Hmdb loader

Showing metabocard for 3,4-Dihydroxybenzaldehyde (HMDB0059965)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Show more...Show more...Show more...
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-04-09 21:16:38 UTC
Update Date2023-02-21 17:29:39 UTC
HMDB IDHMDB0059965
Secondary Accession Numbers
  • HMDB59965
Metabolite Identification
Common Name3,4-Dihydroxybenzaldehyde
Description3,4-Dihydroxybenzaldehyde, also known as protocatechualdehyde or 1,2-dihydroxy-4-formylbenzene, belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. 3,4-Dihydroxybenzaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-Dihydroxybenzaldehyde is an almond, bitter, and dry tasting compound. Outside of the human body, 3,4-Dihydroxybenzaldehyde is found, on average, in the highest concentration within vinegars and grape wines. 3,4-Dihydroxybenzaldehyde has also been detected, but not quantified in, several different foods, such as orange bell peppers, common wheats, spelts, horseradish tree, and muskmelons. This could make 3,4-dihydroxybenzaldehyde a potential biomarker for the consumption of these foods.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0059965 (3,4-Dihydroxybenzaldehyde)

  Mrv0541 02241219242D          

 10 10  0  0  0  0            999 V2000
   -0.0417    1.6523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417    0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417   -0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460    0.8258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460   -0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460   -1.6523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
Download

3D MOL for HMDB0059965 (3,4-Dihydroxybenzaldehyde)

HMDB0059965
     RDKit          3D
3,4-Dihydroxybenzaldehyde
 16 16  0  0  0  0  0  0  0  0999 V2000
   -3.2401    1.1360    0.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6660    0.0241    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2116   -0.0840    0.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -1.3350    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584   -1.4538    0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5240   -0.3083    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8986   -0.3719    0.3933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031    0.9306    0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6730    2.0851    0.4585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4632    1.0543    0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2823   -0.8633    0.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2854   -2.1894    0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2276   -2.4237    0.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4068   -1.2377    0.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2972    3.0012    0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9151    2.0357    0.3990 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
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10  3  1  0
  2 11  1  0
  4 12  1  0
  5 13  1  0
  7 14  1  0
  9 15  1  0
 10 16  1  0
M  END
Download

3D SDF for HMDB0059965 (3,4-Dihydroxybenzaldehyde)

  Mrv0541 02241219242D          

 10 10  0  0  0  0            999 V2000
   -0.0417    1.6523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417    0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417   -0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460    0.8258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460   -0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460   -1.6523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059965

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H

> <INCHI_KEY>
IBGBGRVKPALMCQ-UHFFFAOYSA-N

> <FORMULA>
C7H6O3

> <MOLECULAR_WEIGHT>
138.1207

> <EXACT_MASS>
138.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
12.865164462048833

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4-dihydroxybenzaldehyde

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
1.0786175173333334

> <ALOGPS_LOGS>
-0.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.884399904920077

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.459808177531965

> <JCHEM_PKA_STRONGEST_BASIC>
-6.325186624643433

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
36.6038

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxybenzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0059965 (3,4-Dihydroxybenzaldehyde)

HMDB0059965
     RDKit          3D
3,4-Dihydroxybenzaldehyde
 16 16  0  0  0  0  0  0  0  0999 V2000
   -3.2401    1.1360    0.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6660    0.0241    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2116   -0.0840    0.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -1.3350    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584   -1.4538    0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5240   -0.3083    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8986   -0.3719    0.3933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031    0.9306    0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6730    2.0851    0.4585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4632    1.0543    0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2823   -0.8633    0.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2854   -2.1894    0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2276   -2.4237    0.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4068   -1.2377    0.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2972    3.0012    0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9151    2.0357    0.3990 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
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10  3  1  0
  2 11  1  0
  4 12  1  0
  5 13  1  0
  7 14  1  0
  9 15  1  0
 10 16  1  0
M  END
Download

PDB for HMDB0059965 (3,4-Dihydroxybenzaldehyde)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.078   3.084   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.078   1.541   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.311   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.311  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.078  -1.541   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.311  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.311   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.699   1.541   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.699  -1.541   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.699  -3.084   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    2    6    8                                                  
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
Download

3D PDB for HMDB0059965 (3,4-Dihydroxybenzaldehyde)

COMPND    HMDB0059965
HETATM    1  O1  UNL     1      -3.240   1.136   0.313  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.666   0.024   0.284  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.212  -0.084   0.312  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.625  -1.335   0.278  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.758  -1.454   0.305  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.524  -0.308   0.365  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.899  -0.372   0.393  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.903   0.931   0.398  1.00  0.00           C  
HETATM    9  O3  UNL     1       1.673   2.085   0.459  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.463   1.054   0.372  1.00  0.00           C  
HETATM   11  H1  UNL     1      -3.282  -0.863   0.237  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.285  -2.189   0.232  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.228  -2.424   0.279  1.00  0.00           H  
HETATM   14  H4  UNL     1       3.407  -1.238   0.372  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.297   3.001   0.485  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.915   2.036   0.399  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4   10
CONECT    4    5   12
CONECT    5    6    6   13
CONECT    6    7    8
CONECT    7   14
CONECT    8    9   10   10
CONECT    9   15
CONECT   10   16
END
Download

SMILES for HMDB0059965 (3,4-Dihydroxybenzaldehyde)

OC1=CC=C(C=O)C=C1O
Download

INCHI for HMDB0059965 (3,4-Dihydroxybenzaldehyde)

InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H
Download
View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1,2-Dihydroxy-4-formylbenzeneChEBI
3,4-DihydroxybenzenecarbonalChEBI
4-Formyl-1,2-benzenediolChEBI
4-Formyl-1,2-dihydroxybenzeneChEBI
ProtocatechualdehydeChEBI
Protocatechuic aldehydeChEBI
Protocatechualdehyde, 3H-labeledMeSH
Rancinamycin IVMeSH
Protocatechualdehyde, formyl-14C-labeledMeSH
3,4-DihydroxybenzaldehydeHMDB
Chemical FormulaC7H6O3
Average Molecular Weight138.1207
Monoisotopic Molecular Weight138.031694058
IUPAC Name3,4-dihydroxybenzaldehyde
Traditional Name3,4-dihydroxybenzaldehyde
CAS Registry Number139-85-5
SMILES
OC1=CC=C(C=O)C=C1O
InChI Identifier
InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H
InChI KeyIBGBGRVKPALMCQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentHydroxybenzaldehydes
Alternative Parents
Substituents
  • Hydroxybenzaldehyde
  • Catechol
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot 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 LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.577 +/- 0.566 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11268
Phenol Explorer Compound ID723
FooDB IDFDB012060
KNApSAcK IDC00018099
Chemspider ID8438
KEGG Compound IDC16700
BioCyc IDCPD-7616
BiGG IDNot Available
Wikipedia LinkProtocatechuic aldehyde
METLIN IDNot Available
PubChem Compound8768
PDB IDNot Available
ChEBI ID50205
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. Loke WM, Jenner AM, Proudfoot JM, McKinley AJ, Hodgson JM, Halliwell B, Croft KD: A metabolite profiling approach to identify biomarkers of flavonoid intake in humans. J Nutr. 2009 Dec;139(12):2309-14. doi: 10.3945/jn.109.113613. Epub 2009 Oct 7. [PubMed:19812218 ]