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Showing metabocard for Arecoline (HMDB0030353)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:18 UTC
Update Date2023-02-21 17:19:33 UTC
HMDB IDHMDB0030353
Secondary Accession Numbers
  • HMDB30353
Metabolite Identification
Common NameArecoline
DescriptionArecoline is found in nuts. Arecoline is isolated from betel nuts Arecoline is an alkaloid natural product found in the areca nut, the fruit of the areca palm (Areca catechu). It is an oily liquid that is soluble in water, alcohols, and ether. Owing to its muscarinic and nicotinic agonist properties, arecoline has shown improvement in the learning ability of healthy volunteers. Since one of the hallmarks of Alzheimer's disease is a cognitive decline, arecoline was suggested as a treatment to slow down this process and arecoline administered via i.v. route did indeed show modest verbal and spatial memory improvement in Alzheimer's patients, though due to arecoline's possible carcinogenic properties, it is not the first drug of choice for this degenerative disease
Structure
Data?1676999973
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0030353 (Arecoline)


  Mrv0541 02231217382D          

 11 11  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  5 11  1  0  0  0  0
M  END
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3D MOL for HMDB0030353 (Arecoline)

HMDB0030353
     RDKit          3D
Arecoline
 24 24  0  0  0  0  0  0  0  0999 V2000
    4.1563    0.1722   -0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7852    0.5232   -0.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8384   -0.3574   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2746   -1.4599    0.3452 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4257   -0.0107   -0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0653    1.1657   -0.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3739    1.5147   -0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1240    0.2207   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8838   -0.7957    0.1625 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6531   -0.5346    1.3647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5170   -1.0020    0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4051   -0.4582   -1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7767    1.0812   -0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3567   -0.4101    0.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8283    1.8159   -0.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6664    2.2834   -1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6776    1.7709    0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1976    0.4681   -0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7682   -0.0671   -1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9109   -1.5002    1.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5388    0.0586    1.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0016    0.0195    2.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142   -1.9994    0.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3854   -1.1347    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
 10 20  1  0
 10 21  1  0
 10 22  1  0
 11 23  1  0
 11 24  1  0
M  END
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3D SDF for HMDB0030353 (Arecoline)


  Mrv0541 02231217382D          

 11 11  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  5 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030353

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1=CCCN(C)C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3

> <INCHI_KEY>
HJJPJSXJAXAIPN-UHFFFAOYSA-N

> <FORMULA>
C8H13NO2

> <MOLECULAR_WEIGHT>
155.1943

> <EXACT_MASS>
155.094628665

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.102589891012038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate

> <ALOGPS_LOGP>
0.55

> <JCHEM_LOGP>
0.6488026606666668

> <ALOGPS_LOGS>
0.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.225681392301013

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
43.861000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.46e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
arecoline

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0030353 (Arecoline)

HMDB0030353
     RDKit          3D
Arecoline
 24 24  0  0  0  0  0  0  0  0999 V2000
    4.1563    0.1722   -0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7852    0.5232   -0.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8384   -0.3574   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2746   -1.4599    0.3452 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4257   -0.0107   -0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0653    1.1657   -0.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3739    1.5147   -0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1240    0.2207   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8838   -0.7957    0.1625 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6531   -0.5346    1.3647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5170   -1.0020    0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4051   -0.4582   -1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7767    1.0812   -0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3567   -0.4101    0.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8283    1.8159   -0.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6664    2.2834   -1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6776    1.7709    0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1976    0.4681   -0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7682   -0.0671   -1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9109   -1.5002    1.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5388    0.0586    1.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0016    0.0195    2.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142   -1.9994    0.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3854   -1.1347    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
 10 20  1  0
 10 21  1  0
 10 22  1  0
 11 23  1  0
 11 24  1  0
M  END
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PDB for HMDB0030353 (Arecoline)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0030353 (Arecoline)

COMPND    HMDB0030353
HETATM    1  C1  UNL     1       4.156   0.172  -0.606  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.785   0.523  -0.579  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.838  -0.357  -0.075  1.00  0.00           C  
HETATM    4  O2  UNL     1       2.275  -1.460   0.345  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.426  -0.011  -0.040  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.065   1.166  -0.502  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.374   1.515  -0.465  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.124   0.221  -0.809  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.884  -0.796   0.162  1.00  0.00           N  
HETATM   10  C7  UNL     1      -2.653  -0.535   1.365  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.517  -1.002   0.512  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.405  -0.458  -1.493  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.777   1.081  -0.684  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.357  -0.410   0.315  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.828   1.816  -0.882  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.666   2.283  -1.183  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.678   1.771   0.580  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.198   0.468  -0.840  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.768  -0.067  -1.817  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.911  -1.500   1.835  1.00  0.00           H  
HETATM   21  H10 UNL     1      -3.539   0.059   1.077  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.002   0.020   2.088  1.00  0.00           H  
HETATM   23  H12 UNL     1      -0.214  -1.999   0.077  1.00  0.00           H  
HETATM   24  H13 UNL     1      -0.385  -1.135   1.618  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   11
CONECT    6    7   15
CONECT    7    8   16   17
CONECT    8    9   18   19
CONECT    9   10   11
CONECT   10   20   21   22
CONECT   11   23   24
END
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SMILES for HMDB0030353 (Arecoline)

COC(=O)C1=CCCN(C)C1
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INCHI for HMDB0030353 (Arecoline)

InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Arecaidine methyl esterChEBI
ArecalineChEBI
ArecholineChEBI
ArekolinChEBI
MethylarecaidenChEBI
MethylarecaidinChEBI
1,2,5,6-Tetrahydro-1-methylnicotinic acid, methyl esterHMDB
ArecholinHMDB
ArecolinHMDB
Arecoline baseHMDB
Arecoline hydrobromideHMDB
Methyl 1,2,5, 6-tetrahydro-1-methylnicotinateHMDB
Methyl 1,2,5,6-tetrahydro-1-methylnicotinateHMDB
Methyl 1-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylateHMDB
Methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylateHMDB
Methyl 1-methyl-5,6-dihydro-2H-pyridine-3-carboxylateHMDB
Methyl N-methyl-1,2,5, 6-tetrahydronicotinateHMDB
Methyl N-methyl-1,2,5,6-tetrahydronicotinateHMDB
Methyl N-methyltetrahydronicotinateHMDB
N-Methyl-beta -carboxylic acid methyl esterHMDB
N-Methyltetrahydronicotinic acid, methyl esterHMDB
Nicotinic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl esterHMDB
Chemical FormulaC8H13NO2
Average Molecular Weight155.1943
Monoisotopic Molecular Weight155.094628665
IUPAC Namemethyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
Traditional Namearecoline
CAS Registry Number63-75-2
SMILES
COC(=O)C1=CCCN(C)C1
InChI Identifier
InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3
InChI KeyHJJPJSXJAXAIPN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Alkaloid or derivatives
  • Hydropyridine
  • Methyl ester
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point209.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP0.350The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility446 g/LALOGPS
logP0.55ALOGPS
logP0.65ChemAxon
logS0.46ALOGPS
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.86 m³·mol⁻¹ChemAxon
Polarizability17.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.90331661259
DarkChem[M-H]-132.94831661259
DeepCCS[M+H]+137.80930932474
DeepCCS[M-H]-135.14430932474
DeepCCS[M-2H]-171.51130932474
DeepCCS[M+Na]+146.82930932474
AllCCS[M+H]+132.532859911
AllCCS[M+H-H2O]+128.032859911
AllCCS[M+NH4]+136.632859911
AllCCS[M+Na]+137.832859911
AllCCS[M-H]-134.732859911
AllCCS[M+Na-2H]-136.332859911
AllCCS[M+HCOO]-138.132859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.9 minutes32390414
Predicted by Siyang on May 30, 20228.7688 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.0 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid156.9 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid525.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid272.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid95.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid172.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid45.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid258.5 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid253.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)681.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid615.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid37.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid622.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid182.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid195.3 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate645.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA435.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water179.6 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ArecolineCOC(=O)C1=CCCN(C)C11636.2Standard polar33892256
ArecolineCOC(=O)C1=CCCN(C)C11189.9Standard non polar33892256
ArecolineCOC(=O)C1=CCCN(C)C11180.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Arecoline GC-MS (Non-derivatized) - 70eV, Positivesplash10-006w-9400000000-98b26a9d2867d710059e2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Arecoline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9400000000-c2ac70d939302e3f979b2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arecoline 10V, Positive-QTOFsplash10-0a4i-0900000000-13bcb3825f7244e9bfd32016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arecoline 20V, Positive-QTOFsplash10-05fr-5900000000-4c54ca467a6647c618702016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arecoline 40V, Positive-QTOFsplash10-00rw-9000000000-ff7785df405dc6c7b1362016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arecoline 10V, Negative-QTOFsplash10-0udi-0900000000-1de11420c61028c653082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arecoline 20V, Negative-QTOFsplash10-0udi-1900000000-ff4ff3298d65bc8e1a2b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arecoline 40V, Negative-QTOFsplash10-05fu-9300000000-f368ae9f151a5d63114c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arecoline 10V, Negative-QTOFsplash10-0udi-2900000000-938088a337b250c4c45d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arecoline 20V, Negative-QTOFsplash10-0fdk-7900000000-eacff4cd88f94b61cec02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arecoline 40V, Negative-QTOFsplash10-0a5c-9000000000-39cbbf9119989e64dd6e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arecoline 10V, Positive-QTOFsplash10-0a4i-2900000000-9d51360c21b50a4980fc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arecoline 20V, Positive-QTOFsplash10-05fs-8900000000-84101b2b84e59517def62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arecoline 40V, Positive-QTOFsplash10-0007-9100000000-330ea72f81622bbe2ec12021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04365
Phenol Explorer Compound IDNot Available
FooDB IDFDB002198
KNApSAcK IDC00002020
Chemspider ID13872064
KEGG Compound IDC10129
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkArecoline
METLIN IDNot Available
PubChem Compound2230
PDB IDNot Available
ChEBI ID2814
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1389511
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shih YT, Chen PS, Wu CH, Tseng YT, Wu YC, Lo YC: Arecoline, a major alkaloid of the areca nut, causes neurotoxicity through enhancement of oxidative stress and suppression of the antioxidant protective system. Free Radic Biol Med. 2010 Nov 30;49(10):1471-9. doi: 10.1016/j.freeradbiomed.2010.07.017. Epub 2010 Aug 4. [PubMed:20691257 ]
  2. Yang YR, Chang KC, Chen CL, Chiu TH: Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor. Chin J Physiol. 2000 Mar 31;43(1):23-8. [PubMed:10857465 ]
  3. Wang SW, Hwang GS, Chen TJ, Wang PS: Effects of arecoline on testosterone release in rats. Am J Physiol Endocrinol Metab. 2008 Aug;295(2):E497-504. doi: 10.1152/ajpendo.00045.2008. Epub 2008 Jun 17. [PubMed:18559981 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details
1. Muscarinic acetylcholine receptor M1
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular weight:
51420.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]