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Showing NP-Card for Liriodenine (NP0045597)

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Record Information
Version2.0
Created at2022-03-17 19:32:28 UTC
Updated at2022-03-17 19:32:28 UTC
NP-MRD IDNP0045597
Secondary Accession NumbersNone
Natural Product Identification
Common NameLiriodenine
Description Liriodenine is found in Alphonsea mollis, Anisocycla racemosa, Annickia polycarpa, Annona acuminata, Annona ambotay, Annona cherimolia, Annona dioica, Annona diversifolia, Annona emarginata, Annona foetida, Annona glabra , Annona montana , Annona neosericea, Annona purpurea , Annona senegalensis , Annona squamosa , Aquilaria agallocha , Artabotrys hexapetalus , Artabotrys maingayi, Artabotrys uncinatus , Artabotrys zeylanicus, Asimina triloba, Atherosperma moschatum, Atrabotrys maingayi, Beilschmiedia alloiophylla, Broussonetia papyrifera, Cananga odorata, Cardiopetalum calophyllum, Cissampelos sympodialis, Cleistopholis patens, Dasymaschalon longiflorum, Desfontainia spinosa, Desmos longifolia, Disepalum anomalum, Disepalum pulchrum, Doryphora sassafras, Enantia chlorantha , Eupomatia bennettii, Eupomatia laurina, Fissistigma glaucescens , Friesodielsia velutina, Glossocalyx brevipes, Goniothalamus amuyon, Goniothalamus cheliensis, Goniothalamus scortechinii, Goniothalamus scortephanine, Goniothalamus topis, Greenwayodendron oliveri, Guatteria amplifolia, Guatteria blepharophylla, Guatteriopsis friesiana, Guatteria modesta, Guatteria multivenia, Guatteria oliviformis, Hexalobus crispiflorus, Hexalobus monopetalus, Illigera luzonensis, Isolona congolana, Laurelia novae-zelandiae, Lettowianthus stellatus, Licaria triandra, Liriodendron tulipfera, Liriodendron tulipifera , Magnolia abovata, Magnolia coco, Magnolia elegans, Magnolia grandiflora , Magnolia kobus, Magnolia liliifera, Magnolia mexicana, Magnolia obovata , Magnolia odora, Magnolia officinalis, Magnolia salicifolia, Magnolia soulangeana, Meiogyne monosperma, Meiogyne virgata, Magnolia alba, Magnolia baillonii, Magnolia champaca, Magnolia compressa, Magnolia lanuginosa, Michellia alba, Michellia champaca, Microcos paniculata, Miliusa cuneata, Miliusa horsfieldii, Miliusa velutina , Mitrephora glabra, Mitrephora maingayi, Mitrephora tomentosa, Mollinedia schottiana, Monodora junodii, Monodora tenuifolia, Nelumbo nucifera , Neolitsea acuminatissima, Neolitsea sericea, Oncodostigma monosperma, Oxandra asbeckii, Oxandra xylopioides, Pachygone ovata, Papaver caucasicum, Phoebe formosana, Piptostigma fugax, Polyalthia insignis, Polyalthia longifolia , Polyalthia macropoda, Polyalthia stenopetala, Porcelia macrocarpa, Pseuduvaria rugosa, Pseuduvaria trimera, Rhigiocarya racemifera, Annona mucosa, Annona papilionella, Sapranthus palanga, Sinomenium acutum, Siparuna guianensis, Siparuna thecaphora, Siparuna tonduziana, Stephania dinklagei, Stephania venosa, Talauma gitigensis, Talauma mexicana Don., Thalictrum javanicum, Trivalvaria costata, Trivalvaria macrophylla, Tsoomgiodendron odorum, Unonopsis guatterioides, Unonopsis spectabilis, Uvaria argentea, Uvaria mocali, Uvaria mocoli, Uvaria rufa, Uvaria versicolor, Xanthorhiza simplicissima, Xylopia aethiopica , Xylopia amazonica, Xylopia brasiliensis, Xylopia buxifolia, Xylopia frutescens , Xylopia pancheri, Zanthoxylum caudatum, Zanthoxylum cuspidatum, Zanthoxylum nitidum , Zanthoxylum simulans and Zanthoxylum tetraspermum . Liriodenine was first documented in 1980 (PMID: 7420287).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0045597 (Liriodenine)


