Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-09 16:05:06 UTC |
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Update Date | 2021-09-14 15:46:16 UTC |
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HMDB ID | HMDB0060883 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 7-Hydroxy-R-acenocoumarol |
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Description | 7-Hydroxy-R-acenocoumarol belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. It is a derivative of coumarin and is marketed under the brand names Sintrom and Sinthrome. 7-Hydroxy-R-acenocoumarol is an extremely weak basic (essentially neutral) compound (based on its pKa). 7-Hydroxy-R-acenocoumarol is a metabolite of acenocoumarol. Acenocoumarol is an anticoagulant that functions as a vitamin K antagonist. |
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Structure | CC(=O)C[C@@H](C1=CC=C(C=C1)N(=O)=O)C1=C(O)C2=C(OC1=O)C=C(O)C=C2 InChI=1S/C19H15NO7/c1-10(21)8-15(11-2-4-12(5-3-11)20(25)26)17-18(23)14-7-6-13(22)9-16(14)27-19(17)24/h2-7,9,15,22-23H,8H2,1H3/t15-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C19H15NO7 |
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Average Molecular Weight | 369.3249 |
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Monoisotopic Molecular Weight | 369.084851839 |
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IUPAC Name | 4,7-dihydroxy-3-[(1S)-1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one |
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Traditional Name | 4,7-dihydroxy-3-[(1S)-1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)C[C@@H](C1=CC=C(C=C1)N(=O)=O)C1=C(O)C2=C(OC1=O)C=C(O)C=C2 |
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InChI Identifier | InChI=1S/C19H15NO7/c1-10(21)8-15(11-2-4-12(5-3-11)20(25)26)17-18(23)14-7-6-13(22)9-16(14)27-19(17)24/h2-7,9,15,22-23H,8H2,1H3/t15-/m0/s1 |
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InChI Key | JTCREUDLEYTCAB-HNNXBMFYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Coumarins and derivatives |
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Sub Class | Hydroxycoumarins |
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Direct Parent | 7-hydroxycoumarins |
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Alternative Parents | |
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Substituents | - 4-hydroxycoumarin
- 7-hydroxycoumarin
- Benzopyran
- 1-benzopyran
- Nitrobenzene
- Nitroaromatic compound
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- Monocyclic benzene moiety
- Pyran
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Organic nitro compound
- Ketone
- Lactone
- C-nitro compound
- Propargyl-type 1,3-dipolar organic compound
- Allyl-type 1,3-dipolar organic compound
- Organoheterocyclic compound
- Oxacycle
- Organic 1,3-dipolar compound
- Organic oxoazanium
- Organic oxygen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Carbonyl group
- Organic oxide
- Organopnictogen compound
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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7-Hydroxy-R-acenocoumarol,1TMS,isomer #1 | CC(=O)C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=C(O)C=C2OC1=O | 3327.8 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,1TMS,isomer #2 | CC(=O)C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=C(O[Si](C)(C)C)C=C2OC1=O | 3360.8 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,1TMS,isomer #3 | CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=C(O)C=C2OC1=O)O[Si](C)(C)C | 3400.5 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,1TMS,isomer #4 | C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=C(O)C=C2OC1=O)O[Si](C)(C)C | 3386.1 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,2TMS,isomer #1 | CC(=O)C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2OC1=O | 3381.8 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,2TMS,isomer #2 | CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=C(O)C=C2OC1=O)O[Si](C)(C)C | 3344.0 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,2TMS,isomer #3 | C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=C(O)C=C2OC1=O)O[Si](C)(C)C | 3338.2 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,2TMS,isomer #4 | CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=C(O[Si](C)(C)C)C=C2OC1=O)O[Si](C)(C)C | 3430.4 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,2TMS,isomer #5 | C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=C(O[Si](C)(C)C)C=C2OC1=O)O[Si](C)(C)C | 3392.1 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,3TMS,isomer #1 | CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2OC1=O)O[Si](C)(C)C | 3442.8 