Record Information |
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Version | 1.0 |
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Created at | 2022-09-09 22:13:08 UTC |
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Updated at | 2022-09-09 22:13:08 UTC |
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NP-MRD ID | NP0291212 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 11-hydroxy-1-[2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate |
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Description | 16-Hydroxy-14-[2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-3-en-9-yl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate 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. 11-hydroxy-1-[2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is found in Azadirachta indica. 16-Hydroxy-14-[2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-3-en-9-yl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | COC1=CC(C=CC(=O)OC2CC3C(C)(C)C(=O)C=CC3(C)C3CC(O)C4(C)C(CCC4C23C)C2CC(CO)OC2O)=CC=C1O InChI=1S/C37H50O9/c1-34(2)27-18-31(46-32(42)12-8-20-7-10-24(39)25(15-20)44-6)37(5)26-11-9-23(22-16-21(19-38)45-33(22)43)36(26,4)30(41)17-28(37)35(27,3)14-13-29(34)40/h7-8,10,12-15,21-23,26-28,30-31,33,38-39,41,43H,9,11,16-19H2,1-6H3 |
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Synonyms | Value | Source |
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16-Hydroxy-14-[2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadec-3-en-9-yl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid | Generator | 16-Hydroxy-14-[2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-9-yl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid | Generator |
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Chemical Formula | C37H50O9 |
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Average Mass | 638.7980 Da |
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Monoisotopic Mass | 638.34548 Da |
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IUPAC Name | 16-hydroxy-14-[2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-9-yl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate |
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Traditional Name | 16-hydroxy-14-[2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-9-yl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC(C=CC(=O)OC2CC3C(C)(C)C(=O)C=CC3(C)C3CC(O)C4(C)C(CCC4C23C)C2CC(CO)OC2O)=CC=C1O |
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InChI Identifier | InChI=1S/C37H50O9/c1-34(2)27-18-31(46-32(42)12-8-20-7-10-24(39)25(15-20)44-6)37(5)26-11-9-23(22-16-21(19-38)45-33(22)43)36(26,4)30(41)17-28(37)35(27,3)14-13-29(34)40/h7-8,10,12-15,21-23,26-28,30-31,33,38-39,41,43H,9,11,16-19H2,1-6H3 |
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InChI Key | JBNMGQJPHZENKR-UHFFFAOYSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| 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 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 | - Limonoid skeleton
- 24-hydroxysteroid
- Steroid ester
- Androgen-skeleton
- Androstane-skeleton
- 3-oxo-delta-1-steroid
- Hydroxysteroid
- 12-hydroxysteroid
- Oxosteroid
- 3-oxosteroid
- Delta-1-steroid
- Steroid
- Coumaric acid or derivatives
- Cinnamic acid ester
- Cinnamic acid or derivatives
- Hydroxycinnamic acid or derivatives
- Methoxyphenol
- Phenoxy compound
- Methoxybenzene
- Anisole
- Phenol ether
- Styrene
- Cyclohexenone
- Alkyl aryl ether
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Monocyclic benzene moiety
- Enoate ester
- Cyclic alcohol
- Alpha,beta-unsaturated carboxylic ester
- Tetrahydrofuran
- Cyclic ketone
- Secondary alcohol
- Carboxylic acid ester
- Ketone
- Hemiacetal
- Carboxylic acid derivative
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Ether
- Oxacycle
- Primary alcohol
- Alcohol
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- 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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