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Showing metabocard for cis-Citral (HMDB0035092)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:02:08 UTC
Update Date2022-03-07 02:54:21 UTC
HMDB IDHMDB0035092
Secondary Accession Numbers
  • HMDB35092
Metabolite Identification
Common Namecis-Citral
Descriptioncis-Citral, also known as citral b or lemonal, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, cis-citral is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on cis-Citral.
Structure
Data?1563862664
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0035092 (cis-Citral)


  Mrv1652303202019022D          

 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
10006.603710006.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.316710004.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.031310004.0604    0.0000 O   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  9  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 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
Download

3D MOL for HMDB0035092 (cis-Citral)

HMDB0035092
     RDKit          3D
cis-Citral
 27 26  0  0  0  0  0  0  0  0999 V2000
   -3.3718   -1.4850   -1.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3992   -0.5708   -0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8620    0.1952    0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1689   -0.4722   -1.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1373    0.4089   -0.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0782   -0.4106    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0817    0.5004    0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227    1.3340    1.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2873    0.6019    0.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7365   -0.1570   -1.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9465    0.0373   -1.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0052   -1.7267   -2.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4335   -2.4040   -0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3707   -1.0462   -1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1192    0.2076    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8409   -0.2023    0.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0821    1.2380    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9092   -1.0592   -1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5575    0.9787    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1518    1.1412   -1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3969   -0.9734   -0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7331   -1.1683    0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    2.3421    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814    1.4692    2.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9530    0.7779    2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9878    1.3069    0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2066   -0.8638   -1.6228 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 HMDB0035092 (cis-Citral)


  Mrv1652303202019022D          

 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
10006.603710006.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.316710004.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.031310004.0604    0.0000 O   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  9  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 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035092

> <DATABASE_NAME>
hmdb

> <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-YFHOEESVSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.237

> <EXACT_MASS>
152.120115135

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.66383348733558

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-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>
50.1241

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
neral

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0035092 (cis-Citral)

HMDB0035092
     RDKit          3D
cis-Citral
 27 26  0  0  0  0  0  0  0  0999 V2000
   -3.3718   -1.4850   -1.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3992   -0.5708   -0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8620    0.1952    0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1689   -0.4722   -1.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1373    0.4089   -0.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0782   -0.4106    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0817    0.5004    0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227    1.3340    1.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2873    0.6019    0.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7365   -0.1570   -1.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9465    0.0373   -1.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0052   -1.7267   -2.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4335   -2.4040   -0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3707   -1.0462   -1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1192    0.2076    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8409   -0.2023    0.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0821    1.2380    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9092   -1.0592   -1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5575    0.9787    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1518    1.1412   -1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3969   -0.9734   -0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7331   -1.1683    0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    2.3421    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814    1.4692    2.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9530    0.7779    2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9878    1.3069    0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2066   -0.8638   -1.6228 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

PDB for HMDB0035092 (cis-Citral)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         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    8678.9948678.867   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8680.3258675.017   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8681.6588674.246   0.000  0.00  0.00           O+0
CONECT    1    2    8    9                                                  
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   10                                                       
CONECT    9    1                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for HMDB0035092 (cis-Citral)

COMPND    HMDB0035092
HETATM    1  C1  UNL     1      -3.372  -1.485  -1.229  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.399  -0.571  -0.566  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.862   0.195   0.619  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.169  -0.472  -1.050  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.137   0.409  -0.458  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.078  -0.411   0.006  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.082   0.500   0.588  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.723   1.334   1.772  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.287   0.602   0.096  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.737  -0.157  -1.044  1.00  0.00           C  
HETATM   11  O1  UNL     1       4.946   0.037  -1.428  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.005  -1.727  -2.248  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.434  -2.404  -0.592  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.371  -1.046  -1.345  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.119   0.208   1.443  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.841  -0.202   0.945  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.082   1.238   0.245  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.909  -1.059  -1.912  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.558   0.979   0.392  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.152   1.141  -1.224  1.00  0.00           H  
HETATM   21  H10 UNL     1       1.397  -0.973  -0.858  1.00  0.00           H  
HETATM   22  H11 UNL     1       0.733  -1.168   0.765  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.394   2.342   1.463  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.581   1.469   2.463  1.00  0.00           H  
HETATM   25  H14 UNL     1       0.953   0.778   2.350  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.988   1.307   0.585  1.00  0.00           H  
HETATM   27  H16 UNL     1       3.207  -0.864  -1.623  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 HMDB0035092 (cis-Citral)

CC(C)=CCC\C(C)=C/C=O
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INCHI for HMDB0035092 (cis-Citral)

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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View in JSmolView Stereo Labels
Synonyms
ValueSource
Citral bChEBI
LemonalChEBI
NeralKegg
cis-CitralChEBI
(Z)-CitralMeSH, HMDB
CitralMeSH, HMDB
(2Z)-3,7-Dimethyl-2,6-octadien-1-alHMDB
(2Z)-3,7-Dimethyl-2,6-octadienalHMDB
(Z)-3,7-Dimethyl-2,6-octadienalHMDB
(Z)-NeralHMDB
2-cis-3,7-Dimethyl-2,6-octadienalHMDB
3,7-Dimethyl-2,6-octadien-1-alHMDB
3,7-Dimethyl-2,6-octadienalHMDB
beta-CitralHMDB
cis-3,7-Dimethyl-2,6-octadienalHMDB
cis-GeranialHMDB
β-CitralHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.237
Monoisotopic Molecular Weight152.120115135
IUPAC Name(2Z)-3,7-dimethylocta-2,6-dienal
Traditional Nameneral
CAS Registry Number106-26-3
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-YFHOEESVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Medium-chain aldehyde
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point228.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility84.71 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.170The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP3.37ALOGPS
logP2.66ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.12 m³·mol⁻¹ChemAxon
Polarizability18.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+140.65230932474
DeepCCS[M-H]-138.09830932474
DeepCCS[M-2H]-174.42530932474
DeepCCS[M+Na]+149.71330932474
AllCCS[M+H]+135.832859911
AllCCS[M+H-H2O]+131.732859911
AllCCS[M+NH4]+139.632859911
AllCCS[M+Na]+140.732859911
AllCCS[M-H]-135.732859911
AllCCS[M+Na-2H]-137.632859911
AllCCS[M+HCOO]-139.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.7.03 minutes32390414
Predicted by Siyang on May 30, 202214.3576 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.55 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2181.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid444.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid184.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid282.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid71.1 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid490.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid626.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)78.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1198.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid455.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid998.9 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid408.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid333.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate388.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA508.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water11.6 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cis-CitralCC(C)=CCC\C(C)=C/C=O1681.3Standard polar33892256
cis-CitralCC(C)=CCC\C(C)=C/C=O1212.4Standard non polar33892256
cis-CitralCC(C)=CCC\C(C)=C/C=O1257.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - cis-Citral GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-9300000000-625c688e32f3edaf287c2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Citral GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 10V, Positive-QTOFsplash10-0udi-1900000000-84bd30b4e03200f6db522016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 20V, Positive-QTOFsplash10-1010-8900000000-8aa62bcc7a1bcaa41a1e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 40V, Positive-QTOFsplash10-0gb9-9000000000-79a3e6745a117da8309b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 10V, Negative-QTOFsplash10-0udi-0900000000-21d238fd55ee29af690f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 20V, Negative-QTOFsplash10-0udi-1900000000-b84583833bad67467cf02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 40V, Negative-QTOFsplash10-052f-9700000000-a5e231c57e7f56a65d6d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 10V, Negative-QTOFsplash10-0pb9-0900000000-70e7a03f5a911f54f0982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 20V, Negative-QTOFsplash10-00di-0900000000-3128155f72d867d463182021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 40V, Negative-QTOFsplash10-014i-9100000000-9b92fab117afca4b3a0a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 10V, Positive-QTOFsplash10-05o0-9100000000-9c5fcd575fed478bccf62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 20V, Positive-QTOFsplash10-05qc-9000000000-85ae79bf95f3094e7a852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 40V, Positive-QTOFsplash10-00kf-9000000000-1a9a16cf8ea66689ce6a2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013575
KNApSAcK IDC00003036
Chemspider ID558878
KEGG Compound IDC09847
BioCyc IDCPD-9762
BiGG IDNot Available
Wikipedia LinkNeral
METLIN IDNot Available
PubChem Compound643779
PDB IDNot Available
ChEBI ID29020
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1331191
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Dudai N, Weinstein Y, Krup M, Rabinski T, Ofir R: Citral is a new inducer of caspase-3 in tumor cell lines. Planta Med. 2005 May;71(5):484-8. [PubMed:15931590 ]
  2. Ortiz MI, Ramirez-Montiel ML, Gonzalez-Garcia MP, Ponce-Monter HA, Castaneda-Hernandez G, Carino-Cortes R: The combination of naproxen and citral reduces nociception and gastric damage in rats. Arch Pharm Res. 2010 Oct;33(10):1691-7. doi: 10.1007/s12272-010-1020-9. Epub 2010 Oct 30. [PubMed:21052946 ]
  3. Lee HJ, Jeong HS, Kim DJ, Noh YH, Yuk DY, Hong JT: Inhibitory effect of citral on NO production by suppression of iNOS expression and NF-kappa B activation in RAW264.7 cells. Arch Pharm Res. 2008 Mar;31(3):342-9. doi: 10.1007/s12272-001-1162-0. Epub 2008 Apr 13. [PubMed:18409048 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.