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Showing NP-Card for 4-Hydroxybenzaldehyde (NP0000963)

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Record Information
Version2.0
Created at2009-02-24 16:13:29 UTC
Updated at2024-09-03 04:16:58 UTC
NP-MRD IDNP0000963
Natural Product DOIhttps://doi.org/10.57994/0876
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Hydroxybenzaldehyde
Description4-Hydroxybenzaldehyde, also known as 4-formylphenol or 4-hydroxybenzenecarbonal, 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. A hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. 4-Hydroxybenzaldehyde exists in all living organisms, ranging from bacteria to humans. 4-Hydroxybenzaldehyde is a sweet, almond, and balsam tasting compound. 4-Hydroxybenzaldehyde is found, on average, in the highest concentration within vinegars and oats. 4-Hydroxybenzaldehyde has also been detected, but not quantified, in several different foods, such as cardoons, colorado pinyons, oyster mushrooms, common chokecherries, and potato. This could make 4-hydroxybenzaldehyde a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0000963 (4-Hydroxybenzaldehyde)


  Mrv1652309272007332D          

  9  9  0  0  0  0            999 V2000
 9980.7078 9978.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.9970 9978.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.2825 9978.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.5679 9978.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.5679 9977.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.2823 9977.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.9970 9977.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.8549 9977.2085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.4208 9978.4443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  2  1  0  0  0  0
  2  1  1  0  0  0  0
  5  8  1  0  0  0  0
  1  9  2  0  0  0  0
M  END
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3D MOL for NP0000963 (4-Hydroxybenzaldehyde)

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3D SDF for NP0000963 (4-Hydroxybenzaldehyde)

  Mrv1652309272007332D          

  9  9  0  0  0  0            999 V2000
 9980.7078 9978.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.9970 9978.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.2825 9978.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.5679 9978.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.5679 9977.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.2823 9977.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.9970 9977.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.8549 9977.2085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.4208 9978.4443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  2  1  0  0  0  0
  2  1  1  0  0  0  0
  5  8  1  0  0  0  0
  1  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000963

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H

> <INCHI_KEY>
RGHHSNMVTDWUBI-UHFFFAOYSA-N

> <FORMULA>
C7H6O2

> <MOLECULAR_WEIGHT>
122.1213

> <EXACT_MASS>
122.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.975088213270887

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxybenzaldehyde

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
1.382182839

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.320724001562799

> <JCHEM_PKA_STRONGEST_BASIC>
-7.095242156206047

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
34.6229

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
P-hydroxybenzaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0000963 (4-Hydroxybenzaldehyde)
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PDB for NP0000963 (4-Hydroxybenzaldehyde)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8630.6558627.198   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8629.3288626.431   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8627.9948627.201   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8626.6608626.431   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8626.6608624.891   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8627.9948624.121   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8629.3288624.891   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8625.3298624.123   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8631.9858626.429   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    3    7    1                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5                                                            
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0000963 (4-Hydroxybenzaldehyde)
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SMILES for NP0000963 (4-Hydroxybenzaldehyde)
OC1=CC=C(C=O)C=C1
Download
INCHI for NP0000963 (4-Hydroxybenzaldehyde)
InChI=1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H
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View in JSmol
Synonyms
ValueSource
4-FormylphenolChEBI
p-FormylphenolChEBI
p-HydroxybenzaldehydeChEBI
4-Hydroxy-benzaldehydeHMDB
4-HydroxybenzenecarbonalHMDB
p-Hydroxy-benzaldehydeHMDB
p-OxybenzaldehydeHMDB
ParahydroxybenzaldehydeHMDB
Usaf m-6HMDB
Para-hydroxybenzaldehydeHMDB
4-HydroxybenzaldehydePhytoBank
Chemical FormulaC7H6O2
Average Mass122.1213 Da
Monoisotopic Mass122.03678 Da
IUPAC Name4-hydroxybenzaldehyde
Traditional NameP-hydroxybenzaldehyde
CAS Registry Number123-08-0
SMILES
OC1=CC=C(C=O)C=C1
InChI Identifier
InChI=1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H
InChI KeyRGHHSNMVTDWUBI-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)wuhonghua2011@tjutcm.edu.cnTianjin University of Traditional Chinese MedicineHong-Hua Wu2023-09-08View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)wuhonghua2011@tjutcm.edu.cnTianjin University of Traditional Chinese MedicineHong-Hua Wu2023-09-08View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
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Abies nephrolepis
Abutilon indicumPlant
Aeginetia indica
Ailanthus altissima
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Alpinia roxburghii
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Beta vulgaris
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Chelonanthus albus
Chenopodium album
Cinnamomum kotoense
Cinnamomum reticulatum
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Citrus aurantium
Columba
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Croton draco Schltdl.& Cham.Plant
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Cryptomeria japonicaPlant
Cucubalus baccifer
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Cullen corylifoliumPlant
Curculigo capitulataPlant
Curcuma comosaPlant
Cyathobasis fruticulosa
Daucus carota ssp. sativusFooDB
    • Adrian J. Parr, Annie Ng, and Keith W. Waldron Ester-Linked Phenolic Components of Carrot Cell Wa...
Dendrobium falconeri
Dianthus longicalyx
Dianthus superbus
Dianthus superbus var.longicalycinus (MAXIM.) WILLPlant
Diospyros maritima
Dorstenia prorepensPlant
Dorstenia zenkeri
Dracaena cambodiana
Dromaius novaehollandiae
Drymaria cordataPlant
Dumortiera hirsuta
Dytiscus marginalis
Eleusine coracana
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Enhalus acoroidesPlant
Epichloe typhina
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Gymnadenia conopsea R.BR.Plant
Gynura japonica
Haplopteris anguste-elongata
Hibiscus cannabinus
Hornstedtia reticulata
Houttuynia cordata
Humulus lupulus
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Hymedesmia paupertas
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Lagopus muta
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Ligularia przewalskii
Ligularia stenocephala
Ligularia stenocephala Matsum.et Koidz.Plant
Litsea hypophaea
Litsea szemaois
Lycopodium spp.Plant
Macrococculus pomiferusPlant
Magnolia officinalis
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Marchantia polymorpha
Maytenus boaria
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Melanitta fusca
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Microtropis fokienensisPlant
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Neurospora kobi
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Numida meleagris
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Oryctolagus
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Peniophora polygonia
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Phellodendron amurensePlant
Phellodendron chinense
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Phoebe formosanaPlant
Phoenix dactyliferaFooDB
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Phragmites australis
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Picea glauca
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Populus alba
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Populus deltoides
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Rhizophora mucronata
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Rosa taiwanensis
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Sus scrofa
Sus scrofa domestica
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VanillaFooDB
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Vanilla x tahitensis
Viburnum dilatatum
Viscum articulactumPlant
Viscum articulatum
Viscum coloratumPlant
Visnea mocanera
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Wiesnerella denudata
Wikstroemia canescens
Xanthium strumarium
Zanthoxylum ailanthoidesPlant
Zanthoxylum nitidum
Zanthoxylum wutaiensePlant
Zea mays L.FooDB
Zingiber zerumbet
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
    • 

  • Benzoyl
    • 

  • 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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point117 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility8.45 mg/mL at 25 °CNot Available
LogP1.35Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility9.51 g/LALOGPS
logP1.27ALOGPS
logP1.38ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)7.32ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.62 m³·mol⁻¹ChemAxon
Polarizability11.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011718  
DrugBank IDDB03560  
Phenol Explorer Compound ID725  
FoodDB IDFDB010504  
KNApSAcK IDC00002657  
Chemspider ID123  
KEGG Compound IDC00633  
BioCyc ID4-HYDROXYBENZALDEHYDE  
BiGG IDNot Available
Wikipedia Link4-Hydroxybenzaldehyde  
METLIN IDNot Available
PubChem Compound126  
PDB IDHBA  
ChEBI ID17597  
Good Scents IDNot Available
References
General References
  1. Hext PM, Rose FA: The Sulphation of p-hydroxyphenylpyruvic acid and related compounds by the rat liver cytosol. Biochem J. 1975 Aug;150(2):175-81. [PubMed:1180912  ] 
  2. Sirimanne SR, Herman HH, May SW: Interaction of dopamine beta-mono-oxygenase with substituted imidazoles and pyrazoles. Catalysis and inhibition. Biochem J. 1987 Feb 15;242(1):227-33. doi: 10.1042/bj2420227. [PubMed:3593236  ]