  Mrv0541 02241221442D          

 21 25  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 O   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
    2.1434    1.2375    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
    2.7565    2.6145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4209    3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6005    3.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    1.4289    0.8250    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
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    4.2868    0.8250    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  5 13  2  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
M  END
Download

3D MOL for NP0045597 (Liriodenine)

Download
3D SDF for NP0045597 (Liriodenine)

  Mrv0541 02241221442D          

 21 25  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 O   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
    2.1434    1.2375    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
    2.7565    2.6145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4209    3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6005    3.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    1.4289    0.8250    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
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    4.2868    0.8250    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  5 13  2  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045597

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C2=C(C=CC=C2)C2=C3C(C=CN=C13)=CC1=C2OCO1

> <INCHI_IDENTIFIER>
InChI=1S/C17H9NO3/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12/h1-7H,8H2

> <INCHI_KEY>
MUMCCPUVOAUBAN-UHFFFAOYSA-N

> <FORMULA>
C17H9NO3

> <MOLECULAR_WEIGHT>
275.2583

> <EXACT_MASS>
275.058243159

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.865671533315016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <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),7,9,11,14(19),15,17-octaen-13-one

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
2.8874665223333333

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.473867071137937

> <JCHEM_POLAR_SURFACE_AREA>
48.42

> <JCHEM_REFRACTIVITY>
75.39990000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,9,11,14(19),15,17-octaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0045597 (Liriodenine)
Download
PDB for NP0045597 (Liriodenine)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.145   4.880   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.519   6.287   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.988   6.126   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12    5   14                                                  
CONECT   14   13    2   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    4   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    3                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

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3D PDB for NP0045597 (Liriodenine)
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SMILES for NP0045597 (Liriodenine)
O=C1C2=C(C=CC=C2)C2=C3C(C=CN=C13)=CC1=C2OCO1
Download
INCHI for NP0045597 (Liriodenine)
InChI=1S/C17H9NO3/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12/h1-7H,8H2
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View in JSmol
Synonyms
ValueSource
Micheline bChEBI
OxoushinsunineChEBI
SpermatheridineChEBI
Chemical FormulaC17H9NO3
Average Mass275.2583 Da
Monoisotopic Mass275.05824 Da
IUPAC Name3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,9,11,14(19),15,17-octaen-13-one
Traditional Name3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,9,11,14(19),15,17-octaen-13-one
CAS Registry Number475-75-2
SMILES
O=C1C2=C(C=CC=C2)C2=C3C(C=CN=C13)=CC1=C2OCO1
InChI Identifier
InChI=1S/C17H9NO3/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12/h1-7H,8H2
InChI KeyMUMCCPUVOAUBAN-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Alphonsea mollisPlant
Anisocycla racemosaPlant
Annickia polycarpaLOTUS Database
Annona acuminataLOTUS Database
Annona ambotayLOTUS Database
Annona cherimolaFooDB
Annona cherimoliaPlant
Annona dioicaPlant
Annona diversifoliaPlant
Annona emarginataLOTUS Database
Annona foetidaPlant
Annona glabraPlant
Annona montanaPlant
Annona neosericeaLOTUS Database
Annona purpureaPlant
Annona reticulataFooDB
Annona senegalensisPlant
Annona squamosaPlant
Aquilaria agallochaPlant
Artabotrys hexapetalusPlant
Artabotrys maingayiLOTUS Database
Artabotrys uncinatusPlant
Artabotrys zeylanicusLOTUS Database
Asimina trilobaLOTUS Database
Atherosperma moschatumLOTUS Database
Atrabotrys maingayiPlant
Beilschmiedia alloiophyllaLOTUS Database
Broussonetia papyriferaLOTUS Database
Cananga odorataLOTUS Database
Cardiopetalum calophyllumPlant
Cissampelos sympodialisPlant
Cleistopholis patensPlant
Dasymaschalon longiflorumLOTUS Database
Desfontainia spinosaLOTUS Database
Desmos longifoliaPlant
Disepalum anomalumLOTUS Database
Disepalum pulchrumPlant
Doryphora sassafrasLOTUS Database
Enantia chloranthaPlant
Eupomatia bennettiiLOTUS Database
Eupomatia laurinaLOTUS Database
Fissistigma glaucescensPlant
Friesodielsia velutinaLOTUS Database
Glossocalyx brevipesPlant
Goniothalamus amuyonPlant
Goniothalamus cheliensisLOTUS Database
Goniothalamus scortechiniiLOTUS Database
Goniothalamus scortephaninePlant
Goniothalamus topisPlant
Greenwayodendron oliveriLOTUS Database
Guatteria amplifoliaLOTUS Database
Guatteria blepharophyllaLOTUS Database
Guatteria friesianaPlant
Guatteria modestaLOTUS Database
Guatteria multiveniaPlant
Guatteria oliviformisPlant
Hexalobus crispiflorusLOTUS Database
Hexalobus monopetalusLOTUS Database
Illigera luzonensisPlant
Isolona congolanaLOTUS Database
Laurelia novae-zelandiaeLOTUS Database
Lettowianthus stellatusPlant
Licaria triandraLOTUS Database
Liriodendron tulipferaPlant
Liriodendron tulipiferaPlant
Magnolia abovataPlant
Magnolia cocoPlant
Magnolia elegansLOTUS Database
Magnolia grandifloraPlant
Magnolia kobusLOTUS Database
Magnolia liliiferaLOTUS Database
Magnolia mexicanaLOTUS Database
Magnolia obovataPlant
Magnolia odoraLOTUS Database
Magnolia officinalisLOTUS Database
Magnolia salicifoliaLOTUS Database
Magnolia soulangeanaLOTUS Database
Meiogyne monospermaLOTUS Database
Meiogyne virgataLOTUS Database
Michelia albaLOTUS Database
Michelia bailloniiLOTUS Database
Michelia champacaLOTUS Database
Michelia compressaLOTUS Database
Michelia lanuginosaLOTUS Database
Michellia alba-
Michellia champaca-
Microcos paniculataLOTUS Database
Miliusa cuneataPlant
Miliusa horsfieldiiLOTUS Database
Miliusa velutinaPlant
Mitrephora glabraPlant
Mitrephora maingayiLOTUS Database
Mitrephora tomentosaLOTUS Database
Mollinedia schottianaLOTUS Database
Monodora junodiiLOTUS Database
Monodora tenuifoliaLOTUS Database
Nelumbo nuciferaPlant
Neolitsea acuminatissimaPlant
Neolitsea sericeaLOTUS Database
Oncodostigma monospermaPlant
Oxandra asbeckiiLOTUS Database
Oxandra xylopioidesLOTUS Database
Pachygone ovataLOTUS Database
Papaver caucasicumPlant
Phoebe formosanaLOTUS Database
Piptostigma fugaxPlant
Polyalthia insignisPlant
Polyalthia longifoliaPlant
Polyalthia macropodaPlant
Polyalthia stenopetalaPlant
Porcelia macrocarpaPlant
Pseuduvaria rugosaLOTUS Database
Pseuduvaria trimeraLOTUS Database
Rhigiocarya racemifera MiersLOTUS Database
Rollinia mucosaLOTUS Database
Rollinia pittieriLOTUS Database
Sapranthus palangaPlant
Sinomenium acutumLOTUS Database
Siparuna guianensisLOTUS Database
Siparuna thecaphoraLOTUS Database
Siparuna tonduzianaPlant
Stephania dinklageiPlant
Stephania venosaLOTUS Database
Talauma gitigensisPlant
Talauma mexicana Don.Plant
Thalictrum javanicum BlumeLOTUS Database
Trivalvaria costataLOTUS Database
Trivalvaria macrophyllaPlant
Tsoomgiodendron odorum-
Unonopsis guatterioidesLOTUS Database
Unonopsis spectabilisLOTUS Database
Uvaria argenteaLOTUS Database
Uvaria mocaliPlant
Uvaria mocoliLOTUS Database
Uvaria rufaLOTUS Database
Uvaria versicolorLOTUS Database
Xanthorhiza simplicissimaPlant
Xylopia aethiopicaPlant
Xylopia amazonicaPlant
Xylopia brasiliensisPlant
Xylopia buxifoliaPlant
Xylopia frutescensPlant
Xylopia pancheriPlant
Zanthoxylum caudatumPlant
Zanthoxylum cuspidatumPlant
Zanthoxylum nitidumPlant
Zanthoxylum simulansLOTUS Database
Zanthoxylum tetraspermumPlant
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.
KingdomOrganic compounds  
Super ClassAlkaloids and derivatives  
ClassAporphines  
Sub ClassNot Available
Direct ParentAporphines  
Alternative Parents
Substituents
  • Aporphine
    • 

