| 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 20:03:11 UTC |
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| Update Date | 2022-03-07 02:54:22 UTC |
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| HMDB ID | HMDB0035109 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Diosbulbin D |
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| Description | Diosbulbin 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. Diosbulbin D is an extremely weak basic (essentially neutral) compound (based on its pKa). Diosbulbin D is found in root vegetables and is a constituent of Dioscorea bulbifera (air potato). |
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| Structure | [H][C@]12CC(=O)[C@]3([H])[C@H]4C[C@@H](C[C@@]3([H])[C@]1(C)C[C@H](OC2=O)C1=COC=C1)OC4=O InChI=1S/C19H20O6/c1-19-7-15(9-2-3-23-8-9)25-18(22)13(19)6-14(20)16-11-4-10(5-12(16)19)24-17(11)21/h2-3,8,10-13,15-16H,4-7H2,1H3/t10-,11+,12+,13+,15-,16+,19-/m0/s1 |
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| Synonyms | | Value | Source |
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| Neodiosbulbin | HMDB | | Diosbulbin D | HMDB |
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| Chemical Formula | C19H20O6 |
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| Average Molecular Weight | 344.363 |
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| Monoisotopic Molecular Weight | 344.125988364 |
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| IUPAC Name | (1R,2S,5S,8S,10S,11R,13R)-8-(furan-3-yl)-10-methyl-7,14-dioxatetracyclo[11.2.1.0^{2,11}.0^{5,10}]hexadecane-3,6,15-trione |
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| Traditional Name | (1R,2S,5S,8S,10S,11R,13R)-8-(furan-3-yl)-10-methyl-7,14-dioxatetracyclo[11.2.1.0^{2,11}.0^{5,10}]hexadecane-3,6,15-trione |
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| CAS Registry Number | 66756-57-8 |
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| SMILES | [H][C@]12CC(=O)[C@]3([H])[C@H]4C[C@@H](C[C@@]3([H])[C@]1(C)C[C@H](OC2=O)C1=COC=C1)OC4=O |
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| InChI Identifier | InChI=1S/C19H20O6/c1-19-7-15(9-2-3-23-8-9)25-18(22)13(19)6-14(20)16-11-4-10(5-12(16)19)24-17(11)21/h2-3,8,10-13,15-16H,4-7H2,1H3/t10-,11+,12+,13+,15-,16+,19-/m0/s1 |
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| InChI Key | FJCWYLRNGKSUCH-OXIVVSFQSA-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
- Naphthalene
- Caprolactone
- Delta valerolactone
- Delta_valerolactone
- Oxepane
- Dicarboxylic acid or derivatives
- Gamma butyrolactone
- Oxane
- Pyran
- Heteroaromatic compound
- Furan
- Oxolane
- Lactone
- Ketone
- Carboxylic acid ester
- Oxacycle
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- Carbonyl group
- 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 | 229 - 230 °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 IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| Diosbulbin D,1TMS,isomer #1 | C[C@@]12C[C@@H](C3=COC=C3)OC(=O)[C@H]1CC(O[Si](C)(C)C)=C1[C@H]2C[C@@H]2C[C@H]1C(=O)O2 | 2936.0 | Semi standard non polar | 33892256 | | Diosbulbin D,1TMS,isomer #1 | C[C@@]12C[C@@H](C3=COC=C3)OC(=O)[C@H]1CC(O[Si](C)(C)C)=C1[C@H]2C[C@@H]2C[C@H]1C(=O)O2 | 2729.5 | Standard non polar | 33892256 | | Diosbulbin D,1TMS,isomer #2 | C[C@@]12C[C@@H](C3=COC=C3)OC(=O)[C@H]1C=C(O[Si](C)(C)C)[C@@H]1[C@H]3C[C@@H](C[C@H]12)OC3=O | 2888.8 | Semi standard non polar | 33892256 | | Diosbulbin D,1TMS,isomer #2 | C[C@@]12C[C@@H](C3=COC=C3)OC(=O)[C@H]1C=C(O[Si](C)(C)C)[C@@H]1[C@H]3C[C@@H](C[C@H]12)OC3=O | 2691.3 | Standard non polar | 33892256 | | Diosbulbin D,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=C2[C@@H](C[C@@H]3C[C@H]2C(=O)O3)[C@]2(C)C[C@@H](C3=COC=C3)OC(=O)[C@H]2C1 | 3186.0 | Semi standard non polar | 33892256 | | Diosbulbin D,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=C2[C@@H](C[C@@H]3C[C@H]2C(=O)O3)[C@]2(C)C[C@@H](C3=COC=C3)OC(=O)[C@H]2C1 | 2979.1 | Standard non polar | 33892256 | | Diosbulbin D,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=C[C@@H]2C(=O)O[C@H](C3=COC=C3)C[C@@]2(C)[C@@H]2C[C@@H]3C[C@@H](C(=O)O3)[C@@H]12 | 3125.8 | Semi standard non polar | 33892256 | | Diosbulbin D,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=C[C@@H]2C(=O)O[C@H](C3=COC=C3)C[C@@]2(C)[C@@H]2C[C@@H]3C[C@@H](C(=O)O3)[C@@H]12 | 2912.0 | Standard non polar | 33892256 |
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