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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 02:59:22 UTC

Update Date

2021-09-23 02:59:23 UTC

HMDB ID

HMDB0301844

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Liriodenine

Description

Liriodenine, also known as oxoushinsunine or micheline b, is a member of the class of compounds known as aporphines. Aporphines are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Liriodenine is practically insoluble (in water) and a strong basic compound (based on its pKa). Liriodenine can be found in cherimoya and custard apple, which makes liriodenine a potential biomarker for the consumption of these food products. Liriodenine is a bio-active isolate of the Chinese medicinal herb Zanthoxylum nitidum .

Structure

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

HMDB0301844
     RDKit          3D
Liriodenine
 30 34  0  0  0  0  0  0  0  0999 V2000
   -1.1831   -3.4626    1.1923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8452   -2.3197    0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -1.2889    0.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1351   -1.5979    0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0224   -0.6138    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6099    0.6135   -0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2557    0.9109   -0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3419   -0.0438   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0898    0.2239   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5516    1.4531   -0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9096    1.7072   -0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7788    0.7113   -0.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.5184    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2504   -1.4737    0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8349   -2.7041    0.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155   -2.9285    1.0114 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658   -2.0316    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9619   -0.7909    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1208    3.0131   -1.1382 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8918    3.7002   -1.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373    2.6344   -1.0109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4823   -2.5603    0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1102   -0.7805    0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3384    1.3942   -0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9661    1.8788   -0.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8553    0.9214   -0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2942   -1.2113    0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5637   -3.4812    1.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8565    4.2758   -0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7576    4.3694   -1.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 11 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
  8  3  1  0
 18  9  2  0
 21 10  1  0
 18 13  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 20 29  1  0
 20 30  1  0
M  END


  Mrv0541 02241221442D          

 21 25  0  0  0  0            999 V2000
    2.1434   -1.2375    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565    2.6145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4209    3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6005    3.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   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
    0.7145    1.2375    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  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
  6 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  5 13  2  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301844

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1C2=C(C=CC=C2)C2=C3C(C=CN=C13)=CC1=C2OCO1

> <INCHI_IDENTIFIER>
InChI=1S/C17H9NO3/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12/h1-7H,8H2

> <INCHI_KEY>
MUMCCPUVOAUBAN-UHFFFAOYSA-N

> <FORMULA>
C17H9NO3

> <MOLECULAR_WEIGHT>
275.2583

> <EXACT_MASS>
275.058243159

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.865671533315016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,9,11,14(19),15,17-octaen-13-one

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
2.8874665223333333

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.473867071137937

> <JCHEM_POLAR_SURFACE_AREA>
48.42

> <JCHEM_REFRACTIVITY>
75.39990000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,9,11,14(19),15,17-octaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301844
     RDKit          3D
Liriodenine
 30 34  0  0  0  0  0  0  0  0999 V2000
   -1.1831   -3.4626    1.1923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8452   -2.3197    0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -1.2889    0.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1351   -1.5979    0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0224   -0.6138    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6099    0.6135   -0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2557    0.9109   -0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3419   -0.0438   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0898    0.2239   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5516    1.4531   -0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9096    1.7072   -0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7788    0.7113   -0.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.5184    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2504   -1.4737    0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8349   -2.7041    0.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155   -2.9285    1.0114 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658   -2.0316    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9619   -0.7909    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1208    3.0131   -1.1382 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8918    3.7002   -1.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373    2.6344   -1.0109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4823   -2.5603    0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1102   -0.7805    0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3384    1.3942   -0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9661    1.8788   -0.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8553    0.9214   -0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2942   -1.2113    0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5637   -3.4812    1.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8565    4.2758   -0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7576    4.3694   -1.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 11 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
  8  3  1  0
 18  9  2  0
 21 10  1  0
 18 13  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 20 29  1  0
 20 30  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.145   4.880   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.519   6.287   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.988   6.126   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12    5   14                                                  
CONECT   14   13    2   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    4   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    3                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

COMPND    HMDB0301844
HETATM    1  O1  UNL     1      -1.183  -3.463   1.192  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.845  -2.320   0.780  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.793  -1.289   0.402  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.135  -1.598   0.508  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.022  -0.614   0.147  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.610   0.613  -0.295  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.256   0.911  -0.397  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.342  -0.044  -0.047  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.090   0.224  -0.137  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.552   1.453  -0.580  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.910   1.707  -0.666  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.779   0.711  -0.301  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.322  -0.518   0.142  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.250  -1.474   0.492  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.835  -2.704   0.936  1.00  0.00           C  
HETATM   16  N1  UNL     1       1.515  -2.929   1.011  1.00  0.00           N  
HETATM   17  C15 UNL     1       0.566  -2.032   0.682  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.962  -0.791   0.235  1.00  0.00           C  
HETATM   19  O2  UNL     1       2.121   3.013  -1.138  1.00  0.00           O  
HETATM   20  C17 UNL     1       0.892   3.700  -1.009  1.00  0.00           C  
HETATM   21  O3  UNL     1      -0.037   2.634  -1.011  1.00  0.00           O  
HETATM   22  H1  UNL     1      -3.482  -2.560   0.855  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.110  -0.781   0.202  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.338   1.394  -0.582  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.966   1.879  -0.746  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.855   0.921  -0.372  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.294  -1.211   0.402  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.564  -3.481   1.221  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.857   4.276  -0.044  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.758   4.369  -1.883  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   17
CONECT    3    4    4    8
CONECT    4    5   22
CONECT    5    6    6   23
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9
CONECT    9   10   18   18
CONECT   10   11   11   21
CONECT   11   12   19
CONECT   12   13   13   26
CONECT   13   14   18
CONECT   14   15   15   27
CONECT   15   16   28
CONECT   16   17   17
CONECT   17   18
CONECT   19   20
CONECT   20   21   29   30
END

HMDB0301844
     RDKit          3D
Liriodenine
 30 34  0  0  0  0  0  0  0  0999 V2000
   -1.1831   -3.4626    1.1923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8452   -2.3197    0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -1.2889    0.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1351   -1.5979    0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0224   -0.6138    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6099    0.6135   -0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2557    0.9109   -0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3419   -0.0438   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0898    0.2239   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5516    1.4531   -0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9096    1.7072   -0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7788    0.7113   -0.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.5184    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2504   -1.4737    0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8349   -2.7041    0.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155   -2.9285    1.0114 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658   -2.0316    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9619   -0.7909    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1208    3.0131   -1.1382 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8918    3.7002   -1.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373    2.6344   -1.0109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4823   -2.5603    0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1102   -0.7805    0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3384    1.3942   -0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9661    1.8788   -0.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8553    0.9214   -0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2942   -1.2113    0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5637   -3.4812    1.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8565    4.2758   -0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7576    4.3694   -1.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 11 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
  8  3  1  0
 18  9  2  0
 21 10  1  0
 18 13  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 20 29  1  0
 20 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Micheline b	ChEBI
Oxoushinsunine	ChEBI
Spermatheridine	ChEBI

Chemical Formula

C₁₇H₉NO₃

Average Molecular Weight

275.2583

Monoisotopic Molecular Weight

275.058243159

IUPAC Name

3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,9,11,14(19),15,17-octaen-13-one

Traditional Name

3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,9,11,14(19),15,17-octaen-13-one

CAS Registry Number

Not Available

SMILES

O=C1C2=C(C=CC=C2)C2=C3C(C=CN=C13)=CC1=C2OCO1

InChI Identifier

InChI=1S/C17H9NO3/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12/h1-7H,8H2

InChI Key

MUMCCPUVOAUBAN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Isoquinoline
Naphthalene
Quinoline
Benzodioxole
Aryl ketone
Pyridine
Benzenoid
Heteroaromatic compound
Ketone
Azacycle
Oxacycle
Acetal
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:70649 )
organic heteropentacyclic compound (CHEBI:70649 )
oxacycle (CHEBI:70649 )
isoquinoline alkaloid (CHEBI:70649 )
alkaloid antibiotic (CHEBI:70649 )

Ontology

Not Available

Exogenous (HMDB: HMDB0301844)

Food

Fruit

Tropical fruit

Cherimoya (FooDB: FOOD00326)
Custard apple (FooDB: FOOD00014)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.74	ALOGPS
logP	2.89	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	3.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48.42 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.4 m³·mol⁻¹	ChemAxon
Polarizability	27.87 Å³	ChemAxon
Number of Rings	5	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
AllCCS	[M+H]+	161.292	32859911
AllCCS	[M+H-H2O]+	157.444	32859911
AllCCS	[M+Na]+	165.898	32859911
AllCCS	[M+NH4]+	164.869	32859911
AllCCS	[M-H]-	166.462	32859911
AllCCS	[M+Na-2H]-	165.12	32859911
AllCCS	[M+HCOO]-	163.772	32859911
DeepCCS	[M-2H]-	195.174	30932474
DeepCCS	[M+Na]+	170.57	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	12.2296 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.89 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2414.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	330.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	145.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	200.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	143.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	449.1 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	547.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	105.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	954.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	353.6 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	1623.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	386.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	435.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	400.0 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	134.6 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liriodenine 10V, Positive-QTOF	splash10-004i-0090000000-d116764a1b549566ddc2	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liriodenine 20V, Positive-QTOF	splash10-004i-0090000000-a812cfdc22b3b974a571	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liriodenine 40V, Positive-QTOF	splash10-0h0r-1090000000-4ab9af70321d2452c2ed	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liriodenine 10V, Negative-QTOF	splash10-00di-0090000000-1cc2bb661a5f7d127cab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liriodenine 20V, Negative-QTOF	splash10-00di-0090000000-eccfb2a6124ec79bf0c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liriodenine 40V, Negative-QTOF	splash10-00di-0090000000-6018d8b7c05325657d51	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liriodenine 10V, Positive-QTOF	splash10-004i-0090000000-8c2ae4f25793ef3df058	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liriodenine 20V, Positive-QTOF	splash10-004i-0090000000-8c2ae4f25793ef3df058	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liriodenine 40V, Positive-QTOF	splash10-004i-0090000000-64a6c3e76f87232752c4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liriodenine 10V, Negative-QTOF	splash10-00di-0090000000-9aa519e5953f4135a53a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liriodenine 20V, Negative-QTOF	splash10-00di-0090000000-9aa519e5953f4135a53a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liriodenine 40V, Negative-QTOF	splash10-00dj-0090000000-433b339890d9f33847b6	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Liriodenine

METLIN ID

Not Available

PubChem Compound

10144

PDB ID

Not Available

ChEBI ID

70649

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1814151

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Liriodenine (HMDB0301844)

MOL for HMDB0301844 (Liriodenine)

3D MOL for HMDB0301844 (Liriodenine)

3D SDF for HMDB0301844 (Liriodenine)

3D-SDF for HMDB0301844 (Liriodenine)

PDB for HMDB0301844 (Liriodenine)

3D PDB for HMDB0301844 (Liriodenine)

SMILES for HMDB0301844 (Liriodenine)

INCHI for HMDB0301844 (Liriodenine)

Structure for HMDB0301844 (Liriodenine)

3D Structure for HMDB0301844 (Liriodenine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra