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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:17 UTC

Update Date

2022-03-07 02:52:31 UTC

HMDB ID

HMDB0030350

Secondary Accession Numbers

HMDB30350

Metabolite Identification

Common Name

Dehydroanonaine

Description

Dehydroanonaine 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. Dehydroanonaine is a strong basic compound (based on its pKa). Outside of the human body, dehydroanonaine has been detected, but not quantified in, coffee and coffee products and root vegetables. This could make dehydroanonaine a potential biomarker for the consumption of these foods.

Structure

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

HMDB0030350
     RDKit          3D
Dehydroanonaine
 33 37  0  0  0  0  0  0  0  0999 V2000
   -3.3777    2.6245   -0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7455    1.2973   -0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7768    0.2977   -0.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487    0.6548   -0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673    1.9890   -0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0423    2.9690   -0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2717    2.3007   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532    1.3509   -0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8983    0.0195   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8994   -0.9254   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5241   -2.2553   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2055   -2.6444   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -1.6694   -0.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4651   -0.3156   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884   -2.3884   -0.1157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903   -3.6547    0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4204   -3.8964   -0.1473 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3439   -0.6606   -0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6872    0.7585    0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6395    1.6765   -0.1227 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0962    3.4260   -0.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7978    1.0495   -0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1539   -0.6954   -0.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7160    4.0176   -0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871    3.3427   -0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -3.0445   -0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5392   -3.4932    1.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4353   -4.4151    0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8722   -1.3639    0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7191   -0.8956   -1.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6411    1.0800   -0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8410    0.8137    1.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9112    2.6501   -0.4011 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 10 18  1  0
 18 19  1  0
 19 20  1  0
  6  1  1  0
 20  8  1  0
 14  4  1  0
 14  9  1  0
 17 12  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
 11 26  1  0
 16 27  1  0
 16 28  1  0
 18 29  1  0
 18 30  1  0
 19 31  1  0
 19 32  1  0
 20 33  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  2  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>
HMDB0030350

> <DATABASE_NAME>
hmdb

> <SMILES>
C1OC2=C(O1)C1=C3C(CCNC3=CC3=CC=CC=C13)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H13NO2/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/h1-4,7-8,18H,5-6,9H2

> <INCHI_KEY>
VNNKFCMTGJUPOQ-UHFFFAOYSA-N

> <FORMULA>
C17H13NO2

> <MOLECULAR_WEIGHT>
263.2906

> <EXACT_MASS>
263.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.606664718127153

> <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),7,12,14,16,18-heptaene

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
3.0880994306666665

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.129891778222366

> <JCHEM_POLAR_SURFACE_AREA>
30.49

> <JCHEM_REFRACTIVITY>
78.2287

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-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),7,12,14,16,18-heptaene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030350
     RDKit          3D
Dehydroanonaine
 33 37  0  0  0  0  0  0  0  0999 V2000
   -3.3777    2.6245   -0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7455    1.2973   -0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7768    0.2977   -0.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487    0.6548   -0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673    1.9890   -0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0423    2.9690   -0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2717    2.3007   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532    1.3509   -0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8983    0.0195   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8994   -0.9254   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5241   -2.2553   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2055   -2.6444   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -1.6694   -0.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4651   -0.3156   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884   -2.3884   -0.1157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903   -3.6547    0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4204   -3.8964   -0.1473 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3439   -0.6606   -0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6872    0.7585    0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6395    1.6765   -0.1227 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0962    3.4260   -0.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7978    1.0495   -0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1539   -0.6954   -0.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7160    4.0176   -0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871    3.3427   -0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -3.0445   -0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5392   -3.4932    1.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4353   -4.4151    0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8722   -1.3639    0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7191   -0.8956   -1.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6411    1.0800   -0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8410    0.8137    1.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9112    2.6501   -0.4011 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 10 18  1  0
 18 19  1  0
 19 20  1  0
  6  1  1  0
 20  8  1  0
 14  4  1  0
 14  9  1  0
 17 12  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
 11 26  1  0
 16 27  1  0
 16 28  1  0
 18 29  1  0
 18 30  1  0
 19 31  1  0
 19 32  1  0
 20 33  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    HMDB0030350
HETATM    1  C1  UNL     1      -3.378   2.625  -0.045  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.745   1.297  -0.055  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.777   0.298  -0.077  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.449   0.655  -0.088  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.067   1.989  -0.078  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.042   2.969  -0.056  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.272   2.301  -0.090  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.253   1.351  -0.111  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.898   0.020  -0.121  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.899  -0.925  -0.143  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.524  -2.255  -0.153  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.205  -2.644  -0.142  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.806  -1.669  -0.120  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.465  -0.316  -0.110  1.00  0.00           C  
HETATM   15  O1  UNL     1      -1.988  -2.388  -0.116  1.00  0.00           O  
HETATM   16  C15 UNL     1      -1.690  -3.655   0.433  1.00  0.00           C  
HETATM   17  O2  UNL     1      -0.420  -3.896  -0.147  1.00  0.00           O  
HETATM   18  C16 UNL     1       3.344  -0.661  -0.156  1.00  0.00           C  
HETATM   19  C17 UNL     1       3.687   0.759   0.221  1.00  0.00           C  
HETATM   20  N1  UNL     1       2.640   1.676  -0.123  1.00  0.00           N  
HETATM   21  H1  UNL     1      -4.096   3.426  -0.029  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.798   1.050  -0.046  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.154  -0.695  -0.083  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.716   4.018  -0.049  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.587   3.343  -0.082  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.272  -3.045  -0.170  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.539  -3.493   1.530  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.435  -4.415   0.203  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.872  -1.364   0.545  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.719  -0.896  -1.184  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.641   1.080  -0.237  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.841   0.814   1.334  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.911   2.650  -0.401  1.00  0.00           H  
CONECT    1    2    2    6   21
CONECT    2    3   22
CONECT    3    4    4   23
CONECT    4    5   14
CONECT    5    6    6    7
CONECT    6   24
CONECT    7    8    8   25
CONECT    8    9   20
CONECT    9   10   10   14
CONECT   10   11   18
CONECT   11   12   12   26
CONECT   12   13   17
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   17   27   28
CONECT   18   19   29   30
CONECT   19   20   31   32
CONECT   20   33
END

HMDB0030350
     RDKit          3D
Dehydroanonaine
 33 37  0  0  0  0  0  0  0  0999 V2000
   -3.3777    2.6245   -0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7455    1.2973   -0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7768    0.2977   -0.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487    0.6548   -0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673    1.9890   -0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0423    2.9690   -0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2717    2.3007   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532    1.3509   -0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8983    0.0195   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8994   -0.9254   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5241   -2.2553   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2055   -2.6444   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -1.6694   -0.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4651   -0.3156   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884   -2.3884   -0.1157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903   -3.6547    0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4204   -3.8964   -0.1473 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3439   -0.6606   -0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6872    0.7585    0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6395    1.6765   -0.1227 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0962    3.4260   -0.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7978    1.0495   -0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1539   -0.6954   -0.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7160    4.0176   -0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871    3.3427   -0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -3.0445   -0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5392   -3.4932    1.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4353   -4.4151    0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8722   -1.3639    0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7191   -0.8956   -1.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6411    1.0800   -0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8410    0.8137    1.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9112    2.6501   -0.4011 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 10 18  1  0
 18 19  1  0
 19 20  1  0
  6  1  1  0
 20  8  1  0
 14  4  1  0
 14  9  1  0
 17 12  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
 11 26  1  0
 16 27  1  0
 16 28  1  0
 18 29  1  0
 18 30  1  0
 19 31  1  0
 19 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₃NO₂

Average Molecular Weight

263.2906

Monoisotopic Molecular Weight

263.094628665

IUPAC Name

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

Traditional Name

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

CAS Registry Number

41679-82-7

SMILES

C1OC2=C(O1)C1=C3C(CCNC3=CC3=CC=CC=C13)=C2

InChI Identifier

InChI=1S/C17H13NO2/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/h1-4,7-8,18H,5-6,9H2

InChI Key

VNNKFCMTGJUPOQ-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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030350)

Cellular substructure

Membrane (HMDB: HMDB0030350)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030350)

Source

Endogenous

Endogenous (HMDB: HMDB0030350)

Plant

Plant (HMDB: HMDB0030350)
Coffea (HMDB: HMDB0030350)

Exogenous

Food

Food (HMDB: HMDB0030350)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

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
Water Solubility	0.011 g/L	ALOGPS
logP	3.74	ALOGPS
logP	3.09	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	4.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	30.49 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	78.23 m³·mol⁻¹	ChemAxon
Polarizability	28.61 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]+	160.393	31661259
DarkChem	[M-H]-	157.962	31661259
DeepCCS	[M-2H]-	199.788	30932474
DeepCCS	[M+Na]+	175.353	30932474
AllCCS	[M+H]+	160.2	32859911
AllCCS	[M+H-H2O]+	156.3	32859911
AllCCS	[M+NH4]+	163.8	32859911
AllCCS	[M+Na]+	164.8	32859911
AllCCS	[M-H]-	166.5	32859911
AllCCS	[M+Na-2H]-	165.2	32859911
AllCCS	[M+HCOO]-	163.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydroanonaine	C1OC2=C(O1)C1=C3C(CCNC3=CC3=CC=CC=C13)=C2	4028.1	Standard polar	33892256
Dehydroanonaine	C1OC2=C(O1)C1=C3C(CCNC3=CC3=CC=CC=C13)=C2	2600.6	Standard non polar	33892256
Dehydroanonaine	C1OC2=C(O1)C1=C3C(CCNC3=CC3=CC=CC=C13)=C2	2953.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydroanonaine,1TMS,isomer #1	C[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C4C=CC=CC4=CC1=C23	2775.3	Semi standard non polar	33892256
Dehydroanonaine,1TMS,isomer #1	C[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C4C=CC=CC4=CC1=C23	2659.3	Standard non polar	33892256
Dehydroanonaine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C4C=CC=CC4=CC1=C23	2984.9	Semi standard non polar	33892256
Dehydroanonaine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C4C=CC=CC4=CC1=C23	2848.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroanonaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01pt-0090000000-288e5bd38abefaf40f1e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroanonaine 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 - Dehydroanonaine 10V, Positive-QTOF	splash10-03di-0090000000-5276a6472a48a69682d5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroanonaine 20V, Positive-QTOF	splash10-03di-0090000000-5a78c57b0e4bf866f979	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroanonaine 40V, Positive-QTOF	splash10-0gbi-0390000000-41a4c1db1e27c60a0d26	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroanonaine 10V, Negative-QTOF	splash10-03di-0090000000-dcfb5b9b40ce31dd3079	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroanonaine 20V, Negative-QTOF	splash10-03di-0090000000-0c976bf773bec2639128	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroanonaine 40V, Negative-QTOF	splash10-03xu-2090000000-d0c0c2630bd88a1324e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroanonaine 10V, Positive-QTOF	splash10-03di-0090000000-e474907b40a9feb4630b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroanonaine 20V, Positive-QTOF	splash10-03di-0090000000-e474907b40a9feb4630b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroanonaine 40V, Positive-QTOF	splash10-03di-0090000000-e3aac2a095c0c51dd2cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroanonaine 10V, Negative-QTOF	splash10-03di-0090000000-7efa5c9fe1a915c304ca	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroanonaine 20V, Negative-QTOF	splash10-03di-0090000000-fe80f779714ae85b044d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroanonaine 40V, Negative-QTOF	splash10-0002-0090000000-4c156e67fef6c99e9ab6	2021-09-23	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

FDB002195

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85821358

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 Dehydroanonaine (HMDB0030350)

MOL for HMDB0030350 (Dehydroanonaine)

3D MOL for HMDB0030350 (Dehydroanonaine)

3D SDF for HMDB0030350 (Dehydroanonaine)

3D-SDF for HMDB0030350 (Dehydroanonaine)

PDB for HMDB0030350 (Dehydroanonaine)

3D PDB for HMDB0030350 (Dehydroanonaine)

SMILES for HMDB0030350 (Dehydroanonaine)

INCHI for HMDB0030350 (Dehydroanonaine)

Structure for HMDB0030350 (Dehydroanonaine)

3D Structure for HMDB0030350 (Dehydroanonaine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra