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Showing NP-Card for 2-Acetonyl-3,5-dihydroxy-7-methoxy-1,4-naphthoquinone (NP0082254)

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Record Information
Version2.0
Created at2022-04-29 03:17:53 UTC
Updated at2022-04-29 03:17:53 UTC
NP-MRD IDNP0082254
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Acetonyl-3,5-dihydroxy-7-methoxy-1,4-naphthoquinone
DescriptionPyrrolizidine N-oxide belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. 2-Acetonyl-3,5-dihydroxy-7-methoxy-1,4-naphthoquinone is found in Cylindrocarpon sp. Based on a literature review very few articles have been published on pyrrolizidine N-oxide.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0082254 (2-Acetonyl-3,5-dihydroxy-7-methoxy-1,4-naphthoquinone)


  Mrv1652304292205172D          

  9 10  0  0  0  0            999 V2000
   -0.4849   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    0.5701    0.0000 O   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
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
M  END
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3D MOL for NP0082254 (2-Acetonyl-3,5-dihydroxy-7-methoxy-1,4-naphthoquinone)

     RDKit          3D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -0.0552   -0.1295   -2.1467 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.0398    0.2351   -0.8277 N   0  0  2  0  0  4  0  0  0  0  0  0
    1.1727    1.0097   -0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1565   -0.0898   -0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2847   -0.7005    0.8871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0071   -0.8797    0.0573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2198   -0.9086    0.8897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1242    0.1027    0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1740    1.0398   -0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0777    1.6675    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997    1.5435   -1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0931    0.3013    0.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2047   -0.8337   -1.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6781   -1.6369    1.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407    0.0972    1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1502   -1.8380   -0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7060   -1.9225    0.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0903   -0.6448    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7451    0.6490    0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -0.4038   -0.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6737    1.4811   -1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974    1.8610    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  6  2  1  0
  9  2  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  6
  7 17  1  0
  7 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
M  CHG  2   1  -1   2   1
M  END
Download

3D SDF for NP0082254 (2-Acetonyl-3,5-dihydroxy-7-methoxy-1,4-naphthoquinone)


  Mrv1652304292205172D          

  9 10  0  0  0  0            999 V2000
   -0.4849   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    0.5701    0.0000 O   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
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0082254

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=N12CCCC1CCC2

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO/c9-8-5-1-3-7(8)4-2-6-8/h7H,1-6H2

> <INCHI_KEY>
DGPUVWXQJUQRCZ-UHFFFAOYSA-N

> <FORMULA>
C7H13NO

> <MOLECULAR_WEIGHT>
127.187

> <EXACT_MASS>
127.099714043

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.321343841464174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hexahydro-1H-4lambda5-pyrrolizin-4-one

> <ALOGPS_LOGP>
-0.46

> <JCHEM_LOGP>
-0.06284371433333344

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.706844628570783

> <JCHEM_POLAR_SURFACE_AREA>
26.880000000000003

> <JCHEM_REFRACTIVITY>
36.7852

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexahydro-1H-4lambda5-pyrrolizin-4-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0082254 (2-Acetonyl-3,5-dihydroxy-7-methoxy-1,4-naphthoquinone)

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PDB for NP0082254 (2-Acetonyl-3,5-dihydroxy-7-methoxy-1,4-naphthoquinone)
HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -0.905  -1.246   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -2.492   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.465  -0.476   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0       1.465   1.064   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    3                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   20    0
END

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3D PDB for NP0082254 (2-Acetonyl-3,5-dihydroxy-7-methoxy-1,4-naphthoquinone)
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SMILES for NP0082254 (2-Acetonyl-3,5-dihydroxy-7-methoxy-1,4-naphthoquinone)
O=N12CCCC1CCC2
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INCHI for NP0082254 (2-Acetonyl-3,5-dihydroxy-7-methoxy-1,4-naphthoquinone)
InChI=1S/C7H13NO/c9-8-5-1-3-7(8)4-2-6-8/h7H,1-6H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC7H13NO
Average Mass127.1870 Da
Monoisotopic Mass127.09971 Da
IUPAC Namehexahydro-1H-4lambda5-pyrrolizin-4-one
Traditional Namehexahydro-1H-4lambda5-pyrrolizin-4-one
CAS Registry NumberNot Available
SMILES
O=N12CCCC1CCC2
InChI Identifier
InChI=1S/C7H13NO/c9-8-5-1-3-7(8)4-2-6-8/h7H,1-6H2
InChI KeyDGPUVWXQJUQRCZ-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
Cylindrocarpon sp.Fungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrrolizidines  
Sub ClassNot Available
Direct ParentPyrrolizidines  
Alternative Parents
Substituents
  • Pyrrolizidine
    • 

  • N-alkylpyrrolidine
    • 

  • Trialkyl amine oxide
    • 

  • Pyrrolidine
    • 

  • Azacycle
    • 

  • Trisubstituted n-oxide
    • 

  • N-oxide
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP-0.46ALOGPS
logP-0.063ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)2.71ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.88 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.79 m³·mol⁻¹ChemAxon
Polarizability14.32 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00049076  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12498085  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References