| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:03:09 UTC |
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| Update Date | 2020-04-22 15:11:50 UTC |
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| BMDB ID | BMDB0003218 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Withanolide |
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| Description | Withanolide 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. Withanolide is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C28H38O6 |
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| Average Molecular Weight | 470.606 |
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| Monoisotopic Molecular Weight | 470.266838944 |
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| IUPAC Name | (1S,2R,6S,7R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one |
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| Traditional Name | (1S,2R,6S,7R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one |
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| CAS Registry Number | Not Available |
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| SMILES | [H]C12C[C@@]3([H])[C@]4([H])CC[C@]([H])([C@@](C)(O)[C@@]5([H])CC(C)=C(C)C(=O)O5)[C@@]4(C)CC[C@]3([H])[C@@]3(C)C(=O)C=C[C@]([H])(O)[C@@]13O2 |
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| InChI Identifier | InChI=1S/C28H38O6/c1-14-12-22(33-24(31)15(14)2)27(5,32)19-7-6-17-16-13-23-28(34-23)21(30)9-8-20(29)26(28,4)18(16)10-11-25(17,19)3/h8-9,16-19,21-23,30,32H,6-7,10-13H2,1-5H3/t16-,17-,18-,19-,21-,22+,23?,25-,26-,27+,28+/m0/s1 |
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| InChI Key | SASUFNRGCZMRFD-MOUTUSPFSA-N |
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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 | - Withanolide-skeleton
- 5,6-epoxysteroid
- Cyclohexenone
- Oxepane
- Dihydropyranone
- Pyran
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tertiary alcohol
- Secondary alcohol
- Lactone
- Ketone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Ether
- Oxirane
- Dialkyl ether
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Status | Expected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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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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| Spectra |
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| Spectra | |
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