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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:40:05 UTC

Update Date

2022-03-07 02:52:46 UTC

HMDB ID

HMDB0030963

Secondary Accession Numbers

HMDB30963

Metabolite Identification

Common Name

Punicic acid

Description

Punicic acid, also known as 9t,11C,13t-CLN or punicate, 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. Based on a literature review a significant number of articles have been published on Punicic acid.

Structure

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

HMDB0030963
     RDKit          3D
Punicic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -8.3297   -2.2439   -0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3396   -1.5723   -1.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8122   -0.2949   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8465    0.3321   -1.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7081   -0.5768   -1.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4479   -0.1862   -1.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696   -1.0870   -1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1129   -0.8031   -1.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7293    0.4737   -0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342    0.7943   -0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0112    2.0390   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7597    1.9266    1.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9809    1.0441    0.9706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8054    0.8709    2.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9959    0.0042    1.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9246    0.5343    0.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0760   -0.4684    0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0368   -0.0003   -0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8797    1.0599   -0.8826 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1441   -0.7900   -0.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2687   -3.3276   -0.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1228   -1.9427    0.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3644   -1.9018   -0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8632   -1.4027   -1.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5110   -2.2663   -1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2489   -0.5739    0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6250    0.4076   -0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5030    1.3080   -1.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3989    0.4770   -2.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8419   -1.5571   -2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3601    0.7843   -0.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5714   -2.0680   -2.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3381   -1.5604   -1.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4612    1.1901   -0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2707    0.0412   -0.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1071    2.6851    0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    2.6001   -0.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1991    1.5177    2.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    2.9055    1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6509    1.5433    0.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175    0.0673    0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1698    1.8403    2.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305    0.3983    3.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6950   -1.0316    1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5450   -0.1297    2.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4186    0.5834   -0.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3344    1.5204    1.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6624   -1.4402    0.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5481   -0.6280    1.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7204   -1.0959    0.2513 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  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
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 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 02241217352D          

 20 19  0  0  0  0            999 V2000
    2.5159    2.1034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734    1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734    0.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    0.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734   -0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734   -1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -2.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -2.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133   -1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734   -2.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159   -1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159   -0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734    0.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    0.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709    0.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    2.1034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 20  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030963

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC\C=C\C=C/C=C/CCCCCCCC(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/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5+,8-7-,10-9+

> <INCHI_KEY>
CUXYLFPMQMFGPL-MRZTUZPCSA-N

> <FORMULA>
C18H30O2

> <MOLECULAR_WEIGHT>
278.4296

> <EXACT_MASS>
278.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.911822169017995

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9E,11Z,13E)-octadeca-9,11,13-trienoic acid

> <ALOGPS_LOGP>
6.65

> <JCHEM_LOGP>
6.059955137666666

> <ALOGPS_LOGS>
-6.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.63539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.42e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9t,11c,13t-linolenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030963
     RDKit          3D
Punicic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -8.3297   -2.2439   -0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3396   -1.5723   -1.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8122   -0.2949   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8465    0.3321   -1.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7081   -0.5768   -1.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4479   -0.1862   -1.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696   -1.0870   -1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1129   -0.8031   -1.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7293    0.4737   -0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342    0.7943   -0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0112    2.0390   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7597    1.9266    1.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9809    1.0441    0.9706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8054    0.8709    2.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9959    0.0042    1.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9246    0.5343    0.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0760   -0.4684    0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0368   -0.0003   -0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8797    1.0599   -0.8826 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1441   -0.7900   -0.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2687   -3.3276   -0.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1228   -1.9427    0.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3644   -1.9018   -0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8632   -1.4027   -1.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5110   -2.2663   -1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2489   -0.5739    0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6250    0.4076   -0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5030    1.3080   -1.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3989    0.4770   -2.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8419   -1.5571   -2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3601    0.7843   -0.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5714   -2.0680   -2.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3381   -1.5604   -1.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4612    1.1901   -0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2707    0.0412   -0.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1071    2.6851    0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    2.6001   -0.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1991    1.5177    2.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    2.9055    1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6509    1.5433    0.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175    0.0673    0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1698    1.8403    2.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305    0.3983    3.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6950   -1.0316    1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5450   -0.1297    2.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4186    0.5834   -0.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3344    1.5204    1.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6624   -1.4402    0.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5481   -0.6280    1.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7204   -1.0959    0.2513 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  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
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 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                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       4.696   3.926   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.310   3.156   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.310   1.462   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.078   0.692   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.078  -0.846   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.310  -1.616   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.310  -3.156   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.078  -3.926   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.692  -3.156   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.692  -3.926   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.078  -3.156   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.310  -3.926   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.696  -3.156   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.696  -1.616   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.310  -0.846   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.310   0.692   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.078   1.462   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.692   0.692   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.692  -0.846   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.078   3.926   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
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                                                       
CONECT   19   18                                                            
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0030963
HETATM    1  C1  UNL     1      -8.330  -2.244  -0.069  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.340  -1.572  -1.025  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.812  -0.295  -0.422  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.847   0.332  -1.401  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.708  -0.577  -1.682  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.448  -0.186  -1.401  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.370  -1.087  -1.684  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.113  -0.803  -1.448  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.729   0.474  -0.872  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.534   0.794  -0.620  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.011   2.039  -0.048  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.760   1.927   1.239  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.981   1.044   0.971  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.805   0.871   2.221  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.996   0.004   1.949  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.925   0.534   0.906  1.00  0.00           C  
HETATM   17  C17 UNL     1       7.076  -0.468   0.758  1.00  0.00           C  
HETATM   18  C18 UNL     1       8.037  -0.000  -0.266  1.00  0.00           C  
HETATM   19  O1  UNL     1       7.880   1.060  -0.883  1.00  0.00           O  
HETATM   20  O2  UNL     1       9.144  -0.790  -0.530  1.00  0.00           O  
HETATM   21  H1  UNL     1      -8.269  -3.328  -0.218  1.00  0.00           H  
HETATM   22  H2  UNL     1      -8.123  -1.943   0.977  1.00  0.00           H  
HETATM   23  H3  UNL     1      -9.364  -1.902  -0.321  1.00  0.00           H  
HETATM   24  H4  UNL     1      -7.863  -1.403  -1.974  1.00  0.00           H  
HETATM   25  H5  UNL     1      -6.511  -2.266  -1.221  1.00  0.00           H  
HETATM   26  H6  UNL     1      -6.249  -0.574   0.517  1.00  0.00           H  
HETATM   27  H7  UNL     1      -7.625   0.408  -0.165  1.00  0.00           H  
HETATM   28  H8  UNL     1      -5.503   1.308  -1.024  1.00  0.00           H  
HETATM   29  H9  UNL     1      -6.399   0.477  -2.375  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.842  -1.557  -2.113  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.360   0.784  -0.981  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.571  -2.068  -2.118  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.338  -1.560  -1.698  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.461   1.190  -0.635  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.271   0.041  -0.871  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.107   2.685   0.160  1.00  0.00           H  
HETATM   37  H17 UNL     1       1.584   2.600  -0.814  1.00  0.00           H  
HETATM   38  H18 UNL     1       1.199   1.518   2.071  1.00  0.00           H  
HETATM   39  H19 UNL     1       2.173   2.906   1.558  1.00  0.00           H  
HETATM   40  H20 UNL     1       3.651   1.543   0.215  1.00  0.00           H  
HETATM   41  H21 UNL     1       2.718   0.067   0.567  1.00  0.00           H  
HETATM   42  H22 UNL     1       4.170   1.840   2.601  1.00  0.00           H  
HETATM   43  H23 UNL     1       3.230   0.398   3.042  1.00  0.00           H  
HETATM   44  H24 UNL     1       4.695  -1.032   1.643  1.00  0.00           H  
HETATM   45  H25 UNL     1       5.545  -0.130   2.909  1.00  0.00           H  
HETATM   46  H26 UNL     1       5.419   0.583  -0.084  1.00  0.00           H  
HETATM   47  H27 UNL     1       6.334   1.520   1.134  1.00  0.00           H  
HETATM   48  H28 UNL     1       6.662  -1.440   0.431  1.00  0.00           H  
HETATM   49  H29 UNL     1       7.548  -0.628   1.746  1.00  0.00           H  
HETATM   50  H30 UNL     1       9.720  -1.096   0.251  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    6   30
CONECT    6    7   31
CONECT    7    8    8   32
CONECT    8    9   33
CONECT    9   10   10   34
CONECT   10   11   35
CONECT   11   12   36   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

HMDB0030963
     RDKit          3D
Punicic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -8.3297   -2.2439   -0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3396   -1.5723   -1.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8122   -0.2949   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8465    0.3321   -1.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7081   -0.5768   -1.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4479   -0.1862   -1.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696   -1.0870   -1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1129   -0.8031   -1.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7293    0.4737   -0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342    0.7943   -0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0112    2.0390   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7597    1.9266    1.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9809    1.0441    0.9706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8054    0.8709    2.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9959    0.0042    1.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9246    0.5343    0.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0760   -0.4684    0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0368   -0.0003   -0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8797    1.0599   -0.8826 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1441   -0.7900   -0.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2687   -3.3276   -0.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1228   -1.9427    0.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3644   -1.9018   -0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8632   -1.4027   -1.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5110   -2.2663   -1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2489   -0.5739    0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6250    0.4076   -0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5030    1.3080   -1.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3989    0.4770   -2.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8419   -1.5571   -2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3601    0.7843   -0.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5714   -2.0680   -2.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3381   -1.5604   -1.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4612    1.1901   -0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2707    0.0412   -0.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1071    2.6851    0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    2.6001   -0.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1991    1.5177    2.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    2.9055    1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6509    1.5433    0.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175    0.0673    0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1698    1.8403    2.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305    0.3983    3.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6950   -1.0316    1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5450   -0.1297    2.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4186    0.5834   -0.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3344    1.5204    1.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6624   -1.4402    0.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5481   -0.6280    1.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7204   -1.0959    0.2513 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  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
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 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
(9E,11Z,13E)-9,11,13-Octadecatrienoic acid	ChEBI
(e,Z,e)-9,11,13-Octadecatrienoic acid	ChEBI
9-trans,11-cis,13-trans-Octadecatrienoic acid	ChEBI
9t,11C,13t-CLN	ChEBI
9t,11C,13t-CLnA	ChEBI
9t,11C,13t-Conjugated linolenic acid	ChEBI
9t,11C,13t-Linolenic acid	ChEBI
9trans,11-cis,13trans-Octadecatrienoic acid	ChEBI
C18:3 N-5 trans, 7 cis, 9 trans	ChEBI
Octadeca-9t,11C,13t-trienoic acid	ChEBI
Octadeca-9t,11C,13t-triensaeure	ChEBI
t9,C11,t13-CLN	ChEBI
t9,C11,t13-CLnA	ChEBI
t9,C11,t13-Conjugated linolenic acid	ChEBI
t9,C11,t13-Linolenic acid	ChEBI
(9E,11Z,13E)-9,11,13-Octadecatrienoate	Generator
(e,Z,e)-9,11,13-Octadecatrienoate	Generator
9-trans,11-cis,13-trans-Octadecatrienoate	Generator
9t,11C,13t-Conjugated linolenate	Generator
9t,11C,13t-Linolenate	Generator
9trans,11-cis,13trans-Octadecatrienoate	Generator
Octadeca-9t,11C,13t-trienoate	Generator
t9,C11,t13-Conjugated linolenate	Generator
t9,C11,t13-Linolenate	Generator
Punicate	Generator
(9Z,11E,13Z)-Octadeca-9,11,13-trienoic acid	HMDB
cis-9,trans-11,cis-13-Octadecatrienoic acid	HMDB
Eleostearic acid	HMDB
Punicinic acid	HMDB
Trichosanic acid	HMDB
9E,11Z,13E-Octadecatrienoate	Generator
9,11,13-CLN	MeSH
9C,11t,13t-CLN	MeSH
Eleostearic acid, (e,Z,e)-isomer	MeSH
9,11,13-Octadecatrienoic acid	MeSH
9cis,11trans,13trans-Conjugated linolenic acid	MeSH
Eleostearic acid, (e,e,e)-isomer	MeSH
9,11,13-Conjugated linolenic acid	MeSH
Eleostearic acid, (Z,e,e)-isomer	MeSH
Eleostearic acid, (Z,Z,e)-isomer	MeSH
a-Eleostearate	Generator
a-Eleostearic acid	Generator
alpha-Eleostearate	Generator
Α-eleostearate	Generator
Α-eleostearic acid	Generator

Chemical Formula

C₁₈H₃₀O₂

Average Molecular Weight

278.4296

Monoisotopic Molecular Weight

278.224580204

IUPAC Name

(9E,11Z,13E)-octadeca-9,11,13-trienoic acid

Traditional Name

9t,11c,13t-linolenic acid

CAS Registry Number

544-72-9

SMILES

CCCC\C=C\C=C/C=C/CCCCCCCC(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/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5+,8-7-,10-9+

InChI Key

CUXYLFPMQMFGPL-MRZTUZPCSA-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

9,11,13-octadecatrienoic acid (CHEBI:38383 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030963)
Membrane (HMDB: HMDB0030963)

Fats and oils (FooDB: FOOD00864)

Fruit

Fruits (FooDB: FOOD00871)

Tropical fruit

Pomegranate (FooDB: FOOD00151)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	44 - 45 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.024 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00024 g/L	ALOGPS
logP	6.65	ALOGPS
logP	6.06	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	4.99	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	35.91 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]+	176.609	31661259
DarkChem	[M-H]-	177.718	31661259
DeepCCS	[M+H]+	176.032	30932474
DeepCCS	[M-H]-	173.674	30932474
DeepCCS	[M-2H]-	207.728	30932474
DeepCCS	[M+Na]+	183.136	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
Punicic acid	CCCC\C=C\C=C/C=C/CCCCCCCC(O)=O	3610.3	Standard polar	33892256
Punicic acid	CCCC\C=C\C=C/C=C/CCCCCCCC(O)=O	2186.6	Standard non polar	33892256
Punicic acid	CCCC\C=C\C=C/C=C/CCCCCCCC(O)=O	2309.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Punicic acid,1TMS,isomer #1	CCCC/C=C/C=C\C=C\CCCCCCCC(=O)O[Si](C)(C)C	2358.6	Semi standard non polar	33892256
Punicic acid,1TBDMS,isomer #1	CCCC/C=C/C=C\C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2584.0	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 - Punicic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8960000000-59c083671232b201abc8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Punicic acid GC-MS (1 TMS) - 70eV, Positive	splash10-009j-8922000000-a833082a5dc1b9b8fef6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Punicic 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 - Punicic acid 10V, Negative-QTOF	splash10-004i-0090000000-9017290211373e0fd968	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicic acid 20V, Negative-QTOF	splash10-0059-1090000000-f71ec81e19ca9b6622af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicic acid 40V, Negative-QTOF	splash10-0a4i-9230000000-97b44baaf23d3bde3d46	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicic acid 10V, Negative-QTOF	splash10-004i-0090000000-12da14b99ffff5280158	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicic acid 20V, Negative-QTOF	splash10-056r-1090000000-e58964825ceee9b9ae45	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicic acid 40V, Negative-QTOF	splash10-052f-9510000000-6e24c220dbce17f77c3e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicic acid 10V, Positive-QTOF	splash10-01t9-0090000000-88ce0b28b56f5ae5db9d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicic acid 20V, Positive-QTOF	splash10-02u0-6590000000-30f95b4c2d9566284c4e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicic acid 40V, Positive-QTOF	splash10-014l-8930000000-fe0898dc5088e651e220	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicic acid 10V, Positive-QTOF	splash10-01t9-4690000000-76ea346646e2d3f7b75c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicic acid 20V, Positive-QTOF	splash10-0536-9810000000-b47f33760bad1f74f7dc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicic acid 40V, Positive-QTOF	splash10-05ox-9100000000-f5a89343e9ef6aafee09	2021-09-24	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

FDB012466

KNApSAcK ID

C00001216

Chemspider ID

20118304

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alpha-Eleostearic acid

METLIN ID

Not Available

PubChem Compound

12309425

PDB ID

Not Available

ChEBI ID

38383

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1588761

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Du Plessis LM: Isomerization of the double bonds of a conjugated fatty acid during beta-oxidation. Lipids. 1979 Nov;14(11):943-8. [PubMed:513983 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Punicic acid (HMDB0030963)

MOL for HMDB0030963 (Punicic acid)

3D MOL for HMDB0030963 (Punicic acid)

3D SDF for HMDB0030963 (Punicic acid)

3D-SDF for HMDB0030963 (Punicic acid)

PDB for HMDB0030963 (Punicic acid)

3D PDB for HMDB0030963 (Punicic acid)

SMILES for HMDB0030963 (Punicic acid)

INCHI for HMDB0030963 (Punicic acid)

Structure for HMDB0030963 (Punicic acid)

3D Structure for HMDB0030963 (Punicic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra