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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 23:57:32 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004670

Secondary Accession Numbers

HMDB0010223
HMDB04670
HMDB10223

Metabolite Identification

Common Name

alpha-Dimorphecolic acid

Description

alpha-Dimorphecolic acid or 9(S)-HODE is an endogenous fatty acid (PPAR)gamma agonist synthesized in the body from linoleic acid. alpha-Dimorphecolic acid activates peroxisomal proliferator-activated receptor-gamma (PPAR)gamma in human endothelial cells increasing plasminogen activator inhibitor type-1 expression. Plasminogen activator inhibitor type-1 (PAI-1) is a major physiological inhibitor of fibrinolysis, with its plasma levels correlating with the risk for myocardial infarction and venous thrombosis. The regulation of PAI-1 transcription by endothelial cells (ECs), a major source of PAI-1, remains incompletely understood. Adipocytes also produce PAI-1, suggesting possible common regulatory pathways between adipocytes and ECs. Peroxisomal proliferator-activated receptor-gamma (PPAR)gamma is a ligand-activated transcription factor that regulates gene expression in response to various mediators such as 15-deoxy-delta12, 14-prostaglandin J2 (15d-PGJ2) and oxidized linoleic acid (9- and 13-HODE). alpha-Dimorphecolic acid is a ligand of the G protein-coupled receptor G2A (PMID: 10073956 , 16647253 , 16236715 ). alpha-Dimorphecolic acid inhibits the proliferation of NHEK cells by suppressing DNA synthesis and arresting the cell cycle in the G0/1-phase. alpha-Dimorphecolic acid-G2A signalling plays proinflammatory roles in the skin under oxidative conditions (PMID: 18034171 ).

Structure

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

HMDB0004670
     RDKit          3D
alpha-Dimorphecolic acid
 53 52  0  0  0  0  0  0  0  0999 V2000
    8.2084    1.7074   -0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8662    1.4051    0.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0147    0.1408    0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7746    0.4267   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8906   -0.8033   -0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5099   -1.0917    1.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2629   -1.1019    1.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1623   -0.8379    0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8914   -0.8645    1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -0.5867    0.1680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4859   -1.8196   -0.4622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4152   -0.2205    1.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6435    0.1165    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1278   -1.0199   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4042   -0.6150   -1.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4487   -0.2627   -0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7578    0.1104   -0.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7748    0.4872    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0639    0.8629   -0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6363    0.0618   -1.2778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6577    2.0941   -0.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5737    2.5373   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2905    1.9596   -0.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0920    0.7917   -1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7821    1.2331    1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3120    2.2640    0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8503   -0.1342    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6324   -0.6842    0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955    1.1882    0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9836    0.7959   -1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0600   -0.7055   -0.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5734   -1.6551   -0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3208   -1.3151    1.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1017   -1.3299    2.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291   -0.6048   -0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6905   -1.0830    2.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089    0.1587   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1678   -2.0016   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1785    0.6599    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700   -1.0554    1.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4083    0.4302    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4204    1.0308   -0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3957   -1.3031   -1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521   -1.9022    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1598    0.3290   -1.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7320   -1.4156   -1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5814   -1.0718    0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1861    0.6717    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5133    0.9585   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0590   -0.7493   -1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8976   -0.4202    0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3675    1.3238    0.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0532    2.9096   -0.1472 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  1  0
 10 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  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 21 53  1  0
M  END


  Mrv1652310111919002D          

 21 20  0  0  0  0            999 V2000
 9997.8938 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6086 9998.4816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3238 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0375 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7532 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5780 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2938 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0094 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.7230 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.4387 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.1543 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6086 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1787 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4639 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7491 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0342 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3192 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6044 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8896 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1727 9998.0698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8896 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  2 12  1  6  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  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
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004670

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C=C/[C@@H](O)CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+/t17-/m1/s1

> <INCHI_KEY>
NPDSHTNEKLQQIJ-UINYOVNOSA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.4449

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.228152858699026

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid

> <ALOGPS_LOGP>
5.88

> <JCHEM_LOGP>
5.191065727333333

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.795677864657474

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.676745528848431

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5759708475080179

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
90.0343

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-dimorphecolic

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004670
     RDKit          3D
alpha-Dimorphecolic acid
 53 52  0  0  0  0  0  0  0  0999 V2000
    8.2084    1.7074   -0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8662    1.4051    0.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0147    0.1408    0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7746    0.4267   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8906   -0.8033   -0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5099   -1.0917    1.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2629   -1.1019    1.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1623   -0.8379    0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8914   -0.8645    1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -0.5867    0.1680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4859   -1.8196   -0.4622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4152   -0.2205    1.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6435    0.1165    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1278   -1.0199   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4042   -0.6150   -1.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4487   -0.2627   -0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7578    0.1104   -0.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7748    0.4872    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0639    0.8629   -0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6363    0.0618   -1.2778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6577    2.0941   -0.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5737    2.5373   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2905    1.9596   -0.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0920    0.7917   -1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7821    1.2331    1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3120    2.2640    0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8503   -0.1342    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6324   -0.6842    0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955    1.1882    0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9836    0.7959   -1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0600   -0.7055   -0.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5734   -1.6551   -0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3208   -1.3151    1.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1017   -1.3299    2.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291   -0.6048   -0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6905   -1.0830    2.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089    0.1587   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1678   -2.0016   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1785    0.6599    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700   -1.0554    1.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4083    0.4302    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4204    1.0308   -0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3957   -1.3031   -1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521   -1.9022    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1598    0.3290   -1.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7320   -1.4156   -1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5814   -1.0718    0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1861    0.6717    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5133    0.9585   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0590   -0.7493   -1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8976   -0.4202    0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3675    1.3238    0.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0532    2.9096   -0.1472 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  1  0
 10 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  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 21 53  1  0
M  END

HEADER    PROTEIN                                 11-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-OCT-19         0                                  
HETATM    1  C   UNK     0    8662.7358663.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.0698663.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.4058663.064   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.7378663.832   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8668.0738663.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8669.6128663.064   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.9488663.832   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8672.2848663.064   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8673.6168663.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8674.9528663.064   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8676.2888663.832   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8664.0698665.373   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8661.4008663.832   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.0668663.064   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8658.7328663.832   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8657.3978663.064   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8656.0638663.832   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8654.7288663.064   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8653.3948663.832   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0    8652.0568663.064   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0    8653.3948665.373   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
CONECT    2    1    3   12                                                  
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                                                            
CONECT   12    2                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0004670
HETATM    1  C1  UNL     1       8.208   1.707  -0.930  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.866   1.405   0.512  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.015   0.141   0.576  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.775   0.427  -0.225  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.891  -0.803  -0.220  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.510  -1.092   1.176  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.263  -1.102   1.555  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.162  -0.838   0.665  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.891  -0.865   1.113  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.255  -0.587   0.168  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.486  -1.820  -0.462  1.00  0.00           O  
HETATM   12  C11 UNL     1      -1.415  -0.221   1.041  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.644   0.116   0.290  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.128  -1.020  -0.545  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.404  -0.615  -1.261  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.449  -0.263  -0.239  1.00  0.00           C  
HETATM   17  C16 UNL     1      -6.758   0.110  -0.943  1.00  0.00           C  
HETATM   18  C17 UNL     1      -7.775   0.487   0.119  1.00  0.00           C  
HETATM   19  C18 UNL     1      -9.064   0.863  -0.505  1.00  0.00           C  
HETATM   20  O2  UNL     1      -9.636   0.062  -1.278  1.00  0.00           O  
HETATM   21  O3  UNL     1      -9.658   2.094  -0.255  1.00  0.00           O  
HETATM   22  H1  UNL     1       7.574   2.537  -1.298  1.00  0.00           H  
HETATM   23  H2  UNL     1       9.290   1.960  -0.985  1.00  0.00           H  
HETATM   24  H3  UNL     1       8.092   0.792  -1.543  1.00  0.00           H  
HETATM   25  H4  UNL     1       8.782   1.233   1.111  1.00  0.00           H  
HETATM   26  H5  UNL     1       7.312   2.264   0.947  1.00  0.00           H  
HETATM   27  H6  UNL     1       6.850  -0.134   1.617  1.00  0.00           H  
HETATM   28  H7  UNL     1       7.632  -0.684   0.138  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.195   1.188   0.382  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.984   0.796  -1.234  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.060  -0.706  -0.913  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.573  -1.655  -0.561  1.00  0.00           H  
HETATM   33  H12 UNL     1       5.321  -1.315   1.910  1.00  0.00           H  
HETATM   34  H13 UNL     1       3.102  -1.330   2.625  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.229  -0.605  -0.384  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.691  -1.083   2.127  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.009   0.159  -0.578  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.168  -2.002  -1.169  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.178   0.660   1.694  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.570  -1.055   1.780  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.408   0.430   1.058  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.420   1.031  -0.331  1.00  0.00           H  
HETATM   43  H22 UNL     1      -2.396  -1.303  -1.341  1.00  0.00           H  
HETATM   44  H23 UNL     1      -3.252  -1.902   0.108  1.00  0.00           H  
HETATM   45  H24 UNL     1      -4.160   0.329  -1.813  1.00  0.00           H  
HETATM   46  H25 UNL     1      -4.732  -1.416  -1.934  1.00  0.00           H  
HETATM   47  H26 UNL     1      -5.581  -1.072   0.495  1.00  0.00           H  
HETATM   48  H27 UNL     1      -5.186   0.672   0.339  1.00  0.00           H  
HETATM   49  H28 UNL     1      -6.513   0.958  -1.606  1.00  0.00           H  
HETATM   50  H29 UNL     1      -7.059  -0.749  -1.539  1.00  0.00           H  
HETATM   51  H30 UNL     1      -7.898  -0.420   0.777  1.00  0.00           H  
HETATM   52  H31 UNL     1      -7.367   1.324   0.734  1.00  0.00           H  
HETATM   53  H32 UNL     1      -9.053   2.910  -0.147  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7    7   33
CONECT    7    8   34
CONECT    8    9    9   35
CONECT    9   10   36
CONECT   10   11   12   37
CONECT   11   38
CONECT   12   13   39   40
CONECT   13   14   41   42
CONECT   14   15   43   44
CONECT   15   16   45   46
CONECT   16   17   47   48
CONECT   17   18   49   50
CONECT   18   19   51   52
CONECT   19   20   20   21
CONECT   21   53
END

HMDB0004670
     RDKit          3D
alpha-Dimorphecolic acid
 53 52  0  0  0  0  0  0  0  0999 V2000
    8.2084    1.7074   -0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8662    1.4051    0.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0147    0.1408    0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7746    0.4267   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8906   -0.8033   -0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5099   -1.0917    1.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2629   -1.1019    1.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1623   -0.8379    0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8914   -0.8645    1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -0.5867    0.1680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4859   -1.8196   -0.4622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4152   -0.2205    1.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6435    0.1165    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1278   -1.0199   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4042   -0.6150   -1.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4487   -0.2627   -0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7578    0.1104   -0.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7748    0.4872    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0639    0.8629   -0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6363    0.0618   -1.2778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6577    2.0941   -0.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5737    2.5373   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2905    1.9596   -0.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0920    0.7917   -1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7821    1.2331    1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3120    2.2640    0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8503   -0.1342    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6324   -0.6842    0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955    1.1882    0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9836    0.7959   -1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0600   -0.7055   -0.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5734   -1.6551   -0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3208   -1.3151    1.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1017   -1.3299    2.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291   -0.6048   -0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6905   -1.0830    2.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089    0.1587   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1678   -2.0016   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1785    0.6599    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700   -1.0554    1.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4083    0.4302    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4204    1.0308   -0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3957   -1.3031   -1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521   -1.9022    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1598    0.3290   -1.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7320   -1.4156   -1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5814   -1.0718    0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1861    0.6717    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5133    0.9585   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0590   -0.7493   -1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8976   -0.4202    0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3675    1.3238    0.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0532    2.9096   -0.1472 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  1  0
 10 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  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 21 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(10E,12Z)-(9S)-9-Hydroxyoctadeca-10,12-dienoic acid	ChEBI
(9S)-Hydroxyoctadecadienoic acid	ChEBI
(9S)-Hydroxyoctadecadinoiec acid	ChEBI
(10E,12Z)-(9S)-9-Hydroxyoctadeca-10,12-dienoate	Generator
(9S)-Hydroxyoctadecadienoate	Generator
a-Dimorphecolate	Generator
a-Dimorphecolic acid	Generator
alpha-Dimorphecolate	Generator
Α-dimorphecolate	Generator
Α-dimorphecolic acid	Generator
(9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoate	HMDB
(9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoic acid	HMDB
9(S)-HODE	HMDB
9S-Hydroxy-10E,12Z-octadecadienoate	HMDB
9S-Hydroxy-10E,12Z-octadecadienoic acid	HMDB
alpha-Dimorphecolic	HMDB
[S-(e,Z)]-9-Hydroxy-10,12-octadecadienoate	HMDB
[S-(e,Z)]-9-Hydroxy-10,12-octadecadienoic acid	HMDB
9-Hydroxy-10,12-octadecadienoic acid	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (R-(e,Z))-isomer	HMDB
9-HODE	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-isomer	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (S-(e,Z))-isomer	HMDB
9-Hydroxylinoleic acid	HMDB
Dimorphecolic acid	HMDB
9-OH-18:2DElta(10t,12t)	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-(+-)-isomer	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-isomer	HMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-(+-)-isomer	HMDB
9-Hydroxyoctadecadienoic acid	HMDB
9S-HOD acid	HMDB
(+)-alpha-Dimorphecolic acid	HMDB
(+)-Α-dimorphecolic acid	HMDB
(10E,12Z)-9-Hydroxy-10,12-octadecadienoic acid	HMDB
(9S,10E,12Z)-9-Hydroxy-10,12-octadecadienoic acid	HMDB
(±)-alpha-dimorphecolic acid	HMDB
(±)-α-dimorphecolic acid	HMDB
9-(e,Z)-HODE	HMDB
9-Hydroxy-(10E,12Z)-octadeca-10,12-dienoic acid	HMDB
9-Hydroxy-10(e),12(Z)-octadecadienoic acid	HMDB
9-Hydroxy-10-trans,12-cis-octadecadienoic acid	HMDB
9S-HODE	HMDB
alpha-Dimorphecolic acid	HMDB

Chemical Formula

C₁₈H₃₂O₃

Average Molecular Weight

296.4449

Monoisotopic Molecular Weight

296.23514489

IUPAC Name

(9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid

Traditional Name

α-dimorphecolic

CAS Registry Number

73543-67-6

SMILES

CCCCC\C=C/C=C/[C@@H](O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+/t17-/m1/s1

InChI Key

NPDSHTNEKLQQIJ-UINYOVNOSA-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
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

(10E,12Z)-9-HODE (CHEBI:34496 )
Other Octadecanoids (C14767 )
Other Octadecanoids (LMFA02000188 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)
Cerebrospinal Fluid (CSF) (HMDB: HMDB0004670)
Saliva (PMID: 22308371)

Organ

Placenta (HMDB: HMDB0004670)

Excreta

Biofluid or Excreta

Feces (PMID: 25037050)

Cellular substructure

Extracellular (HMDB: HMDB0004670)
Membrane (HMDB: HMDB0004670)

Source

Exogenous

Exogenous (HMDB: HMDB0004670)

Food

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)

Endogenous

Endogenous (HMDB: HMDB0004670)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	0.0032 g/L	ALOGPS
logP	5.88	ALOGPS
logP	5.19	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	90.03 m³·mol⁻¹	ChemAxon
Polarizability	37.23 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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]+	180.171	31661259
DarkChem	[M-H]-	177.501	31661259
DeepCCS	[M+H]+	187.595	30932474
DeepCCS	[M-H]-	185.237	30932474
DeepCCS	[M-2H]-	218.123	30932474
DeepCCS	[M+Na]+	193.688	30932474
AllCCS	[M+H]+	181.2	32859911
AllCCS	[M+H-H2O]+	178.2	32859911
AllCCS	[M+NH4]+	183.9	32859911
AllCCS	[M+Na]+	184.7	32859911
AllCCS	[M-H]-	180.0	32859911
AllCCS	[M+Na-2H]-	181.5	32859911
AllCCS	[M+HCOO]-	183.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	9.1 minutes	32390414
Predicted by Siyang on May 30, 2022	19.7736 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.06 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2898.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	444.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	203.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	239.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	553.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	881.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	602.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	100.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1896.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	590.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1642.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	666.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	459.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	404.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	480.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Dimorphecolic acid	CCCCC\C=C/C=C/[C@@H](O)CCCCCCCC(O)=O	3833.3	Standard polar	33892256
alpha-Dimorphecolic acid	CCCCC\C=C/C=C/[C@@H](O)CCCCCCCC(O)=O	2304.6	Standard non polar	33892256
alpha-Dimorphecolic acid	CCCCC\C=C/C=C/[C@@H](O)CCCCCCCC(O)=O	2428.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
alpha-Dimorphecolic acid,1TMS,isomer #1	CCCCC/C=C\C=C\[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C	2533.2	Semi standard non polar	33892256
alpha-Dimorphecolic acid,1TMS,isomer #2	CCCCC/C=C\C=C\[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C	2480.6	Semi standard non polar	33892256
alpha-Dimorphecolic acid,2TMS,isomer #1	CCCCC/C=C\C=C\[C@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2544.2	Semi standard non polar	33892256
alpha-Dimorphecolic acid,1TBDMS,isomer #1	CCCCC/C=C\C=C\[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	2777.8	Semi standard non polar	33892256
alpha-Dimorphecolic acid,1TBDMS,isomer #2	CCCCC/C=C\C=C\[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2724.3	Semi standard non polar	33892256
alpha-Dimorphecolic acid,2TBDMS,isomer #1	CCCCC/C=C\C=C\[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3044.9	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00965 +/- 0.00278 uM	Adult (>18 years old)	Not Specified	Normal	18953024	details
Blood	Detected and Quantified	0.0068 +/- 0.00167 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.0117 +/- 0.00023 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.011 +/- 0.0061 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0065 +/- 0.00064 uM	Adult (>18 years old)	Both	Normal	John W. Newman, U...	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB07302

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003060

KNApSAcK ID

Not Available

Chemspider ID

4472255

KEGG Compound ID

C14767

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

9-Hydroxyoctadecadienoic_acid

METLIN ID

Not Available

PubChem Compound

5312830

PDB ID

9HO

ChEBI ID

34496

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

Marx N, Bourcier T, Sukhova GK, Libby P, Plutzky J: PPARgamma activation in human endothelial cells increases plasminogen activator inhibitor type-1 expression: PPARgamma as a potential mediator in vascular disease. Arterioscler Thromb Vasc Biol. 1999 Mar;19(3):546-51. [PubMed:10073956 ]
Hampel JK, Brownrigg LM, Vignarajah D, Croft KD, Dharmarajan AM, Bentel JM, Puddey IB, Yeap BB: Differential modulation of cell cycle, apoptosis and PPARgamma2 gene expression by PPARgamma agonists ciglitazone and 9-hydroxyoctadecadienoic acid in monocytic cells. Prostaglandins Leukot Essent Fatty Acids. 2006 May;74(5):283-93. Epub 2006 May 2. [PubMed:16647253 ]
Obinata H, Hattori T, Nakane S, Tatei K, Izumi T: Identification of 9-hydroxyoctadecadienoic acid and other oxidized free fatty acids as ligands of the G protein-coupled receptor G2A. J Biol Chem. 2005 Dec 9;280(49):40676-83. Epub 2005 Oct 19. [PubMed:16236715 ]
Hattori T, Obinata H, Ogawa A, Kishi M, Tatei K, Ishikawa O, Izumi T: G2A plays proinflammatory roles in human keratinocytes under oxidative stress as a receptor for 9-hydroxyoctadecadienoic acid. J Invest Dermatol. 2008 May;128(5):1123-33. Epub 2007 Nov 22. [PubMed:18034171 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for alpha-Dimorphecolic acid (HMDB0004670)

MOL for HMDB0004670 (alpha-Dimorphecolic acid)

3D MOL for HMDB0004670 (alpha-Dimorphecolic acid)

3D SDF for HMDB0004670 (alpha-Dimorphecolic acid)

3D-SDF for HMDB0004670 (alpha-Dimorphecolic acid)

PDB for HMDB0004670 (alpha-Dimorphecolic acid)

3D PDB for HMDB0004670 (alpha-Dimorphecolic acid)

SMILES for HMDB0004670 (alpha-Dimorphecolic acid)

INCHI for HMDB0004670 (alpha-Dimorphecolic acid)

Structure for HMDB0004670 (alpha-Dimorphecolic acid)

3D Structure for HMDB0004670 (alpha-Dimorphecolic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized