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Showing NP-Card for Phthalaldehydic acid (NP0002749)

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Record Information
Version1.0
Created at2020-11-23 19:39:27 UTC
Updated at2021-08-12 19:52:02 UTC
NP-MRD IDNP0002749
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhthalaldehydic acid
Provided ByBMRBBMRB logo
Description2-Formylbenzoic acid, also known as phthalaldehydic acid or 2-carboxybenzaldehyde, belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group. 2-Formylbenzoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 2002 (PMID: 12123834). Based on a literature review a significant number of articles have been published on 2-formylbenzoic acid (PMID: 12604212) (PMID: 17984079) (PMID: 28166217) (PMID: 24862007).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002749 (Phthalaldehydic acid)


     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    0.9021   -3.3255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1922   -1.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0628   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3568   -1.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4862   -0.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1961    1.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7765    1.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3529    0.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7725    1.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626    2.5612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9019    0.1024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6118   -1.3693    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6469   -2.8230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9058   -0.8488    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3256    2.0945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4864    3.0637    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3215    0.5870    0.0000 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
  9 11  1  0
  8  3  1  0
  2 12  1  0
  4 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
 11 17  1  0
M  END
Download

3D MOL for NP0002749 (Phthalaldehydic acid)

NP0002749
     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
    0.5629    2.6068    1.6177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2686    1.8774    0.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432    0.6528    0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5979    0.3107    0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455   -0.8375    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3686   -1.7100   -0.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0529   -1.3912   -0.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5340   -0.2199   -0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9458    0.0012   -0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6126   -0.8556   -1.2596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6297    1.0845   -0.1284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2558    2.2522    0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1928    1.0191    1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -1.0634    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7589   -2.6331   -1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5695   -2.0776   -1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073    0.9837    0.6339 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
  9 11  1  0
  8  3  1  0
  2 12  1  0
  4 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
 11 17  1  0
M  END
Download

3D SDF for NP0002749 (Phthalaldehydic acid)


     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    0.9021   -3.3255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1922   -1.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0628   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3568   -1.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4862   -0.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1961    1.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7765    1.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3529    0.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7725    1.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626    2.5612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9019    0.1024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6118   -1.3693    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6469   -2.8230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9058   -0.8488    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3256    2.0945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4864    3.0637    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3215    0.5870    0.0000 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
  9 11  1  0
  8  3  1  0
  2 12  1  0
  4 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
 11 17  1  0
M  END
> <DATABASE_ID>
NP0002749

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC=CC=C1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H6O3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5H,(H,10,11)

> <INCHI_KEY>
DYNFCHNNOHNJFG-UHFFFAOYSA-N

> <FORMULA>
C8H6O3

> <MOLECULAR_WEIGHT>
150.133

> <EXACT_MASS>
150.031694053

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
14.041176603407347

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-formylbenzoic acid

> <JCHEM_LOGP>
1.3433310686666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.160326250136123

> <JCHEM_PKA_STRONGEST_BASIC>
-7.226713328236157

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
39.8982

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-carboxybenzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002749 (Phthalaldehydic acid)

NP0002749
     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
    0.5629    2.6068    1.6177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2686    1.8774    0.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432    0.6528    0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5979    0.3107    0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455   -0.8375    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3686   -1.7100   -0.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0529   -1.3912   -0.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5340   -0.2199   -0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9458    0.0012   -0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6126   -0.8556   -1.2596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6297    1.0845   -0.1284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2558    2.2522    0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1928    1.0191    1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -1.0634    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7589   -2.6331   -1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5695   -2.0776   -1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073    0.9837    0.6339 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
  9 11  1  0
  8  3  1  0
  2 12  1  0
  4 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
 11 17  1  0
M  END
Download

PDB for NP0002749 (Phthalaldehydic acid)

