| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-12 14:48:53 UTC |
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| Updated at | 2022-09-12 14:48:54 UTC |
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| NP-MRD ID | NP0329936 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 5-(acetyloxy)-2-{[1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-8-hydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-2-yl]oxy}-4-hydroxy-6-methyloxan-3-yl acetate |
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| Description | 5-(Acetyloxy)-2-{[14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-4-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-13-yl]oxy}-4-hydroxy-6-methyloxan-3-yl acetate belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. 5-(acetyloxy)-2-{[1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-8-hydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-2-yl]oxy}-4-hydroxy-6-methyloxan-3-yl acetate is found in Datisca glomerata. 5-(Acetyloxy)-2-{[14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-4-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-13-yl]oxy}-4-hydroxy-6-methyloxan-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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| Structure | CC1OC(OC2CC3(C)C4CC=C5C(CC(O)C(=O)C5(C)C)C4(C)C(=O)CC3(C)C2C(C)(O)C(=O)C=CC(C)(C)O)C(OC(C)=O)C(O)C1OC(C)=O InChI=1S/C40H58O13/c1-19-30(51-20(2)41)29(46)31(52-21(3)42)34(50-19)53-25-17-37(8)26-13-12-22-23(16-24(43)33(47)36(22,6)7)39(26,10)28(45)18-38(37,9)32(25)40(11,49)27(44)14-15-35(4,5)48/h12,14-15,19,23-26,29-32,34,43,46,48-49H,13,16-18H2,1-11H3 |
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| Synonyms | | Value | Source |
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| 5-(Acetyloxy)-2-{[14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-4-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0,.0,]heptadec-7-en-13-yl]oxy}-4-hydroxy-6-methyloxan-3-yl acetic acid | Generator | | 5-(Acetyloxy)-2-{[14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-4-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-yl]oxy}-4-hydroxy-6-methyloxan-3-yl acetic acid | Generator |
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| Chemical Formula | C40H58O13 |
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| Average Mass | 746.8910 Da |
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| Monoisotopic Mass | 746.38774 Da |
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| IUPAC Name | 5-(acetyloxy)-2-{[14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-4-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-yl]oxy}-4-hydroxy-6-methyloxan-3-yl acetate |
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| Traditional Name | 5-(acetyloxy)-2-{[14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-4-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-yl]oxy}-4-hydroxy-6-methyloxan-3-yl acetate |
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| CAS Registry Number | Not Available |
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| SMILES | CC1OC(OC2CC3(C)C4CC=C5C(CC(O)C(=O)C5(C)C)C4(C)C(=O)CC3(C)C2C(C)(O)C(=O)C=CC(C)(C)O)C(OC(C)=O)C(O)C1OC(C)=O |
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| InChI Identifier | InChI=1S/C40H58O13/c1-19-30(51-20(2)41)29(46)31(52-21(3)42)34(50-19)53-25-17-37(8)26-13-12-22-23(16-24(43)33(47)36(22,6)7)39(26,10)28(45)18-38(37,9)32(25)40(11,49)27(44)14-15-35(4,5)48/h12,14-15,19,23-26,29-32,34,43,46,48-49H,13,16-18H2,1-11H3 |
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| InChI Key | GIJVJTQJDQMZKO-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 cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. |
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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 | Steroidal glycosides |
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| Direct Parent | Cucurbitacin glycosides |
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| Alternative Parents | |
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| Substituents | - Cucurbitacin glycoside skeleton
- Cucurbitacin skeleton
- Triterpenoid
- 25-hydroxysteroid
- 22-oxosteroid
- 21-oxosteroid
- 20-hydroxysteroid
- 3-oxo-delta-5-steroid
- 3-oxosteroid
- 2-hydroxysteroid
- Hydroxysteroid
- 11-oxosteroid
- Oxosteroid
- Delta-5-steroid
- Hexose monosaccharide
- O-glycosyl compound
- Glycosyl compound
- Acyloin
- Oxane
- Monosaccharide
- Dicarboxylic acid or derivatives
- Tertiary alcohol
- Alpha,beta-unsaturated ketone
- Alpha-hydroxy ketone
- Cyclic alcohol
- Enone
- Acryloyl-group
- Carboxylic acid ester
- Secondary alcohol
- Ketone
- Cyclic ketone
- Carboxylic acid derivative
- Organoheterocyclic compound
- Oxacycle
- Acetal
- Organooxygen compound
- Alcohol
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- 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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