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 | CCCCC\C=C/C=C/[C@@H](O)CCCCCCCC(O)=O 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 |
---|
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 |
| Show more...
---|
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 | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
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 | | Show more...
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative 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 |
| Show more...
---|
Spectra |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - alpha-Dimorphecolic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udi-4930000000-e1186c721ea6fb1169c7 | 2017-08-28 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - alpha-Dimorphecolic acid GC-MS (2 TMS) - 70eV, Positive | splash10-00b9-9133100000-615fce6d28e837fb087e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - alpha-Dimorphecolic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Dimorphecolic acid 10V, Positive-QTOF | splash10-004j-0090000000-9edfb0d1ce954a62c742 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Dimorphecolic acid 20V, Positive-QTOF | splash10-003r-6590000000-bf044894de0d32745a88 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Dimorphecolic acid 40V, Positive-QTOF | splash10-0536-9210000000-3859d2d1305a9293e4ce | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Dimorphecolic acid 10V, Negative-QTOF | splash10-0002-0090000000-cb87e5a91d0ade94a4da | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Dimorphecolic acid 20V, Negative-QTOF | splash10-002b-1290000000-b10feffea7912d994743 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Dimorphecolic acid 40V, Negative-QTOF | splash10-0a4i-9620000000-a030dd65d92c57156f49 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Dimorphecolic acid 10V, Negative-QTOF | splash10-0002-0090000000-ac1c086be68f1b68836b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Dimorphecolic acid 20V, Negative-QTOF | splash10-002b-0190000000-8b6429d79d5d2e8d903d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Dimorphecolic acid 40V, Negative-QTOF | splash10-05ox-7970000000-39d40a54c2868e155bbe | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Dimorphecolic acid 10V, Positive-QTOF | splash10-004i-1390000000-84c6212593eb31771c8e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Dimorphecolic acid 20V, Positive-QTOF | splash10-08j0-6930000000-7d820298630f06567efd | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Dimorphecolic acid 40V, Positive-QTOF | splash10-0api-9100000000-0659e7446120fadecc13 | 2021-09-23 | Wishart Lab | View Spectrum |
| Show more...
---|
Biological Properties |
---|
Cellular Locations | |
---|
Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
|
---|
Tissue Locations | |
---|
Pathways | |
---|
Normal Concentrations |
---|
| |
Blood | Detected and Quantified | 0.0068 +/- 0.00167 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.00965 +/- 0.00278 uM | Adult (>18 years old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 0.0117 +/- 0.00023 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.011 +/- 0.0061 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.0065 +/- 0.00064 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details |
| Show more...
---|
Abnormal Concentrations |
---|
| |
Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | 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 | |
---|
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 ]
|
---|