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Showing NP-Card for 6-hydroxy-4h,6h-furo[3,2-c]pyran-2-one (NP0202508)

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Record Information
Version2.0
Created at2022-09-04 21:44:02 UTC
Updated at2022-09-04 21:44:02 UTC
NP-MRD IDNP0202508
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-hydroxy-4h,6h-furo[3,2-c]pyran-2-one
DescriptionIsopatulin belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds. Isopatulin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 6-hydroxy-4h,6h-furo[3,2-c]pyran-2-one is found in Penicillium solitum and Penicillium urticae. 6-hydroxy-4h,6h-furo[3,2-c]pyran-2-one was first documented in 1989 (PMID: 2605253). Based on a literature review a small amount of articles have been published on isopatulin (PMID: 1518888) (PMID: 19583231).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0202508 (6-hydroxy-4h,6h-furo[3,2-c]pyran-2-one)


  Mrv1652309042223442D          

 11 12  0  0  0  0            999 V2000
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   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
    4.0668   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   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
    1.1387   -1.3654    0.0000 O   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
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
M  END
Download

3D MOL for NP0202508 (6-hydroxy-4h,6h-furo[3,2-c]pyran-2-one)

     RDKit          3D

 17 18  0  0  0  0  0  0  0  0999 V2000
    4.0303    0.4355    0.2677 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7607    0.3408    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0156   -0.8834   -0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7176   -0.5526   -0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -1.3566   -0.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5412   -0.8055    0.4015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8170    0.4670   -0.1217 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9620    0.9241    0.5254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541    1.3839    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5641    0.8731    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8462    1.3774    0.2738 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3948   -1.8897   -0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3141   -2.4107   -0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194   -1.3187   -1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0569    0.3647   -1.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9369    0.6274    1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8052    2.4234    0.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 11  1  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
 10  4  1  0
  8 16  1  0
  7 15  1  6
  5 13  1  0
  5 14  1  0
  3 12  1  0
  9 17  1  0
M  END
Download

3D SDF for NP0202508 (6-hydroxy-4h,6h-furo[3,2-c]pyran-2-one)


  Mrv1652309042223442D          

 11 12  0  0  0  0            999 V2000
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   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
    4.0668   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   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
    1.1387   -1.3654    0.0000 O   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
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0202508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1OCC2=CC(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O4/c8-6-2-5-4(3-10-6)1-7(9)11-5/h1-2,6,8H,3H2

> <INCHI_KEY>
ZGBMSNKHUHZKEP-UHFFFAOYSA-N

> <FORMULA>
C7H6O4

> <MOLECULAR_WEIGHT>
154.121

> <EXACT_MASS>
154.026608673

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.7311578940611

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-hydroxy-2H,4H,6H-furo[3,2-c]pyran-2-one

> <JCHEM_LOGP>
-0.37724500566666697

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.215390912465704

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.968765150661097

> <JCHEM_PKA_STRONGEST_BASIC>
-4.124661863080832

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
37.03480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-4H,6H-furo[3,2-c]pyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0202508 (6-hydroxy-4h,6h-furo[3,2-c]pyran-2-one)

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PDB for NP0202508 (6-hydroxy-4h,6h-furo[3,2-c]pyran-2-one)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.126  -2.549   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10    2                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0202508 (6-hydroxy-4h,6h-furo[3,2-c]pyran-2-one)
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SMILES for NP0202508 (6-hydroxy-4h,6h-furo[3,2-c]pyran-2-one)
OC1OCC2=CC(=O)OC2=C1
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INCHI for NP0202508 (6-hydroxy-4h,6h-furo[3,2-c]pyran-2-one)
InChI=1S/C7H6O4/c8-6-2-5-4(3-10-6)1-7(9)11-5/h1-2,6,8H,3H2
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View in JSmol
Synonyms
ValueSource
3-Hydroxy-4,9-dioxabicyclo[4.3.0]nona-1,6-dien-8-oneChEBI
NeopatulinChEBI
Chemical FormulaC7H6O4
Average Mass154.1210 Da
Monoisotopic Mass154.02661 Da
IUPAC Name6-hydroxy-2H,4H,6H-furo[3,2-c]pyran-2-one
Traditional Name6-hydroxy-4H,6H-furo[3,2-c]pyran-2-one
CAS Registry NumberNot Available
SMILES
OC1OCC2=CC(=O)OC2=C1
InChI Identifier
InChI=1S/C7H6O4/c8-6-2-5-4(3-10-6)1-7(9)11-5/h1-2,6,8H,3H2
InChI KeyZGBMSNKHUHZKEP-UHFFFAOYSA-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
Penicillium urticaeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and  two ring double bonds.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassNot Available
Direct ParentPyrans  
Alternative Parents
Substituents
  • 2-furanone
    • 

  • Pyran
    • 

  • Dihydrofuran
    • 

  • Enol ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Hemiacetal
    • 

  • 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-0.38ChemAxon
pKa (Strongest Acidic)11.97ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37.03 m³·mol⁻¹ChemAxon
Polarizability13.73 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 ID136980  
KEGG Compound IDNot Available
BioCyc IDCPD-16725  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound155497  
PDB IDNot Available
ChEBI ID145111  
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. Seigle-Murandi F, Steiman R, Krivobok S, Beriel H, Benoit-Guyod JL: Antitumor activity of patulin and structural analogs. Pharmazie. 1992 Apr;47(4):288-91. [PubMed:1518888  ] 
  3. Lykakis IN, Zaravinos IP, Raptis C, Stratakis M: Divergent synthesis of the co-isolated mycotoxins longianone, isopatulin, and (Z)-ascladiol via furan oxidation. J Org Chem. 2009 Aug 21;74(16):6339-42. doi: 10.1021/jo900855e. [PubMed:19583231  ] 
  4. LOTUS database [Link]