Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2012-09-11 18:21:16 UTC |
---|
Update Date | 2022-03-07 02:53:47 UTC |
---|
HMDB ID | HMDB0033607 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Artemoin D |
---|
Description | Artemoin D belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Based on a literature review a significant number of articles have been published on Artemoin D. |
---|
Structure | CCCCCCCCCCCCCCCCC(O)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O InChI=1S/C35H66O4/c1-3-4-5-6-7-8-9-10-11-12-16-19-22-25-28-33(36)34(37)29-26-23-20-17-14-13-15-18-21-24-27-32-30-31(2)39-35(32)38/h30-31,33-34,36-37H,3-29H2,1-2H3 |
---|
Synonyms | Value | Source |
---|
3-(13,14-Dihydroxytriacontyl)-5-methyl-2(5H)-furanone | HMDB |
|
---|
Chemical Formula | C35H66O4 |
---|
Average Molecular Weight | 550.8961 |
---|
Monoisotopic Molecular Weight | 550.4961106 |
---|
IUPAC Name | 3-(13,14-dihydroxytriacontyl)-5-methyl-2,5-dihydrofuran-2-one |
---|
Traditional Name | 3-(13,14-dihydroxytriacontyl)-5-methyl-5H-furan-2-one |
---|
CAS Registry Number | Not Available |
---|
SMILES | CCCCCCCCCCCCCCCCC(O)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O |
---|
InChI Identifier | InChI=1S/C35H66O4/c1-3-4-5-6-7-8-9-10-11-12-16-19-22-25-28-33(36)34(37)29-26-23-20-17-14-13-15-18-21-24-27-32-30-31(2)39-35(32)38/h30-31,33-34,36-37H,3-29H2,1-2H3 |
---|
InChI Key | CAGLXILDKKCMCR-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Fatty Acyls |
---|
Sub Class | Fatty alcohols |
---|
Direct Parent | Annonaceous acetogenins |
---|
Alternative Parents | |
---|
Substituents | - Annonaceae acetogenin skeleton
- Long chain fatty alcohol
- 2-furanone
- Dihydrofuran
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Lactone
- 1,2-diol
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organoheterocyclic compound
- Oxacycle
- Alcohol
- Organooxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- Aliphatic heteromonocyclic compound
|
---|
Molecular Framework | Aliphatic heteromonocyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | |
---|
Role | |
---|
Physical Properties |
---|
State | Not Available |
---|
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 | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
Artemoin D,1TMS,isomer #1 | CCCCCCCCCCCCCCCCC(O[Si](C)(C)C)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O | 4187.6 | Semi standard non polar | 33892256 | Artemoin D,1TMS,isomer #2 | CCCCCCCCCCCCCCCCC(O)C(CCCCCCCCCCCCC1=CC(C)OC1=O)O[Si](C)(C)C | 4187.4 | Semi standard non polar | 33892256 | Artemoin D,2TMS,isomer #1 | CCCCCCCCCCCCCCCCC(O[Si](C)(C)C)C(CCCCCCCCCCCCC1=CC(C)OC1=O)O[Si](C)(C)C | 4118.8 | Semi standard non polar | 33892256 | Artemoin D,1TBDMS,isomer #1 | CCCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O | 4445.1 | Semi standard non polar | 33892256 | Artemoin D,1TBDMS,isomer #2 | CCCCCCCCCCCCCCCCC(O)C(CCCCCCCCCCCCC1=CC(C)OC1=O)O[Si](C)(C)C(C)(C)C | 4444.9 | Semi standard non polar | 33892256 | Artemoin D,2TBDMS,isomer #1 | CCCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(CCCCCCCCCCCCC1=CC(C)OC1=O)O[Si](C)(C)C(C)(C)C | 4626.5 | Semi standard non polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin D GC-MS (Non-derivatized) - 70eV, Positive | splash10-0pc1-2190110000-301424c6108cda5dd00a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin D GC-MS (2 TMS) - 70eV, Positive | splash10-004i-8706809000-b97157c9ce2088a19f13 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin D GC-MS ("Artemoin D,1TMS,#1" TMS) - 70eV, Positive | Not Available | 2021-10-14 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin D GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin D GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin D GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin D GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin D GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin D 10V, Positive-QTOF | splash10-0udi-0010190000-94dccb7dae160e54d615 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin D 20V, Positive-QTOF | splash10-016r-2490130000-39adfbcfaa9e52a6b6f6 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin D 40V, Positive-QTOF | splash10-004i-3960200000-966316d44cff4ed699fa | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin D 10V, Negative-QTOF | splash10-0002-0010090000-655a18c3d9e8bf700bd8 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin D 20V, Negative-QTOF | splash10-052b-1090060000-dc6a25f5f71586fe4352 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin D 40V, Negative-QTOF | splash10-0kcr-2090000000-6ac706b6299a162fc9a8 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin D 10V, Positive-QTOF | splash10-0159-1020190000-218716ec151cd2ba60e1 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin D 20V, Positive-QTOF | splash10-0f89-2000190000-8206749ededec3b55b1c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin D 40V, Positive-QTOF | splash10-052f-9001000000-02b7c1be001b562672e5 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin D 10V, Negative-QTOF | splash10-0002-0013090000-728d172cb2bfe65016f3 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin D 20V, Negative-QTOF | splash10-0002-2062090000-2be9f3ebd341812d05a9 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin D 40V, Negative-QTOF | splash10-054n-3291010000-8acac13b2e68f1b4417a | 2021-09-25 | Wishart Lab | View Spectrum |
|
---|
General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
|
---|