  • Benzoquinoline
    • 

  • Phenanthrene
    • 

  • Isoquinoline
    • 

  • Naphthalene
    • 

  • Quinoline
    • 

  • Benzodioxole
    • 

  • Aryl ketone
    • 

  • Pyridine
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Ketone
    • 

  • Azacycle
    • 

  • Oxacycle
    • 

  • Acetal
    • 

  • Organoheterocyclic compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.74ALOGPS
logP2.89ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)3.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.42 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity75.4 m³·mol⁻¹ChemAxon
Polarizability27.87 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001503  
KNApSAcK IDC00001878  
Chemspider IDNot Available
KEGG Compound IDC09567  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLiriodenine  
METLIN IDNot Available
PubChem Compound10144  
PDB IDNot Available
ChEBI ID70649  
Good Scents IDNot Available
References
General References
  1. Mohamed SM, Hassan EM, Ibrahim NA: Cytotoxic and antiviral activities of aporphine alkaloids of Magnolia grandiflora L. Nat Prod Res. 2010 Sep;24(15):1395-402. doi: 10.1080/14786410902906959. [PubMed:19764006  ] 
  2. de la Cruz Chacon I, Gonzalez-Esquinca AR: Liriodenine alkaloid in Annona diversifolia during early development. Nat Prod Res. 2012;26(1):42-9. doi: 10.1080/14786419.2010.533373. Epub 2011 Jul 27. [PubMed:21790492  ] 
  3. De la Cruz-Chacon I, Gonzalez-Esquinca AR, Guevara Fefer P, Jimenez Garcia LF: Liriodenine, early antimicrobial defence in Annona diversifolia. Z Naturforsch C J Biosci. 2011 Jul-Aug;66(7-8):377-84. doi: 10.1515/znc-2011-7-809. [PubMed:21950162  ] 
  4. Chen ZF, Liu YC, Peng Y, Hong X, Wang HH, Zhang MM, Liang H: Synthesis, characterization, and in vitro antitumor properties of gold(III) compounds with the traditional Chinese medicine (TCM) active ingredient liriodenine. J Biol Inorg Chem. 2012 Feb;17(2):247-61. doi: 10.1007/s00775-011-0846-z. Epub 2011 Sep 30. [PubMed:21960256  ] 
  5. Mollataghi A, Coudiere E, Hadi AH, Mukhtar MR, Awang K, Litaudon M, Ata A: Anti-acetylcholinesterase, anti-alpha-glucosidase, anti-leishmanial and anti-fungal activities of chemical constituents of Beilschmiedia species. Fitoterapia. 2012 Mar;83(2):298-302. doi: 10.1016/j.fitote.2011.11.009. Epub 2011 Nov 17. [PubMed:22119096  ] 
  6. Hufford CD, Sharma AS, Oguntimein BO: Antibacterial and antifungal activity of liriodenine and related oxoaporphine alkaloids. J Pharm Sci. 1980 Oct;69(10):1180-3. doi: 10.1002/jps.2600691016. [PubMed:7420287  ]