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Showing NP-Card for 2-Hydroxybenzaldehyde (NP0001232)

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Record Information
Version1.0
Created at2012-09-11 18:57:50 UTC
Updated at2021-08-19 23:58:56 UTC
NP-MRD IDNP0001232
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Hydroxybenzaldehyde
Description2-Hydroxybenzaldehyde, also known as salicylal or O-formylphenol, 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. 2-Hydroxybenzaldehyde is a cinnamon, cooling, and medical tasting compound. 2-Hydroxybenzaldehyde is found, on average, in the highest concentration within peppermints. 2-Hydroxybenzaldehyde has also been detected, but not quantified, in several different foods, such as common buckwheats, garden tomato (var.), Herbs and spices, and tea. This could make 2-hydroxybenzaldehyde a potential biomarker for the consumption of these foods. 2-Hydroxybenzaldehyde is a potentially toxic compound.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001232 (2-Hydroxybenzaldehyde)


  Mrv1652309272007352D          

  9  9  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  5  2  0  0  0  0
  9  7  1  0  0  0  0
M  END
Download

3D MOL for NP0001232 (2-Hydroxybenzaldehyde)

HMDB0034170
     RDKit          3D
2-Hydroxybenzaldehyde
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.4584    1.9856   -0.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1483    0.7703   -0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    0.4134   -0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2275    1.3727   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5636    1.0733    0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9524   -0.2558    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9705   -1.2203    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711   -0.9155   -0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559   -1.8805   -0.1171 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9463    0.0507   -0.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0883    2.4224   -0.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304    1.8333    0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9908   -0.5134    0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2846   -2.2672    0.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1935   -2.8691   -0.0764 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
  8  3  1  0
  2 10  1  0
  4 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  9 15  1  0
M  END
Download

3D SDF for NP0001232 (2-Hydroxybenzaldehyde)


  Mrv1652309272007352D          

  9  9  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  5  2  0  0  0  0
  9  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001232

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
SMQUZDBALVYZAC-UHFFFAOYSA-N

> <FORMULA>
C7H6O2

> <MOLECULAR_WEIGHT>
122.1213

> <EXACT_MASS>
122.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.886411741635492

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxybenzaldehyde

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
2.032182839

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.403256552441606

> <JCHEM_PKA_STRONGEST_BASIC>
-5.985596393103912

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
34.6229

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
salicylaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0001232 (2-Hydroxybenzaldehyde)

HMDB0034170
     RDKit          3D
2-Hydroxybenzaldehyde
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.4584    1.9856   -0.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1483    0.7703   -0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    0.4134   -0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2275    1.3727   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5636    1.0733    0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9524   -0.2558    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9705   -1.2203    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711   -0.9155   -0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559   -1.8805   -0.1171 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9463    0.0507   -0.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0883    2.4224   -0.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304    1.8333    0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9908   -0.5134    0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2846   -2.2672    0.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1935   -2.8691   -0.0764 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
  8  3  1  0
  2 10  1  0
  4 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  9 15  1  0
M  END
Download

PDB for NP0001232 (2-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      -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  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334   3.850   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    8                                                       
CONECT    6    3    5    7                                                  
CONECT    7    4    6    9                                                  
CONECT    8    5                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0001232 (2-Hydroxybenzaldehyde)

COMPND    HMDB0034170
HETATM    1  O1  UNL     1       2.458   1.986  -0.331  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.148   0.770  -0.268  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.758   0.413  -0.098  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.228   1.373  -0.004  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.564   1.073   0.159  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.952  -0.256   0.234  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.971  -1.220   0.140  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.371  -0.915  -0.023  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.356  -1.881  -0.117  1.00  0.00           O  
HETATM   10  H1  UNL     1       2.946   0.051  -0.345  1.00  0.00           H  
HETATM   11  H2  UNL     1       0.088   2.422  -0.064  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.330   1.833   0.232  1.00  0.00           H  
HETATM   13  H4  UNL     1      -2.991  -0.513   0.361  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.285  -2.267   0.200  1.00  0.00           H  
HETATM   15  H6  UNL     1       1.194  -2.869  -0.076  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4    4    8
CONECT    4    5   11
CONECT    5    6    6   12
CONECT    6    7   13
CONECT    7    8    8   14
CONECT    8    9
CONECT    9   15
END
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SMILES for NP0001232 (2-Hydroxybenzaldehyde)

OC1=C(C=O)C=CC=C1
Download

INCHI for NP0001232 (2-Hydroxybenzaldehyde)

InChI=1S/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H
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View in JSmolView NMR Assignments
Synonyms
ValueSource
O-FormylphenolChEBI
O-HydroxybenzaldehydeChEBI
SalicylalChEBI
SalicylaldehydChEBI
SalizylaldehydChEBI
2-FormylphenolHMDB
FEMA 3004HMDB
Salicylaldehyde, 8ciHMDB
Salicylic aldehydeHMDB
Salicylaldehyde esterHMDB
2-Hydroxy-1-benzaldehydeHMDB
SalicylaldehydeHMDB
2-HydroxybenzaldehydeChEBI
Chemical FormulaC7H6O2
Average Mass122.1213 Da
Monoisotopic Mass122.03678 Da
IUPAC Name2-hydroxybenzaldehyde
Traditional Namesalicylaldehyde
CAS Registry Number90-02-8
SMILES
OC1=CC=CC=C1C=O
InChI Identifier
InChI=1S/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H
InChI KeySMQUZDBALVYZAC-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anthemis aciphyllaLOTUS Database
Anthemis aciphylla BOISS.var.discoidea BOISSKNApSAcK Database
Aspalathus linearisLOTUS Database
Brassica rapaKNApSAcK Database
Camellia sinensisKNApSAcK Database
Cannabis sativaCannabisDB
      Not Available
Castanopsis cuspidataLOTUS Database
Ceanothus velutinusLOTUS Database
Cinnamomum burmanniLOTUS Database
Cinnamomum versumKNApSAcK Database
Decalepis hamiltoniiLOTUS Database
Fagopyrum esculentumFooDB
Festuca rubraLOTUS Database
Filipendula camtschaticaLOTUS Database
Filipendula ulmariaLOTUS Database
Mentha x piperitaFooDB
Paeonia lactifloraLOTUS Database
Photinia melanocarpaLOTUS Database
Salix babylonicaPlant
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaKNApSAcK Database
Vitis viniferaLOTUS Database
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-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point0.7 °CNot Available
Boiling Point196.00 to 197.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility17 mg/mL at 86 °CNot Available
LogP1.81Not Available
Predicted Properties
PropertyValueSource
Water Solubility10.3 g/LALOGPS
logP1.22ALOGPS
logP2.03ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)8.4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.62 m³·mol⁻¹ChemAxon
Polarizability11.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034170
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003871
KNApSAcK IDC00031273
Chemspider ID13863618
KEGG Compound IDC06202
BioCyc IDSALICYLALDEHYDE
BiGG IDNot Available
Wikipedia LinkSalicylaldehyde
METLIN IDNot Available
PubChem Compound6998
PDB IDNK
ChEBI ID16008
Good Scents IDrw1028641
References
General References
  1. Kim HK, Yun YK, Ahn YJ: Fumigant toxicity of cassia bark and cassia and cinnamon oil compounds to Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae). Exp Appl Acarol. 2008 Jan;44(1):1-9. doi: 10.1007/s10493-008-9129-y. Epub 2008 Feb 5. [PubMed:18247142 ]
  2. Caboni P, Aissani N, Cabras T, Falqui A, Marotta R, Liori B, Ntalli N, Sarais G, Sasanelli N, Tocco G: Potent nematicidal activity of phthalaldehyde, salicylaldehyde, and cinnamic aldehyde against Meloidogyne incognita. J Agric Food Chem. 2013 Feb 27;61(8):1794-803. doi: 10.1021/jf305164m. Epub 2013 Feb 15. [PubMed:23379671 ]
  3. Montalbano F, Cal PM, Carvalho MA, Goncalves LM, Lucas SD, Guedes RC, Veiros LF, Moreira R, Gois PM: Discovery of new heterocycles with activity against human neutrophile elastase based on a boron promoted one-pot assembly reaction. Org Biomol Chem. 2013 Jul 21;11(27):4465-72. doi: 10.1039/c3ob40614h. [PubMed:23715243 ]
  4. May NV, Jancso A, Enyedy EA: Binding Models of Copper(II) Thiosemicarbazone Complexes with Human Serum Albumin: A Speciation Study. Molecules. 2021 May 5;26(9). pii: molecules26092711. doi: 10.3390/molecules26092711. [PubMed:34063080 ]
  5. Yu M, Liu Y, Feng J, Chen D, Yang Y, Liu P, Yu Z, Wei J: Remarkable Phytochemical Characteristics of Chi-Nan Agarwood Induced from New-Found Chi-Nan Germplasm of Aquilaria sinensis Compared with Ordinary Agarwood. Int J Anal Chem. 2021 Apr 10;2021:5593730. doi: 10.1155/2021/5593730. eCollection 2021. [PubMed:33927765 ]
  6. Sibuh BZ, Khanna S, Taneja P, Sarkar P, Taneja NK: Molecular docking, synthesis and anticancer activity of thiosemicarbazone derivatives against MCF-7 human breast cancer cell line. Life Sci. 2021 May 15;273:119305. doi: 10.1016/j.lfs.2021.119305. Epub 2021 Mar 3. [PubMed:33675898 ]
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