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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-14 01:55:43 UTC

Update Date

2022-09-22 17:43:53 UTC

HMDB ID

HMDB0004705

Secondary Accession Numbers

HMDB04705

Metabolite Identification

Common Name

12,13-DHOME

Description

12,13-DHOME (CAS: 263399-35-5), also known as 12,13-dihydroxy-9-octadecenoic acid or 12,13-DiHOME, is the epoxide hydrolase metabolite of the leukotoxin 12,13-EpOME. 12,13-EpOME acts as a protoxin, with the corresponding epoxide hydrolase 12,13-DHOME specifically exerting toxicity. Both the EpOME and the DHOME are shown to have neutrophil chemotactic activity. 12,13-DHOME suppress the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4, which inhibit multiple aspects of neutrophil activation. 12,13-DHOME is a derivative of the linoleic acid diol that has been reported to be toxic in human tissue preparations. 12,13-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation (PMID: 17435320 , 12021203 , 12127265 ).

Structure

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

HMDB0004705
     RDKit          3D
12,13-DHOME
 56 55  0  0  0  0  0  0  0  0999 V2000
    1.9561    2.0912   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3366    2.6123    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479    1.6659    0.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6676    0.5704   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194   -0.4582   -0.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3347   -1.2601    0.4151 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5008   -1.9484    0.8368 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2977   -2.3090    0.2272 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0377   -3.0269    1.3900 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9393   -1.7657   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0630   -2.9259   -0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0399   -3.1026    0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5913   -2.1328    1.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907   -1.8101    0.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0028   -1.1979   -0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241    0.1242   -0.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9768    1.1294    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4078    1.3465   -0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6376    1.8654   -1.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0121    3.1751   -1.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0867    3.6639   -2.8154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3502    3.8652   -0.6735 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7927    1.2458    0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2429    2.8916    0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163    1.9645   -1.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6079    3.2667   -0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556    3.3446    0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3782    1.3450    1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3952    2.2929    0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8391    1.0252   -1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6273    0.0399   -0.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6978   -0.1167   -1.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0456   -1.2092   -1.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0498   -0.5975    1.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5791   -1.9200    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6287   -3.0179   -0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8778   -3.1117    1.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204   -0.9479    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1040   -1.3248   -1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3777   -3.7159   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6446   -4.0418    0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0647   -1.1882    1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7136   -2.5853    2.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5548   -1.2303    1.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5077   -2.8111    0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4327   -1.8817   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0172   -1.1566   -1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3759    0.5585   -1.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2667    0.0620   -0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9487    0.7457    1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3737    2.0309    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8309    2.0607    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9846    0.4072    0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7324    1.9952   -1.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3129    1.0967   -2.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8559    4.3116    0.0940 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  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  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  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  1
  7 35  1  0
  8 36  1  6
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
M  END

  Mrv1652303062020172D          

 22 21  0  0  0  0            999 V2000
10009.876910007.8977    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10009.161410007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.445910007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.621510007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.906810007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.192010007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.477310007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.762610007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.047910007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.333110007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.618310007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.903710007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.186910007.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.903710008.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.590410007.4857    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10011.305810007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.021410007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.734810007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.450310007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.165810007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.590410006.6603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.876910008.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 15  1  0  0  0  0
  1 22  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 15 16  1  0  0  0  0
 15 21  1  6  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
M  END
> <DATABASE_ID>
HMDB0004705

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H34O4/c1-2-3-10-13-16(19)17(20)14-11-8-6-4-5-7-9-12-15-18(21)22/h8,11,16-17,19-20H,2-7,9-10,12-15H2,1H3,(H,21,22)/b11-8-/t16-,17-/m0/s1

> <INCHI_KEY>
CQSLTKIXAJTQGA-BTDPBSJTSA-N

> <FORMULA>
C18H34O4

> <MOLECULAR_WEIGHT>
314.466

> <EXACT_MASS>
314.245709575

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.50993978920626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,12S,13S)-12,13-dihydroxyoctadec-9-enoic acid

> <ALOGPS_LOGP>
5.20

> <JCHEM_LOGP>
4.322176317

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.874418583842726

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283339478

> <JCHEM_PKA_STRONGEST_BASIC>
-3.148519520984263

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
90.43319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9Z,12S,13S)-12,13-dihydroxyoctadec-9-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004705
     RDKit          3D
12,13-DHOME
 56 55  0  0  0  0  0  0  0  0999 V2000
    1.9561    2.0912   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3366    2.6123    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479    1.6659    0.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6676    0.5704   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194   -0.4582   -0.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3347   -1.2601    0.4151 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5008   -1.9484    0.8368 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2977   -2.3090    0.2272 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0377   -3.0269    1.3900 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9393   -1.7657   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0630   -2.9259   -0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0399   -3.1026    0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5913   -2.1328    1.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907   -1.8101    0.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0028   -1.1979   -0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241    0.1242   -0.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9768    1.1294    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4078    1.3465   -0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6376    1.8654   -1.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0121    3.1751   -1.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0867    3.6639   -2.8154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3502    3.8652   -0.6735 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7927    1.2458    0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2429    2.8916    0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163    1.9645   -1.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6079    3.2667   -0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556    3.3446    0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3782    1.3450    1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3952    2.2929    0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8391    1.0252   -1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6273    0.0399   -0.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6978   -0.1167   -1.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0456   -1.2092   -1.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0498   -0.5975    1.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5791   -1.9200    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6287   -3.0179   -0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8778   -3.1117    1.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204   -0.9479    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1040   -1.3248   -1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3777   -3.7159   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6446   -4.0418    0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0647   -1.1882    1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7136   -2.5853    2.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5548   -1.2303    1.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5077   -2.8111    0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4327   -1.8817   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0172   -1.1566   -1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3759    0.5585   -1.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2667    0.0620   -0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9487    0.7457    1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3737    2.0309    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8309    2.0607    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9846    0.4072    0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7324    1.9952   -1.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3129    1.0967   -2.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8559    4.3116    0.0940 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  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  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  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  1
  7 35  1  0
  8 36  1  6
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8685.1048681.409   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8683.7688680.640   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8682.4328681.409   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8680.8938681.409   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8679.5598680.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8678.2258681.409   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8676.8918680.640   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8675.5578681.409   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8674.2238680.640   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8672.8888681.409   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8671.5548680.640   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8670.2208681.409   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8668.8828680.640   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8670.2208682.948   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8686.4358680.640   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8687.7718681.409   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8689.1078680.640   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8690.4388681.409   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8691.7748680.640   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8693.1098681.409   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8686.4358679.099   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8685.1048682.948   0.000  0.00  0.00           O+0
CONECT    1    2   15   22                                                  
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   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    1   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   15                                                            
CONECT   22    1                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0004705
HETATM    1  C1  UNL     1       1.956   2.091  -0.013  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.337   2.612   0.055  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.448   1.666   0.302  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.668   0.570  -0.655  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.619  -0.458  -0.826  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.335  -1.260   0.415  1.00  0.00           C  
HETATM    7  O1  UNL     1       4.501  -1.948   0.837  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.298  -2.309   0.227  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.038  -3.027   1.390  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.939  -1.766  -0.224  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.063  -2.926  -0.345  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.040  -3.103   0.297  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.591  -2.133   1.264  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.991  -1.810   0.795  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.003  -1.198  -0.545  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.324   0.124  -0.610  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.977   1.129   0.323  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.408   1.346  -0.020  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.638   1.865  -1.406  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.012   3.175  -1.669  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.087   3.664  -2.815  1.00  0.00           O  
HETATM   22  O4  UNL     1      -3.350   3.865  -0.673  1.00  0.00           O  
HETATM   23  H1  UNL     1       1.793   1.246   0.643  1.00  0.00           H  
HETATM   24  H2  UNL     1       1.243   2.892   0.379  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.616   1.965  -1.066  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.608   3.267  -0.812  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.356   3.345   0.926  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.378   1.345   1.366  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.395   2.293   0.290  1.00  0.00           H  
HETATM   30  H8  UNL     1       4.839   1.025  -1.675  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.627   0.040  -0.447  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.698  -0.117  -1.310  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.046  -1.209  -1.563  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.050  -0.597   1.254  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.579  -1.920   1.808  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.629  -3.018  -0.550  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.878  -3.112   1.889  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.620  -0.948   0.413  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.104  -1.325  -1.245  1.00  0.00           H  
HETATM   40  H18 UNL     1       0.378  -3.716  -1.050  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.645  -4.042   0.136  1.00  0.00           H  
HETATM   42  H20 UNL     1      -1.065  -1.188   1.356  1.00  0.00           H  
HETATM   43  H21 UNL     1      -1.714  -2.585   2.282  1.00  0.00           H  
HETATM   44  H22 UNL     1      -3.555  -1.230   1.564  1.00  0.00           H  
HETATM   45  H23 UNL     1      -3.508  -2.811   0.715  1.00  0.00           H  
HETATM   46  H24 UNL     1      -2.433  -1.882  -1.251  1.00  0.00           H  
HETATM   47  H25 UNL     1      -4.017  -1.157  -1.012  1.00  0.00           H  
HETATM   48  H26 UNL     1      -2.376   0.559  -1.639  1.00  0.00           H  
HETATM   49  H27 UNL     1      -1.267   0.062  -0.360  1.00  0.00           H  
HETATM   50  H28 UNL     1      -2.949   0.746   1.373  1.00  0.00           H  
HETATM   51  H29 UNL     1      -2.374   2.031   0.308  1.00  0.00           H  
HETATM   52  H30 UNL     1      -4.831   2.061   0.738  1.00  0.00           H  
HETATM   53  H31 UNL     1      -4.985   0.407   0.126  1.00  0.00           H  
HETATM   54  H32 UNL     1      -5.732   1.995  -1.612  1.00  0.00           H  
HETATM   55  H33 UNL     1      -4.313   1.097  -2.153  1.00  0.00           H  
HETATM   56  H34 UNL     1      -3.856   4.312   0.094  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7    8   34
CONECT    7   35
CONECT    8    9   10   36
CONECT    9   37
CONECT   10   11   38   39
CONECT   11   12   12   40
CONECT   12   13   41
CONECT   13   14   42   43
CONECT   14   15   44   45
CONECT   15   16   46   47
CONECT   16   17   48   49
CONECT   17   18   50   51
CONECT   18   19   52   53
CONECT   19   20   54   55
CONECT   20   21   21   22
CONECT   22   56
END

HMDB0004705
     RDKit          3D
12,13-DHOME
 56 55  0  0  0  0  0  0  0  0999 V2000
    1.9561    2.0912   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3366    2.6123    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479    1.6659    0.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6676    0.5704   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194   -0.4582   -0.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3347   -1.2601    0.4151 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5008   -1.9484    0.8368 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2977   -2.3090    0.2272 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0377   -3.0269    1.3900 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9393   -1.7657   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0630   -2.9259   -0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0399   -3.1026    0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5913   -2.1328    1.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907   -1.8101    0.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0028   -1.1979   -0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241    0.1242   -0.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9768    1.1294    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4078    1.3465   -0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6376    1.8654   -1.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0121    3.1751   -1.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0867    3.6639   -2.8154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3502    3.8652   -0.6735 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7927    1.2458    0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2429    2.8916    0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163    1.9645   -1.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6079    3.2667   -0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556    3.3446    0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3782    1.3450    1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3952    2.2929    0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8391    1.0252   -1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6273    0.0399   -0.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6978   -0.1167   -1.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0456   -1.2092   -1.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0498   -0.5975    1.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5791   -1.9200    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6287   -3.0179   -0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8778   -3.1117    1.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204   -0.9479    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1040   -1.3248   -1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3777   -3.7159   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6446   -4.0418    0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0647   -1.1882    1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7136   -2.5853    2.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5548   -1.2303    1.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5077   -2.8111    0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4327   -1.8817   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0172   -1.1566   -1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3759    0.5585   -1.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2667    0.0620   -0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9487    0.7457    1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3737    2.0309    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8309    2.0607    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9846    0.4072    0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7324    1.9952   -1.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3129    1.0967   -2.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8559    4.3116    0.0940 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  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  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  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  1
  7 35  1  0
  8 36  1  6
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12,13-Dihydroxyoleate	HMDB
(-)-Threo-12,13-dihydroxyoleic acid	HMDB
(9Z)-12,13-Dihydroxy-9-octadecenoic acid	HMDB
(9Z,12S,13S)-12,13-Dihydroxy-9-octadecenoic acid	HMDB
12,13-DiHOME	HMDB
FA(18:1(9Z,12S,13S))	HMDB
FA(18:1(9Z,12S-OH,13S-OH))	HMDB
12,13-DHOME	HMDB

Chemical Formula

C₁₈H₃₄O₄

Average Molecular Weight

314.466

Monoisotopic Molecular Weight

314.245709575

IUPAC Name

(9Z,12S,13S)-12,13-dihydroxyoctadec-9-enoic acid

Traditional Name

(9Z,12S,13S)-12,13-dihydroxyoctadec-9-enoic acid

CAS Registry Number

7293-40-5

SMILES

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

InChI Identifier

InChI=1S/C18H34O4/c1-2-3-10-13-16(19)17(20)14-11-8-6-4-5-7-9-12-15-18(21)22/h8,11,16-17,19-20H,2-7,9-10,12-15H2,1H3,(H,21,22)/b11-8-/t16-,17-/m0/s1

InChI Key

CQSLTKIXAJTQGA-BTDPBSJTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)
Cerebrospinal Fluid (CSF) (HMDB: HMDB0004705)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)

Cellular substructure

Extracellular (HMDB: HMDB0004705)
Membrane (HMDB: HMDB0004705)

Source

Exogenous

Exogenous (HMDB: HMDB0004705)

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: HMDB0004705)

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	0.036 g/L	ALOGPS
logP	5.2	ALOGPS
logP	4.32	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	90.43 m³·mol⁻¹	ChemAxon
Polarizability	38.51 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
DeepCCS	[M+H]+	188.969	30932474
DeepCCS	[M-H]-	186.611	30932474
DeepCCS	[M-2H]-	219.497	30932474
DeepCCS	[M+Na]+	195.062	30932474
AllCCS	[M+H]+	186.7	32859911
AllCCS	[M+H-H2O]+	183.9	32859911
AllCCS	[M+NH4]+	189.3	32859911
AllCCS	[M+Na]+	190.1	32859911
AllCCS	[M-H]-	183.3	32859911
AllCCS	[M+Na-2H]-	184.9	32859911
AllCCS	[M+HCOO]-	186.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
12,13-DHOME	CCCCC[C@H](O)[C@@H](O)C\C=C/CCCCCCCC(O)=O	3886.1	Standard polar	33892256
12,13-DHOME	CCCCC[C@H](O)[C@@H](O)C\C=C/CCCCCCCC(O)=O	2371.2	Standard non polar	33892256
12,13-DHOME	CCCCC[C@H](O)[C@@H](O)C\C=C/CCCCCCCC(O)=O	2508.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12,13-DHOME,1TMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C)[C@@H](O)C/C=C\CCCCCCCC(=O)O	2513.5	Semi standard non polar	33892256
12,13-DHOME,1TMS,isomer #2	CCCCC[C@H](O)[C@H](C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C	2529.7	Semi standard non polar	33892256
12,13-DHOME,1TMS,isomer #3	CCCCC[C@H](O)[C@@H](O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C	2537.0	Semi standard non polar	33892256
12,13-DHOME,2TMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C)[C@H](C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C	2532.7	Semi standard non polar	33892256
12,13-DHOME,2TMS,isomer #2	CCCCC[C@H](O[Si](C)(C)C)[C@@H](O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C	2545.9	Semi standard non polar	33892256
12,13-DHOME,2TMS,isomer #3	CCCCC[C@H](O)[C@H](C/C=C\CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2554.9	Semi standard non polar	33892256
12,13-DHOME,3TMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C)[C@H](C/C=C\CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2542.8	Semi standard non polar	33892256
12,13-DHOME,1TBDMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C/C=C\CCCCCCCC(=O)O	2754.6	Semi standard non polar	33892256
12,13-DHOME,1TBDMS,isomer #2	CCCCC[C@H](O)[C@H](C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	2757.4	Semi standard non polar	33892256
12,13-DHOME,1TBDMS,isomer #3	CCCCC[C@H](O)[C@@H](O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2779.6	Semi standard non polar	33892256
12,13-DHOME,2TBDMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3027.1	Semi standard non polar	33892256
12,13-DHOME,2TBDMS,isomer #2	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	3020.1	Semi standard non polar	33892256
12,13-DHOME,2TBDMS,isomer #3	CCCCC[C@H](O)[C@H](C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3038.6	Semi standard non polar	33892256
12,13-DHOME,3TBDMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3276.0	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 - 12,13-DHOME 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 - 12,13-DHOME 10V, Negative-QTOF	splash10-03di-0119000000-4c868de0f3de6c07f549	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-DHOME 20V, Negative-QTOF	splash10-03dj-3985000000-11f56948c3f5b836b850	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-DHOME 40V, Negative-QTOF	splash10-0002-9510000000-44b29fc1dc61e8abffec	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-DHOME 10V, Positive-QTOF	splash10-00mk-0492000000-08dc8525353e9939cf8d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-DHOME 20V, Positive-QTOF	splash10-00pj-9650000000-e6462e60e7ab620364b5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-DHOME 40V, Positive-QTOF	splash10-0apl-9200000000-bd2c48bf7ac9bd897d4a	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00502 +/- 0.00019 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.0166 (0.00440 - 0.0287) uM	Adult (>18 years old)	Not Specified	Normal	18953024	details
Blood	Detected and Quantified	0.00769 +/- 0.00059 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.00582 +/- 0.003 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00062 +/- 0.00044 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	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB023416

KNApSAcK ID

Not Available

Chemspider ID

26324122

KEGG Compound ID

C14829

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25320870

PDB ID

Not Available

ChEBI ID

72665

Food Biomarker Ontology

Not Available

VMH ID

CE2049

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lecka-Czernik B, Moerman EJ, Grant DF, Lehmann JM, Manolagas SC, Jilka RL: Divergent effects of selective peroxisome proliferator-activated receptor-gamma 2 ligands on adipocyte versus osteoblast differentiation. Endocrinology. 2002 Jun;143(6):2376-84. [PubMed:12021203 ]
Ha J, Dobretsov M, Kurten RC, Grant DF, Stimers JR: Effect of linoleic acid metabolites on Na(+)/K(+) pump current in N20.1 oligodendrocytes: role of membrane fluidity. Toxicol Appl Pharmacol. 2002 Jul 1;182(1):76-83. [PubMed:12127265 ]
Thompson DA, Hammock BD: Dihydroxyoctadecamonoenoate esters inhibit the neutrophil respiratory burst. J Biosci. 2007 Mar;32(2):279-91. [PubMed:17435320 ]

Showing metabocard for 12,13-DHOME (HMDB0004705)

MOL for HMDB0004705 (12,13-DHOME)

3D MOL for HMDB0004705 (12,13-DHOME)

3D SDF for HMDB0004705 (12,13-DHOME)

3D-SDF for HMDB0004705 (12,13-DHOME)

PDB for HMDB0004705 (12,13-DHOME)

3D PDB for HMDB0004705 (12,13-DHOME)

SMILES for HMDB0004705 (12,13-DHOME)

INCHI for HMDB0004705 (12,13-DHOME)

Structure for HMDB0004705 (12,13-DHOME)

3D Structure for HMDB0004705 (12,13-DHOME)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra