2-[4-Hydroxy-2-(hydroxymethyl)-6-[(10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl)oxy]-5-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol

Details

• Internal ID: 80f0a7d4-e31b-49eb-b864-6eac86fc6c78
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: 2-[4-hydroxy-2-(hydroxymethyl)-6-[(10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl)oxy]-5-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1CCC2C(C3C(N2C1)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C
• SMILES (Isomeric): CC1CCC2C(C3C(N2C1)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C
• InChI: InChI=1S/C45H73NO14/c1-19-7-10-28-20(2)31-29(46(28)17-19)16-27-25-9-8-23-15-24(11-13-44(23,5)26(25)12-14-45(27,31)6)57-43-40(60-42-37(53)35(51)33(49)22(4)56-42)38(54)39(30(18-47)58-43)59-41-36(52)34(50)32(48)21(3)55-41/h8,19-22,24-43,47-54H,7,9-18H2,1-6H3
• InChI Key: TYNQWWGVEGFKRU-UHFFFAOYSA-N
• Popularity: 123 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₃NO₁₄
• Molecular Weight: 852.10 g/mol
• Exact Mass: 851.50310600 g/mol
• Topological Polar Surface Area (TPSA): 221.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.18
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• 2-[4-hydroxy-2-(hydroxymethyl)-6-[(10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl)oxy]-5-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• 20562-03-2
• a-Chaconine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5433	54.33%
Caco-2	-	0.8845	88.45%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5015	50.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8773	87.73%
OATP1B3 inhibitior	+	0.9358	93.58%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.8243	82.43%
P-glycoprotein inhibitior	+	0.7255	72.55%
P-glycoprotein substrate	+	0.5778	57.78%
CYP3A4 substrate	+	0.7458	74.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7546	75.46%
CYP3A4 inhibition	-	0.9600	96.00%
CYP2C9 inhibition	-	0.9394	93.94%
CYP2C19 inhibition	-	0.9285	92.85%
CYP2D6 inhibition	-	0.9048	90.48%
CYP1A2 inhibition	-	0.9142	91.42%
CYP2C8 inhibition	+	0.6484	64.84%
CYP inhibitory promiscuity	-	0.8908	89.08%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Danger	0.5161	51.61%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.9179	91.79%
Skin irritation	-	0.7004	70.04%
Skin corrosion	-	0.9237	92.37%
Ames mutagenesis	-	0.9800	98.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7804	78.04%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.8623	86.23%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6899	68.99%
Acute Oral Toxicity (c)	III	0.7950	79.50%
Estrogen receptor binding	+	0.8627	86.27%
Androgen receptor binding	+	0.7279	72.79%
Thyroid receptor binding	-	0.5720	57.20%
Glucocorticoid receptor binding	-	0.6506	65.06%
Aromatase binding	+	0.6453	64.53%
PPAR gamma	+	0.7274	72.74%
Honey bee toxicity	-	0.6174	61.74%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.7950	79.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.16%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.47%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	97.28%	95.93%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	96.73%	89.05%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.76%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.22%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.97%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.62%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.43%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.86%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.95%	95.89%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	88.91%	98.46%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.58%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.34%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.95%	94.00%
CHEMBL1914	P06276	Butyrylcholinesterase	82.52%	95.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.48%	92.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.45%	96.90%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.80%	94.45%
CHEMBL332	P03956	Matrix metalloproteinase-1	81.52%	94.50%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.47%	86.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.28%	97.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.07%	100.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.85%	92.86%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.28%	92.94%
CHEMBL1871	P10275	Androgen Receptor	80.21%	96.43%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.05%	95.56%

Plants that contains it

• Solanum stoloniferum
• Solanum tuberosum

Cross-Links

• PubChem: 4115417
• LOTUS: LTS0017813
• wikiData: Q105323915