Record Information |
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Version | 2.0 |
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Created at | 2022-09-05 23:12:10 UTC |
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Updated at | 2022-09-05 23:12:10 UTC |
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NP-MRD ID | NP0221581 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 5-(2-{3a,7,8-trihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1,2-dihydroxypropyl)-4-ethyl-4-hydroxy-3-methyloxolan-2-one |
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Description | 5-(1,2-Dihydroxy-2-{4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-14-yl}propyl)-4-ethyl-4-hydroxy-3-methyloxolan-2-one belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. 5-(2-{3a,7,8-trihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1,2-dihydroxypropyl)-4-ethyl-4-hydroxy-3-methyloxolan-2-one is found in Ajuga reptans. 5-(1,2-Dihydroxy-2-{4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-14-yl}propyl)-4-ethyl-4-hydroxy-3-methyloxolan-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CCC1(O)C(C)C(=O)OC1C(O)C(C)(O)C1CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C InChI=1S/C29H44O9/c1-6-28(36)14(2)24(34)38-23(28)22(33)27(5,35)21-8-10-29(37)16-11-18(30)17-12-19(31)20(32)13-25(17,3)15(16)7-9-26(21,29)4/h11,14-15,17,19-23,31-33,35-37H,6-10,12-13H2,1-5H3 |
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Synonyms | Not Available |
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Chemical Formula | C29H44O9 |
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Average Mass | 536.6620 Da |
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Monoisotopic Mass | 536.29853 Da |
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IUPAC Name | 5-(1,2-dihydroxy-2-{4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-14-yl}propyl)-4-ethyl-4-hydroxy-3-methyloxolan-2-one |
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Traditional Name | 5-(1,2-dihydroxy-2-{4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-14-yl}propyl)-4-ethyl-4-hydroxy-3-methyloxolan-2-one |
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CAS Registry Number | Not Available |
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SMILES | CCC1(O)C(C)C(=O)OC1C(O)C(C)(O)C1CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C |
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InChI Identifier | InChI=1S/C29H44O9/c1-6-28(36)14(2)24(34)38-23(28)22(33)27(5,35)21-8-10-29(37)16-11-18(30)17-12-19(31)20(32)13-25(17,3)15(16)7-9-26(21,29)4/h11,14-15,17,19-23,31-33,35-37H,6-10,12-13H2,1-5H3 |
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InChI Key | JWAUYPGAZQEFKS-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 withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Steroid lactones |
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Direct Parent | Withanolides and derivatives |
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Alternative Parents | |
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Substituents | - Triterpenoid
- Hexahydroxy bile acid, alcohol, or derivatives
- Withanolide-skeleton
- Ecdysteroid
- 24-hydroxysteroid
- Hydroxy bile acid, alcohol, or derivatives
- Bile acid, alcohol, or derivatives
- 22-hydroxysteroid
- 20-hydroxysteroid
- 3-hydroxy-delta-7-steroid
- 3-hydroxysteroid
- 6-oxosteroid
- 2-hydroxysteroid
- 14-hydroxysteroid
- Oxosteroid
- Hydroxysteroid
- Delta-7-steroid
- Cyclohexenone
- Gamma butyrolactone
- Cyclic alcohol
- Tetrahydrofuran
- Tertiary alcohol
- Ketone
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Polyol
- Alcohol
- Organic oxide
- Hydrocarbon derivative
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- 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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