Record Information |
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Version | 1.0 |
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Created at | 2021-06-19 22:47:02 UTC |
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Updated at | 2021-06-30 00:00:37 UTC |
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NP-MRD ID | NP0031806 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | ent-18-(E)-caffeoyloxy-8(17)-labden-15-oic acid |
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Provided By | JEOL Database |
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Description | (5Beta,9alpha,10alpha,13S)-19-[(3,4-Dihydroxy-trans-cinnamoyl)oxy]labd-8(20)-en-15-oic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. ent-18-(E)-caffeoyloxy-8(17)-labden-15-oic acid is found in Nuxia sphaerocephala. It was first documented in 2006 (Mambu, L., et al.). Based on a literature review very few articles have been published on (5beta,9alpha,10alpha,13S)-19-[(3,4-Dihydroxy-trans-cinnamoyl)oxy]labd-8(20)-en-15-oic acid. |
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Structure | [H]OC(=O)C([H])([H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@]2([H])[C@@](C([H])([H])[H])(C([H])([H])OC(=O)C(\[H])=C(/[H])C3=C([H])C(O[H])=C(O[H])C([H])=C3[H])C([H])([H])C([H])([H])C([H])([H])[C@@]12C([H])([H])[H] InChI=1S/C29H40O6/c1-19(16-26(32)33)6-10-22-20(2)7-12-25-28(3,14-5-15-29(22,25)4)18-35-27(34)13-9-21-8-11-23(30)24(31)17-21/h8-9,11,13,17,19,22,25,30-31H,2,5-7,10,12,14-16,18H2,1,3-4H3,(H,32,33)/b13-9+/t19-,22+,25+,28+,29-/m0/s1 |
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Synonyms | Value | Source |
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(5b,9a,10a,13S)-19-[(3,4-Dihydroxy-trans-cinnamoyl)oxy]labd-8(20)-en-15-Oate | Generator | (5b,9a,10a,13S)-19-[(3,4-Dihydroxy-trans-cinnamoyl)oxy]labd-8(20)-en-15-Oic acid | Generator | (5beta,9alpha,10alpha,13S)-19-[(3,4-Dihydroxy-trans-cinnamoyl)oxy]labd-8(20)-en-15-Oate | Generator | (5Β,9α,10α,13S)-19-[(3,4-dihydroxy-trans-cinnamoyl)oxy]labd-8(20)-en-15-Oate | Generator | (5Β,9α,10α,13S)-19-[(3,4-dihydroxy-trans-cinnamoyl)oxy]labd-8(20)-en-15-Oic acid | Generator |
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Chemical Formula | C29H40O6 |
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Average Mass | 484.6330 Da |
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Monoisotopic Mass | 484.28249 Da |
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IUPAC Name | (3S)-5-[(1R,4aS,5S,8aS)-5-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]-3-methylpentanoic acid |
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Traditional Name | (3S)-5-[(1R,4aS,5S,8aS)-5-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]-3-methylpentanoic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]OC(=O)C([H])([H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@]2([H])[C@@](C([H])([H])[H])(C([H])([H])OC(=O)C(\[H])=C(/[H])C3=C([H])C(O[H])=C(O[H])C([H])=C3[H])C([H])([H])C([H])([H])C([H])([H])[C@@]12C([H])([H])[H] |
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InChI Identifier | InChI=1S/C29H40O6/c1-19(16-26(32)33)6-10-22-20(2)7-12-25-28(3,14-5-15-29(22,25)4)18-35-27(34)13-9-21-8-11-23(30)24(31)17-21/h8-9,11,13,17,19,22,25,30-31H,2,5-7,10,12,14-16,18H2,1,3-4H3,(H,32,33)/b13-9+/t19-,22+,25+,28+,29-/m0/s1 |
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InChI Key | OGSUKCAEIRKSMH-NVVSKEKZSA-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, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CD3OD, 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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Nuxia sphaerocephala | JEOL database | - Mambu, L., et al, Phytochemistry 67, 444 (2006)
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. |
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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 | Diterpenoids |
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Direct Parent | Diterpenoids |
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Alternative Parents | |
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Substituents | - Labdane diterpenoid
- Diterpenoid
- Cinnamic acid or derivatives
- Coumaric acid or derivatives
- Hydroxycinnamic acid or derivatives
- Cinnamic acid ester
- Carbocyclic fatty acid
- Catechol
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Fatty acid ester
- Hydroxy fatty acid
- Phenol
- Fatty acyl
- Dicarboxylic acid or derivatives
- Monocyclic benzene moiety
- Benzenoid
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Carboxylic acid ester
- Carboxylic acid
- Carboxylic acid derivative
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic 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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