Record Information |
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Version | 2.0 |
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Created at | 2022-09-12 00:14:33 UTC |
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Updated at | 2022-09-12 00:14:34 UTC |
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NP-MRD ID | NP0321825 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (4s,4ar,5r,6r,8ar)-6-(acetyloxy)-3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h,8h,8ah-naphtho[2,3-b]furan-4-yl (2z)-2-methylbut-2-enoate |
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Description | (4S,4aR,5R,6R,8aR)-6-(acetyloxy)-3,4a,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. (4s,4ar,5r,6r,8ar)-6-(acetyloxy)-3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h,8h,8ah-naphtho[2,3-b]furan-4-yl (2z)-2-methylbut-2-enoate is found in Telanthophora grandifolia. Based on a literature review very few articles have been published on (4S,4aR,5R,6R,8aR)-6-(acetyloxy)-3,4a,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate. |
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Structure | C\C=C(\C)C(=O)O[C@@H]1C2=C(OC=C2C)C(=O)[C@@H]2CC[C@@H](OC(C)=O)[C@H](C)[C@@]12C InChI=1S/C22H28O6/c1-7-11(2)21(25)28-20-17-12(3)10-26-19(17)18(24)15-8-9-16(27-14(5)23)13(4)22(15,20)6/h7,10,13,15-16,20H,8-9H2,1-6H3/b11-7-/t13-,15-,16+,20+,22+/m0/s1 |
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Synonyms | Value | Source |
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(4S,4AR,5R,6R,8ar)-6-(acetyloxy)-3,4a,5-trimethyl-9-oxo-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoic acid | Generator |
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Chemical Formula | C22H28O6 |
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Average Mass | 388.4600 Da |
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Monoisotopic Mass | 388.18859 Da |
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IUPAC Name | (4S,4aR,5R,6R,8aR)-6-(acetyloxy)-3,4a,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate |
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Traditional Name | (4S,4aR,5R,6R,8aR)-6-(acetyloxy)-3,4a,5-trimethyl-9-oxo-4H,5H,6H,7H,8H,8aH-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | C\C=C(\C)C(=O)O[C@@H]1C2=C(OC=C2C)C(=O)[C@@H]2CC[C@@H](OC(C)=O)[C@H](C)[C@@]12C |
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InChI Identifier | InChI=1S/C22H28O6/c1-7-11(2)21(25)28-20-17-12(3)10-26-19(17)18(24)15-8-9-16(27-14(5)23)13(4)22(15,20)6/h7,10,13,15-16,20H,8-9H2,1-6H3/b11-7-/t13-,15-,16+,20+,22+/m0/s1 |
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InChI Key | ZBEIDAHTEHJVBJ-HMAFTSSZSA-N |
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Experimental Spectra |
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| Not Available | 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 | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. |
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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 | Sesquiterpenoids |
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Direct Parent | Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids |
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Alternative Parents | |
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Substituents | - Furoeremophilane sesquiterpenoid
- Naphthofuran
- Benzofuran
- Aryl ketone
- Aryl alkyl ketone
- Fatty acid ester
- Dicarboxylic acid or derivatives
- Fatty acyl
- Furan
- Heteroaromatic compound
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Ketone
- Carboxylic acid ester
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- 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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