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,3TMS,isomer #1 | CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2OC1=O)O[Si](C)(C)C | 3253.4 | Standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,3TMS,isomer #1 | CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2OC1=O)O[Si](C)(C)C | 3785.4 | Standard polar | 33892256 | 7-Hydroxy-R-acenocoumarol,3TMS,isomer #2 | C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2OC1=O)O[Si](C)(C)C | 3419.1 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,3TMS,isomer #2 | C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2OC1=O)O[Si](C)(C)C | 3092.8 | Standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,3TMS,isomer #2 | C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2OC1=O)O[Si](C)(C)C | 3785.3 | Standard polar | 33892256 | 7-Hydroxy-R-acenocoumarol,1TBDMS,isomer #1 | CC(=O)C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C2OC1=O | 3588.9 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,1TBDMS,isomer #2 | CC(=O)C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O | 3622.5 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,1TBDMS,isomer #3 | CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=C(O)C=C2OC1=O)O[Si](C)(C)C(C)(C)C | 3692.5 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,1TBDMS,isomer #4 | C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=C(O)C=C2OC1=O)O[Si](C)(C)C(C)(C)C | 3666.5 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,2TBDMS,isomer #1 | CC(=O)C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O | 3879.2 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,2TBDMS,isomer #2 | CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C2OC1=O)O[Si](C)(C)C(C)(C)C | 3883.4 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,2TBDMS,isomer #3 | C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C2OC1=O)O[Si](C)(C)C(C)(C)C | 3863.6 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,2TBDMS,isomer #4 | CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O)O[Si](C)(C)C(C)(C)C | 3974.0 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,2TBDMS,isomer #5 | C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O)O[Si](C)(C)C(C)(C)C | 3920.4 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,3TBDMS,isomer #1 | CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O)O[Si](C)(C)C(C)(C)C | 4196.2 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,3TBDMS,isomer #1 | CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O)O[Si](C)(C)C(C)(C)C | 3889.4 | Standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,3TBDMS,isomer #1 | CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O)O[Si](C)(C)C(C)(C)C | 3922.2 | Standard polar | 33892256 | 7-Hydroxy-R-acenocoumarol,3TBDMS,isomer #2 | C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O)O[Si](C)(C)C(C)(C)C | 4157.7 | Semi standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,3TBDMS,isomer #2 | C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O)O[Si](C)(C)C(C)(C)C | 3701.1 | Standard non polar | 33892256 | 7-Hydroxy-R-acenocoumarol,3TBDMS,isomer #2 | C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O)O[Si](C)(C)C(C)(C)C | 3928.0 | Standard polar | 33892256 |
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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 - 7-Hydroxy-R-acenocoumarol GC-MS (Non-derivatized) - 70eV, Positive | splash10-03dl-3219000000-da88ab03b39416dbb29b | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 7-Hydroxy-R-acenocoumarol GC-MS (2 TMS) - 70eV, Positive | splash10-0007-4130900000-fd3b87a52f6024a2836f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 7-Hydroxy-R-acenocoumarol 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 |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7-Hydroxy-R-acenocoumarol 10V, Positive-QTOF | splash10-0fk9-0009000000-a7d1a5bfb6eb7eb8c1ca | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7-Hydroxy-R-acenocoumarol 20V, Positive-QTOF | splash10-0ul0-0009000000-9a9ec37447fec43d2352 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7-Hydroxy-R-acenocoumarol 40V, Positive-QTOF | splash10-00ei-3917000000-18bd160fd57bc55c299e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7-Hydroxy-R-acenocoumarol 10V, Negative-QTOF | splash10-0gb9-0009000000-f0c057dc31a38298f94d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7-Hydroxy-R-acenocoumarol 20V, Negative-QTOF | splash10-00or-1409000000-d8c3784d630852f81cc5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7-Hydroxy-R-acenocoumarol 40V, Negative-QTOF | splash10-0a4i-7913000000-f0e1604a582357b4ce99 | 2017-10-06 | Wishart Lab | View Spectrum |
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