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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:23 UTC

Update Date

2022-03-07 02:52:27 UTC

HMDB ID

HMDB0030195

Secondary Accession Numbers

HMDB30195

Metabolite Identification

Common Name

gamma-Fagarine

Description

gamma-Fagarine, also known as fagarine or haplopine, belongs to the class of organic compounds known as furanoquinolines. Furanoquinolines are compounds containing a furan ring fused to a quinoline. Based on a literature review a significant number of articles have been published on gamma-Fagarine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0030195
     RDKit          3D
gamma-Fagarine
 28 30  0  0  0  0  0  0  0  0999 V2000
   -2.9375    2.0691    0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291    1.3417   -0.4204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4851    0.3383   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9042   -0.9570   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1657   -1.5038   -0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9804   -2.8504    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983   -3.1147    0.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9949   -2.0017   -0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3330   -1.7668   -0.1588 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7350   -0.4961   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1179   -0.2838   -0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9958   -1.3536   -0.3215 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699   -1.1395   -0.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6021    0.9920   -0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7183    2.0503   -0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    1.8621   -0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.5766   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7731    1.5940    1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    2.3884    1.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3558    3.0287    0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0769   -0.9197   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7997   -3.5457    0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8910   -2.1095   -0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7951   -0.6782    0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6356   -0.4845   -1.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6615    1.2080   -0.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0586    3.0717   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3592    2.6840   -0.6712 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  3  1  0
  8  4  1  0
 17 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
 13 23  1  0
 13 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
M  END


  Mrv0541 05061305042D          

 17 19  0  0  0  0            999 V2000
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  1  0  0  0  0
  9  6  1  0  0  0  0
 10  5  2  0  0  0  0
 11  8  2  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  2  0  0  0  0
 15  1  1  0  0  0  0
 15 10  1  0  0  0  0
 16  2  1  0  0  0  0
 16 12  1  0  0  0  0
 17  7  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030195

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC2=C1N=C1OC=CC1=C2OC

> <INCHI_IDENTIFIER>
InChI=1S/C13H11NO3/c1-15-10-5-3-4-8-11(10)14-13-9(6-7-17-13)12(8)16-2/h3-7H,1-2H3

> <INCHI_KEY>
KFBCTNNQFGONHB-UHFFFAOYSA-N

> <FORMULA>
C13H11NO3

> <MOLECULAR_WEIGHT>
229.2313

> <EXACT_MASS>
229.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.42403527388898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,8-dimethoxyfuro[2,3-b]quinoline

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.3421433956666666

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.5646428368630954

> <JCHEM_POLAR_SURFACE_AREA>
44.49

> <JCHEM_REFRACTIVITY>
61.69940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fagarine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030195
     RDKit          3D
gamma-Fagarine
 28 30  0  0  0  0  0  0  0  0999 V2000
   -2.9375    2.0691    0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291    1.3417   -0.4204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4851    0.3383   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9042   -0.9570   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1657   -1.5038   -0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9804   -2.8504    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983   -3.1147    0.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9949   -2.0017   -0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3330   -1.7668   -0.1588 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7350   -0.4961   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1179   -0.2838   -0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9958   -1.3536   -0.3215 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699   -1.1395   -0.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6021    0.9920   -0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7183    2.0503   -0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    1.8621   -0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.5766   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7731    1.5940    1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    2.3884    1.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3558    3.0287    0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0769   -0.9197   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7997   -3.5457    0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8910   -2.1095   -0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7951   -0.6782    0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6356   -0.4845   -1.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6615    1.2080   -0.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0586    3.0717   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3592    2.6840   -0.6712 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  3  1  0
  8  4  1  0
 17 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
 13 23  1  0
 13 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258  -1.007   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.924   4.383   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       7.591   5.923   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3    4    5                                                       
CONECT    4    3    8                                                       
CONECT    5    3   10                                                       
CONECT    6    7    9                                                       
CONECT    7    6   17                                                       
CONECT    8    4   11   12                                                  
CONECT    9    6   12   13                                                  
CONECT   10    5   11   15                                                  
CONECT   11    8   10   14                                                  
CONECT   12    8    9   16                                                  
CONECT   13    9   14   17                                                  
CONECT   14   11   13                                                       
CONECT   15    1   10                                                       
CONECT   16    2   12                                                       
CONECT   17    7   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0030195
HETATM    1  C1  UNL     1      -2.938   2.069   0.654  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.429   1.342  -0.420  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.485   0.338  -0.338  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.904  -0.957  -0.163  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.166  -1.504  -0.043  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.980  -2.850   0.113  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.698  -3.115   0.091  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.995  -2.002  -0.074  1.00  0.00           C  
HETATM    9  N1  UNL     1       0.333  -1.767  -0.159  1.00  0.00           N  
HETATM   10  C7  UNL     1       0.735  -0.496  -0.330  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.118  -0.284  -0.415  1.00  0.00           C  
HETATM   12  O3  UNL     1       2.996  -1.354  -0.322  1.00  0.00           O  
HETATM   13  C9  UNL     1       4.370  -1.139  -0.406  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.602   0.992  -0.590  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.718   2.050  -0.682  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.356   1.862  -0.601  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.134   0.577  -0.424  1.00  0.00           C  
HETATM   18  H1  UNL     1      -3.773   1.594   1.186  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.176   2.388   1.391  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.356   3.029   0.229  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.077  -0.920  -0.076  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.800  -3.546   0.232  1.00  0.00           H  
HETATM   23  H6  UNL     1       4.891  -2.109  -0.596  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.795  -0.678   0.533  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.636  -0.485  -1.257  1.00  0.00           H  
HETATM   26  H9  UNL     1       3.661   1.208  -0.661  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.059   3.072  -0.820  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.359   2.684  -0.671  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5    8
CONECT    5    6    6   21
CONECT    6    7   22
CONECT    7    8
CONECT    8    9    9
CONECT    9   10
CONECT   10   11   11   17
CONECT   11   12   14
CONECT   12   13
CONECT   13   23   24   25
CONECT   14   15   15   26
CONECT   15   16   27
CONECT   16   17   17   28
END

HMDB0030195
     RDKit          3D
gamma-Fagarine
 28 30  0  0  0  0  0  0  0  0999 V2000
   -2.9375    2.0691    0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291    1.3417   -0.4204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4851    0.3383   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9042   -0.9570   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1657   -1.5038   -0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9804   -2.8504    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983   -3.1147    0.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9949   -2.0017   -0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3330   -1.7668   -0.1588 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7350   -0.4961   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1179   -0.2838   -0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9958   -1.3536   -0.3215 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699   -1.1395   -0.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6021    0.9920   -0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7183    2.0503   -0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    1.8621   -0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.5766   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7731    1.5940    1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    2.3884    1.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3558    3.0287    0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0769   -0.9197   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7997   -3.5457    0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8910   -2.1095   -0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7951   -0.6782    0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6356   -0.4845   -1.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6615    1.2080   -0.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0586    3.0717   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3592    2.6840   -0.6712 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  3  1  0
  8  4  1  0
 17 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
 13 23  1  0
 13 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Fagarine	Kegg
g-Fagarine	Generator
Γ-fagarine	Generator
4,8-Dimethoxy-furo(2,3-b)quinoline	HMDB
4,8-Dimethoxy-furo[2,3-b]quinoline	HMDB
4,8-Dimethoxyfuro[2,3-b]quinoline	HMDB
8-Methoxydictamine	HMDB
8-Methoxydictamnine	HMDB
Haplopine	HMDB

Chemical Formula

C₁₃H₁₁NO₃

Average Molecular Weight

229.2313

Monoisotopic Molecular Weight

229.073893223

IUPAC Name

4,8-dimethoxyfuro[2,3-b]quinoline

Traditional Name

fagarine

CAS Registry Number

524-15-2

SMILES

COC1=CC=CC2=C1N=C1OC=CC1=C2OC

InChI Identifier

InChI=1S/C13H11NO3/c1-15-10-5-3-4-8-11(10)14-13-9(6-7-17-13)12(8)16-2/h3-7H,1-2H3

InChI Key

KFBCTNNQFGONHB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoquinolines. Furanoquinolines are compounds containing a furan ring fused to a quinoline.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Furanoquinolines

Direct Parent

Furanoquinolines

Alternative Parents

Substituents

Furanoquinoline
Furopyridine
Anisole
Alkyl aryl ether
Pyridine
Benzenoid
Furan
Heteroaromatic compound
Oxacycle
Azacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:10562 )
oxacycle (CHEBI:10562 )
organonitrogen heterocyclic compound (CHEBI:10562 )
Quinoline alkaloids (C10676 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030195)
Cell membrane (HMDB: HMDB0030195)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030195)

Source

Endogenous

Endogenous (HMDB: HMDB0030195)

Plant

Plant (HMDB: HMDB0030195)

Exogenous

Food

Food (HMDB: HMDB0030195)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030195)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	142 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	8.78 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	3.09	ALOGPS
logP	2.34	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	1.56	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.49 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.7 m³·mol⁻¹	ChemAxon
Polarizability	23.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	151.219	31661259
DarkChem	[M-H]-	151.108	31661259
DeepCCS	[M+H]+	145.3	30932474
DeepCCS	[M-H]-	142.942	30932474
DeepCCS	[M-2H]-	176.479	30932474
DeepCCS	[M+Na]+	151.404	30932474
AllCCS	[M+H]+	149.3	32859911
AllCCS	[M+H-H2O]+	145.0	32859911
AllCCS	[M+NH4]+	153.2	32859911
AllCCS	[M+Na]+	154.3	32859911
AllCCS	[M-H]-	152.8	32859911
AllCCS	[M+Na-2H]-	152.3	32859911
AllCCS	[M+HCOO]-	151.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	5.14 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0972 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.27 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1904.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	514.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	200.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	295.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	239.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	585.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	598.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	188.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1231.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	466.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1363.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	490.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	498.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	553.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	70.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Fagarine	COC1=CC=CC2=C1N=C1OC=CC1=C2OC	2761.7	Standard polar	33892256
gamma-Fagarine	COC1=CC=CC2=C1N=C1OC=CC1=C2OC	2069.9	Standard non polar	33892256
gamma-Fagarine	COC1=CC=CC2=C1N=C1OC=CC1=C2OC	2227.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Fagarine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01rb-0960000000-c9367d01b5d6009f1321	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Fagarine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Fagarine 10V, Positive-QTOF	splash10-001i-0090000000-24f2a92dfd15f2e5b08a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Fagarine 20V, Positive-QTOF	splash10-001i-0090000000-2b6a6bb452db4bfc509e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Fagarine 40V, Positive-QTOF	splash10-0ue9-0790000000-80457f126ca6561a06a3	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Fagarine 10V, Negative-QTOF	splash10-004i-0090000000-404f8f015fea98ede42f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Fagarine 20V, Negative-QTOF	splash10-004i-0190000000-c2787628a20493751b1b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Fagarine 40V, Negative-QTOF	splash10-03ea-0970000000-a4605699c08614c46c30	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Fagarine 10V, Positive-QTOF	splash10-001i-0090000000-ade84bbaac177e7ac3e9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Fagarine 20V, Positive-QTOF	splash10-001i-0090000000-ade84bbaac177e7ac3e9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Fagarine 40V, Positive-QTOF	splash10-06v1-0980000000-2a871c94d45f049694ac	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Fagarine 10V, Negative-QTOF	splash10-004i-0090000000-ed4a3dc85d622798a3a4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Fagarine 20V, Negative-QTOF	splash10-004i-0190000000-fe622c53ad2dfc379862	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Fagarine 40V, Negative-QTOF	splash10-0002-0920000000-e15ea646206cbaa082f7	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

107936

PDB ID

Not Available

ChEBI ID

521306

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1817831

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for gamma-Fagarine (HMDB0030195)

MOL for HMDB0030195 (gamma-Fagarine)

3D MOL for HMDB0030195 (gamma-Fagarine)

3D SDF for HMDB0030195 (gamma-Fagarine)

3D-SDF for HMDB0030195 (gamma-Fagarine)

PDB for HMDB0030195 (gamma-Fagarine)

3D PDB for HMDB0030195 (gamma-Fagarine)

SMILES for HMDB0030195 (gamma-Fagarine)

INCHI for HMDB0030195 (gamma-Fagarine)

Structure for HMDB0030195 (gamma-Fagarine)

3D Structure for HMDB0030195 (gamma-Fagarine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra