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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:40:04 UTC

Update Date

2022-03-07 02:52:46 UTC

HMDB ID

HMDB0030962

Secondary Accession Numbers

HMDB30962

Metabolite Identification

Common Name

Calendic acid

Description

Calendic acid is isolated from Calendula officinalis (pot marigold) seed oil Calendic acid (sometimes -Calendic acid) is an unsaturated fatty acid, named for the pot marigold (genus Calendula), from which it is obtained. It is chemically similar to the conjugated linoleic acids; laboratory work suggests it may have similar health benefits. Calendic acid is an omega-6 fatty acid. though not usually listed with this group. Calendic acid (8t,10t,12c-18:3) is synthesised in Calendula officinalis from linoleate (9c,12c-18:2) by an unusual 12-oleate desaturase (a FAD 2 variant) that converts the cis-double bond in position 9 to a trans,trans-conjugated double bond system (8t,10t). Calendic acid is an all-trans beta isomer has been described

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0030962
     RDKit          3D
Calendic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
    8.7281   -1.2765    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7298   -0.3596    0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6237   -0.0907   -0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5638    0.8033    0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165    1.0205   -0.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836   -0.2412   -1.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997   -0.5055   -1.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6720    0.4594   -0.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3632    0.1631   -0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5895    1.1128    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8669    0.7844    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8884    1.7317    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131    1.0424    1.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1959   -0.2584    1.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3141   -0.0720    0.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9111   -1.4113    0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0369   -1.3668   -0.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1496   -0.5577   -0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1421   -0.0676    0.9484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2441   -0.3451   -1.0154 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4271   -2.3377    0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7913   -1.0218   -1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7045   -1.1928    0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2371    0.6019    0.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3008   -0.8225    1.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1868   -1.0764   -0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0561    0.3522   -1.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9678    1.7464    0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057    0.3006    1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7839    1.7677   -0.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120    1.4388   -1.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5732   -0.9906   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2837   -1.4794   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9240    1.4357   -0.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667   -0.7967   -0.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2905    2.0775    0.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623   -0.1910   -0.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    2.6460    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6136    2.0465    0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1862    1.7062    2.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6991    0.7617    2.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6156   -0.6670    2.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4842   -0.9984    1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0331    0.6830    0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7955    0.2438   -0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1500   -2.1281   -0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2364   -1.9275    1.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6032   -0.9289   -1.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3773   -2.4000   -0.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6043    0.5853   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
M  END

  Mrv0541 05061305372D          

 20 19  0  0  0  0            999 V2000
   -2.0033   -1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030962

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C=C/C=C/CCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-11H,2-5,12-17H2,1H3,(H,19,20)/b7-6-,9-8+,11-10+

> <INCHI_KEY>
DQGMPXYVZZCNDQ-KBPWROHVSA-N

> <FORMULA>
C18H30O2

> <MOLECULAR_WEIGHT>
278.4296

> <EXACT_MASS>
278.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.0001414985088

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8E,10E,12Z)-octadeca-8,10,12-trienoic acid

> <ALOGPS_LOGP>
6.66

> <JCHEM_LOGP>
6.059955137666666

> <ALOGPS_LOGS>
-6.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.955292456255931

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.63539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.36e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
calendic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030962
     RDKit          3D
Calendic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
    8.7281   -1.2765    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7298   -0.3596    0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6237   -0.0907   -0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5638    0.8033    0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165    1.0205   -0.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836   -0.2412   -1.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997   -0.5055   -1.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6720    0.4594   -0.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3632    0.1631   -0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5895    1.1128    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8669    0.7844    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8884    1.7317    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131    1.0424    1.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1959   -0.2584    1.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3141   -0.0720    0.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9111   -1.4113    0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0369   -1.3668   -0.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1496   -0.5577   -0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1421   -0.0676    0.9484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2441   -0.3451   -1.0154 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4271   -2.3377    0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7913   -1.0218   -1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7045   -1.1928    0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2371    0.6019    0.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3008   -0.8225    1.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1868   -1.0764   -0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0561    0.3522   -1.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9678    1.7464    0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057    0.3006    1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7839    1.7677   -0.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120    1.4388   -1.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5732   -0.9906   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2837   -1.4794   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9240    1.4357   -0.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667   -0.7967   -0.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2905    2.0775    0.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623   -0.1910   -0.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    2.6460    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6136    2.0465    0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1862    1.7062    2.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6991    0.7617    2.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6156   -0.6670    2.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4842   -0.9984    1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0331    0.6830    0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7955    0.2438   -0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1500   -2.1281   -0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2364   -1.9275    1.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6032   -0.9289   -1.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3773   -2.4000   -0.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6043    0.5853   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
M  END

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      -3.739  -2.159   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.406  -2.929   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.072  -2.159   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.262  -2.929   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.595  -2.159   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.929  -2.929   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.263  -2.159   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.263  -0.619   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.596   0.151   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.596   1.691   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.930   2.461   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0030962
HETATM    1  C1  UNL     1       8.728  -1.276   0.082  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.730  -0.360   0.770  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.624  -0.091  -0.234  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.564   0.803   0.306  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.517   1.020  -0.779  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.884  -0.241  -1.202  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.600  -0.506  -1.098  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.672   0.459  -0.538  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.363   0.163  -0.445  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.590   1.113   0.113  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.867   0.784   0.188  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.888   1.732   0.756  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.513   1.042   1.942  1.00  0.00           C  
HETATM   14  C14 UNL     1      -4.196  -0.258   1.581  1.00  0.00           C  
HETATM   15  C15 UNL     1      -5.314  -0.072   0.574  1.00  0.00           C  
HETATM   16  C16 UNL     1      -5.911  -1.411   0.297  1.00  0.00           C  
HETATM   17  C17 UNL     1      -7.037  -1.367  -0.692  1.00  0.00           C  
HETATM   18  C18 UNL     1      -8.150  -0.558  -0.182  1.00  0.00           C  
HETATM   19  O1  UNL     1      -8.142  -0.068   0.948  1.00  0.00           O  
HETATM   20  O2  UNL     1      -9.244  -0.345  -1.015  1.00  0.00           O  
HETATM   21  H1  UNL     1       8.427  -2.338   0.130  1.00  0.00           H  
HETATM   22  H2  UNL     1       8.791  -1.022  -1.002  1.00  0.00           H  
HETATM   23  H3  UNL     1       9.704  -1.193   0.592  1.00  0.00           H  
HETATM   24  H4  UNL     1       8.237   0.602   0.985  1.00  0.00           H  
HETATM   25  H5  UNL     1       7.301  -0.823   1.672  1.00  0.00           H  
HETATM   26  H6  UNL     1       6.187  -1.076  -0.499  1.00  0.00           H  
HETATM   27  H7  UNL     1       7.056   0.352  -1.146  1.00  0.00           H  
HETATM   28  H8  UNL     1       5.968   1.746   0.681  1.00  0.00           H  
HETATM   29  H9  UNL     1       5.006   0.301   1.142  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.784   1.768  -0.492  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.112   1.439  -1.646  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.573  -0.991  -1.641  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.284  -1.479  -1.454  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.924   1.436  -0.167  1.00  0.00           H  
HETATM   35  H15 UNL     1       0.067  -0.797  -0.799  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.291   2.078   0.468  1.00  0.00           H  
HETATM   37  H17 UNL     1      -2.162  -0.191  -0.172  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.398   2.646   1.145  1.00  0.00           H  
HETATM   39  H19 UNL     1      -3.614   2.047   0.005  1.00  0.00           H  
HETATM   40  H20 UNL     1      -4.186   1.706   2.514  1.00  0.00           H  
HETATM   41  H21 UNL     1      -2.699   0.762   2.658  1.00  0.00           H  
HETATM   42  H22 UNL     1      -4.616  -0.667   2.519  1.00  0.00           H  
HETATM   43  H23 UNL     1      -3.484  -0.998   1.168  1.00  0.00           H  
HETATM   44  H24 UNL     1      -6.033   0.683   0.911  1.00  0.00           H  
HETATM   45  H25 UNL     1      -4.796   0.244  -0.374  1.00  0.00           H  
HETATM   46  H26 UNL     1      -5.150  -2.128  -0.126  1.00  0.00           H  
HETATM   47  H27 UNL     1      -6.236  -1.927   1.250  1.00  0.00           H  
HETATM   48  H28 UNL     1      -6.603  -0.929  -1.638  1.00  0.00           H  
HETATM   49  H29 UNL     1      -7.377  -2.400  -0.933  1.00  0.00           H  
HETATM   50  H30 UNL     1      -9.604   0.585  -1.198  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7    7   32
CONECT    7    8   33
CONECT    8    9    9   34
CONECT    9   10   35
CONECT   10   11   11   36
CONECT   11   12   37
CONECT   12   13   38   39
CONECT   13   14   40   41
CONECT   14   15   42   43
CONECT   15   16   44   45
CONECT   16   17   46   47
CONECT   17   18   48   49
CONECT   18   19   19   20
CONECT   20   50
END

HMDB0030962
     RDKit          3D
Calendic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
    8.7281   -1.2765    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7298   -0.3596    0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6237   -0.0907   -0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5638    0.8033    0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165    1.0205   -0.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836   -0.2412   -1.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997   -0.5055   -1.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6720    0.4594   -0.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3632    0.1631   -0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5895    1.1128    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8669    0.7844    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8884    1.7317    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131    1.0424    1.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1959   -0.2584    1.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3141   -0.0720    0.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9111   -1.4113    0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0369   -1.3668   -0.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1496   -0.5577   -0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1421   -0.0676    0.9484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2441   -0.3451   -1.0154 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4271   -2.3377    0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7913   -1.0218   -1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7045   -1.1928    0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2371    0.6019    0.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3008   -0.8225    1.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1868   -1.0764   -0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0561    0.3522   -1.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9678    1.7464    0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057    0.3006    1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7839    1.7677   -0.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120    1.4388   -1.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5732   -0.9906   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2837   -1.4794   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9240    1.4357   -0.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667   -0.7967   -0.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2905    2.0775    0.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623   -0.1910   -0.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    2.6460    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6136    2.0465    0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1862    1.7062    2.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6991    0.7617    2.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6156   -0.6670    2.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4842   -0.9984    1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0331    0.6830    0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7955    0.2438   -0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1500   -2.1281   -0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2364   -1.9275    1.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6032   -0.9289   -1.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3773   -2.4000   -0.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6043    0.5853   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8E,10E,12Z-Octadecatrienoic acid	ChEBI
alpha-Calendic acid	ChEBI
C18:3N-6,8,10	ChEBI
Calendulic acid	ChEBI
trans-8, trans-10, cis-12-Octadecatrienoic acid	ChEBI
8E,10E,12Z-Octadecatrienoate	Generator
a-Calendate	Generator
a-Calendic acid	Generator
alpha-Calendate	Generator
Α-calendate	Generator
Α-calendic acid	Generator
Calendulate	Generator
trans-8, trans-10, cis-12-Octadecatrienoate	Generator
Calendate	Generator
Calendic acid	ChEBI

Chemical Formula

C₁₈H₃₀O₂

Average Molecular Weight

278.4296

Monoisotopic Molecular Weight

278.224580204

IUPAC Name

(8E,10E,12Z)-octadeca-8,10,12-trienoic acid

Traditional Name

calendic acid

CAS Registry Number

28872-28-8

SMILES

CCCCC\C=C/C=C/C=C/CCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-11H,2-5,12-17H2,1H3,(H,19,20)/b7-6-,9-8+,11-10+

InChI Key

DQGMPXYVZZCNDQ-KBPWROHVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

omega-6 fatty acid (CHEBI:86148 )
conjugated linolenic acid (CHEBI:86148 )
Unsaturated fatty acids (LMFA01030144 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0030962)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030962)

Source

Endogenous

Endogenous (HMDB: HMDB0030962)

Animal

Animal (HMDB: HMDB0030962)

Exogenous

Food

Food (HMDB: HMDB0030962)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Exogenous (HMDB: HMDB0030962)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0030962)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0030962)

Lipid metabolism pathway (HMDB: HMDB0030962)

Cellular process

Cell signaling (HMDB: HMDB0030962)

Biochemical process

Lipid transport (HMDB: HMDB0030962)

Role

Biological role

Energy source (HMDB: HMDB0030962)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030962)

