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Showing NP-Card for 3,4-Dihydroxybenzaldehyde (NP0047775)

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Record Information
Version2.0
Created at2022-03-17 20:45:45 UTC
Updated at2025-02-11 15:44:31 UTC
NP-MRD IDNP0047775
Natural Product DOIhttps://doi.org/10.57994/1240
Secondary Accession NumbersNone
Natural Product 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. 3,4-Dihydroxybenzaldehyde is found in Actaea racemosa , Amomum subulatum, Amorphophallus konjac, Amorphophallus konjac K.Koch , Anastatica hierochuntica, Artemisia sacrorum, Beta vulgaris, Bletilla formosana, Calophyllum macrocarpum, Centipeda minima, Chrysanthemum morifolium, Cryptotympana sp., Cullen corylifolium, Dryopteris crassirhizoma, Duhaldea cappa, Ganoderma applanatum, Haplopteris anguste-elongata, Hordeum vulgare , Hydnophytum formicarum, Hymenochaete xerantica, Inonotus obliquus , Ipomoea nil, Joannesia princeps, Keiskea japonica, Magnolia crassipes, Menispermum dauricum, Orobanche pycnostachya, Perilla frutescens, Phellinus igniarius , Picea jezoensis, Polyporus umbellatus, Vertebrata lanosa, Populus ciliata, Populus euphratica, Populus simonii, Posidonia oceanica , Pyrrosia petiolosa, Quercus suber, Ranunculus sceleratus, Salsola collina, Salvia chinensis, Salvia divinorum, Salvia miltiorrhiza, Salvia miltiorrihiza, Streptomyces lincolnensis, Tropicoporus linteus, Visnea mocanera, Vitis vinifera and Vittaria anguste-elongata. This could make 3,4-dihydroxybenzaldehyde a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047775 (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
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3D MOL for NP0047775 (3,4-Dihydroxybenzaldehyde)

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3D SDF for NP0047775 (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>
NP0047775

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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3D-SDF for NP0047775 (3,4-Dihydroxybenzaldehyde)
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PDB for NP0047775 (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

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3D PDB for NP0047775 (3,4-Dihydroxybenzaldehyde)
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SMILES for NP0047775 (3,4-Dihydroxybenzaldehyde)
OC1=CC=C(C=O)C=C1O
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INCHI for NP0047775 (3,4-Dihydroxybenzaldehyde)
InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H
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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
Chemical FormulaC7H6O3
Average Mass138.1207 Da
Monoisotopic Mass138.03169 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-04View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-04View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-04View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-04View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-04View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-04View Spectrum
Species
Species of Origin
Species NameSourceReference
Actaea racemosaPlant
Amomum subulatumLOTUS Database
Amorphophallus konjacLOTUS Database
Amorphophallus konjac K.KochPlant
Anastatica hierochunticaLOTUS Database
Artemisia sacrorumLOTUS Database
Beta vulgarisLOTUS Database
Bletilla formosanaPlant
Calophyllum macrocarpumLOTUS Database
Centipeda minimaLOTUS Database
Chrysanthemum morifoliumLOTUS Database
Cichorium intybusFooDB
Cryptotympana sp.Animalia
Cullen corylifoliumLOTUS Database
Dryopteris crassirhizomaLOTUS Database
Duhaldea cappaLOTUS Database
Fagopyrum esculentumFooDB
Ganoderma applanatumLOTUS Database
Haplopteris anguste-elongataLOTUS Database
Hordeum vulgarePlant
Hydnophytum formicarumLOTUS Database
Hymenochaete xeranticaLOTUS Database
Inonotus obliquusFungi
Ipomoea nilLOTUS Database
Joannesia princepsLOTUS Database
Keiskea japonicaLOTUS Database
Manglietia crassipesLOTUS Database
Menispermum dauricumLOTUS Database
Orobanche pycnostachyaLOTUS Database
Perilla frutescensLOTUS Database
Phellinus igniariusFungi
Picea jezoensisLOTUS Database
Polyporus umbellatusLOTUS Database
Polysiphonia lanosaLOTUS Database
Populus ciliataLOTUS Database
Populus euphraticaLOTUS Database
Populus simoniiLOTUS Database
Posidonia oceanicaPlant
Pyrrosia petiolosaLOTUS Database
Quercus suberLOTUS Database
Ranunculus sceleratusLOTUS Database
Salsola collinaLOTUS Database
Salvia chinensisLOTUS Database
Salvia divinorumLOTUS Database
Salvia miltiorrhizaLOTUS Database
Salvia miltiorrihizaPlant
Streptomyces lincolnensisBacteria
Tropicoporus linteusLOTUS Database
Visnea mocaneraLOTUS Database
Vitis viniferaLOTUS Database
Vitis vinifera L.FooDB
Vittaria anguste-elongataPlant
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
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
logP0.89ALOGPS
logP1.08ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)7.46ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.6 m³·mol⁻¹ChemAxon
Polarizability12.87 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0059965  
DrugBank IDDB11268  
Phenol Explorer Compound ID723  
FoodDB 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  
Good Scents IDNot Available
References
General References