Showing metabocard for Citral (MMDBc0033609)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:55:43 UTC
Update Date2024-10-06 19:05:59 UTC
Metabolite IDMMDBc0033609
Metabolite Identification
Common NameCitral
DescriptionCitral, also known as geranial, 3,7-dimethyl-2,6-octadienal, or lemonal, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, citral is considered to be an isoprenoid lipid. Two different isomers of 3,7-dimethyl-2,6-octadienal exist. The E-isomer or trans-isomer is known as citral or citral A. The Z-isomer or cis-isomer is known as neral or citral B. 3,7-dimethyl-2,6-octadienal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Citral is present in the oils of several plants, including lemon myrtle (90-98%), Litsea citrata (90%), Litsea cubeba, lemongrass (65-80%), lemon tea-tree (70-80%), Ocimum gratissimum, Lindera citriodora, Calypranthes parriculata, petitgrain, lemon verbena, lemon ironbark, lemon balm, lime, lemon and orange. Citral has also been reported to be found in Cannabis sativa (PMID:6991645 , 26657499 ). Citral has a strong lemon (citrus) odor. Neral's lemon odor is less intense, but sweeter. Citral is therefore an aroma compound used in perfumery for its citrus effect. Citral is also used as a flavor and for fortifying lemon oil. It has strong antimicrobial qualities (PMID:28974979 ) and pheromonal effects in nematodes and insects (PMID:26973536 ). Citral is used in the synthesis of vitamin A, lycopene, ionone, and methylionone (a compound used to mask the smell of smoke).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f46dc9edf48>


  Mrv1652305271900132D          

 11 10  0  0  0  0            999 V2000
10006.603710005.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.888210005.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.173410005.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.458710005.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.743710005.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.029010005.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.743710006.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.317210005.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.032710005.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.746310005.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.603710006.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  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
  5  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f46dc9edf48>

HMDB0035078
     RDKit          3D
Geranial
 27 26  0  0  0  0  0  0  0  0999 V2000
   -2.4337    1.3550    0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5950   -0.0157   -0.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8521   -0.4355   -0.9554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094   -0.8827   -0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3465   -0.4465    0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7501   -0.6112   -0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560   -0.1945   -0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508   -0.9116    1.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7513    0.7794   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0409    1.2170    0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6861    2.1585   -0.5193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    1.9725    0.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5564    1.8215   -0.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2081    1.4052    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6865   -1.1743   -1.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5382   -0.9537   -0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4182    0.4014   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7220   -1.8988   -0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101    0.5892    0.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1508   -1.1723    1.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4710   -0.0341   -1.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7360   -1.6902   -0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0779   -1.9088    1.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2366   -0.3289    2.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6504   -1.0806    1.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3709    1.2858   -1.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4973    0.7538    0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f46dc9edf48>


  Mrv1652305271900132D          

 11 10  0  0  0  0            999 V2000
10006.603710005.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.888210005.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.173410005.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.458710005.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.743710005.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.029010005.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.743710006.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.317210005.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.032710005.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.746310005.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.603710006.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  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
  5  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033609

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)=CCC\C(C)=C\C=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+

> <INCHI_KEY>
WTEVQBCEXWBHNA-JXMROGBWSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.237

> <EXACT_MASS>
152.120115135

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.595636664441315

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3,7-dimethylocta-2,6-dienal

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
2.664041581666667

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.056096067340819

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
50.124100000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-citral

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for #<Metabolite:0x00007f46dc9edf48>

HMDB0035078
     RDKit          3D
Geranial
 27 26  0  0  0  0  0  0  0  0999 V2000
   -2.4337    1.3550    0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5950   -0.0157   -0.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8521   -0.4355   -0.9554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094   -0.8827   -0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3465   -0.4465    0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7501   -0.6112   -0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560   -0.1945   -0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508   -0.9116    1.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7513    0.7794   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0409    1.2170    0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6861    2.1585   -0.5193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    1.9725    0.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5564    1.8215   -0.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2081    1.4052    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6865   -1.1743   -1.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5382   -0.9537   -0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4182    0.4014   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7220   -1.8988   -0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101    0.5892    0.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1508   -1.1723    1.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4710   -0.0341   -1.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7360   -1.6902   -0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0779   -1.9088    1.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2366   -0.3289    2.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6504   -1.0806    1.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3709    1.2858   -1.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4973    0.7538    0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
M  END
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PDB for #<Metabolite:0x00007f46dc9edf48>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8678.9948677.327   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8677.6588676.558   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8676.3248677.327   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8674.9908676.558   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8673.6558677.327   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8672.3218676.558   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8673.6558678.867   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8680.3258676.558   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8681.6618677.327   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8682.9938676.558   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8678.9948678.867   0.000  0.00  0.00           C+0
CONECT    1    2    8   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    1                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for #<Metabolite:0x00007f46dc9edf48>

COMPND    HMDB0035078
HETATM    1  C1  UNL     1      -2.434   1.355   0.221  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.595  -0.016  -0.306  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.852  -0.435  -0.955  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.609  -0.883  -0.200  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.346  -0.446   0.457  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.750  -0.611  -0.596  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.056  -0.195  -0.019  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.551  -0.912   1.161  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.751   0.779  -0.538  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.041   1.217   0.004  1.00  0.00           C  
HETATM   11  O1  UNL     1       4.686   2.159  -0.519  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.348   1.972   0.082  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.556   1.821  -0.303  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.208   1.405   1.298  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.686  -1.174  -1.784  1.00  0.00           H  
HETATM   16  H5  UNL     1      -4.538  -0.954  -0.241  1.00  0.00           H  
HETATM   17  H6  UNL     1      -4.418   0.401  -1.388  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.722  -1.899  -0.588  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.410   0.589   0.831  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.151  -1.172   1.287  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.471  -0.034  -1.481  1.00  0.00           H  
HETATM   22  H11 UNL     1       0.736  -1.690  -0.868  1.00  0.00           H  
HETATM   23  H12 UNL     1       2.078  -1.909   1.239  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.237  -0.329   2.068  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.650  -1.081   1.154  1.00  0.00           H  
HETATM   26  H15 UNL     1       2.371   1.286  -1.395  1.00  0.00           H  
HETATM   27  H16 UNL     1       4.497   0.754   0.874  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    4
CONECT    3   15   16   17
CONECT    4    5   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8    9    9
CONECT    8   23   24   25
CONECT    9   10   26
CONECT   10   11   11   27
END
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SMILES for #<Metabolite:0x00007f46dc9edf48>

CC(C)=CCC\C(C)=C\C=O
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INCHI for #<Metabolite:0x00007f46dc9edf48>

InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+
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Synonyms
ValueSource
(2E)-GeranialChEBI
(e)-CitralChEBI
(e)-GeranialChEBI
alpha-CitralChEBI
Citral aChEBI
LemonalChEBI
trans-CitralChEBI
a-CitralGenerator
Α-citralGenerator
(2E)-3,7-Dimethyl-2,6-octadienalHMDB
(e)-3,7-Dimethyl-2,6-octadienalHMDB
(e)-3,7-Dimethylocta-2,6-dienalHMDB
3,7-Dimethyl-(2E)-2,6-octadienalHMDB
3,7-Dimethyl-(e)-2,6-octadienalHMDB
3,7-Dimethyl-trans-2,6-octadienalHMDB
alpha -CitralHMDB
beta-GeranialHMDB
Citral-aHMDB
GenanialHMDB
GeranalHMDB
trans-3,7-Dimethyl-2,6-octadienalHMDB
(Z)-CitralMeSH, HMDB
CitralMeSH, HMDB
(2E)-3,7-Dimethyl-2,6-octadien-1-alHMDB
(E)-3,7-Dimethyl-2,6-octadienalHMDB
(E)-NeralHMDB
GeranaldehydeHMDB
GeranialHMDB
beta-NeralHMDB
trans-3,7-Dimethyl-2,6-octadien-1-alHMDB
trans-GeranialHMDB
β-GeranialHMDB
β-NeralHMDB
3,7-Dimethyl-2,6-octadien-1-alHMDB
3,7-Dimethyl-2,6-octadienalHMDB
Molecular FormulaC10H16O
Average Mass152.237
Monoisotopic Mass152.120115135
IUPAC Name(2E)-3,7-dimethylocta-2,6-dienal
Traditional Nameα-citral
CAS Registry Number5392-40-5
SMILES
CC(C)=CCC\C(C)=C\C=O
InChI Identifier
InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+
InChI KeyWTEVQBCEXWBHNA-JXMROGBWSA-N