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Showing NP-Card for Isopatulin (NP0066459)

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Record Information
Version2.0
Created at2022-04-28 10:43:26 UTC
Updated at2022-04-28 10:43:26 UTC
NP-MRD IDNP0066459
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsopatulin
DescriptionISOCLAVICIN, also known as isopatulin, belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. Isopatulin is found in Penicillium urticae 2159k. Based on a literature review very few articles have been published on ISOCLAVICIN.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0066459 (Isopatulin)


  Mrv1652304282212432D          

 11 12  0  0  0  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 O   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
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
Download

3D MOL for NP0066459 (Isopatulin)

     RDKit          3D

 17 18  0  0  0  0  0  0  0  0999 V2000
    0.9443   -2.3166   -0.5334 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8219   -1.0847   -0.3191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9951   -0.1611   -0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5820    0.9339    0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4510    1.5790    0.1566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456    0.7827   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5271   -0.5529   -0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8898   -1.1009   -0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643   -0.1014   -0.6893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328    1.1266   -0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000    2.2882   -0.5671 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8996   -0.6906    0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1729    0.3586   -1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4065    1.6196    0.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1871    0.4409    1.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328   -2.0944   -0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1680   -1.0270    1.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  2  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  6 10  1  0
  2  7  1  0
  8 16  1  0
  8 17  1  0
  4 14  1  0
  4 15  1  0
  3 12  1  0
  3 13  1  0
M  END
Download

3D SDF for NP0066459 (Isopatulin)


  Mrv1652304282212432D          

 11 12  0  0  0  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 O   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
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0066459

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1OCC2=C1OCCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O4/c8-5-1-2-10-6-4(5)3-11-7(6)9/h1-3H2

> <INCHI_KEY>
CGCAHEDRSBRAIM-UHFFFAOYSA-N

> <FORMULA>
C7H6O4

> <MOLECULAR_WEIGHT>
154.121

> <EXACT_MASS>
154.026608673

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.545605460733501

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2H,3H,4H,5H,7H-furo[3,4-b]pyran-4,7-dione

> <ALOGPS_LOGP>
-0.29

> <JCHEM_LOGP>
-0.16619355100000033

> <ALOGPS_LOGS>
-0.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.347079808361867

> <JCHEM_PKA_STRONGEST_BASIC>
-5.041788353280007

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
35.656600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.34e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2H,3H,5H-furo[3,4-b]pyran-4,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0066459 (Isopatulin)

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PDB for NP0066459 (Isopatulin)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.924   1.303   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.220   2.843   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0066459 (Isopatulin)
Download
SMILES for NP0066459 (Isopatulin)
O=C1OCC2=C1OCCC2=O
Download
INCHI for NP0066459 (Isopatulin)
InChI=1S/C7H6O4/c8-5-1-2-10-6-4(5)3-11-7(6)9/h1-3H2
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View in JSmol
Synonyms
ValueSource
IsopatulinMeSH
Chemical FormulaC7H6O4
Average Mass154.1210 Da
Monoisotopic Mass154.02661 Da
IUPAC Name2H,3H,4H,5H,7H-furo[3,4-b]pyran-4,7-dione
Traditional Name2H,3H,5H-furo[3,4-b]pyran-4,7-dione
CAS Registry NumberNot Available
SMILES
O=C1OCC2=C1OCCC2=O
InChI Identifier
InChI=1S/C7H6O4/c8-5-1-2-10-6-4(5)3-11-7(6)9/h1-3H2
InChI KeyCGCAHEDRSBRAIM-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
Penicillium urticae 2159kFungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassPyranones and derivatives  
Direct ParentDihydropyranones  
Alternative Parents
Substituents
  • Dihydropyranone
    • 

  • 2-furanone
    • 

  • Dihydrofuran
    • 

  • Enoate ester
    • 

  • Vinylogous ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Carboxylic acid ester
    • 

  • Ketone
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Oxacycle
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen 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-0.29ALOGPS
logP-0.17ChemAxon
logS-0.27ALOGPS
pKa (Strongest Acidic)10.35ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.66 m³·mol⁻¹ChemAxon
Polarizability13.55 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 IDC00024001  
Chemspider ID91476  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101239  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available