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Showing metabocard for Cinnamaldehyde (HMDB0003441)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-12 20:46:08 UTC
Update Date2023-02-21 17:16:40 UTC
HMDB IDHMDB0003441
Secondary Accession Numbers
  • HMDB03441
Metabolite Identification
Common NameCinnamaldehyde
DescriptionCinnamaldehyde is the aldehyde that gives cinnamon its flavor and odor. Cinnamaldehyde occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum like camphor and cassia. These trees are the natural source of cinnamon, and the essential oil of cinnamon bark is about 90% cinnamaldehyde. Cinnamaldehyde is also used as a fungicide. Proven effective on over 40 different crops, cinnamaldehyde is typically applied to the root systems of plants. Its low toxicity and well-known properties make it ideal for agriculture. To a lesser extent, cinnamaldehyde is an effective insecticide, and its scent is also known to repel animals like cats and dogs. Cinnamaldehyde is also known as a corrosion inhibitor for steel and other ferrous alloys in corrosive fluids. It can be used in combination with additional components such as dispersing agents, solvents and other surfactants. Concentrated cinnamaldehyde is a skin irritant, and the chemical is toxic in large doses, but no agencies suspect the compound is a carcinogen or poses a long-term health hazard. Most cinnamaldehyde is excreted in urine as cinnamic acid, an oxidized form of cinnamaldehyde.
Structure
Data?1676999800
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003441 (Cinnamaldehyde)

  Mrv1652309272007362D          

 10 10  0  0  0  0            999 V2000
10000.004810000.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.720510000.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.434110000.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.149810000.3998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.290210000.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.575810000.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.861210000.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8612 9999.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5757 9999.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2902 9999.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  1  5  1  0  0  0  0
M  END
Download

3D MOL for HMDB0003441 (Cinnamaldehyde)

HMDB0003441
     RDKit          3D
Cinnamaldehyde
 18 18  0  0  0  0  0  0  0  0999 V2000
   -4.3723    1.1333   -0.3388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5617    0.1906   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1386    0.5195   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3077   -0.4804    0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1274   -0.2596    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688   -1.3768    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3210   -1.1758    0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8361    0.0997    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0154    1.1787    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417    1.0011    0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9112   -0.8234   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467    1.5494   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796   -1.5168    0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5539   -2.3601    0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9801   -2.0196    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.2347    0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171    2.2052    0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0299    1.9001   -0.0926 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
  9 10  2  0
 10  5  1  0
  2 11  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
M  END
Download

3D SDF for HMDB0003441 (Cinnamaldehyde)

  Mrv1652309272007362D          

 10 10  0  0  0  0            999 V2000
10000.004810000.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.720510000.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.434110000.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.149810000.3998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.290210000.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.575810000.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.861210000.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8612 9999.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5757 9999.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2902 9999.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  1  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003441

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+

> <INCHI_KEY>
KJPRLNWUNMBNBZ-QPJJXVBHSA-N

> <FORMULA>
C9H8O

> <MOLECULAR_WEIGHT>
132.1592

> <EXACT_MASS>
132.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.476246951483136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-phenylprop-2-enal

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
1.9774700076666665

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.439447314621728

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
42.1345

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cinnamal

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0003441 (Cinnamaldehyde)

HMDB0003441
     RDKit          3D
Cinnamaldehyde
 18 18  0  0  0  0  0  0  0  0999 V2000
   -4.3723    1.1333   -0.3388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5617    0.1906   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1386    0.5195   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3077   -0.4804    0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1274   -0.2596    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688   -1.3768    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3210   -1.1758    0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8361    0.0997    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0154    1.1787    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417    1.0011    0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9112   -0.8234   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467    1.5494   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796   -1.5168    0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5539   -2.3601    0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9801   -2.0196    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.2347    0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171    2.2052    0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0299    1.9001   -0.0926 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
  9 10  2  0
 10  5  1  0
  2 11  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
M  END
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PDB for HMDB0003441 (Cinnamaldehyde)

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    8666.6768668.179   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.0128667.413   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.3448668.179   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8670.6808667.413   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8665.3428667.411   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8664.0088668.181   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8662.6748667.411   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.6748665.871   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.0088665.101   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.3428665.871   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    6   10    1                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0003441 (Cinnamaldehyde)

