gamma-Chaconine

Details

• Internal ID: 6055c210-aeb3-4e7d-a030-61a18cc9494c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]oxane-3,4,5-triol
• SMILES (Canonical): CC1CCC2C(C3C(N2C1)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)O)O)C)C)C
• SMILES (Isomeric): C[C@H]1CC[C@@H]2[C@H]([C@H]3[C@@H](N2C1)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)C)C
• InChI: InChI=1S/C33H53NO6/c1-17-5-8-24-18(2)27-25(34(24)15-17)14-23-21-7-6-19-13-20(9-11-32(19,3)22(21)10-12-33(23,27)4)39-31-30(38)29(37)28(36)26(16-35)40-31/h6,17-18,20-31,35-38H,5,7-16H2,1-4H3/t17-,18+,20-,21+,22-,23-,24+,25-,26+,27-,28+,29-,30+,31+,32-,33-/m0/s1
• InChI Key: IDGKMGZVTKHZDA-OSCYGWHCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₃NO₆
• Molecular Weight: 559.80 g/mol
• Exact Mass: 559.38728841 g/mol
• Topological Polar Surface Area (TPSA): 103.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 3.48
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 511-36-4
• GGO73MR9P5
• (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]oxane-3,4,5-triol
• UNII-GGO73MR9P5
• beta-D-Glucopyranoside, (3beta)-solanid-5-en-3-yl
• .GAMMA.-CHACONINE
• DTXSID90965376
• CHEBI:176052
• SOLANIDINE-3-O-.BETA.-D-GLUCOPYRANOSIDE
• (3beta)-Solanid-5-en-3-yl beta-D-glucopyranoside
• Q27279097
• .BETA.-D-GLUCOPYRANOSIDE, (3.BETA.)-SOLANID-5-EN-3-YL

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6414	64.14%
Caco-2	-	0.8385	83.85%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5229	52.29%
OATP2B1 inhibitior	-	0.7182	71.82%
OATP1B1 inhibitior	+	0.8777	87.77%
OATP1B3 inhibitior	+	0.9273	92.73%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.6894	68.94%
P-glycoprotein inhibitior	+	0.6071	60.71%
P-glycoprotein substrate	-	0.5127	51.27%
CYP3A4 substrate	+	0.7366	73.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7546	75.46%
CYP3A4 inhibition	-	0.9623	96.23%
CYP2C9 inhibition	-	0.9280	92.80%
CYP2C19 inhibition	-	0.9301	93.01%
CYP2D6 inhibition	-	0.9137	91.37%
CYP1A2 inhibition	-	0.9272	92.72%
CYP2C8 inhibition	+	0.5714	57.14%
CYP inhibitory promiscuity	-	0.9012	90.12%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Danger	0.4950	49.50%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.9458	94.58%
Skin irritation	-	0.7078	70.78%
Skin corrosion	-	0.9264	92.64%
Ames mutagenesis	-	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7351	73.51%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8677	86.77%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.5643	56.43%
Acute Oral Toxicity (c)	III	0.7971	79.71%
Estrogen receptor binding	+	0.6540	65.40%
Androgen receptor binding	+	0.7170	71.70%
Thyroid receptor binding	-	0.6303	63.03%
Glucocorticoid receptor binding	-	0.5131	51.31%
Aromatase binding	+	0.5430	54.30%
PPAR gamma	-	0.5366	53.66%
Honey bee toxicity	-	0.6955	69.55%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8207	82.07%

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	99.20%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.21%	97.25%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	96.85%	89.05%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.42%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	95.38%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.36%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.47%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.70%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.51%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.58%	95.89%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	86.06%	86.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.56%	89.00%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	85.53%	98.46%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.10%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.82%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	83.12%	92.50%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.71%	92.86%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.05%	96.90%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.32%	92.94%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.16%	95.50%

Plants that contains it

• Solanum tuberosum

Cross-Links

• PubChem: 21123844
• LOTUS: LTS0179167
• wikiData: Q27279097