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Showing NP-Card for desoxyphyllostin (NP0309635)

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Record Information
Version2.0
Created at2022-09-11 04:22:10 UTC
Updated at2022-09-11 04:22:11 UTC
NP-MRD IDNP0309635
Secondary Accession NumbersNone
Natural Product Identification
Common Namedesoxyphyllostin
DescriptionDesoxyphyllostine belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. desoxyphyllostin is found in Penicillium solitum. desoxyphyllostin was first documented in 1989 (PMID: 2605253). Based on a literature review very few articles have been published on desoxyphyllostine.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0309635 (desoxyphyllostin)


  Mrv1652309112206222D          

 10 11  0  0  1  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    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    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  1  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
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  7  1  1  0  0  0
  8  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
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3D MOL for NP0309635 (desoxyphyllostin)

     RDKit          3D

 16 17  0  0  0  0  0  0  0  0999 V2000
    2.3158    0.3414    0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8582    0.1086   -0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4228   -1.1457    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9936   -1.4528   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226   -2.6312   -0.4291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0032   -0.4062    0.0230 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9386    0.4466    1.1404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5425    0.9437   -0.1767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0985    1.1612   -0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3247    2.3169   -0.4911 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6651   -0.0097    1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9175   -0.2026   -0.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5182    1.4365    0.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524   -1.9516    0.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0481   -0.6481   -0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2277    1.6928   -0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9  2  1  0
  8  6  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  6 15  1  6
  8 16  1  6
M  END
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3D SDF for NP0309635 (desoxyphyllostin)


  Mrv1652309112206222D          

 10 11  0  0  1  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    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    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  1  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
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  7  1  1  0  0  0
  8  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0309635

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)[C@H]2O[C@H]2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O3/c1-3-2-4(8)6-7(10-6)5(3)9/h2,6-7H,1H3/t6-,7+/m1/s1

> <INCHI_KEY>
QMPGHDQKVHABLV-RQJHMYQMSA-N

> <FORMULA>
C7H6O3

> <MOLECULAR_WEIGHT>
138.122

> <EXACT_MASS>
138.031694053

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.58604860676088

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,6S)-3-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

> <JCHEM_LOGP>
0.7934823156666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.928617867864318

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3192798057873265

> <JCHEM_POLAR_SURFACE_AREA>
46.67

> <JCHEM_REFRACTIVITY>
33.482200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6S)-3-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0309635 (desoxyphyllostin)

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PDB for NP0309635 (desoxyphyllostin)
HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6    8                                                       
CONECT    8    7    6    9                                                  
CONECT    9    8    2   10                                                  
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0309635 (desoxyphyllostin)
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SMILES for NP0309635 (desoxyphyllostin)
CC1=CC(=O)[C@H]2O[C@H]2C1=O
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INCHI for NP0309635 (desoxyphyllostin)
InChI=1S/C7H6O3/c1-3-2-4(8)6-7(10-6)5(3)9/h2,6-7H,1H3/t6-,7+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC7H6O3
Average Mass138.1220 Da
Monoisotopic Mass138.03169 Da
IUPAC Name(1R,6S)-3-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
Traditional Name(1R,6S)-3-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
CAS Registry NumberNot Available
SMILES
CC1=CC(=O)[C@H]2O[C@H]2C1=O
InChI Identifier
InChI=1S/C7H6O3/c1-3-2-4(8)6-7(10-6)5(3)9/h2,6-7H,1H3/t6-,7+/m1/s1
InChI KeyQMPGHDQKVHABLV-RQJHMYQMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Penicillium solitumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentCyclohexenones  
Alternative Parents
Substituents
  • Cyclohexenone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Dialkyl ether
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP0.79ChemAxon
pKa (Strongest Acidic)16.93ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.67 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.48 m³·mol⁻¹ChemAxon
Polarizability12.59 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID58828398  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound90657428  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Priest JW, Light RJ: Patulin biosynthesis: epoxidation of toluquinol and gentisyl alcohol by particulate preparations from Penicillium patulum. Biochemistry. 1989 Nov 14;28(23):9192-200. doi: 10.1021/bi00449a035. [PubMed:2605253  ] 
  2. LOTUS database [Link]