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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:04:58 UTC

Update Date

2022-03-07 02:53:41 UTC

HMDB ID

HMDB0033367

Secondary Accession Numbers

HMDB33367

Metabolite Identification

Common Name

Oxonantenine

Description

Oxonantenine 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. Oxonantenine is a strong basic compound (based on its pKa). Outside of the human body, oxonantenine has been detected, but not quantified in, a few different foods, such as cherimoya, custard apples, and herbs and spices. This could make oxonantenine a potential biomarker for the consumption of these foods. An oxoaporphine alkaloid isolated from Annona glabra and has been shown to exhibit acetylcholinesterase inhibitory activity.

Structure

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


  Mrv0541 05061307052D          

 25 29  0  0  0  0            999 V2000
    1.4289   -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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2708    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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    2.0625    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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
    1.4289    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859    2.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14  5  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 16 15  2  0  0  0  0
 17 15  1  0  0  0  0
 18 11  1  0  0  0  0
 18 17  1  0  0  0  0
 19 14  2  0  0  0  0
 19 16  1  0  0  0  0
 20  4  1  0  0  0  0
 20 17  2  0  0  0  0
 21 18  2  0  0  0  0
 22  1  1  0  0  0  0
 22 14  1  0  0  0  0
 23  2  1  0  0  0  0
 23 19  1  0  0  0  0
 24  8  1  0  0  0  0
 24 12  1  0  0  0  0
 25  8  1  0  0  0  0
 25 13  1  0  0  0  0
M  END

HMDB0033367
     RDKit          3D
Oxonantenine
 38 42  0  0  0  0  0  0  0  0999 V2000
   -4.5863    1.8778    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1940    1.8000    0.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4633    0.6415    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0238   -0.5959    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1922   -1.6935    0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7902   -2.9462   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854   -4.0579   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6484   -3.9605   -0.1675 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0524   -2.7504   -0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8074   -1.6032    0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2432   -0.3036    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0627    0.7910    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937    2.0759    0.2182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5137    2.9479   -0.8997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2242   -0.2137    0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355    1.0082    0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2342    1.0993    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9820   -0.0237    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3954   -1.2759    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0247   -1.3410   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811   -2.6329   -0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0794   -3.6757   -0.1912 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3144    0.3533    0.2052 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3789    1.7596    0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0438    2.2035    0.3583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0096    1.8648   -0.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8524    2.8709    0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0448    1.1009    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1086   -0.7310    0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8689   -3.0243   -0.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530   -5.0474   -0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1034    3.8137   -0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4543    3.3033   -1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327    2.4025   -1.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090    1.8951    0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9503   -2.1913   -0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311    2.0157   -0.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0285    2.2432    0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 12  3  1  0
 20 15  1  0
 10  5  1  0
 25 17  1  0
 21  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 19 36  1  0
 24 37  1  0
 24 38  1  0
M  END


  Mrv0541 05061307052D          

 25 29  0  0  0  0            999 V2000
    1.4289   -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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2708    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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    2.0625    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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
    1.4289    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859    2.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14  5  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 16 15  2  0  0  0  0
 17 15  1  0  0  0  0
 18 11  1  0  0  0  0
 18 17  1  0  0  0  0
 19 14  2  0  0  0  0
 19 16  1  0  0  0  0
 20  4  1  0  0  0  0
 20 17  2  0  0  0  0
 21 18  2  0  0  0  0
 22  1  1  0  0  0  0
 22 14  1  0  0  0  0
 23  2  1  0  0  0  0
 23 19  1  0  0  0  0
 24  8  1  0  0  0  0
 24 12  1  0  0  0  0
 25  8  1  0  0  0  0
 25 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033367

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C2=C3C(C=CN=C3C(=O)C3=CC4=C(OCO4)C=C23)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H13NO5/c1-22-14-5-9-3-4-20-17-15(9)16(19(14)23-2)10-6-12-13(25-8-24-12)7-11(10)18(17)21/h3-7H,8H2,1-2H3

> <INCHI_KEY>
NFDVJYPMLVMXRR-UHFFFAOYSA-N

> <FORMULA>
C19H13NO5

> <MOLECULAR_WEIGHT>
335.3102

> <EXACT_MASS>
335.079372531

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.91308050073911

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(20),2,4(8),9,12,14,16,18-octaen-11-one

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
2.572123991

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.6629951364285596

> <JCHEM_POLAR_SURFACE_AREA>
66.88000000000001

> <JCHEM_REFRACTIVITY>
88.32629999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(20),2,4(8),9,12,14,16,18-octaen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033367
     RDKit          3D
Oxonantenine
 38 42  0  0  0  0  0  0  0  0999 V2000
   -4.5863    1.8778    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1940    1.8000    0.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4633    0.6415    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0238   -0.5959    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1922   -1.6935    0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7902   -2.9462   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854   -4.0579   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6484   -3.9605   -0.1675 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0524   -2.7504   -0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8074   -1.6032    0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2432   -0.3036    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0627    0.7910    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937    2.0759    0.2182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5137    2.9479   -0.8997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2242   -0.2137    0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355    1.0082    0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2342    1.0993    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9820   -0.0237    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3954   -1.2759    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0247   -1.3410   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811   -2.6329   -0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0794   -3.6757   -0.1912 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3144    0.3533    0.2052 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3789    1.7596    0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0438    2.2035    0.3583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0096    1.8648   -0.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8524    2.8709    0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0448    1.1009    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1086   -0.7310    0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8689   -3.0243   -0.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530   -5.0474   -0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1034    3.8137   -0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4543    3.3033   -1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327    2.4025   -1.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090    1.8951    0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9503   -2.1913   -0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311    2.0157   -0.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0285    2.2432    0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 12  3  1  0
 20 15  1  0
 10  5  1  0
 25 17  1  0
 21  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 19 36  1  0
 24 37  1  0
 24 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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.705   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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -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       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.667   4.620   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.800   1.834   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.800   4.326   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3    4    9                                                       
CONECT    4    3   20                                                       
CONECT    5    9   14                                                       
CONECT    6   10   12                                                       
CONECT    7   11   13                                                       
CONECT    8   24   25                                                       
CONECT    9    3    5   15                                                  
CONECT   10    6   11   16                                                  
CONECT   11    7   10   18                                                  
CONECT   12    6   13   24                                                  
CONECT   13    7   12   25                                                  
CONECT   14    5   19   22                                                  
CONECT   15    9   16   17                                                  
CONECT   16   10   15   19                                                  
CONECT   17   15   18   20                                                  
CONECT   18   11   17   21                                                  
CONECT   19   14   16   23                                                  
CONECT   20    4   17                                                       
CONECT   21   18                                                            
CONECT   22    1   14                                                       
CONECT   23    2   19                                                       
CONECT   24    8   12                                                       
CONECT   25    8   13                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

COMPND    HMDB0033367
HETATM    1  C1  UNL     1      -4.586   1.878   0.314  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.194   1.800   0.276  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.463   0.642   0.183  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.024  -0.596   0.115  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.192  -1.693   0.024  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.790  -2.946  -0.051  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.985  -4.058  -0.146  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.648  -3.960  -0.167  1.00  0.00           N  
HETATM    9  C7  UNL     1      -0.052  -2.750  -0.095  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.807  -1.603   0.001  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.243  -0.304   0.076  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.063   0.791   0.161  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.594   2.076   0.218  1.00  0.00           O  
HETATM   14  C11 UNL     1      -0.514   2.948  -0.900  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.224  -0.214   0.072  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.836   1.008   0.203  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.234   1.099   0.238  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.982  -0.024   0.145  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.395  -1.276   0.015  1.00  0.00           C  
HETATM   20  C17 UNL     1       2.025  -1.341  -0.017  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.381  -2.633  -0.105  1.00  0.00           C  
HETATM   22  O3  UNL     1       2.079  -3.676  -0.191  1.00  0.00           O  
HETATM   23  O4  UNL     1       5.314   0.353   0.205  1.00  0.00           O  
HETATM   24  C19 UNL     1       5.379   1.760   0.073  1.00  0.00           C  
HETATM   25  O5  UNL     1       4.044   2.204   0.358  1.00  0.00           O  
HETATM   26  H1  UNL     1      -5.010   1.865  -0.707  1.00  0.00           H  
HETATM   27  H2  UNL     1      -4.852   2.871   0.751  1.00  0.00           H  
HETATM   28  H3  UNL     1      -5.045   1.101   0.965  1.00  0.00           H  
HETATM   29  H4  UNL     1      -4.109  -0.731   0.132  1.00  0.00           H  
HETATM   30  H5  UNL     1      -3.869  -3.024  -0.034  1.00  0.00           H  
HETATM   31  H6  UNL     1      -2.453  -5.047  -0.206  1.00  0.00           H  
HETATM   32  H7  UNL     1       0.103   3.814  -0.592  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.454   3.303  -1.286  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.033   2.403  -1.693  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.309   1.895   0.333  1.00  0.00           H  
HETATM   36  H11 UNL     1       3.950  -2.191  -0.061  1.00  0.00           H  
HETATM   37  H12 UNL     1       5.631   2.016  -0.975  1.00  0.00           H  
HETATM   38  H13 UNL     1       6.028   2.243   0.813  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5   29
CONECT    5    6    6   10
CONECT    6    7   30
CONECT    7    8    8   31
CONECT    8    9
CONECT    9   10   10   21
CONECT   10   11
CONECT   11   12   12   15
CONECT   12   13
CONECT   13   14
CONECT   14   32   33   34
CONECT   15   16   16   20
CONECT   16   17   35
CONECT   17   18   18   25
CONECT   18   19   23
CONECT   19   20   20   36
CONECT   20   21
CONECT   21   22   22
CONECT   23   24
CONECT   24   25   37   38
END

HMDB0033367
     RDKit          3D
Oxonantenine
 38 42  0  0  0  0  0  0  0  0999 V2000
   -4.5863    1.8778    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1940    1.8000    0.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4633    0.6415    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0238   -0.5959    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1922   -1.6935    0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7902   -2.9462   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854   -4.0579   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6484   -3.9605   -0.1675 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0524   -2.7504   -0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8074   -1.6032    0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2432   -0.3036    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0627    0.7910    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937    2.0759    0.2182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5137    2.9479   -0.8997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2242   -0.2137    0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355    1.0082    0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2342    1.0993    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9820   -0.0237    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3954   -1.2759    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0247   -1.3410   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811   -2.6329   -0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0794   -3.6757   -0.1912 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3144    0.3533    0.2052 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3789    1.7596    0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0438    2.2035    0.3583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0096    1.8648   -0.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8524    2.8709    0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0448    1.1009    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1086   -0.7310    0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8689   -3.0243   -0.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530   -5.0474   -0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1034    3.8137   -0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4543    3.3033   -1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327    2.4025   -1.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090    1.8951    0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9503   -2.1913   -0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311    2.0157   -0.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0285    2.2432    0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 12  3  1  0
 20 15  1  0
 10  5  1  0
 25 17  1  0
 21  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 19 36  1  0
 24 37  1  0
 24 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Dimethoxy-4,5,6,6a-tetradehydro-9,10-(methylenedioxy)noraprophin-7-one	ChEBI
1,2-Dimethoxy-9,10-methylenedioxyoxoaporphine	HMDB

Chemical Formula

C₁₉H₁₃NO₅

Average Molecular Weight

335.3102

Monoisotopic Molecular Weight

335.079372531

IUPAC Name

18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(20),2,4(8),9,12,14,16,18-octaen-11-one

Traditional Name

18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(20),2,4(8),9,12,14,16,18-octaen-11-one

CAS Registry Number

15358-38-0

SMILES

COC1=C(OC)C2=C3C(C=CN=C3C(=O)C3=CC4=C(OCO4)C=C23)=C1

InChI Identifier

InChI=1S/C19H13NO5/c1-22-14-5-9-3-4-20-17-15(9)16(19(14)23-2)10-6-12-13(25-8-24-12)7-11(10)18(17)21/h3-7H,8H2,1-2H3

InChI Key

NFDVJYPMLVMXRR-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: HMDB0033367)

Cellular substructure

Membrane (HMDB: HMDB0033367)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033367)

Source

Exogenous

Food

Food (HMDB: HMDB0033367)

Fruit

Tropical fruit

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

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033367)

Not Available

Nutrient (HMDB: HMDB0033367)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	297 - 299 °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	0.3 g/L	ALOGPS
logP	2.61	ALOGPS
logP	2.57	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	3.66	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.88 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.33 m³·mol⁻¹	ChemAxon
Polarizability	33.91 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	178.459	31661259
DarkChem	[M-H]-	176.932	31661259
DeepCCS	[M-2H]-	223.104	30932474
DeepCCS	[M+Na]+	198.332	30932474
AllCCS	[M+H]+	176.1	32859911
AllCCS	[M+H-H2O]+	172.8	32859911
AllCCS	[M+NH4]+	179.3	32859911
AllCCS	[M+Na]+	180.2	32859911
AllCCS	[M-H]-	181.8	32859911
AllCCS	[M+Na-2H]-	180.7	32859911
AllCCS	[M+HCOO]-	179.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oxonantenine	COC1=C(OC)C2=C3C(C=CN=C3C(=O)C3=CC4=C(OCO4)C=C23)=C1	3835.1	Standard polar	33892256
Oxonantenine	COC1=C(OC)C2=C3C(C=CN=C3C(=O)C3=CC4=C(OCO4)C=C23)=C1	2968.0	Standard non polar	33892256
Oxonantenine	COC1=C(OC)C2=C3C(C=CN=C3C(=O)C3=CC4=C(OCO4)C=C23)=C1	3323.0	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 - Oxonantenine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-0149000000-1d6ef2c5b94c85adb365	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxonantenine 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 - Oxonantenine 10V, Positive-QTOF	splash10-000i-0009000000-ccd6a9460492ed8a4222	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxonantenine 20V, Positive-QTOF	splash10-000i-0009000000-365a9ef26b6bd6830cea	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxonantenine 40V, Positive-QTOF	splash10-056u-0098000000-0fcbf3ff6b616cd71ea9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxonantenine 10V, Negative-QTOF	splash10-001i-0009000000-8abd3f26aab90eac37e1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxonantenine 20V, Negative-QTOF	splash10-001i-0009000000-30c8bd296f185e8f93ec	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxonantenine 40V, Negative-QTOF	splash10-0gbi-0079000000-efbe249cee2ce79bc2a9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxonantenine 10V, Positive-QTOF	splash10-000i-0009000000-9402c14bc783925c244f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxonantenine 20V, Positive-QTOF	splash10-000i-0009000000-9402c14bc783925c244f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxonantenine 40V, Positive-QTOF	splash10-052o-0059000000-da0c603c743658129219	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxonantenine 10V, Negative-QTOF	splash10-001i-0009000000-2f7ce3c1250b2ddc4d81	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxonantenine 20V, Negative-QTOF	splash10-001i-0009000000-2f7ce3c1250b2ddc4d81	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxonantenine 40V, Negative-QTOF	splash10-0udi-0049000000-dfbe1c56f6bd4715fd4a	2021-09-22	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

FDB011395

KNApSAcK ID

C00025995

Chemspider ID

2341323

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3084224

PDB ID

Not Available

ChEBI ID

70651

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 Oxonantenine (HMDB0033367)

MOL for HMDB0033367 (Oxonantenine)

3D MOL for HMDB0033367 (Oxonantenine)

3D SDF for HMDB0033367 (Oxonantenine)

3D-SDF for HMDB0033367 (Oxonantenine)

PDB for HMDB0033367 (Oxonantenine)

3D PDB for HMDB0033367 (Oxonantenine)

SMILES for HMDB0033367 (Oxonantenine)

INCHI for HMDB0033367 (Oxonantenine)

Structure for HMDB0033367 (Oxonantenine)

3D Structure for HMDB0033367 (Oxonantenine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra