NP-MRD: Showing NP-Card for lettowianthine (NP0029808)

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Record Information

Version

2.0

Created at

2021-06-19 21:20:18 UTC

Updated at

2021-06-29 23:57:24 UTC

NP-MRD ID

NP0029808

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lettowianthine

Provided By

JEOL Database JEOL Logo

Description

Lettowianthine, also known as annobraine, 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. Lettowianthine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, lettowianthine has been detected, but not quantified in, alcoholic beverages and fruits. lettowianthine is found in Annona glabra , Annona squamosa and Lettowianthus stellatus. lettowianthine was first documented in 2000 (Nkunya, M. H. H., et al.). This could make lettowianthine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123203D          

 35 40  0  0  0  0            999 V2000
   -1.9084   -2.0573   -5.3744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565   -1.6712   -4.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3521   -1.3363   -4.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9914   -1.4753   -5.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644   -0.9021   -3.4556 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1180   -0.6451   -3.0163 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1752    0.2483   -1.7693 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0890   -0.0683   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2535    0.2769    0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870    0.0650    1.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0237   -0.4453    0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2723   -0.8020   -0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1485   -0.6099   -1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -0.9559   -2.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556   -1.4301   -3.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012   -1.6226   -2.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7991   -2.1121   -2.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9319   -2.3085   -2.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8831   -2.0203   -0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018   -1.5347   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5214   -1.3160   -0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091   -0.5353    2.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1327   -0.0411    3.1331 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1979    0.3490    2.7594 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6944   -0.2135   -3.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638   -1.6232   -2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667    0.1606   -1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413    1.2946   -2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750    0.7101    0.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8646   -2.3484   -3.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8467   -2.6861   -2.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7626   -2.1703   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7306   -1.3273    0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6467    0.8260    3.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -0.8250    3.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0  0  0  0
  5  6  1  0  0  0  0
 19 18  2  0  0  0  0
  6  7  1  0  0  0  0
 18 17  1  0  0  0  0
 17 16  2  0  0  0  0
 14 15  2  0  0  0  0
 14 13  1  0  0  0  0
  9 10  2  0  0  0  0
  8 13  2  0  0  0  0
 13 12  1  0  0  0  0
 12 21  1  0  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
  5 14  1  0  0  0  0
 15  2  1  0  0  0  0
 16 15  1  0  0  0  0
  3  4  2  0  0  0  0
 11 12  2  0  0  0  0
  2  1  2  0  0  0  0
 11 10  1  0  0  0  0
 16 21  1  0  0  0  0
  8  9  1  0  0  0  0
 21 20  2  0  0  0  0
  8  7  1  0  0  0  0
 10 24  1  0  0  0  0
 24 23  1  0  0  0  0
 23 22  1  0  0  0  0
 22 11  1  0  0  0  0
  9 29  1  0  0  0  0
  6 25  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
 20 33  1  0  0  0  0
 19 32  1  0  0  0  0
 18 31  1  0  0  0  0
 17 30  1  0  0  0  0
 23 34  1  0  0  0  0
 23 35  1  0  0  0  0
M  END

     RDKit          3D

 35 40  0  0  0  0  0  0  0  0999 V2000
   -1.9084   -2.0573   -5.3744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565   -1.6712   -4.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3521   -1.3363   -4.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9914   -1.4753   -5.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644   -0.9021   -3.4556 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1180   -0.6451   -3.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752    0.2483   -1.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0890   -0.0683   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2535    0.2769    0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870    0.0650    1.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0237   -0.4453    0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2723   -0.8020   -0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1485   -0.6099   -1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -0.9559   -2.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556   -1.4301   -3.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012   -1.6226   -2.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7991   -2.1121   -2.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9319   -2.3085   -2.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8831   -2.0203   -0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018   -1.5347   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5214   -1.3160   -0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091   -0.5353    2.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1327   -0.0411    3.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979    0.3490    2.7594 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6944   -0.2135   -3.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638   -1.6232   -2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667    0.1606   -1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413    1.2946   -2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750    0.7101    0.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8646   -2.3484   -3.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8467   -2.6861   -2.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7626   -2.1703   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7306   -1.3273    0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6467    0.8260    3.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -0.8250    3.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
  5  6  1  0
 19 18  2  0
  6  7  1  0
 18 17  1  0
 17 16  2  0
 14 15  2  0
 14 13  1  0
  9 10  2  0
  8 13  2  0
 13 12  1  0
 12 21  1  0
  2  3  1  0
  3  5  1  0
  5 14  1  0
 15  2  1  0
 16 15  1  0
  3  4  2  0
 11 12  2  0
  2  1  2  0
 11 10  1  0
 16 21  1  0
  8  9  1  0
 21 20  2  0
  8  7  1  0
 10 24  1  0
 24 23  1  0
 23 22  1  0
 22 11  1  0
  9 29  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
 20 33  1  0
 19 32  1  0
 18 31  1  0
 17 30  1  0
 23 34  1  0
 23 35  1  0
M  END


  Mrv1652306192123203D          

 35 40  0  0  0  0            999 V2000
   -1.9084   -2.0573   -5.3744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565   -1.6712   -4.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3521   -1.3363   -4.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9914   -1.4753   -5.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644   -0.9021   -3.4556 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1180   -0.6451   -3.0163 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1752    0.2483   -1.7693 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0890   -0.0683   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2535    0.2769    0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870    0.0650    1.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0237   -0.4453    0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2723   -0.8020   -0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1485   -0.6099   -1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -0.9559   -2.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556   -1.4301   -3.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012   -1.6226   -2.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7991   -2.1121   -2.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9319   -2.3085   -2.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8831   -2.0203   -0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018   -1.5347   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5214   -1.3160   -0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091   -0.5353    2.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1327   -0.0411    3.1331 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1979    0.3490    2.7594 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6944   -0.2135   -3.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638   -1.6232   -2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667    0.1606   -1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413    1.2946   -2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750    0.7101    0.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8646   -2.3484   -3.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8467   -2.6861   -2.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7626   -2.1703   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7306   -1.3273    0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6467    0.8260    3.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -0.8250    3.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0  0  0  0
  5  6  1  0  0  0  0
 19 18  2  0  0  0  0
  6  7  1  0  0  0  0
 18 17  1  0  0  0  0
 17 16  2  0  0  0  0
 14 15  2  0  0  0  0
 14 13  1  0  0  0  0
  9 10  2  0  0  0  0
  8 13  2  0  0  0  0
 13 12  1  0  0  0  0
 12 21  1  0  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
  5 14  1  0  0  0  0
 15  2  1  0  0  0  0
 16 15  1  0  0  0  0
  3  4  2  0  0  0  0
 11 12  2  0  0  0  0
  2  1  2  0  0  0  0
 11 10  1  0  0  0  0
 16 21  1  0  0  0  0
  8  9  1  0  0  0  0
 21 20  2  0  0  0  0
  8  7  1  0  0  0  0
 10 24  1  0  0  0  0
 24 23  1  0  0  0  0
 23 22  1  0  0  0  0
 22 11  1  0  0  0  0
  9 29  1  0  0  0  0
  6 25  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
 20 33  1  0  0  0  0
 19 32  1  0  0  0  0
 18 31  1  0  0  0  0
 17 30  1  0  0  0  0
 23 34  1  0  0  0  0
 23 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029808

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C([H])=C2C(=C1[H])C1=C3N(C(=O)C1=O)C([H])([H])C([H])([H])C1=C3C2=C2OC([H])([H])OC2=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H11NO4/c21-17-15-11-4-2-1-3-10(11)14-13-9(7-12-18(14)24-8-23-12)5-6-20(16(13)15)19(17)22/h1-4,7H,5-6,8H2

> <INCHI_KEY>
FMLHJJVSHOCVAU-UHFFFAOYSA-N

> <FORMULA>
C19H11NO4

> <MOLECULAR_WEIGHT>
317.2949

> <EXACT_MASS>
317.068807845

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
32.360658849454644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-dioxa-11-azahexacyclo[9.9.2.0^{2,6}.0^{8,21}.0^{14,22}.0^{15,20}]docosa-1(21),2(6),7,14(22),15,17,19-heptaene-12,13-dione

