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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:16 UTC

Update Date

2022-03-07 02:52:31 UTC

HMDB ID

HMDB0030348

Secondary Accession Numbers

HMDB30348

Metabolite Identification

Common Name

Anonaine

Description

Anonaine 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. Anonaine is found, on average, in the highest concentration within custard apples (Annona reticulata). Anonaine has also been detected, but not quantified in, several different foods, such as fruits, red tea, teas (Camellia sinensis), sacred lotus (Nelumbo nucifera), and cherimoyas (Annona cherimola). This could make anonaine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Anonaine.

Structure

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

HMDB0030348
     RDKit          3D
Anonaine
 35 39  0  0  0  0  0  0  0  0999 V2000
   -2.3918    3.5112   -0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599    2.4218   -0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5853    1.1839    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2179    1.0464   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4187    2.1159   -0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360    3.3572   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458    2.0099   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6280    0.6686   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9692    0.5769    0.1552 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557   -0.6519   -0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8646   -1.8500    0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4101   -1.6301    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6142   -2.6834    0.6662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7396   -2.5440    0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3615   -1.3435    0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6149   -0.2561    0.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7740   -0.4372    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6760   -1.5571    0.8019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9613   -2.9399    0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123   -3.4694    1.1942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571    4.4944   -0.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2319    2.5298   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2135    0.4084    0.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789    4.1825   -0.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5184    2.6185    0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408    2.5896   -1.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415    0.4065   -1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5119    1.3595   -0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -0.6344   -1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6352   -0.6257   -0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2307   -2.0276    1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600   -2.7498   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1080   -3.6523    0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3143   -3.3195   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7387   -3.1090    1.6102 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
  6  1  1  0
 17  8  1  0
 16  4  1  0
 17 12  2  0
 20 14  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 19 34  1  0
 19 35  1  0
M  END


  Mrv0541 05061305102D          

 20 24  0  0  0  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    0.7145   -0.4125    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
    2.8579   -1.6500    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
    3.1354    2.1307    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
    1.4289    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
    2.1434   -1.2375    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   -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
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3149    2.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
 10  3  2  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  2  0  0  0  0
 12  4  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 16 15  2  0  0  0  0
 17 14  2  0  0  0  0
 17 16  1  0  0  0  0
 18  6  1  0  0  0  0
 18 13  1  0  0  0  0
 19  9  1  0  0  0  0
 19 14  1  0  0  0  0
 20  9  1  0  0  0  0
 20 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030348

> <DATABASE_NAME>
hmdb

> <SMILES>
C1OC2=C(O1)C1=C3C(CC4=CC=CC=C14)NCCC3=C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H15NO2/c1-2-4-12-10(3-1)7-13-15-11(5-6-18-13)8-14-17(16(12)15)20-9-19-14/h1-4,8,13,18H,5-7,9H2

> <INCHI_KEY>
VZTUKBKUWSHDFM-UHFFFAOYSA-N

> <FORMULA>
C17H15NO2

> <MOLECULAR_WEIGHT>
265.3065

> <EXACT_MASS>
265.110278729

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.11176530392553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <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),7,14,16,18-hexaene

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
2.9415975579999993

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.4909785873816

> <JCHEM_POLAR_SURFACE_AREA>
30.49

> <JCHEM_REFRACTIVITY>
76.49849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030348
     RDKit          3D
Anonaine
 35 39  0  0  0  0  0  0  0  0999 V2000
   -2.3918    3.5112   -0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599    2.4218   -0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5853    1.1839    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2179    1.0464   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4187    2.1159   -0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360    3.3572   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458    2.0099   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6280    0.6686   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9692    0.5769    0.1552 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557   -0.6519   -0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8646   -1.8500    0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4101   -1.6301    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6142   -2.6834    0.6662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7396   -2.5440    0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3615   -1.3435    0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6149   -0.2561    0.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7740   -0.4372    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6760   -1.5571    0.8019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9613   -2.9399    0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123   -3.4694    1.1942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571    4.4944   -0.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2319    2.5298   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2135    0.4084    0.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789    4.1825   -0.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5184    2.6185    0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408    2.5896   -1.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415    0.4065   -1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5119    1.3595   -0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -0.6344   -1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6352   -0.6257   -0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2307   -2.0276    1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600   -2.7498   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1080   -3.6523    0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3143   -3.3195   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7387   -3.1090    1.6102 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
  6  1  1  0
 17  8  1  0
 16  4  1  0
 17 12  2  0
 20 14  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 19 34  1  0
 19 35  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       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.853   3.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       4.321   3.816   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.479   2.570   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   10                                                       
CONECT    4    2   12                                                       
CONECT    5    6   11                                                       
CONECT    6    5   18                                                       
CONECT    7   10   13                                                       
CONECT    8   11   14                                                       
CONECT    9   19   20                                                       
CONECT   10    3    7   12                                                  
CONECT   11    5    8   15                                                  
CONECT   12    4   10   16                                                  
CONECT   13    7   15   18                                                  
CONECT   14    8   17   19                                                  
CONECT   15   11   13   16                                                  
CONECT   16   12   15   17                                                  
CONECT   17   14   16   20                                                  
CONECT   18    6   13                                                       
CONECT   19    9   14                                                       
CONECT   20    9   17                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   48    0
END

COMPND    HMDB0030348
HETATM    1  C1  UNL     1      -2.392   3.511  -0.527  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.160   2.422  -0.193  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.585   1.184   0.053  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.218   1.046  -0.041  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.419   2.116  -0.371  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.036   3.357  -0.615  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.046   2.010  -0.438  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.628   0.669  -0.450  1.00  0.00           C  
HETATM    9  N1  UNL     1       2.969   0.577   0.155  1.00  0.00           N  
HETATM   10  C9  UNL     1       3.556  -0.652  -0.367  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.865  -1.850   0.148  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.410  -1.630   0.270  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.614  -2.683   0.666  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.740  -2.544   0.810  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.361  -1.344   0.566  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.615  -0.256   0.168  1.00  0.00           C  
HETATM   17  C16 UNL     1       0.774  -0.437   0.028  1.00  0.00           C  
HETATM   18  O1  UNL     1      -2.676  -1.557   0.802  1.00  0.00           O  
HETATM   19  C17 UNL     1      -2.961  -2.940   0.848  1.00  0.00           C  
HETATM   20  O2  UNL     1      -1.712  -3.469   1.194  1.00  0.00           O  
HETATM   21  H1  UNL     1      -2.857   4.494  -0.722  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.232   2.530  -0.120  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.214   0.408   0.296  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.379   4.182  -0.875  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.518   2.618   0.379  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.341   2.590  -1.372  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.841   0.407  -1.537  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.512   1.359  -0.300  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.502  -0.634  -1.469  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.635  -0.626  -0.053  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.231  -2.028   1.200  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.060  -2.750  -0.477  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.108  -3.652   0.865  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.314  -3.319  -0.132  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.739  -3.109   1.610  1.00  0.00           H  
CONECT    1    2    2    6   21
CONECT    2    3   22
CONECT    3    4    4   23
CONECT    4    5   16
CONECT    5    6    6    7
CONECT    6   24
CONECT    7    8   25   26
CONECT    8    9   17   27
CONECT    9   10   28
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   17   17
CONECT   13   14   14   33
CONECT   14   15   20
CONECT   15   16   16   18
CONECT   16   17
CONECT   18   19
CONECT   19   20   34   35
END

HMDB0030348
     RDKit          3D
Anonaine
 35 39  0  0  0  0  0  0  0  0999 V2000
   -2.3918    3.5112   -0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599    2.4218   -0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5853    1.1839    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2179    1.0464   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4187    2.1159   -0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360    3.3572   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458    2.0099   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6280    0.6686   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9692    0.5769    0.1552 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557   -0.6519   -0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8646   -1.8500    0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4101   -1.6301    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6142   -2.6834    0.6662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7396   -2.5440    0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3615   -1.3435    0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6149   -0.2561    0.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7740   -0.4372    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6760   -1.5571    0.8019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9613   -2.9399    0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123   -3.4694    1.1942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571    4.4944   -0.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2319    2.5298   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2135    0.4084    0.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789    4.1825   -0.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5184    2.6185    0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408    2.5896   -1.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415    0.4065   -1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5119    1.3595   -0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -0.6344   -1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6352   -0.6257   -0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2307   -2.0276    1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600   -2.7498   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1080   -3.6523    0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3143   -3.3195   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7387   -3.1090    1.6102 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
  6  1  1  0
 17  8  1  0
 16  4  1  0
 17 12  2  0
 20 14  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 19 34  1  0
 19 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Annonaine	HMDB
1,2-Methylenedioxynoraporphine	HMDB
Anonain	HMDB

Chemical Formula

C₁₇H₁₅NO₂

Average Molecular Weight

265.3065

Monoisotopic Molecular Weight

265.110278729

IUPAC Name

3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaene

Traditional Name

3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaene

CAS Registry Number

1862-41-5

SMILES

C1OC2=C(O1)C1=C3C(CC4=CC=CC=C14)NCCC3=C2

InChI Identifier

InChI=1S/C17H15NO2/c1-2-4-12-10(3-1)7-13-15-11(5-6-18-13)8-14-17(16(12)15)20-9-19-14/h1-4,8,13,18H,5-7,9H2

InChI Key

VZTUKBKUWSHDFM-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
Naphthalene
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Aralkylamine
Benzenoid
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary aliphatic amine
Acetal
Secondary amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030348)
Cytoplasm (HMDB: HMDB0030348)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030348)

Source

Endogenous

Endogenous (HMDB: HMDB0030348)

Plant

Plant (HMDB: HMDB0030348)

Exogenous

Food

Food (HMDB: HMDB0030348)

Fruit

Tropical fruit

Fruits (FooDB: FOOD00871)

Tea

Vegetable

Other vegetable

Sacred lotus (FooDB: FOOD00402)

Exogenous (HMDB: HMDB0030348)

Process

Not Available

Role

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0030348)
Insecticide (HMDB: HMDB0030348)

Pesticide (HMDB: HMDB0030348)

Dopamine-adenylate-cyclase inhibitor (HMDB: HMDB0030348)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	122 - 123 °C	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
Water Solubility	0.034 g/L	ALOGPS
logP	2.22	ALOGPS
logP	2.94	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	9.49	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	30.49 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	76.5 m³·mol⁻¹	ChemAxon
Polarizability	29.11 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	160.767	31661259
DarkChem	[M-H]-	158.731	31661259
DeepCCS	[M-2H]-	195.662	30932474
DeepCCS	[M+Na]+	170.828	30932474
AllCCS	[M+H]+	162.0	32859911
AllCCS	[M+H-H2O]+	158.2	32859911
AllCCS	[M+NH4]+	165.5	32859911
AllCCS	[M+Na]+	166.5	32859911
AllCCS	[M-H]-	169.2	32859911
AllCCS	[M+Na-2H]-	168.1	32859911
AllCCS	[M+HCOO]-	167.1	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.	4.98 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9615 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.37 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	52.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1431.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	274.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	159.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	105.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	345.5 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	386.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	283.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	913.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	379.0 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	1116.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	278.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	275.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	392.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	304.7 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	40.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Anonaine	C1OC2=C(O1)C1=C3C(CC4=CC=CC=C14)NCCC3=C2	3630.8	Standard polar	33892256
Anonaine	C1OC2=C(O1)C1=C3C(CC4=CC=CC=C14)NCCC3=C2	2372.7	Standard non polar	33892256
Anonaine	C1OC2=C(O1)C1=C3C(CC4=CC=CC=C14)NCCC3=C2	2590.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Anonaine,1TMS,isomer #1	C[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC=CC=C13	2533.6	Semi standard non polar	33892256
Anonaine,1TMS,isomer #1	C[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC=CC=C13	2513.4	Standard non polar	33892256
Anonaine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC=CC=C13	2759.2	Semi standard non polar	33892256
Anonaine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC=CC=C13	2756.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Anonaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kr-0290000000-eef0189b19c023e62512	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anonaine 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 - Anonaine 10V, Positive-QTOF	splash10-014i-0090000000-e9a2afab256159ae2699	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anonaine 20V, Positive-QTOF	splash10-014i-0090000000-f7ca3522e83754962ac6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anonaine 40V, Positive-QTOF	splash10-00pl-1980000000-a0014a6236a9bf51d76e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anonaine 10V, Negative-QTOF	splash10-03di-0090000000-74185903329bd522c04a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anonaine 20V, Negative-QTOF	splash10-03di-0090000000-7de3784592381bb7a862	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anonaine 40V, Negative-QTOF	splash10-014m-1490000000-2f75c30aa943164353af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anonaine 10V, Positive-QTOF	splash10-014i-0090000000-4ceb63c2dd5efc77f44c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anonaine 20V, Positive-QTOF	splash10-014i-0090000000-4ceb63c2dd5efc77f44c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anonaine 40V, Positive-QTOF	splash10-00ds-0190000000-9a10adc3866934e256bc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anonaine 10V, Negative-QTOF	splash10-03di-0090000000-f67efedff389fe87473b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anonaine 20V, Negative-QTOF	splash10-03di-0090000000-e7468aac66a5ed55954f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anonaine 40V, Negative-QTOF	splash10-000t-0090000000-d457525b01f969160b5d	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

Anonaine

METLIN ID

Not Available

PubChem Compound

3462225

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1819201

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Paulo Mde Q, Barbosa-Filho JM, Lima EO, Maia RF, Barbosa Rde C, Kaplan MA: Antimicrobial activity of benzylisoquinoline alkaloids from Annona salzmanii D.C. J Ethnopharmacol. 1992 Feb;36(1):39-41. [PubMed:1501491 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Anonaine (HMDB0030348)

MOL for HMDB0030348 (Anonaine)

3D MOL for HMDB0030348 (Anonaine)

3D SDF for HMDB0030348 (Anonaine)

3D-SDF for HMDB0030348 (Anonaine)

PDB for HMDB0030348 (Anonaine)

3D PDB for HMDB0030348 (Anonaine)

SMILES for HMDB0030348 (Anonaine)

INCHI for HMDB0030348 (Anonaine)

Structure for HMDB0030348 (Anonaine)

3D Structure for HMDB0030348 (Anonaine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra