Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 20:44:51 UTC |
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Update Date | 2022-03-07 02:54:36 UTC |
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HMDB ID | HMDB0035732 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Dukunolide D |
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Description | Dukunolide D belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Dukunolide D is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, dukunolide D has been detected, but not quantified in, fruits. This could make dukunolide D a potential biomarker for the consumption of these foods. |
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Structure | CC12OC(=O)CC1C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C1 InChI=1S/C26H28O8/c1-22(2)15-10-16(27)34-24(15,4)26(31)18-17-13(11-25(26,30)21(22)29)6-5-8-23(17,3)19(33-20(18)28)14-7-9-32-12-14/h6-7,9,12,15,19,30-31H,5,8,10-11H2,1-4H3 |
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Synonyms | Value | Source |
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(+)-Dukunolide D | HMDB | 1,1'-Dimethyl-2,2'-oxydiethyl dibenzoate | HMDB | Dipropylene glycol dibenzoate | HMDB | Oxydipropane-1,2-diyl dibenzoate | HMDB | Propanol, oxybis-, dibenzoate | HMDB |
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Chemical Formula | C26H28O8 |
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Average Molecular Weight | 468.4957 |
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Monoisotopic Molecular Weight | 468.178417872 |
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IUPAC Name | 17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione |
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Traditional Name | 17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione |
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CAS Registry Number | 101560-02-5 |
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SMILES | CC12OC(=O)CC1C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C1 |
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InChI Identifier | InChI=1S/C26H28O8/c1-22(2)15-10-16(27)34-24(15,4)26(31)18-17-13(11-25(26,30)21(22)29)6-5-8-23(17,3)19(33-20(18)28)14-7-9-32-12-14/h6-7,9,12,15,19,30-31H,5,8,10-11H2,1-4H3 |
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InChI Key | WUQGZJQZKDLECQ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Naphthopyrans |
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Sub Class | Not Available |
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Direct Parent | Naphthopyrans |
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Alternative Parents | |
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Substituents | - Naphthopyran
- Naphthofuran
- Naphthalene
- Dihydropyranone
- Dicarboxylic acid or derivatives
- Gamma butyrolactone
- Pyran
- Cyclic alcohol
- Furan
- Heteroaromatic compound
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tertiary alcohol
- Tetrahydrofuran
- Lactone
- Ketone
- Carboxylic acid ester
- 1,2-diol
- Oxacycle
- Carboxylic acid derivative
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Organooxygen 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 | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 295.5 - 298 °C | 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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Dukunolide D,1TMS,isomer #1 | CC1(C)C(=O)C2(O[Si](C)(C)C)CC3=CCCC4(C)C3=C(C(=O)OC4C3=COC=C3)C2(O)C2(C)OC(=O)CC12 | 3658.7 | Semi standard non polar | 33892256 | Dukunolide D,1TMS,isomer #2 | CC1(C)C(=O)C2(O)CC3=CCCC4(C)C3=C(C(=O)OC4C3=COC=C3)C2(O[Si](C)(C)C)C2(C)OC(=O)CC12 | 3662.8 | Semi standard non polar | 33892256 | Dukunolide D,2TMS,isomer #1 | CC1(C)C(=O)C2(O[Si](C)(C)C)CC3=CCCC4(C)C3=C(C(=O)OC4C3=COC=C3)C2(O[Si](C)(C)C)C2(C)OC(=O)CC12 | 3609.3 | Semi standard non polar | 33892256 | Dukunolide D,1TBDMS,isomer #1 | CC1(C)C(=O)C2(O[Si](C)(C)C(C)(C)C)CC3=CCCC4(C)C3=C(C(=O)OC4C3=COC=C3)C2(O)C2(C)OC(=O)CC12 | 3907.0 | Semi standard non polar | 33892256 | Dukunolide D,1TBDMS,isomer #2 | CC1(C)C(=O)C2(O)CC3=CCCC4(C)C3=C(C(=O)OC4C3=COC=C3)C2(O[Si](C)(C)C(C)(C)C)C2(C)OC(=O)CC12 | 3904.1 | Semi standard non polar | 33892256 | Dukunolide D,2TBDMS,isomer #1 | CC1(C)C(=O)C2(O[Si](C)(C)C(C)(C)C)CC3=CCCC4(C)C3=C(C(=O)OC4C3=COC=C3)C2(O[Si](C)(C)C(C)(C)C)C2(C)OC(=O)CC12 | 4101.0 | Semi standard non 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 - Dukunolide D GC-MS (Non-derivatized) - 70eV, Positive | splash10-0005-8265900000-c34c57fb27d3982e3758 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dukunolide D GC-MS (2 TMS) - 70eV, Positive | splash10-0gi4-9210080000-5ea1e8a9def7bfc53f75 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dukunolide D GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dukunolide D GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dukunolide D GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dukunolide D GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dukunolide D GC-MS ("Dukunolide D,1TMS,#2" TMS) - 70eV, Positive | Not Available | 2021-10-14 | 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 - Dukunolide D 10V, Positive-QTOF | splash10-014i-0000900000-05fe7f8d93d043bf3433 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dukunolide D 20V, Positive-QTOF | splash10-0uxr-0000900000-6fdaa93c85af22bc5e1c | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dukunolide D 40V, Positive-QTOF | splash10-00kk-9501000000-2a02a2ad319d0a5f3dd4 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dukunolide D 10V, Negative-QTOF | splash10-01b9-0000900000-8b9d04d5395dfda91981 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dukunolide D 20V, Negative-QTOF | splash10-01b9-1001900000-8eeebfd2f38b366c0b46 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dukunolide D 40V, Negative-QTOF | splash10-0006-9406200000-9bbd100d16ee7179b3c1 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dukunolide D 10V, Positive-QTOF | splash10-014i-0000900000-cc33c2bebaeb72d73a58 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dukunolide D 20V, Positive-QTOF | splash10-0gdi-0100900000-8a3998899426dbf3542a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dukunolide D 40V, Positive-QTOF | splash10-0007-5491400000-57a12129d86a786ec452 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dukunolide D 10V, Negative-QTOF | splash10-014i-0000900000-7dccc54e01e7cdbb03b9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dukunolide D 20V, Negative-QTOF | splash10-014i-0000900000-9e5d2ae0d9d409a74039 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dukunolide D 40V, Negative-QTOF | splash10-01dj-7079600000-fbb87fc0e88f252b9485 | 2021-09-22 | Wishart Lab | View Spectrum |
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