Record Information |
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Version | 1.0 |
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Created at | 2023-03-17 17:21:34 UTC |
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Updated at | 2024-04-19 09:45:06 UTC |
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NP-MRD ID | NP0331539 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Tetrahydro-cucurbitacin I |
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Description | 23,24-Dihydrocucurbitacin D belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. It was first documented in 2004 (PMID: 14752064). Based on a literature review a small amount of articles have been published on 23,24-dihydrocucurbitacin D (PMID: 17674793) (PMID: 34592371). |
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Structure | CC(C)(O)CCC(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3CC=C4[C@@H](C[C@H](O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C InChI=1S/C30H46O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,17-20,23,31-32,36-37H,10-15H2,1-8H3/t17-,18+,19-,20+,23+,27+,28-,29+,30+/m1/s1 |
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Synonyms | Value | Source |
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2beta,16alpha,20,25- Tetrahydroxy-9beta-methyl-19-nor-10alpha-lanost-5-ene-3,11,22-trione | ChEBI | 2beta,16alpha,20,25-Tetrahydroxy-10alpha-cucurbit-5-ene-3,11,22-trione | ChEBI | 2b,16a,20,25- Tetrahydroxy-9b-methyl-19-nor-10a-lanost-5-ene-3,11,22-trione | Generator | 2Β,16α,20,25- tetrahydroxy-9β-methyl-19-nor-10α-lanost-5-ene-3,11,22-trione | Generator | 2b,16a,20,25-Tetrahydroxy-10a-cucurbit-5-ene-3,11,22-trione | Generator | 2Β,16α,20,25-tetrahydroxy-10α-cucurbit-5-ene-3,11,22-trione | Generator |
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Chemical Formula | C30H46O7 |
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Average Mass | 518.6910 Da |
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Monoisotopic Mass | 518.32435 Da |
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IUPAC Name | (1R,2R,4S,10S,11S,13R,14R,15R)-14-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-4,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,17-dione |
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Traditional Name | (1R,2R,4S,10S,11S,13R,14R,15R)-14-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-4,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,17-dione |
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CAS Registry Number | Not Available |
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SMILES | CC(C)(O)CCC(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3CC=C4[C@@H](C[C@H](O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C |
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InChI Identifier | InChI=1S/C30H46O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,17-20,23,31-32,36-37H,10-15H2,1-8H3/t17-,18+,19-,20+,23+,27+,28-,29+,30+/m1/s1 |
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InChI Key | ITMUUFDDBRYVNJ-VOKXYEOFSA-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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HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | toussaintgnaore@gmail.com | Not Available | Not Available | 2023-03-17 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | toussaintgnaore@gmail.com | Not Available | Not Available | 2023-03-17 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | toussaintgnaore@gmail.com | Not Available | Not Available | 2023-03-17 | View Spectrum | 1D NMR | [1H, ] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | toussaintgnaore@gmail.com | Not Available | Not Available | 2023-03-17 | View Spectrum | 1D NMR | [13C, ] NMR Spectrum (2D, 126 MHz, CD3OD, experimental) | toussaintgnaore@gmail.com | Not Available | Not Available | 2023-03-17 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125.77 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500.11 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| 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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. |
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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 | Cucurbitacins |
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Direct Parent | Cucurbitacins |
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Alternative Parents | |
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Substituents | - Cucurbitacin skeleton
- Triterpenoid
- 25-hydroxysteroid
- 22-oxosteroid
- 21-oxosteroid
- 20-hydroxysteroid
- 14-alpha-methylsteroid
- 3-oxo-delta-5-steroid
- 16-hydroxysteroid
- 16-alpha-hydroxysteroid
- 3-oxosteroid
- Oxosteroid
- 11-oxosteroid
- 2-hydroxysteroid
- Hydroxysteroid
- Delta-5-steroid
- Acyloin
- Alpha-hydroxy ketone
- Cyclic alcohol
- Tertiary alcohol
- Cyclic ketone
- Secondary alcohol
- Ketone
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Alcohol
- Organooxygen compound
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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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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