| Record Information |
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| Version | 2.0 |
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| Created at | 2021-06-20 21:37:08 UTC |
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| Updated at | 2021-06-30 00:12:14 UTC |
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| NP-MRD ID | NP0039093 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | xylomexicanolide B |
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| Provided By | JEOL Database |
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| Description | Xylomexicanolide B belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. xylomexicanolide B is found in Xylocarpus moluccensis. xylomexicanolide B was first documented in 2010 (Zhang, J., et al.). Based on a literature review very few articles have been published on Xylomexicanolide B. |
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| Structure | [H]C1=C([H])C(=C([H])O1)[C@]1([H])OC(=O)C([H])=C2C3=C(C([H])([H])C([H])([H])[C@@]12C([H])([H])[H])[C@]1(C(=O)[C@@]([H])(C3([H])[H])[C@@]([H])(OC(=O)C([H])(C([H])([H])[H])C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]1([H])C([H])([H])C(=O)OC([H])([H])[H])C([H])([H])[H] InChI=1S/C31H38O8/c1-16(2)28(35)39-27-19-12-18-20(31(6,25(19)34)22(29(27,3)4)14-23(32)36-7)8-10-30(5)21(18)13-24(33)38-26(30)17-9-11-37-15-17/h9,11,13,15-16,19,22,26-27H,8,10,12,14H2,1-7H3/t19-,22+,26+,27-,30-,31-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C31H38O8 |
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| Average Mass | 538.6370 Da |
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| Monoisotopic Mass | 538.25667 Da |
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| IUPAC Name | (1S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadeca-2(11),9-dien-14-yl 2-methylpropanoate |
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| Traditional Name | (1S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadeca-2(11),9-dien-14-yl 2-methylpropanoate |
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| CAS Registry Number | Not Available |
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| SMILES | [H]C1=C([H])C(=C([H])O1)[C@]1([H])OC(=O)C([H])=C2C3=C(C([H])([H])C([H])([H])[C@@]12C([H])([H])[H])[C@]1(C(=O)[C@@]([H])(C3([H])[H])[C@@]([H])(OC(=O)C([H])(C([H])([H])[H])C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]1([H])C([H])([H])C(=O)OC([H])([H])[H])C([H])([H])[H] |
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| InChI Identifier | InChI=1S/C31H38O8/c1-16(2)28(35)39-27-19-12-18-20(31(6,25(19)34)22(29(27,3)4)14-23(32)36-7)8-10-30(5)21(18)13-24(33)38-26(30)17-9-11-37-15-17/h9,11,13,15-16,19,22,26-27H,8,10,12,14H2,1-7H3/t19-,22+,26+,27-,30-,31-/m1/s1 |
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| InChI Key | GYYAKSJMMOLBCO-BLXBAJQHSA-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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| 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | 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 | | Species Name | Source | Reference |
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| Xylocarpus moluccensis | JEOL database | - Zhang, J., et al, Chem. Pharm. Bull. 58, 552(2010)
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. |
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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 | Triterpenoids |
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| Direct Parent | Limonoids |
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| Alternative Parents | |
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| Substituents | - Mexicanolide
- Limonoid skeleton
- Naphthopyran
- Naphthalene
- Tricarboxylic acid or derivatives
- Cyclohexenone
- Dihydropyranone
- Pyran
- Heteroaromatic compound
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Methyl ester
- Furan
- Lactone
- Ketone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- 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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| 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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