Commersonine

Details

• Internal ID: 67804285-0e3b-4a1d-9ed3-b9cf994d887b
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[[(1S,2R,5S,7S,10S,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]tetracosan-7-yl]oxy]oxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1CCC2C(C3C(N2C1)CC4C3(CCC5C4CCC6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)OC9C(C(C(C(O9)CO)O)O)O)OC1C(C(C(C(O1)CO)O)O)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[C@@H]6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)C)C)C
• InChI: InChI=1S/C51H85NO21/c1-20-5-8-27-21(2)33-28(52(27)15-20)14-26-24-7-6-22-13-23(9-11-50(22,3)25(24)10-12-51(26,33)4)66-46-42(65)39(62)43(32(19-56)70-46)71-49-45(73-48-41(64)38(61)35(58)30(17-54)68-48)44(36(59)31(18-55)69-49)72-47-40(63)37(60)34(57)29(16-53)67-47/h20-49,53-65H,5-19H2,1-4H3/t20-,21+,22-,23-,24+,25-,26-,27+,28-,29+,30+,31+,32+,33-,34+,35+,36+,37-,38-,39+,40+,41+,42+,43-,44-,45+,46+,47-,48-,49-,50-,51-/m0/s1
• InChI Key: JNFOOEMBPCLHEP-NLRYXJPGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₁H₈₅NO₂₁
• Molecular Weight: 1048.20 g/mol
• Exact Mass: 1047.56140872 g/mol
• Topological Polar Surface Area (TPSA): 340.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -2.97
• H-Bond Acceptor: 22
• H-Bond Donor: 13
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6638	66.38%
Caco-2	-	0.8759	87.59%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Lysosomes	0.5468	54.68%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8638	86.38%
OATP1B3 inhibitior	+	0.9468	94.68%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.7746	77.46%
P-glycoprotein inhibitior	+	0.7286	72.86%
P-glycoprotein substrate	-	0.5409	54.09%
CYP3A4 substrate	+	0.7450	74.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7424	74.24%
CYP3A4 inhibition	-	0.9521	95.21%
CYP2C9 inhibition	-	0.9240	92.40%
CYP2C19 inhibition	-	0.9048	90.48%
CYP2D6 inhibition	-	0.9322	93.22%
CYP1A2 inhibition	-	0.9467	94.67%
CYP2C8 inhibition	+	0.5237	52.37%
CYP inhibitory promiscuity	-	0.9201	92.01%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5488	54.88%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9066	90.66%
Skin irritation	-	0.7655	76.55%
Skin corrosion	-	0.9379	93.79%
Ames mutagenesis	-	0.8415	84.15%
Human Ether-a-go-go-Related Gene inhibition	+	0.8142	81.42%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8925	89.25%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.7095	70.95%
Acute Oral Toxicity (c)	III	0.6093	60.93%
Estrogen receptor binding	+	0.8479	84.79%
Androgen receptor binding	+	0.7221	72.21%
Thyroid receptor binding	-	0.5437	54.37%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6511	65.11%
PPAR gamma	+	0.7481	74.81%
Honey bee toxicity	-	0.5789	57.89%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	-	0.4570	45.70%

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	98.76%	96.09%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	96.26%	89.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.22%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.74%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.29%	91.11%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	92.34%	92.86%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.08%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.01%	100.00%
CHEMBL233	P35372	Mu opioid receptor	88.83%	97.93%
CHEMBL237	P41145	Kappa opioid receptor	88.44%	98.10%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	87.89%	98.46%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.48%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	87.39%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.19%	95.50%
CHEMBL206	P03372	Estrogen receptor alpha	86.56%	97.64%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.32%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.12%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	85.86%	95.93%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.51%	96.21%
CHEMBL2094135	Q96BI3	Gamma-secretase	84.90%	98.05%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	84.41%	95.58%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.97%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.47%	95.89%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	82.46%	97.86%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.18%	100.00%
CHEMBL4581	P52732	Kinesin-like protein 1	81.42%	93.18%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.12%	96.90%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	81.07%	96.67%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.53%	95.89%

Plants that contains it

• Solanum acaule
• Solanum chacoense
• Solanum commersonii

Cross-Links

• PubChem: 185997
• NPASS: NPC139722
• LOTUS: LTS0091816
• wikiData: Q105131886