Laboratory chemical

Laboratory chemical (HMDB: HMDB0030962)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	40 - 40.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00024 g/L	ALOGPS
logP	6.66	ALOGPS
logP	6.06	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	4.96	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	89.64 m³·mol⁻¹	ChemAxon
Polarizability	36 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	179.311	31661259
DarkChem	[M-H]-	177.579	31661259
DeepCCS	[M+H]+	177.971	30932474
DeepCCS	[M-H]-	175.613	30932474
DeepCCS	[M-2H]-	209.641	30932474
DeepCCS	[M+Na]+	185.491	30932474
AllCCS	[M+H]+	175.4	32859911
AllCCS	[M+H-H2O]+	172.3	32859911
AllCCS	[M+NH4]+	178.3	32859911
AllCCS	[M+Na]+	179.2	32859911
AllCCS	[M-H]-	177.0	32859911
AllCCS	[M+Na-2H]-	178.5	32859911
AllCCS	[M+HCOO]-	180.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Calendic acid	CCCCC\C=C/C=C/C=C/CCCCCCC(O)=O	3612.8	Standard polar	33892256
Calendic acid	CCCCC\C=C/C=C/C=C/CCCCCCC(O)=O	2185.7	Standard non polar	33892256
Calendic acid	CCCCC\C=C/C=C/C=C/CCCCCCC(O)=O	2306.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Calendic acid,1TMS,isomer #1	CCCCC/C=C\C=C\C=C\CCCCCCC(=O)O[Si](C)(C)C	2348.4	Semi standard non polar	33892256
Calendic acid,1TBDMS,isomer #1	CCCCC/C=C\C=C\C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2578.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Calendic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9660000000-d828aaab6ed3d3077513	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calendic acid GC-MS (1 TMS) - 70eV, Positive	splash10-01yc-9621000000-89f2294fe8e5a7fa99b1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calendic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calendic acid 10V, Positive-QTOF	splash10-01t9-0190000000-31cd9fbd0511b99abd28	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calendic acid 20V, Positive-QTOF	splash10-001i-5890000000-72f37321b7fde75b1a82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calendic acid 40V, Positive-QTOF	splash10-05mo-8930000000-2ae64d84444e7d3105fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calendic acid 10V, Negative-QTOF	splash10-004i-0090000000-f6df0fd86f077c397e84	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calendic acid 20V, Negative-QTOF	splash10-0059-1090000000-74939ebc0a54bce2e7b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calendic acid 40V, Negative-QTOF	splash10-0a4i-9230000000-abe728a7db5610480673	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calendic acid 10V, Negative-QTOF	splash10-004i-0090000000-12da14b99ffff5280158	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calendic acid 20V, Negative-QTOF	splash10-056r-1090000000-b00c3559d2e5d3b02239	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calendic acid 40V, Negative-QTOF	splash10-052f-9510000000-62ae777e69970ad77555	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calendic acid 10V, Positive-QTOF	splash10-01t9-3690000000-39d79ed7580ed5594c11	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calendic acid 20V, Positive-QTOF	splash10-05pn-9610000000-fb79ee2260a91fce9a2d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calendic acid 40V, Positive-QTOF	splash10-05po-9100000000-24bbf16380c1781b6791	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002944

KNApSAcK ID

C00054959

Chemspider ID

4445945

KEGG Compound ID

Not Available

BioCyc ID

CPD-8228

BiGG ID

Not Available

Wikipedia Link

Calendic_acid

METLIN ID

Not Available

PubChem Compound

5282818

PDB ID

Not Available

ChEBI ID

86148

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Calendic acid (HMDB0030962)

MOL for HMDB0030962 (Calendic acid)

3D MOL for HMDB0030962 (Calendic acid)

3D SDF for HMDB0030962 (Calendic acid)

3D-SDF for HMDB0030962 (Calendic acid)

PDB for HMDB0030962 (Calendic acid)

3D PDB for HMDB0030962 (Calendic acid)

SMILES for HMDB0030962 (Calendic acid)

INCHI for HMDB0030962 (Calendic acid)

Structure for HMDB0030962 (Calendic acid)

3D Structure for HMDB0030962 (Calendic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra