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Showing metabocard for Cuminaldehyde (HMDB0002214)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:42 UTC
Update Date2023-02-21 17:16:16 UTC
HMDB IDHMDB0002214
Secondary Accession Numbers
  • HMDB02214
Metabolite Identification
Common NameCuminaldehyde
DescriptionCuminaldehyde is the biologically active constituent of Cuminum cyminum seed oil. C. cyminum seed-derived materials have an inhibitory effect in vitro against rat lens aldose reductase and alpha-glucosidase. This inhibitory action cuminaldehyde suggest a potential utility as an antidiabetic therapeutic. (PMID:15796577 ). Cuminaldehyde is a volatile compound representative of cumin aroma present in trace amounts in the blood and milk of ewes fed with cumin seed. (PMID:8738023 ). The terpenoid cuminaldehyde, undergoes reduction biotransformation in mammals, but not oxidation. (PMID:2815827 ).
Structure
Data?1676999776
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002214 (Cuminaldehyde)

Cuminaldehyde
  Mrv1652303202019022D          

 12 12  0  0  0  0            999 V2000
    0.4195   -2.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -3.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4195   -1.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0094   -2.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -1.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0094   -1.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7239   -3.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4384   -2.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7240   -3.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1340   -1.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8485   -1.8880    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1340   -0.6504    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
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
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3D MOL for HMDB0002214 (Cuminaldehyde)

HMDB0002214
     RDKit          3D
Cuminaldehyde
 23 23  0  0  0  0  0  0  0  0999 V2000
   -2.4731    0.7309   -1.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8136   -0.3740   -0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2277   -0.2549    1.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320   -0.2899   -0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4330   -1.3102   -0.8736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8221   -1.1696   -0.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4695   -0.0384   -0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9139    0.1028   -0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5024    1.1191   -0.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6951    0.9764    0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145    0.8354    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872    1.0987   -1.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6369    1.6086   -0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4493    0.4164   -1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1946   -1.3324   -0.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3977   -0.5748    1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4989    0.7754    1.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0885   -0.9124    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381   -2.2095   -1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3882   -1.9990   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792   -0.7145   -0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1854    1.8733    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2658    1.6425    0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  7 10  1  0
 10 11  2  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
 10 22  1  0
 11 23  1  0
M  END
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3D SDF for HMDB0002214 (Cuminaldehyde)

Cuminaldehyde
  Mrv1652303202019022D          

 12 12  0  0  0  0            999 V2000
    0.4195   -2.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -3.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4195   -1.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0094   -2.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -1.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0094   -1.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7239   -3.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4384   -2.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7240   -3.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1340   -1.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8485   -1.8880    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1340   -0.6504    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
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002214

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C(=O)C1=CC=C(C=C1)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3

> <INCHI_KEY>
WTWBUQJHJGUZCY-UHFFFAOYSA-N

> <FORMULA>
C10H12O

> <MOLECULAR_WEIGHT>
148.205

> <EXACT_MASS>
148.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.05551663791709

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(propan-2-yl)benzaldehyde

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.9307573113333336

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.103469274977909

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
46.8328

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cuminaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0002214 (Cuminaldehyde)

HMDB0002214
     RDKit          3D
Cuminaldehyde
 23 23  0  0  0  0  0  0  0  0999 V2000
   -2.4731    0.7309   -1.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8136   -0.3740   -0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2277   -0.2549    1.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320   -0.2899   -0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4330   -1.3102   -0.8736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8221   -1.1696   -0.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4695   -0.0384   -0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9139    0.1028   -0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5024    1.1191   -0.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6951    0.9764    0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145    0.8354    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872    1.0987   -1.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6369    1.6086   -0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4493    0.4164   -1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1946   -1.3324   -0.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3977   -0.5748    1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4989    0.7754    1.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0885   -0.9124    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381   -2.2095   -1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3882   -1.9990   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792   -0.7145   -0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1854    1.8733    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2658    1.6425    0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  7 10  1  0
 10 11  2  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
 10 22  1  0
 11 23  1  0
M  END
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PDB for HMDB0002214 (Cuminaldehyde)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Cuminaldehyde                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       0.783  -5.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.550  -5.834   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.783  -3.524   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.884  -5.064   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.550  -2.754   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.884  -3.524   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.218  -5.834   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.552  -5.064   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.218  -7.374   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.117  -2.754   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       3.451  -3.524   0.000  0.00  0.00           H+0
HETATM   12  O   UNK     0       2.117  -1.214   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5   10                                                  
CONECT    4    2    6    7                                                  
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0002214 (Cuminaldehyde)

COMPND    HMDB0002214
HETATM    1  C1  UNL     1      -2.473   0.731  -1.039  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.814  -0.374  -0.244  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.228  -0.255   1.219  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.332  -0.290  -0.348  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.433  -1.310  -0.874  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.822  -1.170  -0.944  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.470  -0.038  -0.504  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.914   0.103  -0.580  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.502   1.119  -0.185  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.695   0.976   0.020  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.315   0.835   0.089  1.00  0.00           C  
HETATM   12  H1  UNL     1      -1.787   1.099  -1.838  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.637   1.609  -0.360  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.449   0.416  -1.428  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.195  -1.332  -0.632  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.398  -0.575   1.884  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.499   0.775   1.484  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.088  -0.912   1.440  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.038  -2.209  -1.227  1.00  0.00           H  
HETATM   20  H9  UNL     1       2.388  -1.999  -1.366  1.00  0.00           H  
HETATM   21  H10 UNL     1       4.479  -0.715  -0.996  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.185   1.873   0.371  1.00  0.00           H  
HETATM   23  H12 UNL     1      -0.266   1.643   0.503  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5    5   11
CONECT    5    6   19
CONECT    6    7    7   20
CONECT    7    8   10
CONECT    8    9    9   21
CONECT   10   11   11   22
CONECT   11   23
END
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SMILES for HMDB0002214 (Cuminaldehyde)

[H]C(=O)C1=CC=C(C=C1)C(C)C
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INCHI for HMDB0002214 (Cuminaldehyde)

InChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-IsopropylbenzaldehydeChEBI
CumaldehydeChEBI
Cumic aldehydeChEBI
Cuminic aldehydeChEBI
Cuminyl aldehydeChEBI
p-Cumic aldehydeChEBI
p-IsopropylbenzaldehydeChEBI
p-IsopropylbenzenecarboxaldehydeChEBI
p-Isopropyl benzaldehydeMeSH
4-(1-Methylethyl)benzaldehydeHMDB
4-IsopropylbenzenecarboxylateHMDB
CuminalHMDB
Cuminal P-(1-methylethyl)benzaldehydeHMDB
P-Cuminic aldehydeHMDB
P-Isopropyl-benzaldehydeHMDB
Chemical FormulaC10H12O
Average Molecular Weight148.205
Monoisotopic Molecular Weight148.088815006
IUPAC Name4-(propan-2-yl)benzaldehyde
Traditional Namecuminaldehyde
CAS Registry Number122-03-2
SMILES
[H]C(=O)C1=CC=C(C=C1)C(C)C
InChI Identifier
InChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3
InChI KeyWTWBUQJHJGUZCY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • P-cymene
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Cumene
  • Phenylpropane
  • Benzaldehyde
  • Benzoyl
  • Aryl-aldehyde
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Aldehyde
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • 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
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point235.5 °CNot Available
Water Solubility282 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP3.170The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008724
KNApSAcK IDC00003039
Chemspider ID21106431
KEGG Compound IDC06577
BioCyc IDCPD-1003
BiGG IDNot Available
Wikipedia LinkCuminaldehyde
METLIN IDNot Available
PubChem Compound326
PDB IDNot Available
ChEBI ID28671
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1004031
References
Synthesis ReferenceLebedev, I. M.; Gorker, I. A.; Mochalin, V. B. A new method for the preparation of cuminaldehyde and for the simultaneous preparation of p-isopropyl-a-methylcinnamaldehyde. Masloboino-Zhirovaya Promyshlennost (1961), 27(2), 33-5.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lee HS: Cuminaldehyde: Aldose Reductase and alpha-Glucosidase Inhibitor Derived from Cuminum cyminum L. Seeds. J Agric Food Chem. 2005 Apr 6;53(7):2446-50. [PubMed:15796577 ]
  2. Desage M, Schaal B, Soubeyrand J, Orgeur P, Brazier JL: Gas chromatographic-mass spectrometric method to characterise the transfer of dietary odorous compounds into plasma and milk. J Chromatogr B Biomed Appl. 1996 Apr 12;678(2):205-10. [PubMed:8738023 ]
  3. Ishida T, Toyota M, Asakawa Y: Terpenoid biotransformation in mammals. V. Metabolism of (+)-citronellal, (+-)-7-hydroxycitronellal, citral, (-)-perillaldehyde, (-)-myrtenal, cuminaldehyde, thujone, and (+-)-carvone in rabbits. Xenobiotica. 1989 Aug;19(8):843-55. [PubMed:2815827 ]