COMPND    HMDB0003441
HETATM    1  O1  UNL     1      -4.372   1.133  -0.339  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.562   0.191  -0.190  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.139   0.520  -0.118  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.308  -0.480   0.039  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.127  -0.260   0.122  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.969  -1.377   0.290  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.321  -1.176   0.369  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.836   0.100   0.284  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.015   1.179   0.121  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.642   1.001   0.038  1.00  0.00           C  
HETATM   11  H1  UNL     1      -3.911  -0.823  -0.118  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.847   1.549  -0.195  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.680  -1.517   0.111  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.554  -2.360   0.354  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.980  -2.020   0.498  1.00  0.00           H  
HETATM   16  H6  UNL     1       3.926   0.235   0.350  1.00  0.00           H  
HETATM   17  H7  UNL     1       2.417   2.205   0.052  1.00  0.00           H  
HETATM   18  H8  UNL     1       0.030   1.900  -0.093  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4   12
CONECT    4    5   13
CONECT    5    6    6   10
CONECT    6    7   14
CONECT    7    8    8   15
CONECT    8    9   16
CONECT    9   10   10   17
CONECT   10   18
END
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SMILES for HMDB0003441 (Cinnamaldehyde)

O=C\C=C\C1=CC=CC=C1
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INCHI for HMDB0003441 (Cinnamaldehyde)

InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC9H8O
Average Molecular Weight132.1592
Monoisotopic Molecular Weight132.057514878
IUPAC Name(2E)-3-phenylprop-2-enal
Traditional Namecinnamal
CAS Registry Number104-55-2
SMILES
O=C\C=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+
InChI KeyKJPRLNWUNMBNBZ-QPJJXVBHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamaldehydes
Sub ClassNot Available
Direct ParentCinnamaldehydes
Alternative Parents
Substituents
  • Cinnamaldehyde
  • Styrene
  • Benzenoid
  • Monocyclic benzene moiety
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-7.5 °CNot Available
Boiling Point248.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.42 mg/mL at 25 °CNot Available
LogP1.90HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Baker134.25130932474
[M+H]+Not Available134.251http://allccs.zhulab.cn/database/detail?ID=AllCCS00002051
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue Locations
  • Epidermis
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected 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 IDFDB030727
KNApSAcK IDC00002725
Chemspider ID553117
KEGG Compound IDC00903
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCinnamaldehyde
METLIN ID6931
PubChem Compound637511
PDB IDNot Available
ChEBI ID16731
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1092691
References
Synthesis ReferenceLiu, Xue-mei. Synthesis of cinnamaldehyde. Qufu Shifan Daxue Xuebao, Ziran Kexueban (2005), 31(2), 96-98.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bandell M, Story GM, Hwang SW, Viswanath V, Eid SR, Petrus MJ, Earley TJ, Patapoutian A: Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. Neuron. 2004 Mar 25;41(6):849-57. [PubMed:15046718 ]
  2. Muller G, Biering A, Graubaum K, Jeschkeit H, Neubert K, Kleine R, Klapperstuck M: [The PABA test]. Dtsch Z Verdau Stoffwechselkr. 1984;44(5):219-31. [PubMed:6334604 ]
  3. Smith CK, Moore CA, Elahi EN, Smart AT, Hotchkiss SA: Human skin absorption and metabolism of the contact allergens, cinnamic aldehyde, and cinnamic alcohol. Toxicol Appl Pharmacol. 2000 Nov 1;168(3):189-99. [PubMed:11042091 ]
  4. Smith CK, Cheung C, Elahi EN, Hotchkiss SA: High-performance liquid chromatography method for the quantification of non-radiolabelled cinnamic compounds in analytes derived from human skin absorption and metabolism experiments. J Chromatogr B Biomed Sci Appl. 2001 Jul 15;758(2):249-64. [PubMed:11486835 ]
  5. Bruze M, Johansen JD, Andersen KE, Frosch P, Lepoittevin JP, Rastogi S, Wakelin S, White I, Menne T: Deodorants: an experimental provocation study with cinnamic aldehyde. J Am Acad Dermatol. 2003 Feb;48(2):194-200. [PubMed:12582388 ]