| Record Information |
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| Version | 2.0 |
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| Created at | 2024-06-25 12:20:40 UTC |
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| Updated at | 2024-09-03 04:22:44 UTC |
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| NP-MRD ID | NP0333509 |
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| Natural Product DOI | https://doi.org/10.57994/2963 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Carabrolate I |
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| Description | Carabrolate I, also known as carabrolic acid I, belongs to the class of organic compounds known as xanthanolides. These are sesquiterpenoids with a structure based on the xanthanolide skeleton consistsing of a cycloheptane ring usually attached to a four-carbon chain (at carbon 1 ) and a methyl group (at carbon 10), and fused to a five-member lactone ring (sharing carbons 7 and 8). The lactone ring can be conjugated with a methyl or methylene group at position 11. Based on a literature review very few articles have been published on Carabrolate I. |
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| Structure | [H][C@@]12C[C@]3([H])C(=C)C(=O)O[C@]3([H])C[C@]1(C)C2CC[C@@H](C)OC(=O)C[C@@H](O)CCCCCCCCCCCCCC InChI=1S/C32H54O5/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-25(33)20-30(34)36-23(2)18-19-27-28-21-26-24(3)31(35)37-29(26)22-32(27,28)4/h23,25-29,33H,3,5-22H2,1-2,4H3/t23-,25+,26-,27?,28+,29-,32-/m1/s1 |
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| Synonyms | | Value | Source |
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| Carabrolic acid I | Generator |
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| Chemical Formula | C32H54O5 |
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| Average Mass | 518.7790 Da |
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| Monoisotopic Mass | 518.39712 Da |
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| IUPAC Name | (2R)-4-[(1R,3S,5R,7R)-5-methyl-10-methylidene-9-oxo-8-oxatricyclo[5.3.0.0^{3,5}]decan-4-yl]butan-2-yl (3S)-3-hydroxyheptadecanoate |
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| Traditional Name | (2R)-4-[(1R,3S,5R,7R)-5-methyl-10-methylidene-9-oxo-8-oxatricyclo[5.3.0.0^{3,5}]decan-4-yl]butan-2-yl (3S)-3-hydroxyheptadecanoate |
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| CAS Registry Number | Not Available |
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| SMILES | [H][C@@]12C[C@]3([H])C(=C)C(=O)O[C@]3([H])C[C@]1(C)C2CC[C@@H](C)OC(=O)C[C@@H](O)CCCCCCCCCCCCCC |
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| InChI Identifier | InChI=1S/C32H54O5/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-25(33)20-30(34)36-23(2)18-19-27-28-21-26-24(3)31(35)37-29(26)22-32(27,28)4/h23,25-29,33H,3,5-22H2,1-2,4H3/t23-,25+,26-,27?,28+,29-,32-/m1/s1 |
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| InChI Key | YHYPVIBHTXXRRX-KFBXYJQZSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | lufu_kclz110@126.com | 20081993fulu | Lu Fu | 2024-06-25 | View Spectrum | | NOESY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | lufu_kclz110@126.com | 20081993fulu | Lu Fu | 2024-06-25 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | lufu_kclz110@126.com | 20081993fulu | Lu Fu | 2024-06-25 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | lufu_kclz110@126.com | 20081993fulu | Lu Fu | 2024-06-25 | View Spectrum | | 1D_DEPT NMR | 13C NMR Spectrum (1D, 151 MHz, CDCl3, experimental) | lufu_kclz110@126.com | 20081993fulu | Lu Fu | 2024-06-25 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, CDCl3, experimental) | lufu_kclz110@126.com | 20081993fulu | Lu Fu | 2024-06-25 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental) | lufu_kclz110@126.com | 20081993fulu | Lu Fu | 2024-06-25 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | | Species Name | Source | Reference |
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| Carpesium Carpesium. abrotanoides | | |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of organic compounds known as xanthanolides. These are sesquiterpenoids with a structure based on the xanthanolide skeleton consistsing of a cycloheptane ring usually attached to a four-carbon chain (at carbon 1 ) and a methyl group (at carbon 10), and fused to a five-member lactone ring (sharing carbons 7 and 8). The lactone ring can be conjugated with a methyl or methylene group at position 11. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Terpene lactones |
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| Direct Parent | Xanthanolides |
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| Alternative Parents | |
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| Substituents | - Xanthanolide-skeleton
- Carabrane sesquiterpenoid
- Sesquiterpenoid
- Fatty alcohol ester
- Fatty acid ester
- Beta-hydroxy acid
- Fatty acyl
- Hydroxy acid
- Gamma butyrolactone
- Dicarboxylic acid or derivatives
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic 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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