HEADER    PROTEIN                                 23-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-20         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    7                                                       
CONECT    5    6    9                                                       
CONECT    6    3    5    7                                                  
CONECT    7    4    6    8                                                  
CONECT    8    7   10   11                                                  
CONECT    9    5                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0002749 (Phthalaldehydic acid)

COMPND    NP0002749
HETATM    1  O1  UNL     1       0.563   2.607   1.618  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.269   1.877   0.968  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.243   0.653   0.388  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.598   0.311   0.551  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.145  -0.838   0.025  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.369  -1.710  -0.693  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.053  -1.391  -0.859  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.534  -0.220  -0.331  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.946   0.001  -0.579  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.613  -0.856  -1.260  1.00  0.00           O  
HETATM   11  O3  UNL     1      -2.630   1.084  -0.128  1.00  0.00           O  
HETATM   12  H1  UNL     1      -1.256   2.252   0.923  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.193   1.019   1.125  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.201  -1.063   0.176  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.759  -2.633  -1.129  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.570  -2.078  -1.428  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.307   0.984   0.634  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4    8
CONECT    4    5   13
CONECT    5    6    6   14
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   17
END
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SMILES for NP0002749 (Phthalaldehydic acid)

OC(=O)C1=CC=CC=C1C=O
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INCHI for NP0002749 (Phthalaldehydic acid)

InChI=1S/C8H6O3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5H,(H,10,11)
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View in JSmol
Synonyms
ValueSource
2-CarboxybenzaldehydeChEBI
O-Formylbenzoic acidChEBI
Phthalaldehydic acidChEBI
2-FormylbenzoateKegg
O-FormylbenzoateGenerator
PhthalaldehydateGenerator
2-Formylbenzoic acidKEGG
Chemical FormulaC8H6O3
Average Mass150.1330 Da
Monoisotopic Mass150.03169 Da
IUPAC Name2-formylbenzoic acid
Traditional Name2-carboxybenzaldehyde
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC=CC=C1C=O
InChI Identifier
InChI=1S/C8H6O3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5H,(H,10,11)
InChI KeyDYNFCHNNOHNJFG-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acids
Alternative Parents
Substituents
  • Benzoic acid
  • Benzoyl
  • Benzaldehyde
  • Aryl-aldehyde
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP1.34ChemAxon
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.9 m³·mol⁻¹ChemAxon
Polarizability14.04 ųChemAxon
Number of Rings1ChemAxon
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 ID8099
KEGG Compound IDC03057
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17605
Good Scents IDNot Available
References
General References
  1. Hinshelwood A, McGarvie G, Ellis EM: Substrate specificity of mouse aldo-keto reductase AKR7A5. Chem Biol Interact. 2003 Feb 1;143-144:263-9. [PubMed:12604212 ]
  2. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  3. Keller AN, Eckle SB, Xu W, Liu L, Hughes VA, Mak JY, Meehan BS, Pediongco T, Birkinshaw RW, Chen Z, Wang H, D'Souza C, Kjer-Nielsen L, Gherardin NA, Godfrey DI, Kostenko L, Corbett AJ, Purcell AW, Fairlie DP, McCluskey J, Rossjohn J: Drugs and drug-like molecules can modulate the function of mucosal-associated invariant T cells. Nat Immunol. 2017 Apr;18(4):402-411. doi: 10.1038/ni.3679. Epub 2017 Feb 6. [PubMed:28166217 ]
  4. Hinshelwood A, McGarvie G, Ellis E: Characterisation of a novel mouse liver aldo-keto reductase AKR7A5. FEBS Lett. 2002 Jul 17;523(1-3):213-8. doi: 10.1016/s0014-5793(02)02982-4. [PubMed:12123834 ]
  5. Mishra S, Singh SN, Pande V: Bacteria induced degradation of fluoranthene in minimal salt medium mediated by catabolic enzymes in vitro condition. Bioresour Technol. 2014 Jul;164:299-308. doi: 10.1016/j.biortech.2014.04.076. Epub 2014 May 9. [PubMed:24862007 ]