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Showing NP-Card for Oxonantenine (NP0047630)

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Record Information
Version2.0
Created at2022-03-17 20:43:21 UTC
Updated at2022-03-17 20:43:21 UTC
NP-MRD IDNP0047630
Secondary Accession NumbersNone
Natural Product Identification
Common NameOxonantenine
DescriptionOxonantenine 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. Oxonantenine is found in Annona glabra, Corydalis solida, Illigera pentaphylla, Laurelia sempervirens, Litsea cubeba, Platycapnos spicata, Siparuna tonduziana and Stephania tetrandra S.Moore . Oxonantenine was first documented in 1981 (PMID: 17401850). An oxoaporphine alkaloid isolated from Annona glabra and has been shown to exhibit acetylcholinesterase inhibitory activity (PMID: 20944522) (PMID: 17402008).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047630 (Oxonantenine)


  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
Download

3D MOL for NP0047630 (Oxonantenine)

Download
3D SDF for NP0047630 (Oxonantenine)

  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>
NP0047630

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

Download
3D-SDF for NP0047630 (Oxonantenine)
Download
PDB for NP0047630 (Oxonantenine)
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

Download
3D PDB for NP0047630 (Oxonantenine)
Download
SMILES for NP0047630 (Oxonantenine)
COC1=C(OC)C2=C3C(C=CN=C3C(=O)C3=CC4=C(OCO4)C=C23)=C1
Download
INCHI for NP0047630 (Oxonantenine)
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
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View in JSmol
Synonyms
ValueSource
1,2-Dimethoxy-4,5,6,6a-tetradehydro-9,10-(methylenedioxy)noraprophin-7-oneChEBI
1,2-Dimethoxy-9,10-methylenedioxyoxoaporphineHMDB
Chemical FormulaC19H13NO5
Average Mass335.3102 Da
Monoisotopic Mass335.07937 Da
IUPAC Name18,19-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 Name18,19-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 Number15358-38-0
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 KeyNFDVJYPMLVMXRR-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Annona cherimolaFooDB
Annona glabraLOTUS Database
Annona reticulataFooDB
Corydalis solidaLOTUS Database
Illigera pentaphyllaLOTUS Database
Laurelia sempervirensPlant
Litsea cubebaLOTUS Database
Platycapnos spicataPlant
Siparuna tonduzianaPlant
Stephania tetrandraPlant
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP2.61ALOGPS
logP2.57ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)3.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.88 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.33 m³·mol⁻¹ChemAxon
Polarizability33.91 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033367  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011395  
KNApSAcK IDC00025995  
Chemspider ID2341323  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3084224  
PDB IDNot Available
ChEBI ID70651  
Good Scents IDNot Available
References
General References
  1. Yang Y, Jiang J, Qimei L, Yan X, Zhao J, Yuan H, Qin Z, Wang M: The fungicidal terpenoids and essential oil from Litsea cubeba in Tibet. Molecules. 2010 Oct 13;15(10):7075-82. doi: 10.3390/molecules15107075. [PubMed:20944522  ] 
  2. Kiryakov HG, Iskrenova E, Kuzmanov B, Evstatieva L: Alkaloids from Corydalis marschalliana. Planta Med. 1981 Mar;41(3):298-302. doi: 10.1055/s-2007-971718. [PubMed:17401850  ] 
  3. Kiryakov HG, Iskrenova E, Kuzmanov B, Evstatieva L: Alkaloids from Corydalis bulbosa. Planta Med. 1981 Sep;43(1):51-5. doi: 10.1055/s-2007-971472. [PubMed:17402008  ]