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
2.457685117333333

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.507041615929681

> <JCHEM_POLAR_SURFACE_AREA>
55.84

> <JCHEM_REFRACTIVITY>
85.56779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dioxa-11-azahexacyclo[9.9.2.0^{2,6}.0^{8,21}.0^{14,22}.0^{15,20}]docosa-1(21),2(6),7,14(22),15,17,19-heptaene-12,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 40  0  0  0  0  0  0  0  0999 V2000
   -1.9084   -2.0573   -5.3744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565   -1.6712   -4.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3521   -1.3363   -4.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9914   -1.4753   -5.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644   -0.9021   -3.4556 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1180   -0.6451   -3.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752    0.2483   -1.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0890   -0.0683   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2535    0.2769    0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870    0.0650    1.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0237   -0.4453    0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2723   -0.8020   -0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1485   -0.6099   -1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -0.9559   -2.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556   -1.4301   -3.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012   -1.6226   -2.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7991   -2.1121   -2.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9319   -2.3085   -2.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8831   -2.0203   -0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018   -1.5347   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5214   -1.3160   -0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091   -0.5353    2.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1327   -0.0411    3.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979    0.3490    2.7594 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6944   -0.2135   -3.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638   -1.6232   -2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667    0.1606   -1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413    1.2946   -2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750    0.7101    0.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8646   -2.3484   -3.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8467   -2.6861   -2.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7626   -2.1703   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7306   -1.3273    0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6467    0.8260    3.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -0.8250    3.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
  5  6  1  0
 19 18  2  0
  6  7  1  0
 18 17  1  0
 17 16  2  0
 14 15  2  0
 14 13  1  0
  9 10  2  0
  8 13  2  0
 13 12  1  0
 12 21  1  0
  2  3  1  0
  3  5  1  0
  5 14  1  0
 15  2  1  0
 16 15  1  0
  3  4  2  0
 11 12  2  0
  2  1  2  0
 11 10  1  0
 16 21  1  0
  8  9  1  0
 21 20  2  0
  8  7  1  0
 10 24  1  0
 24 23  1  0
 23 22  1  0
 22 11  1  0
  9 29  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
 20 33  1  0
 19 32  1  0
 18 31  1  0
 17 30  1  0
 23 34  1  0
 23 35  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0      -1.908  -2.057  -5.374  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.157  -1.671  -4.508  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.352  -1.336  -4.693  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.991  -1.475  -5.712  0.00  0.00           O+0
HETATM    5  N   UNK     0       0.764  -0.902  -3.456  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.118  -0.645  -3.016  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.175   0.248  -1.769  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.089  -0.068  -0.755  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.254   0.277   0.585  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.187   0.065   1.428  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.024  -0.445   0.989  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.272  -0.802  -0.352  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.149  -0.610  -1.199  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.278  -0.956  -2.527  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.456  -1.430  -3.083  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.601  -1.623  -2.319  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.799  -2.112  -2.882  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.932  -2.309  -2.099  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.883  -2.020  -0.746  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.702  -1.535  -0.175  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.521  -1.316  -0.926  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.909  -0.535   2.028  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.133  -0.041   3.133  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.198   0.349   2.759  0.00  0.00           O+0
HETATM   25  H   UNK     0       2.694  -0.214  -3.842  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.564  -1.623  -2.795  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.167   0.161  -1.310  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.041   1.295  -2.072  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.175   0.710   0.959  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.865  -2.348  -3.943  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.847  -2.686  -2.549  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.763  -2.170  -0.125  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.731  -1.327   0.891  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.647   0.826   3.563  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.069  -0.825   3.897  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    3   15    1                                                  
CONECT    3    2    5    4                                                  
CONECT    4    3                                                            
CONECT    5    6    3   14                                                  
CONECT    6    5    7   25   26                                             
CONECT    7    6    8   27   28                                             
CONECT    8   13    9    7                                                  
CONECT    9   10    8   29                                                  
CONECT   10    9   11   24                                                  
CONECT   11   12   10   22                                                  
CONECT   12   13   21   11                                                  
CONECT   13   14    8   12                                                  
CONECT   14   15   13    5                                                  
CONECT   15   14    2   16                                                  
CONECT   16   17   15   21                                                  
CONECT   17   18   16   30                                                  
CONECT   18   19   17   31                                                  
CONECT   19   20   18   32                                                  
CONECT   20   19   21   33                                                  
CONECT   21   12   16   20                                                  
CONECT   22   23   11                                                       
CONECT   23   24   22   34   35                                             
CONECT   24   10   23                                                       
CONECT   25    6                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    7                                                            
CONECT   29    9                                                            
CONECT   30   17                                                            
CONECT   31   18                                                            
CONECT   32   19                                                            
CONECT   33   20                                                            
CONECT   34   23                                                            
CONECT   35   23                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

RDKit          3D

35 40  0  0  0  0  0  0  0  0999 V2000
   -1.9084   -2.0573   -5.3744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565   -1.6712   -4.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3521   -1.3363   -4.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9914   -1.4753   -5.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644   -0.9021   -3.4556 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1180   -0.6451   -3.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752    0.2483   -1.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0890   -0.0683   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2535    0.2769    0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870    0.0650    1.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0237   -0.4453    0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2723   -0.8020   -0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1485   -0.6099   -1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -0.9559   -2.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556   -1.4301   -3.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012   -1.6226   -2.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7991   -2.1121   -2.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9319   -2.3085   -2.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8831   -2.0203   -0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018   -1.5347   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5214   -1.3160   -0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091   -0.5353    2.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1327   -0.0411    3.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979    0.3490    2.7594 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6944   -0.2135   -3.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638   -1.6232   -2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667    0.1606   -1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413    1.2946   -2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750    0.7101    0.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8646   -2.3484   -3.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8467   -2.6861   -2.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7626   -2.1703   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7306   -1.3273    0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6467    0.8260    3.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -0.8250    3.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
  5  6  1  0
 19 18  2  0
  6  7  1  0
 18 17  1  0
 17 16  2  0
 14 15  2  0
 14 13  1  0
  9 10  2  0
  8 13  2  0
 13 12  1  0
 12 21  1  0
  2  3  1  0
  3  5  1  0
  5 14  1  0
 15  2  1  0
 16 15  1  0
  3  4  2  0
 11 12  2  0
  2  1  2  0
 11 10  1  0
 16 21  1  0
  8  9  1  0
 21 20  2  0
  8  7  1  0
 10 24  1  0
 24 23  1  0
 23 22  1  0
 22 11  1  0
  9 29  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
 20 33  1  0
 19 32  1  0
 18 31  1  0
 17 30  1  0
 23 34  1  0
 23 35  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
Annobraine	HMDB
Lettowianthine	MeSH

Chemical Formula

C₁₉H₁₁NO₄

Average Mass

317.2949 Da

Monoisotopic Mass

317.06881 Da

IUPAC Name

3,5-dioxa-11-azahexacyclo[9.9.2.0^{2,6}.0^{8,21}.0^{14,22}.0^{15,20}]docosa-1(21),2(6),7,14(22),15,17,19-heptaene-12,13-dione

Traditional Name

3,5-dioxa-11-azahexacyclo[9.9.2.0^{2,6}.0^{8,21}.0^{14,22}.0^{15,20}]docosa-1(21),2(6),7,14(22),15,17,19-heptaene-12,13-dione

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])C([H])=C2C(=C1[H])C1=C3N(C(=O)C1=O)C([H])([H])C([H])([H])C1=C3C2=C2OC([H])([H])OC2=C1[H]

InChI Identifier

InChI=1S/C19H11NO4/c21-17-15-11-4-2-1-3-10(11)14-13-9(7-12-18(14)24-8-23-12)5-6-20(16(13)15)19(17)22/h1-4,7H,5-6,8H2

InChI Key

FMLHJJVSHOCVAU-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 360 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 360 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Annona glabra	Plant	KNApSAcK
Annona squamosa	LOTUS Database	35616633
Lettowianthus stellatus	JEOL database	Nkunya, M. H. H., et al, Phytochemistry 53, 1067 (2000)

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
Indole or derivatives
Aryl ketone
Benzenoid
Vinylogous amide
Tertiary carboxylic acid amide
Carboxamide group
Ketone
Lactam
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	2.24	ALOGPS
logP	2.46	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.84 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.57 m³·mol⁻¹	ChemAxon
Polarizability	32.36 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034923

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013509

KNApSAcK ID

C00027280

Chemspider ID

10216687

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21593830

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nkunya, M. H. H., et al. (2000). Nkunya, M. H. H., et al, Phytochemistry 53, 1067 (2000). Phytochem..

Showing NP-Card for lettowianthine (NP0029808)

MOL for NP0029808 (lettowianthine)

3D MOL for NP0029808 (lettowianthine)

3D SDF for NP0029808 (lettowianthine)

3D-SDF for NP0029808 (lettowianthine)

PDB for NP0029808 (lettowianthine)

3D PDB for NP0029808 (lettowianthine)

SMILES for NP0029808 (lettowianthine)

INCHI for NP0029808 (lettowianthine)

Structure for NP0029808 (lettowianthine)

3D Structure for NP0029808 (lettowianthine)