Record Information |
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Version | 2.0 |
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Created at | 2024-05-03 03:51:40 UTC |
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Updated at | 2024-09-03 04:20:49 UTC |
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NP-MRD ID | NP0332981 |
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Natural Product DOI | https://doi.org/10.57994/2262 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Withastramonolide A |
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Description | Withastramonolide A 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. Withastramonolide A was first documented in 2024 (PMID: 38084071). Based on a literature review very few articles have been published on Withastramonolide A. |
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Structure | [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4CC=CC(=O)[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@@]1([H])CC(C)=C(CO[C@@H]2O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)C(O)[C@H]2O)C(=O)O1 InChI=1S/C43H54O12/c1-22-18-32(23(2)28-13-14-29-36-30(16-17-42(28,29)3)43(4)25(19-31(36)45)6-5-7-34(43)46)54-40(51)27(22)20-53-41-39(50)38(49)37(48)33(55-41)21-52-35(47)15-10-24-8-11-26(44)12-9-24/h5,7-12,15,19,23,28-33,36-39,41,44-45,48-50H,6,13-14,16-18,20-21H2,1-4H3/b15-10+/t23-,28+,29-,30-,31+,32+,33+,36-,37+,38?,39+,41+,42+,43-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C43H54O12 |
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Average Mass | 762.8930 Da |
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Monoisotopic Mass | 762.36153 Da |
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IUPAC Name | [(2R,3S,5R,6R)-6-{[(6R)-6-[(1S)-1-[(1R,3aS,3bS,4S,9aR,9bS,11aR)-4-hydroxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,6H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]ethyl]-4-methyl-2-oxo-5,6-dihydro-2H-pyran-3-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate |
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Traditional Name | [(2R,3S,5R,6R)-6-{[(6R)-6-[(1S)-1-[(1R,3aS,3bS,4S,9aR,9bS,11aR)-4-hydroxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,6H,9bH,10H,11H-cyclopenta[a]phenanthren-1-yl]ethyl]-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4CC=CC(=O)[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@@]1([H])CC(C)=C(CO[C@@H]2O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)C(O)[C@H]2O)C(=O)O1 |
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InChI Identifier | InChI=1S/C43H54O12/c1-22-18-32(23(2)28-13-14-29-36-30(16-17-42(28,29)3)43(4)25(19-31(36)45)6-5-7-34(43)46)54-40(51)27(22)20-53-41-39(50)38(49)37(48)33(55-41)21-52-35(47)15-10-24-8-11-26(44)12-9-24/h5,7-12,15,19,23,28-33,36-39,41,44-45,48-50H,6,13-14,16-18,20-21H2,1-4H3/b15-10+/t23-,28+,29-,30-,31+,32+,33+,36-,37+,38?,39+,41+,42+,43-/m0/s1 |
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InChI Key | XLHUMJNCPFKSNR-PPOKXSMESA-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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| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600, CD3OD, simulated) | 570075670@qq.com | 黑龙江中医药大学 | Pan juan | 2024-05-03 | View Spectrum |
| Species |
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Species of Origin | Species Name | Source | Reference |
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stramonium | | |
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Chemical Taxonomy |
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Description | This compound 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 | - Withanolide-skeleton
- Monohydroxy bile acid, alcohol, or derivatives
- Hydroxy bile acid, alcohol, or derivatives
- Bile acid, alcohol, or derivatives
- Steroid ester
- Diterpenoid
- Diterpene lactone
- Saccharolipid
- 7-hydroxysteroid
- 7-alpha-hydroxysteroid
- Oxosteroid
- 1-oxosteroid
- Hydroxysteroid
- Fatty acyl glycoside of mono- or disaccharide
- Fatty acyl glycoside
- Coumaric acid ester
- Cinnamic acid ester
- Hydroxycinnamic acid or derivatives
- Fatty alcohol ester
- Coumaric acid or derivatives
- Cinnamic acid or derivatives
- Alkyl glycoside
- Quinomethane
- M-quinomethane
- 1-hydroxy-2-unsubstituted benzenoid
- Cyclohexenone
- Phenol
- Dihydropyranone
- Fatty acyl
- Benzenoid
- Pyran
- Oxane
- Monosaccharide
- Dicarboxylic acid or derivatives
- Monocyclic benzene moiety
- Alpha,beta-unsaturated ketone
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Enone
- Acryloyl-group
- Secondary alcohol
- Lactone
- Ketone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- 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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