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Showing metabocard for 1-Oxo-1H-2-benzopyran-3-carboxaldehyde (HMDB0030577)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:44 UTC
Update Date2023-02-21 17:19:39 UTC
HMDB IDHMDB0030577
Secondary Accession Numbers
  • HMDB30577
Metabolite Identification
Common Name1-Oxo-1H-2-benzopyran-3-carboxaldehyde
Description1-Oxo-1H-2-benzopyran-3-carboxaldehyde, also known as 3-formylisocoumarin or artemidinal, belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. Based on a literature review very few articles have been published on 1-Oxo-1H-2-benzopyran-3-carboxaldehyde.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

  Mrv0541 05061305212D          

 13 14  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  6  2  0  0  0  0
 12 10  2  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
M  END
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3D MOL for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

HMDB0030577
     RDKit          3D
1-Oxo-1H-2-benzopyran-3-carboxaldehyde
 19 20  0  0  0  0  0  0  0  0999 V2000
    4.4044    0.9876   -0.0374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5864    0.0711   -0.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1648    0.2977   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2351   -0.7100   -0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1210   -0.5204   -0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0660   -1.5066   -0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4160   -1.2724   -0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8732   -0.0344    0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230    0.9558    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619    0.7125    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951    1.6855    0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0216    2.8166    0.8335 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777    1.4566    0.3049 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9587   -0.8824   -0.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5877   -1.6753   -0.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6906   -2.4684   -0.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548   -2.0412   -0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9186    0.1988    0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2632    1.9291    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13  3  1  0
 10  5  1  0
  2 14  1  0
  4 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
M  END
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3D SDF for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

  Mrv0541 05061305212D          

 13 14  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  6  2  0  0  0  0
 12 10  2  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030577

> <DATABASE_NAME>
hmdb

> <SMILES>
O=CC1=CC2=CC=CC=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C10H6O3/c11-6-8-5-7-3-1-2-4-9(7)10(12)13-8/h1-6H

> <INCHI_KEY>
ALHVSADYXQWYJH-UHFFFAOYSA-N

> <FORMULA>
C10H6O3

> <MOLECULAR_WEIGHT>
174.1528

> <EXACT_MASS>
174.031694058

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
16.57403805907387

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-oxo-1H-isochromene-3-carbaldehyde

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
1.5224005779999998

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.700459967174671

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
47.86590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-oxoisochromene-3-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

HMDB0030577
     RDKit          3D
1-Oxo-1H-2-benzopyran-3-carboxaldehyde
 19 20  0  0  0  0  0  0  0  0999 V2000
    4.4044    0.9876   -0.0374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5864    0.0711   -0.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1648    0.2977   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2351   -0.7100   -0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1210   -0.5204   -0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0660   -1.5066   -0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4160   -1.2724   -0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8732   -0.0344    0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230    0.9558    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619    0.7125    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951    1.6855    0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0216    2.8166    0.8335 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777    1.4566    0.3049 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9587   -0.8824   -0.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5877   -1.6753   -0.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6906   -2.4684   -0.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548   -2.0412   -0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9186    0.1988    0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2632    1.9291    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13  3  1  0
 10  5  1  0
  2 14  1  0
  4 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
M  END
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PDB for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    9                                                       
CONECT    5    7    8                                                       
CONECT    6    8   11                                                       
CONECT    7    3    5    9                                                  
CONECT    8    5    6   13                                                  
CONECT    9    4    7   10                                                  
CONECT   10    9   12   13                                                  
CONECT   11    6                                                            
CONECT   12   10                                                            
CONECT   13    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

COMPND    HMDB0030577
HETATM    1  O1  UNL     1       4.404   0.988  -0.037  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.586   0.071  -0.247  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.165   0.298  -0.074  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.235  -0.710  -0.302  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.121  -0.520  -0.145  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.066  -1.507  -0.365  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.416  -1.272  -0.195  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.873  -0.034   0.205  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.923   0.956   0.426  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.562   0.713   0.252  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.395   1.685   0.468  1.00  0.00           C  
HETATM   12  O2  UNL     1      -0.022   2.817   0.834  1.00  0.00           O  
HETATM   13  O3  UNL     1       1.678   1.457   0.305  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.959  -0.882  -0.556  1.00  0.00           H  
HETATM   15  H2  UNL     1       1.588  -1.675  -0.613  1.00  0.00           H  
HETATM   16  H3  UNL     1      -0.691  -2.468  -0.677  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.155  -2.041  -0.367  1.00  0.00           H  
HETATM   18  H5  UNL     1      -3.919   0.199   0.352  1.00  0.00           H  
HETATM   19  H6  UNL     1      -2.263   1.929   0.739  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   14
CONECT    3    4    4   13
CONECT    4    5   15
CONECT    5    6    6   10
CONECT    6    7   16
CONECT    7    8    8   17
CONECT    8    9   18
CONECT    9   10   10   19
CONECT   10   11
CONECT   11   12   12   13
END
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SMILES for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

O=CC1=CC2=CC=CC=C2C(=O)O1
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INCHI for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

InChI=1S/C10H6O3/c11-6-8-5-7-3-1-2-4-9(7)10(12)13-8/h1-6H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3-FormylisocoumarinHMDB
ArtemidinalHMDB
Isocoumarin-3-carboxaldehydeHMDB
Chemical FormulaC10H6O3
Average Molecular Weight174.1528
Monoisotopic Molecular Weight174.031694058
IUPAC Name1-oxo-1H-isochromene-3-carbaldehyde
Traditional Name1-oxoisochromene-3-carbaldehyde
CAS Registry Number34328-51-3
SMILES
O=CC1=CC2=CC=CC=C2C(=O)O1
InChI Identifier
InChI=1S/C10H6O3/c11-6-8-5-7-3-1-2-4-9(7)10(12)13-8/h1-6H
InChI KeyALHVSADYXQWYJH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsocoumarins and derivatives
Sub ClassNot Available
Direct ParentIsocoumarins and derivatives
Alternative Parents
Substituents
  • Isocoumarin
  • Benzopyran
  • 2-benzopyran
  • Pyranone
  • Aryl-aldehyde
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aldehyde
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point178 - 179 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002467
KNApSAcK IDC00054903
Chemspider ID27021040
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12582097
PDB IDNot Available
ChEBI ID173471
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details
1. Carbonyl reductase [NADPH] 1
General function:
Involved in oxidoreductase activity
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:
CBR1
Uniprot ID:
P16152
Molecular weight:
30374.73
Reactions
1-Oxo-1H-2-benzopyran-3-carboxaldehyde → 3-(hydroxymethyl)-1H-isochromen-1-onedetails