 inhibitior	-	0.7224	72.24%
OATP1B1 inhibitior	+	0.9094	90.94%
OATP1B3 inhibitior	+	0.8898	88.98%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.9042	90.42%
P-glycoprotein inhibitior	-	0.5790	57.90%
P-glycoprotein substrate	-	0.8873	88.73%
CYP3A4 substrate	+	0.6463	64.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8203	82.03%
CYP3A4 inhibition	-	0.9684	96.84%
CYP2C9 inhibition	-	0.8810	88.10%
CYP2C19 inhibition	-	0.8825	88.25%
CYP2D6 inhibition	-	0.9594	95.94%
CYP1A2 inhibition	-	0.9096	90.96%
CYP2C8 inhibition	-	0.8127	81.27%
CYP inhibitory promiscuity	-	0.9516	95.16%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6776	67.76%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9095	90.95%
Skin irritation	-	0.7492	74.92%
Skin corrosion	-	0.9571	95.71%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6459	64.59%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.7299	72.99%
skin sensitisation	-	0.9401	94.01%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.7966	79.66%
Acute Oral Toxicity (c)	I	0.5240	52.40%
Estrogen receptor binding	+	0.5717	57.17%
Androgen receptor binding	+	0.5972	59.72%
Thyroid receptor binding	+	0.5261	52.61%
Glucocorticoid receptor binding	-	0.5054	50.54%
Aromatase binding	+	0.5947	59.47%
PPAR gamma	+	0.6031	60.31%
Honey bee toxicity	-	0.7767	77.67%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.8399	83.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.89%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.68%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.02%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	96.01%	95.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.61%	96.61%
CHEMBL1937	Q92769	Histone deacetylase 2	93.75%	94.75%
CHEMBL237	P41145	Kappa opioid receptor	93.18%	98.10%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.65%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.65%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	89.39%	90.17%
CHEMBL220	P22303	Acetylcholinesterase	89.16%	94.45%
CHEMBL1871	P10275	Androgen Receptor	87.84%	96.43%
CHEMBL2581	P07339	Cathepsin D	87.79%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.17%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.07%	100.00%
CHEMBL4581	P52732	Kinesin-like protein 1	85.40%	93.18%
CHEMBL5103	Q969S8	Histone deacetylase 10	85.28%	90.08%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.19%	96.47%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.03%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.54%	96.21%
CHEMBL4072	P07858	Cathepsin B	84.06%	93.67%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.10%	96.38%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.65%	100.00%
CHEMBL2996	Q05655	Protein kinase C delta	82.64%	97.79%
CHEMBL2360	P00492	Hypoxanthine-guanine phosphoribosyltransferase	82.52%	87.38%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.57%	95.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.24%	96.77%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.20%	89.05%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.03%	93.04%
CHEMBL5255	O00206	Toll-like receptor 4	80.60%	92.50%

Plants that contains it

• Corydalis conspersa
• Dendrobium nobile
• Gynochthodes parvifolia
• Ligustrum ovalifolium
• Mespilus germanica
• Mikania luetzelburgii
• Pittosporum brevicalyx
• Sideritis grandiflora
• Solanum euacanthum
• Ungernia victoris

Cross-Links

• PubChem: 10030799
• NPASS: NPC50146
• LOTUS: LTS0231441
• wikiData: Q104950783