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Trigonelline
- Family: Plantae - Dichapetalaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | C[n+]1cccc(c1)C(=O)[O-] |
|---|---|
| InChI | InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3 |
| InChIKey | WWNNZCOKKKDOPX-UHFFFAOYSA-N |
| Formula | C7H7NO2 |
| HBA | 2 |
| HBD | 0 |
| MW | 137.14 |
| Rotatable Bonds | 1 |
| TPSA | 44.01 |
| LogP | -1.13 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 10 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.14 |
| Exact Mass | 137.05 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Dichapetalum michelsonii | Dichapetalaceae | Plantae | 4314 |
Showing of synonyms
Trigonelline
535-83-1
Trigenolline
N-Methylnicotinate
Caffearine
Gynesine
1-methylpyridinium-3-carboxylate
Coffearine
Betain nicotinate
Coffearin
Trigonellin
Betaine nicotinate
Nicotinic acid N-methylbetaine
Trigenelline
Caffearin
1-Methyl-3-pyridiniumcarboxylate
N'-Methylnicotinate
3-Carboxy-1-methylpyridinium hydroxide inner salt
CCRIS 1332
CHEBI:18123
1-methylnicotinate
EINECS 208-620-5
N-methyl-nicotinate
UNII-3NQ9N60I00
BRN 3905114
HSDB 7684
3NQ9N60I00
3-Carboxy-1-methylpyridinium hydroxide, inner salt
3-Carboxy-1-methylpyridinium inner salt
N-Methylnicotinic acid betaine
Pyridinium, 3-carboxy-1-methyl-, hydroxide, inner salt
DTXSID2026230
5-22-02-00143 (Beilstein Handbook Reference)
TRIGONELLINE (USP-RS)
TRIGONELLINE [USP-RS]
DTXCID906230
TRIGONELLINE (CONSTITUENT OF FENUGREEK SEED)
208-620-5
1-methylpyridin-1-ium-3-carboxylate
1-Methylpyridinio-3-carboxylate
1-Methyl-Nicotinic Acid Anion(Trigonelline)
3-Carboxy-1-methylpyridin-1-ium hydroxide
6138-40-5
Trigonelline?
MFCD00054262
N'-Methylnicotinic acid
Trigonelline (Standard)
TRIGONELLINE [MI]
TRIGONELLINE [HSDB]
MLS002153895
SCHEMBL195666
SPECTRUM1500880
CHEMBL350675
HY-N0414R
HMS2096H08
HMS2234K22
HMS3371K21
HY-N0414
MSK40340
BDBM50548713
CCG-38517
NSC714350
AKOS005067859
FT32681
NSC-714350
SDCCGMLS-0066739.P001
NCGC00095649-01
NCGC00095649-02
NCGC00095649-03
NCGC00095649-04
NCGC00095649-07
AC-34290
AS-17722
SMR001233244
AB00052974
CS-0008944
NS00014578
Pyridinium, 3-carboxy-1-methyl-, inner salt
C01004
3-carboxy-1-methyl-Pyridinium hydroxide inner salt
AP-163/40806827
Q928965
3-Carboxy-1-methylpyridinium, Hydroxide, Inner salt
TrigonellineN-Methylnicotinate
TRIGONELLINE (CONSTITUENT OF FENUGREEK SEED) [DSC]
- Esters V, Karangwa C, et al. (2013). Unusual amino acids and monofluoroacetate from Dichapetalum michelsonii (Umutambasha), a toxic plant from Rwanda.. Planta medica, 2013, 79(5), 334–337. [View]
Pubchem:
5570
Cas:
535-83-1
Gnps:
CCMSLIB00000220925
Kegg Ligand:
C01004
Chebi:
18123
Nmrshiftdb2:
60019473
Metabolights:
MTBLC18123
Chembl:
CHEMBL350675
Comptox:
DTXSID2026230
Bindingdb:
50480286
CPRiL:
60121
SMILES: c1cc[nH+]cc1
Level: 0
Mol. Weight: 137.14 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.0
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.19
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.85
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.11
- Plasma Protein Binding
- 20.58
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.59
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -0.27
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.54
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 2.17
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 1.75
- Rat (Acute)
- 1.97
- Rat (Chronic Oral)
- 2.66
- Fathead Minnow
- 3.21
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 251.4
- Hydration Free Energy
- -9.04
- Log(D) at pH=7.4
- -1.42
- Log(P)
- -3.24
- Log S
- -0.13
- Log(Vapor Pressure)
- -2.74
- Melting Point
- 207.38
- pKa Acid
- 4.19
- pKa Basic
- 2.64
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| L-lactate dehydrogenase (cytochrome) | P00175 | CYB2_YEAST | Saccharomyces cerevisiae | 3 | 0.9440 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.8773 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.8018 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 2 | 0.7684 |
