Trigonelline

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	ddd161c5-394d-4ddf-89d0-78885cb68987
Taxonomy	Alkaloids and derivatives
IUPAC Name	1-methylpyridin-1-ium-3-carboxylate
SMILES (Canonical)	C[N+]1=CC=CC(=C1)C(=O)[O-]
SMILES (Isomeric)	C[N+]1=CC=CC(=C1)C(=O)[O-]
InChI	InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3
InChI Key	WWNNZCOKKKDOPX-UHFFFAOYSA-N
Popularity	1,660 references in papers

Physical and Chemical Properties

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Molecular Formula	C₇H₇NO₂
Molecular Weight	137.14 g/mol
Exact Mass	137.047678466 g/mol
Topological Polar Surface Area (TPSA)	44.00 Å²
XlogP	1.20
Atomic LogP (AlogP)	-1.13
H-Bond Acceptor	2
H-Bond Donor	0
Rotatable Bonds	1

Synonyms

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535-83-1

Trigenolline

N-Methylnicotinate

Caffearine

Gynesine

Coffearine

Betain nicotinate

Coffearin

Trigonellin

1-methylpyridinium-3-carboxylate

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7939	79.39%
Caco-2	+	0.9665	96.65%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8127	81.27%
OATP2B1 inhibitior	-	0.8792	87.92%
OATP1B1 inhibitior	+	0.9453	94.53%
OATP1B3 inhibitior	+	0.9602	96.02%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.9319	93.19%
P-glycoprotein inhibitior	-	0.9861	98.61%
P-glycoprotein substrate	-	0.9700	97.00%
CYP3A4 substrate	-	0.7178	71.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8962	89.62%
CYP3A4 inhibition	-	0.9743	97.43%
CYP2C9 inhibition	-	0.9385	93.85%
CYP2C19 inhibition	-	0.9679	96.79%
CYP2D6 inhibition	-	0.9493	94.93%
CYP1A2 inhibition	-	0.8691	86.91%
CYP2C8 inhibition	-	0.9471	94.71%
CYP inhibitory promiscuity	-	0.9472	94.72%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7636	76.36%
Carcinogenicity (trinary)	Non-required	0.5435	54.35%
Eye corrosion	-	0.8164	81.64%
Eye irritation	+	0.9809	98.09%
Skin irritation	+	0.7078	70.78%
Skin corrosion	-	0.7718	77.18%
Ames mutagenesis	-	0.7170	71.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.9221	92.21%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8651	86.51%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	-	0.7333	73.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5398	53.98%
Acute Oral Toxicity (c)	IV	0.4690	46.90%
Estrogen receptor binding	-	0.9735	97.35%
Androgen receptor binding	-	0.8941	89.41%
Thyroid receptor binding	-	0.8732	87.32%
Glucocorticoid receptor binding	-	0.9207	92.07%
Aromatase binding	-	0.8898	88.98%
PPAR gamma	-	0.8170	81.70%
Honey bee toxicity	-	0.9860	98.60%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	-	0.8774	87.74%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	12589.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.99%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.70%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	82.96%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.92%	86.33%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Abrus precatorius

Achillea erba-rotta subsp. moschata

Achillea millefolium

Ageratina saltillensis

Amaranthus retroflexus