Showing metabocard for neopatulin (MMDBc0056212)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-17 20:19:41 UTC
Update Date2025-10-07 16:09:39 UTC
Metabolite IDMMDBc0056212
Metabolite Identification
Common Nameneopatulin
DescriptionNeopatulin is a secondary metabolite belonging to the class of polyketides. Its chemical structure features a complex arrangement of carbon rings and functional groups, characteristic of many fungal metabolites. Neopatulin is biosynthesized through a series of enzymatic reactions involving polyketide synthases, which facilitate the assembly of its carbon skeleton from acetyl-CoA and malonyl-CoA precursors. This compound is notably involved in various metabolic pathways, including those related to the synthesis of other bioactive compounds. In particular, neopatulin has been shown to be further converted to other metabolites by enzymatic extracts, highlighting its role in the intricate network of secondary metabolism (PMID:2605253 ). The study of neopatulin and its derivatives contributes to the understanding of fungal biochemistry and the potential applications of these metabolites in pharmaceuticals and agriculture.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007faddd865c80>


  Mrv1652306172222192D          

 11 12  0  0  0  0            999 V2000
    1.1387   -1.3654    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
    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
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   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
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  4  3  1  0  0  0  0
  5  2  2  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  7  1  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  3  1  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 11  7  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007faddd865c80>

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3D SDF for #<Metabolite:0x00007faddd865c80>

  Mrv1652306172222192D          

 11 12  0  0  0  0            999 V2000
    1.1387   -1.3654    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
    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
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   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
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  4  3  1  0  0  0  0
  5  2  2  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  7  1  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  3  1  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 11  7  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0056212

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007faddd865c80>
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PDB for #<Metabolite:0x00007faddd865c80>
HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+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  -0.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
CONECT    1    4    7                                                       
CONECT    2    5    6                                                       
CONECT    3    4   10                                                       
CONECT    4    1    3    5                                                  
CONECT    5    2    4   11                                                  
CONECT    6    2    8   10                                                  
CONECT    7    1    9   11                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
CONECT   10    3    6                                                       
CONECT   11    5    7                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for #<Metabolite:0x00007faddd865c80>
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SMILES for #<Metabolite:0x00007faddd865c80>
OC1OCC2=CC(=O)OC2=C1
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INCHI for #<Metabolite:0x00007faddd865c80>
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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Synonyms
ValueSource
3-Hydroxy-4,9-dioxabicyclo[4.3.0]nona-1,6-dien-8-oneChEBI
IsopatulinMeSH
Molecular FormulaC7H6O4
Average Mass154.121
Monoisotopic Mass154.026608673
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