| Mandelate racemase | P11444 | MANR_PSEPU | Pseudomonas putida | 2 | 0.7675 |
| Neutrophil gelatinase-associated lipocalin | P80188 | NGAL_HUMAN | Homo sapiens | 3 | 0.7622 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7588 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7540 |
| Chloramphenicol 3-O phosphotransferase | Q56148 | CPT_STRVP | Streptomyces venezuelae | 2 | 0.7437 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7429 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 2 | 0.7424 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7408 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 2 | 0.7398 |
| Ceramide transfer protein | Q9Y5P4 | CERT_HUMAN | Homo sapiens | 2 | 0.7380 |
| 3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase | O33877 | FABA_PSEAE | Pseudomonas aeruginosa | 2 | 0.7379 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 2 | 0.7373 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 2 | 0.7371 |
| Tryptophan synthase alpha chain | P00929 | TRPA_SALTY | Salmonella typhimurium | 2 | 0.7368 |
| Prostaglandin F2a synthase | Q8I6L9 | Q8I6L9_TRYCR | Trypanosoma cruzi | 2 | 0.7316 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7303 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7278 |
| Neutrophil gelatinase-associated lipocalin | P80188 | NGAL_HUMAN | Homo sapiens | 3 | 0.7277 |
| D-alanyl-D-alanine carboxypeptidase | P15555 | DAC_STRSR | Streptomyces sp | 2 | 0.7273 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 2 | 0.7265 |
| Anthranilate phosphoribosyltransferase | P50384 | TRPD_SACS2 | Saccharolobus solfataricus | 2 | 0.7254 |
| Putative FAD-dependent oxygenase EncM | Q9KHK2 | Q9KHK2_9ACTN | Streptomyces maritimus | 2 | 0.7252 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 2 | 0.7241 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 2 | 0.7234 |
| Egl nine homolog 1 | Q9GZT9 | EGLN1_HUMAN | Homo sapiens | 2 | 0.7222 |
| Isochorismate pyruvate lyase | Q51507 | PCHB_PSEAE | Pseudomonas aeruginosa | 2 | 0.7221 |
| Ribosome-inactivating protein 3 | P25891 | RIP3_MAIZE | Zea mays | 2 | 0.7220 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7218 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7209 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7186 |
| Benzoylformate decarboxylase | P20906 | MDLC_PSEPU | Pseudomonas putida | 2 | 0.7173 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 2 | 0.7148 |
| Acidic mammalian chitinase | Q9BZP6 | CHIA_HUMAN | Homo sapiens | 2 | 0.7141 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7140 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7134 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7130 |
| ADP compounds hydrolase NudE | P45799 | NUDE_ECOLI | Escherichia coli | 2 | 0.7106 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 2 | 0.7097 |
| Protein mono-ADP-ribosyltransferase PARP14 | Q460N5 | PAR14_HUMAN | Homo sapiens | 2 | 0.7094 |
| Proline iminopeptidase | O32449 | PIP_SERMA | Serratia marcescens | 2 | 0.7084 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7072 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7065 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 2 | 0.7057 |
| p-hydroxyphenylacetate 3-hydroxylase, oxygenase component | Q6Q272 | HPAH_ACIBA | Acinetobacter baumannii | 2 | 0.7054 |
| Carbonic anhydrase 5A, mitochondrial | P23589 | CAH5A_MOUSE | Mus musculus | 2 | 0.7051 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | P0AF12 | MTNN_ECOLI | Escherichia coli | 2 | 0.7050 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7047 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7045 |
| VioE domain-containing protein | Q7NSZ5 | Q7NSZ5_CHRVO | Chromobacterium violaceum | 2 | 0.7040 |
| L-lactate dehydrogenase | Q27743 | LDH_PLAFD | Plasmodium falciparum | 2 | 0.7005 |