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Showing metabocard for 4-Hydroxybenzaldehyde (HMDB0011718)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-02-24 16:13:29 UTC
Update Date2023-02-21 17:17:34 UTC
HMDB IDHMDB0011718
Secondary Accession Numbers
  • HMDB11718
Metabolite 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0011718 (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 HMDB0011718 (4-Hydroxybenzaldehyde)

HMDB0011718
     RDKit          3D
4-Hydroxybenzaldehyde
 15 15  0  0  0  0  0  0  0  0999 V2000
    3.4190   -0.5569   -0.2724 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5990    0.3620   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566    0.1767   -0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2916    1.2209    0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0740    1.0222    0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462   -0.2073   -0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0283   -0.3638   -0.0603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820   -1.2523   -0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5833   -1.0620   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9862    1.3456    0.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7103    2.2015    0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7589    1.8377    0.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5438   -0.6115    0.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2024   -2.2333   -0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2895   -1.8794   -0.5107 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  2  0
  9  3  1  0
  2 10  1  0
  4 11  1  0
  5 12  1  0
  7 13  1  0
  8 14  1  0
  9 15  1  0
M  END
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3D SDF for HMDB0011718 (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>
HMDB0011718

> <DATABASE_NAME>
hmdb

> <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 HMDB0011718 (4-Hydroxybenzaldehyde)

HMDB0011718
     RDKit          3D
4-Hydroxybenzaldehyde
 15 15  0  0  0  0  0  0  0  0999 V2000
    3.4190   -0.5569   -0.2724 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5990    0.3620   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566    0.1767   -0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2916    1.2209    0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0740    1.0222    0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462   -0.2073   -0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0283   -0.3638   -0.0603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820   -1.2523   -0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5833   -1.0620   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9862    1.3456    0.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7103    2.2015    0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7589    1.8377    0.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5438   -0.6115    0.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2024   -2.2333   -0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2895   -1.8794   -0.5107 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  2  0
  9  3  1  0
  2 10  1  0
  4 11  1  0
  5 12  1  0
  7 13  1  0
  8 14  1  0
  9 15  1  0
M  END
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PDB for HMDB0011718 (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 HMDB0011718 (4-Hydroxybenzaldehyde)

COMPND    HMDB0011718
HETATM    1  O1  UNL     1       3.419  -0.557  -0.272  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.599   0.362  -0.046  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.157   0.177  -0.050  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.292   1.221   0.205  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.074   1.022   0.197  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.646  -0.207  -0.062  1.00  0.00           C  
HETATM    7  O2  UNL     1      -3.028  -0.364  -0.060  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.782  -1.252  -0.317  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.583  -1.062  -0.310  1.00  0.00           C  
HETATM   10  H1  UNL     1       2.986   1.346   0.162  1.00  0.00           H  
HETATM   11  H2  UNL     1       0.710   2.201   0.412  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.759   1.838   0.396  1.00  0.00           H  
HETATM   13  H4  UNL     1      -3.544  -0.612   0.780  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.202  -2.233  -0.524  1.00  0.00           H  
HETATM   15  H6  UNL     1       1.289  -1.879  -0.511  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4    4    9
CONECT    4    5   11
CONECT    5    6    6   12
CONECT    6    7    8
CONECT    7   13
CONECT    8    9    9   14
CONECT    9   15
END
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SMILES for HMDB0011718 (4-Hydroxybenzaldehyde)

OC1=CC=C(C=O)C=C1
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INCHI for HMDB0011718 (4-Hydroxybenzaldehyde)

InChI=1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
4-FormylphenolChEBI
p-FormylphenolChEBI
p-HydroxybenzaldehydeChEBI
4-Hydroxy-benzaldehydeHMDB
4-HydroxybenzenecarbonalHMDB
P-Hydroxy-benzaldehydeHMDB
p-OxybenzaldehydeHMDB
ParahydroxybenzaldehydeHMDB
Usaf m-6HMDB
Para-hydroxybenzaldehydeMeSH, HMDB
4-HydroxybenzaldehydePhytoBank
Chemical FormulaC7H6O2
Average Molecular Weight122.1213
Monoisotopic Molecular Weight122.036779436
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
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
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point117 °CNot Available
Boiling Point310.00 to 311.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility8.45 mg/mL at 25 °CNot Available
LogP1.35HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available119.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00002108
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified16.961 +/- 2.481 umol/mmol creatinineAdolescent (13-18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Prostate Cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified6.703 +/- 1.305 umol/mmol creatinineAdolescent (13-18 years old)Both
Obese		 details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Obesity
  1. Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]
Associated OMIM IDs
DrugBank IDDB03560
Phenol Explorer Compound ID725
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000845
Good Scents IDrw1040191
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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 ]