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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:13:42 UTC

Update Date

2022-03-07 02:57:03 UTC

HMDB ID

HMDB0041537

Secondary Accession Numbers

HMDB41537

Metabolite Identification

Common Name

N-Acetyldehydroanonaine

Description

N-Acetyldehydroanonaine 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. N-Acetyldehydroanonaine has been detected, but not quantified in, fruits and herbs and spices. This could make N-acetyldehydroanonaine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-Acetyldehydroanonaine.

Structure

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

HMDB0041537
     RDKit          3D
N-Acetyldehydroanonaine
 38 42  0  0  0  0  0  0  0  0999 V2000
    4.8390    0.5725   -0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023    1.0140   -0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2318    2.1626   -0.8326 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4074    0.1196    0.0272 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484   -1.2164    0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9236   -2.2429   -0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4919   -1.8197   -0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4296   -2.8173   -0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7698   -2.5367   -0.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1840   -1.2091   -0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2808   -0.1972   -0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851   -0.5059   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0442    0.4926    0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6461    1.8001    0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6965    2.0874    0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0896    3.3893    0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4169    3.7589    0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3569    2.7628    0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026    1.4399   -0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6663    1.1148   -0.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5586   -1.2741   -0.5265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9415   -2.5758   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9171   -3.3326   -0.7803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5241    1.3539   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0319    0.2048    0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0056   -0.2988   -0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4452   -1.3087    1.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8299   -1.3771    0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3511   -2.3497   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -3.1933    0.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019   -3.8591   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069    2.5441    0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304    4.1600    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7096    4.7910    0.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3996    3.0942    0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8146    0.7611   -0.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9449   -2.8564   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556   -2.6529    0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  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
 18 19  2  0
 19 20  1  0
 10 21  1  0
 21 22  1  0
 22 23  1  0
 13  4  1  0
 20 15  1  0
 12  7  1  0
 23  9  1  0
 20 11  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 22 37  1  0
 22 38  1  0
M  END


  Mrv0541 05061312442D          

 23 27  0  0  0  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    1.4289   -2.4750    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
    2.1434   -2.8875    0.0000 O   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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
 11  1  1  0  0  0  0
 12  4  2  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  0  0  0  0
 13  9  2  0  0  0  0
 14  5  2  0  0  0  0
 14 12  1  0  0  0  0
 15  8  2  0  0  0  0
 16  9  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 14  1  0  0  0  0
 18 17  2  0  0  0  0
 19 16  2  0  0  0  0
 19 18  1  0  0  0  0
 20  7  1  0  0  0  0
 20 11  1  0  0  0  0
 20 15  1  0  0  0  0
 21 11  2  0  0  0  0
 22 10  1  0  0  0  0
 22 16  1  0  0  0  0
 23 10  1  0  0  0  0
 23 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041537

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)N1CCC2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31

> <INCHI_IDENTIFIER>
InChI=1S/C19H15NO3/c1-11(21)20-7-6-13-9-16-19(23-10-22-16)18-14-5-3-2-4-12(14)8-15(20)17(13)18/h2-5,8-9H,6-7,10H2,1H3

> <INCHI_KEY>
FNUSCCFSHRMQQM-UHFFFAOYSA-N

> <FORMULA>
C19H15NO3

> <MOLECULAR_WEIGHT>
305.3273

> <EXACT_MASS>
305.105193351

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.872709222382554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaen-11-yl}ethan-1-one

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
2.7170977393333335

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6092362840324257

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
86.01379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaen-11-yl}ethanone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0041537
     RDKit          3D
N-Acetyldehydroanonaine
 38 42  0  0  0  0  0  0  0  0999 V2000
    4.8390    0.5725   -0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023    1.0140   -0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2318    2.1626   -0.8326 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4074    0.1196    0.0272 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484   -1.2164    0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9236   -2.2429   -0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4919   -1.8197   -0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4296   -2.8173   -0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7698   -2.5367   -0.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1840   -1.2091   -0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2808   -0.1972   -0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851   -0.5059   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0442    0.4926    0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6461    1.8001    0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6965    2.0874    0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0896    3.3893    0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4169    3.7589    0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3569    2.7628    0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026    1.4399   -0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6663    1.1148   -0.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5586   -1.2741   -0.5265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9415   -2.5758   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9171   -3.3326   -0.7803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5241    1.3539   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0319    0.2048    0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0056   -0.2988   -0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4452   -1.3087    1.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8299   -1.3771    0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3511   -2.3497   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -3.1933    0.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019   -3.8591   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069    2.5441    0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304    4.1600    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7096    4.7910    0.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3996    3.0942    0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8146    0.7611   -0.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9449   -2.8564   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556   -2.6529    0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  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
 18 19  2  0
 19 20  1  0
 10 21  1  0
 21 22  1  0
 22 23  1  0
 13  4  1  0
 20 15  1  0
 12  7  1  0
 23  9  1  0
 20 11  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 22 37  1  0
 22 38  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       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.853   3.977   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.321   3.816   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.479   2.570   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   12                                                       
CONECT    5    3   14                                                       
CONECT    6    7   13                                                       
CONECT    7    6   20                                                       
CONECT    8   12   15                                                       
CONECT    9   13   16                                                       
CONECT   10   22   23                                                       
CONECT   11    1   20   21                                                  
CONECT   12    4    8   14                                                  
CONECT   13    6    9   17                                                  
CONECT   14    5   12   18                                                  
CONECT   15    8   17   20                                                  
CONECT   16    9   19   22                                                  
CONECT   17   13   15   18                                                  
CONECT   18   14   17   19                                                  
CONECT   19   16   18   23                                                  
CONECT   20    7   11   15                                                  
CONECT   21   11                                                            
CONECT   22   10   16                                                       
CONECT   23   10   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0041537
HETATM    1  C1  UNL     1       4.839   0.572  -0.266  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.402   1.014  -0.378  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.232   2.163  -0.833  1.00  0.00           O  
HETATM    4  N1  UNL     1       2.407   0.120   0.027  1.00  0.00           N  
HETATM    5  C3  UNL     1       2.748  -1.216   0.457  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.924  -2.243  -0.311  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.492  -1.820  -0.356  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.430  -2.817  -0.555  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.770  -2.537  -0.597  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.184  -1.209  -0.432  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.281  -0.197  -0.232  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.085  -0.506  -0.193  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.044   0.493   0.004  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.646   1.800   0.167  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.697   2.087   0.129  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.090   3.389   0.292  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.417   3.759   0.265  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.357   2.763   0.067  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.003   1.440  -0.101  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.666   1.115  -0.068  1.00  0.00           C  
HETATM   21  O2  UNL     1      -3.559  -1.274  -0.526  1.00  0.00           O  
HETATM   22  C19 UNL     1      -3.941  -2.576  -0.139  1.00  0.00           C  
HETATM   23  O3  UNL     1      -2.917  -3.333  -0.780  1.00  0.00           O  
HETATM   24  H1  UNL     1       5.524   1.354  -0.601  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.032   0.205   0.751  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.006  -0.299  -0.961  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.445  -1.309   1.522  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.830  -1.377   0.304  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.351  -2.350  -1.322  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.952  -3.193   0.255  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.102  -3.859  -0.685  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.407   2.544   0.327  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.330   4.160   0.447  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.710   4.791   0.396  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.400   3.094   0.052  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.815   0.761  -0.246  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.945  -2.856  -0.449  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.756  -2.653   0.954  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    4
CONECT    4    5   13
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8    8   12
CONECT    8    9   31
CONECT    9   10   10   23
CONECT   10   11   21
CONECT   11   12   20   20
CONECT   12   13   13
CONECT   13   14
CONECT   14   15   15   32
CONECT   15   16   20
CONECT   16   17   17   33
CONECT   17   18   34
CONECT   18   19   19   35
CONECT   19   20   36
CONECT   21   22
CONECT   22   23   37   38
END

HMDB0041537
     RDKit          3D
N-Acetyldehydroanonaine
 38 42  0  0  0  0  0  0  0  0999 V2000
    4.8390    0.5725   -0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023    1.0140   -0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2318    2.1626   -0.8326 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4074    0.1196    0.0272 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484   -1.2164    0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9236   -2.2429   -0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4919   -1.8197   -0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4296   -2.8173   -0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7698   -2.5367   -0.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1840   -1.2091   -0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2808   -0.1972   -0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851   -0.5059   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0442    0.4926    0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6461    1.8001    0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6965    2.0874    0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0896    3.3893    0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4169    3.7589    0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3569    2.7628    0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026    1.4399   -0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6663    1.1148   -0.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5586   -1.2741   -0.5265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9415   -2.5758   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9171   -3.3326   -0.7803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5241    1.3539   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0319    0.2048    0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0056   -0.2988   -0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4452   -1.3087    1.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8299   -1.3771    0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3511   -2.3497   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -3.1933    0.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019   -3.8591   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069    2.5441    0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304    4.1600    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7096    4.7910    0.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3996    3.0942    0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8146    0.7611   -0.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9449   -2.8564   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556   -2.6529    0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  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
 18 19  2  0
 19 20  1  0
 10 21  1  0
 21 22  1  0
 22 23  1  0
 13  4  1  0
 20 15  1  0
 12  7  1  0
 23  9  1  0
 20 11  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 22 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₁₅NO₃

Average Molecular Weight

305.3273

Monoisotopic Molecular Weight

305.105193351

IUPAC Name

1-{3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaen-11-yl}ethan-1-one

Traditional Name

1-{3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaen-11-yl}ethanone

CAS Registry Number

132646-11-8

SMILES

CC(=O)N1CCC2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31

InChI Identifier

InChI=1S/C19H15NO3/c1-11(21)20-7-6-13-9-16-19(23-10-22-16)18-14-5-3-2-4-12(14)8-15(20)17(13)18/h2-5,8-9H,6-7,10H2,1H3

InChI Key

FNUSCCFSHRMQQM-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
Benzodioxole
Benzenoid
Tertiary carboxylic acid amide
Acetamide
Carboxamide group
Azacycle
Oxacycle
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
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

Membrane (HMDB: HMDB0041537)
Cell membrane (HMDB: HMDB0041537)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041537)

Source

Exogenous

Exogenous (HMDB: HMDB0041537)

Food

Food (HMDB: HMDB0041537)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0041537)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041537)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	151 - 153 °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	0.021 g/L	ALOGPS
logP	3.27	ALOGPS
logP	2.72	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.01 m³·mol⁻¹	ChemAxon
Polarizability	32.87 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]+	170.897	31661259
DarkChem	[M-H]-	166.109	31661259
DeepCCS	[M-2H]-	196.448	30932474
DeepCCS	[M+Na]+	171.619	30932474
AllCCS	[M+H]+	170.2	32859911
AllCCS	[M+H-H2O]+	166.7	32859911
AllCCS	[M+NH4]+	173.5	32859911
AllCCS	[M+Na]+	174.4	32859911
AllCCS	[M-H]-	178.0	32859911
AllCCS	[M+Na-2H]-	177.0	32859911
AllCCS	[M+HCOO]-	176.0	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.	6.35 minutes	32390414
Predicted by Siyang on May 30, 2022	14.5272 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.04 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2259.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	389.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	175.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	203.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	131.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	613.3 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	670.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	72.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1111.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	502.5 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	1793.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	430.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	388.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	309.9 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	12.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyldehydroanonaine	CC(=O)N1CCC2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31	4168.3	Standard polar	33892256
N-Acetyldehydroanonaine	CC(=O)N1CCC2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31	2818.3	Standard non polar	33892256
N-Acetyldehydroanonaine	CC(=O)N1CCC2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31	3178.0	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 - N-Acetyldehydroanonaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-1090000000-3be673e829379007b4c1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyldehydroanonaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyldehydroanonaine 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 - N-Acetyldehydroanonaine 10V, Positive-QTOF	splash10-0a4i-0039000000-83c85b4aa3856db47e51	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 20V, Positive-QTOF	splash10-0bt9-0096000000-81087b256ded869c6606	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 40V, Positive-QTOF	splash10-02ai-1090000000-9090f6814cf5889e31fc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 10V, Negative-QTOF	splash10-0udi-0029000000-821ad62da85eb995cd65	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 20V, Negative-QTOF	splash10-0ik9-1095000000-62a257d4823339b4c972	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 40V, Negative-QTOF	splash10-03di-2090000000-7d6c990d913f488afc18	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 10V, Negative-QTOF	splash10-0udi-0029000000-0d43d345fce52165f59f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 20V, Negative-QTOF	splash10-0ik9-0097000000-0bc82a3ee74aa2993fd8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 40V, Negative-QTOF	splash10-0il3-1092000000-6c48d0c524a338010bf7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 10V, Positive-QTOF	splash10-0a4i-0009000000-43ab62a80b50d00d6e5f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 20V, Positive-QTOF	splash10-0a4i-0039000000-1a45e8f62fa161f99e43	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 40V, Positive-QTOF	splash10-000i-0090000000-e78fd1902ec5c130217d	2021-09-24	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

FDB021517

KNApSAcK ID

Not Available

Chemspider ID

4474975

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5315739

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 N-Acetyldehydroanonaine (HMDB0041537)

MOL for HMDB0041537 (N-Acetyldehydroanonaine)

3D MOL for HMDB0041537 (N-Acetyldehydroanonaine)

3D SDF for HMDB0041537 (N-Acetyldehydroanonaine)

3D-SDF for HMDB0041537 (N-Acetyldehydroanonaine)

PDB for HMDB0041537 (N-Acetyldehydroanonaine)

3D PDB for HMDB0041537 (N-Acetyldehydroanonaine)

SMILES for HMDB0041537 (N-Acetyldehydroanonaine)

INCHI for HMDB0041537 (N-Acetyldehydroanonaine)

Structure for HMDB0041537 (N-Acetyldehydroanonaine)

3D Structure for HMDB0041537 (N-Acetyldehydroanonaine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra