Record Information |
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Version | 1.0 |
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Created at | 2022-03-17 20:47:23 UTC |
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Updated at | 2022-03-17 20:47:24 UTC |
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NP-MRD ID | NP0047875 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Bullatacinone |
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Description | 2,4-Cis-Trilobacinone, also known as bullatacinone or 2,4-trans-asimicinone, 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. 2,4-Cis-Trilobacinone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2,4-cis-Trilobacinone has been detected, but not quantified in, fruits. Bullatacinone is found in Annona bullata, Annona cherimola, Annona squamosa , Asimina triloba , Annona rensoniana and Rollinia papilionella. It was first documented in 2000 (PMID: 11413487). This could make 2,4-cis-trilobacinone a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567). |
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Structure | CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCC1CC(CC(C)=O)C(=O)O1 InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30-27-29(26-28(2)38)37(41)42-30/h29-36,39-40H,3-27H2,1-2H3 |
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Synonyms | Value | Source |
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2,4-cis-Asimicinone | HMDB | Bullatacinone | HMDB | 2,4-trans-Asimicinone | HMDB | Asimicinone | HMDB | Rollinone | MeSH |
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Chemical Formula | C37H66O7 |
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Average Mass | 622.9157 Da |
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Monoisotopic Mass | 622.48085 Da |
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IUPAC Name | 5-(11-hydroxy-11-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-3-(2-oxopropyl)oxolan-2-one |
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Traditional Name | 5-(11-hydroxy-11-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-3-(2-oxopropyl)oxolan-2-one |
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CAS Registry Number | 189686-30-4 |
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SMILES | CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCC1CC(CC(C)=O)C(=O)O1 |
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InChI Identifier | InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30-27-29(26-28(2)38)37(41)42-30/h29-36,39-40H,3-27H2,1-2H3 |
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InChI Key | KGGVWMAPBXIMEM-UHFFFAOYSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty alcohols |
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Direct Parent | Annonaceous acetogenins |
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Alternative Parents | |
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Substituents | - Annonaceae acetogenin skeleton
- Long chain fatty alcohol
- Gamma butyrolactone
- Tetrahydrofuran
- Carboxylic acid ester
- Ketone
- Lactone
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- Alcohol
- Organooxygen compound
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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