Record Information |
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Version | 1.0 |
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Created at | 2022-09-09 20:23:17 UTC |
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Updated at | 2022-09-09 20:23:17 UTC |
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NP-MRD ID | NP0289951 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | {[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid |
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Description | Sulfolithocholylglycine, also known as glycolithocholate 3-sulfate or sulfoglycolithocholate, belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton. Thus, sulfolithocholylglycine is considered to be a steroid conjugate lipid molecule. Sulfolithocholylglycine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. {[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid is found in Apis cerana. It was first documented in 1975 (PMID: 1097294). The 3-O-sulfo derivative of glycolithocholic acid (PMID: 832799) (PMID: 1150035) (PMID: 12231118) (PMID: 4086945). |
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Structure | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCC(O)=O InChI=1S/C26H43NO7S/c1-16(4-9-23(28)27-15-24(29)30)20-7-8-21-19-6-5-17-14-18(34-35(31,32)33)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22H,4-15H2,1-3H3,(H,27,28)(H,29,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1 |
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Synonyms | Value | Source |
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Glycolithocholate 3-sulfate | ChEBI | Glycolithocholate sulfate | ChEBI | Glycolithocholic acid 3-sulfate | ChEBI | Glycolithocholic acid sulfate | ChEBI | Sulfoglycolithocholate | ChEBI | Glycolithocholate 3-sulphate | Generator | Glycolithocholic acid 3-sulfuric acid | Generator | Glycolithocholic acid 3-sulphuric acid | Generator | Glycolithocholate sulphate | Generator | Glycolithocholic acid sulfuric acid | Generator | Glycolithocholic acid sulphuric acid | Generator | Sulfoglycolithocholic acid | Generator | Sulphoglycolithocholate | Generator | Sulphoglycolithocholic acid | Generator | Sulpholithocholylglycine | Generator | Sulfolithoglycocholine | HMDB | 3alpha-Hydroxy-5beta-cholanoylglycine 3-sulfate | HMDB | 3alpha-Hydroxy-5beta-cholanoylglycine 3-sulphate | HMDB | 3Α-hydroxy-5β-cholanoylglycine 3-sulfate | HMDB | 3Α-hydroxy-5β-cholanoylglycine 3-sulphate | HMDB | Glycolithocholic acid 3-sulphate | HMDB | Glycolithocholic acid 3alpha-sulfate | HMDB | Glycolithocholic acid 3alpha-sulphate | HMDB | Glycolithocholic acid 3α-sulfate | HMDB | Glycolithocholic acid 3α-sulphate | HMDB | Glycolithocholic acid sulphate | HMDB | N-[(3alpha,5beta)-24-oxo-3-(Sulfooxy)cholan-24-yl]glycine | HMDB | N-[(3Α,5β)-24-oxo-3-(sulfooxy)cholan-24-yl]glycine | HMDB | Sulfolithocholylglycine | ChEBI |
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Chemical Formula | C26H43NO7S |
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Average Mass | 513.6900 Da |
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Monoisotopic Mass | 513.27602 Da |
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IUPAC Name | 2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid |
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Traditional Name | [(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCC(O)=O |
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InChI Identifier | InChI=1S/C26H43NO7S/c1-16(4-9-23(28)27-15-24(29)30)20-7-8-21-19-6-5-17-14-18(34-35(31,32)33)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22H,4-15H2,1-3H3,(H,27,28)(H,29,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1 |
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InChI Key | FHXBAFXQVZOILS-OETIFKLTSA-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 glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton. |
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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 | Bile acids, alcohols and derivatives |
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Direct Parent | Glycinated bile acids and derivatives |
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Alternative Parents | |
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Substituents | - Glycinated bile acid
- Sulfated steroid skeleton
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid or derivatives
- Sulfuric acid monoester
- Sulfuric acid ester
- Alkyl sulfate
- Sulfate-ester
- Organic sulfuric acid or derivatives
- Carboximidic acid
- Carboximidic acid derivative
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Carbonyl group
- 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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