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Showing NP-Card for o-Tolualdehyde (NP0002791)

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Record Information
Version1.0
Created at2020-11-23 19:40:32 UTC
Updated at2021-08-19 23:59:23 UTC
NP-MRD IDNP0002791
Secondary Accession NumbersNone
Natural Product Identification
Common Nameo-Tolualdehyde
Provided ByBMRBBMRB logo
Description2-Methylbenzaldehyde, also known as O-toluic aldehyde or 2-formyltoluene, belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-). 2-Methylbenzaldehyde exists in all living organisms, ranging from bacteria to humans. 2-Methylbenzaldehyde is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. o-Tolualdehyde is found in Cichorium endivia and Gossypium hirsutum. It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on 2-Methylbenzaldehyde (PMID: 20016999) (PMID: 24312872) (PMID: 28747743) (PMID: 25434408) (PMID: 31347360) (PMID: 27193865).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002791 (o-Tolualdehyde)


     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    1.8860   -1.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -0.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6783   -1.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0810   -1.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3219    0.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1601    1.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2425    0.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    1.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633    3.3181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4177    0.2792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3544   -2.5261    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2886   -1.6551    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375   -3.0212    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427   -1.9579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7245    1.0031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010    2.9009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8069    1.3059    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  7  2  1  0
  1 10  1  1
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
M  END
Download

3D MOL for NP0002791 (o-Tolualdehyde)

NP0002791
     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
   -1.6738   -1.2019    0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3490   -0.5620    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7901   -1.3302   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181   -0.7404   -0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1152    0.6354   -0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0018    1.3993   -0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539    0.8051    0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4165    1.6349    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5406    1.1441    0.4967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5337   -2.3287    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4228   -0.9221   -0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1164   -1.0092    1.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6351   -2.4026   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8953   -1.3724   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    1.0588   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0900    2.4737   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3388    2.7183    0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  7  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
M  END
Download

3D SDF for NP0002791 (o-Tolualdehyde)


     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    1.8860   -1.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -0.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6783   -1.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0810   -1.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3219    0.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1601    1.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2425    0.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    1.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633    3.3181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4177    0.2792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3544   -2.5261    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2886   -1.6551    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375   -3.0212    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427   -1.9579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7245    1.0031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010    2.9009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8069    1.3059    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  7  2  1  0
  1 10  1  1
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
M  END
> <DATABASE_ID>
NP0002791

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC=CC=C1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O/c1-7-4-2-3-5-8(7)6-9/h2-6H,1H3

> <INCHI_KEY>
BTFQKIATRPGRBS-UHFFFAOYSA-N

> <FORMULA>
C8H8O

> <MOLECULAR_WEIGHT>
120.1485

> <EXACT_MASS>
120.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
13.02461965328535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylbenzaldehyde

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
2.19916955

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.118545287314168

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
37.68320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methylbenzaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002791 (o-Tolualdehyde)

NP0002791
     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
   -1.6738   -1.2019    0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3490   -0.5620    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7901   -1.3302   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181   -0.7404   -0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1152    0.6354   -0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0018    1.3993   -0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539    0.8051    0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4165    1.6349    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5406    1.1441    0.4967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5337   -2.3287    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4228   -0.9221   -0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1164   -1.0092    1.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6351   -2.4026   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8953   -1.3724   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    1.0588   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0900    2.4737   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3388    2.7183    0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  7  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
M  END
Download

PDB for NP0002791 (o-Tolualdehyde)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    8                                                       
CONECT    6    8    9                                                       
CONECT    7    1    4    8                                                  
CONECT    8    5    6    7                                                  
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0002791 (o-Tolualdehyde)

COMPND    NP0002791
HETATM    1  C1  UNL     1      -1.674  -1.202   0.230  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.349  -0.562   0.029  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.790  -1.330  -0.208  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.018  -0.740  -0.394  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.115   0.635  -0.344  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.002   1.399  -0.111  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.254   0.805   0.080  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.416   1.635   0.324  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.541   1.144   0.497  1.00  0.00           O  
HETATM   10  H1  UNL     1      -1.534  -2.329   0.224  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.423  -0.922  -0.537  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.116  -1.009   1.228  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.635  -2.403  -0.233  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.895  -1.372  -0.578  1.00  0.00           H  
HETATM   15  H6  UNL     1       3.100   1.059  -0.495  1.00  0.00           H  
HETATM   16  H7  UNL     1       1.090   2.474  -0.074  1.00  0.00           H  
HETATM   17  H8  UNL     1      -1.339   2.718   0.363  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    7
CONECT    3    4   13
CONECT    4    5    5   14
CONECT    5    6   15
CONECT    6    7    7   16
CONECT    7    8
CONECT    8    9    9   17
END
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SMILES for NP0002791 (o-Tolualdehyde)

CC1=CC=CC=C1C=O
Download

INCHI for NP0002791 (o-Tolualdehyde)

InChI=1S/C8H8O/c1-7-4-2-3-5-8(7)6-9/h2-6H,1H3
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View in JSmol
Synonyms
ValueSource
2-FormyltolueneChEBI
2-TolualdehydeChEBI
O-MethylbenazldehydeChEBI
O-Toluic aldehydeChEBI
O-ToluylaldehydeChEBI
O-TolylaldehydeChEBI
O-TolualdehydeKegg
2-Methyl-benzaldehydeHMDB
O-MethylbenzaldehydeHMDB
O-Tolualdehyde (8ci)HMDB
Toluic aldehydeHMDB
2-MethylbenzaldehydeChEBI
Chemical FormulaC8H8O
Average Mass120.1485 Da
Monoisotopic Mass120.05751 Da
IUPAC Name2-methylbenzaldehyde
Traditional Name2-methylbenzaldehyde
CAS Registry NumberNot Available
SMILES
CC1=CC=CC=C1C=O
InChI Identifier
InChI=1S/C8H8O/c1-7-4-2-3-5-8(7)6-9/h2-6H,1H3
InChI KeyBTFQKIATRPGRBS-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium sativumFooDB
Carum carviFooDB
Cichorium endiviaLOTUS Database
Cinnamomum aromaticumFooDB
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Gossypium hirsutumLOTUS Database
Prunus aviumFooDB
    • Bernalte, M. J., Hernandez, M. T., Vidal-Aragon, M. C. & Sabio, E. (1999) Physical, chemical, fla...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoyl derivatives
Direct ParentBenzoyl derivatives
Alternative Parents
Substituents
  • Benzoyl
  • Benzaldehyde
  • Aryl-aldehyde
  • Toluene
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point200.00 to 201.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1178 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.260The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP1.91ALOGPS
logP2.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.68 m³·mol⁻¹ChemAxon
Polarizability13.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029636
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000806
KNApSAcK IDNot Available
Chemspider ID21106524
KEGG Compound IDC07214
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Methylbenzaldehyde
METLIN IDNot Available
PubChem Compound10722
PDB IDNot Available
ChEBI ID27434
Good Scents IDrw1055241
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Huang J, Feng Y, Fu J, Sheng G: A method of detecting carbonyl compounds in tree leaves in China. Environ Sci Pollut Res Int. 2010 Jun;17(5):1129-36. doi: 10.1007/s11356-009-0277-3. Epub 2009 Dec 17. [PubMed:20016999 ]
  3. Hamedeyazdan S, Asnaashari S, Fathiazad F: Characterization of Non-Terpenoids in Marrubium crassidens Boiss. Essential Oil. Adv Pharm Bull. 2013;3(2):429-32. doi: 10.5681/apb.2013.069. Epub 2013 Aug 20. [PubMed:24312872 ]
  4. Park JH, Lee NH, Yang YC, Lee HS: Food Protective Effects of 3-Methylbenzaldehyde Derived from Myosotis arvensis and Its Analogues against Tyrophagus putrescentiae. Sci Rep. 2017 Jul 26;7(1):6608. doi: 10.1038/s41598-017-07001-5. [PubMed:28747743 ]
  5. Yang JY, Kim MG, Park JH, Hong ST, Lee HS: Evaluation of benzaldehyde derivatives from Morinda officinalis as anti-mite agents with dual function as acaricide and mite indicator. Sci Rep. 2014 Dec 1;4:7149. doi: 10.1038/srep07149. [PubMed:25434408 ]
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