Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-11 08:54:50 UTC |
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Update Date | 2021-09-26 23:03:36 UTC |
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HMDB ID | HMDB0251549 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | Vadimezan |
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Description | Vadimezan, also known as 5,6-mexaa or AS 1404, belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. ASA404 (DMXAA) is a small-molecule vascular disrupting agent which targets the blood vessels that nourish tumours. Vadimezan is an extremely weak basic (essentially neutral) compound (based on its pKa). Vasoactive mediators such as tumor necrosis factor (TNF) may also be implicated. Increased permeability of tumor cell vasculature may allow increased permeation of anticancer treatments such as cytotoxic drugs, antibodies, drug conjugates and gene therapy. The proposed mechanism of action for ASA404 is directly increasing permeability of the tumor's endothelial cells. This compound has been identified in human blood as reported by (PMID: 31557052 ). Vadimezan is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Vadimezan is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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Structure | CC1=C(C)C2=C(C=C1)C(=O)C1=CC=CC(CC(O)=O)=C1O2 InChI=1S/C17H14O4/c1-9-6-7-13-15(20)12-5-3-4-11(8-14(18)19)17(12)21-16(13)10(9)2/h3-7H,8H2,1-2H3,(H,18,19) |
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Synonyms | Value | Source |
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(5,6-Dimethyl-9-oxoxanthen-4-yl)acetic acid | ChEBI | 5,6-Dimethyl-9-oxo-9H-xanthene-4-acetic acid | ChEBI | 5,6-Dimethylxanthenone-4-acetic acid | ChEBI | 5,6-Dimethylxanthenoneacetic acid | ChEBI | 5,6-MeXAA | ChEBI | AS 1404 | ChEBI | AS-1404 | ChEBI | Dimethyloxoxanthene acetic acid | ChEBI | NSC 640488 | ChEBI | Vadimezanum | ChEBI | (5,6-Dimethyl-9-oxoxanthen-4-yl)acetate | Generator | 5,6-Dimethyl-9-oxo-9H-xanthene-4-acetate | Generator | 5,6-Dimethylxanthenone-4-acetate | Generator | 5,6-Dimethylxanthenoneacetate | Generator | Dimethyloxoxanthene acetate | Generator | ASA-404 | MeSH | 5,6-Dimethylxanthenoneacetic acid, sodium salt | MeSH | ASA 404 | MeSH | 5,6-Dimethyl xanthenone acetic acid | MeSH | 2-(5,6-Dimethyl-9-oxo-9H-xanthen-4-yl)acetate | Generator | Vadimezan | MeSH |
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Chemical Formula | C17H14O4 |
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Average Molecular Weight | 282.2907 |
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Monoisotopic Molecular Weight | 282.089208936 |
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IUPAC Name | 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetic acid |
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Traditional Name | vadimezan |
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CAS Registry Number | Not Available |
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SMILES | CC1=C(C)C2=C(C=C1)C(=O)C1=CC=CC(CC(O)=O)=C1O2 |
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InChI Identifier | InChI=1S/C17H14O4/c1-9-6-7-13-15(20)12-5-3-4-11(8-14(18)19)17(12)21-16(13)10(9)2/h3-7H,8H2,1-2H3,(H,18,19) |
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InChI Key | XGOYIMQSIKSOBS-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzopyrans |
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Sub Class | 1-benzopyrans |
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Direct Parent | Xanthones |
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Alternative Parents | |
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Substituents | - Xanthone
- Chromone
- Pyranone
- Pyran
- Benzenoid
- Heteroaromatic compound
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Oxacycle
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Vadimezan GC-MS (Non-derivatized) - 70eV, Positive | splash10-000i-1590000000-d4efa2ba1592bc477025 | 2017-08-28 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Vadimezan GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Vadimezan GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Vadimezan GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vadimezan 10V, Positive-QTOF | splash10-00lr-0090000000-71bb93a6d50c24e356d5 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vadimezan 20V, Positive-QTOF | splash10-000i-0090000000-a3673e1da5352e6bdb54 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vadimezan 40V, Positive-QTOF | splash10-06ri-9260000000-f980944812e96d4fe239 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vadimezan 10V, Negative-QTOF | splash10-001r-0090000000-1455ab7323abbdbd8177 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vadimezan 20V, Negative-QTOF | splash10-0019-1090000000-0189efd89d0cbaf2f9ee | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vadimezan 40V, Negative-QTOF | splash10-0kmr-5790000000-bc847bc1b3e8c194abf6 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vadimezan 10V, Positive-QTOF | splash10-0159-0090000000-1d849ba5ea2b160d11d5 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vadimezan 20V, Positive-QTOF | splash10-000i-0090000000-df0ce6dc9c1a64a9d774 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vadimezan 40V, Positive-QTOF | splash10-0pbi-2960000000-31d7cd2b322c340ec685 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vadimezan 10V, Negative-QTOF | splash10-000i-0090000000-5fed5dd8afcf2a250ae8 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vadimezan 20V, Negative-QTOF | splash10-000i-0090000000-264165165bc48fe0c5b4 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vadimezan 40V, Negative-QTOF | splash10-0kmr-0980000000-9dd30c2643f6ffed38af | 2021-10-12 | Wishart Lab | View Spectrum |
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