| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-11 18:25:38 UTC |
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| Updated at | 2022-05-11 18:25:38 UTC |
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| NP-MRD ID | NP0090905 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 11-beta-Hydroxyandrosterone-3-glucuronide |
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| Description | 6-Hydroxymelatonin, also known as lopac-H-0627, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 6-Hydroxymelatonin is an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Hydroxymelatonin exists in all living organisms, ranging from bacteria to humans. 6-Hydroxymelatonin can be biosynthesized from melatonin; which is catalyzed by the enzyme cytochrome P450 1A1. In humans, 6-hydroxymelatonin is involved in tryptophan metabolism. Outside of the human body, 6-Hydroxymelatonin has been detected, but not quantified in, several different foods, such as lemon grass, papaya, corianders, sparkleberries, and wax gourds. This could make 6-hydroxymelatonin a potential biomarker for the consumption of these foods. It is also an antioxidant and neuroprotective, and is even more potent in this regard relative to melatonin. Similar to melatonin, 6-OHM is a full agonist of the MT1 and MT2 receptors. 11-beta-Hydroxyandrosterone-3-glucuronide was first documented in 1985 (PMID: 3964785). 6-Hydroxymelatonin (6-OHM) is a naturally occurring, endogenous, major active metabolite of melatonin (PMID: 15356035) (PMID: 16300638) (PMID: 22430231) (PMID: 2646423). |
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| Structure | [H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O InChI=1S/C25H38O9/c1-24-8-7-12(33-23-20(30)18(28)19(29)21(34-23)22(31)32)9-11(24)3-4-13-14-5-6-16(27)25(14,2)10-15(26)17(13)24/h11-15,17-21,23,26,28-30H,3-10H2,1-2H3,(H,31,32)/t11-,12+,13-,14-,15-,17+,18-,19-,20+,21-,23+,24-,25-/m0/s1 |
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| Synonyms | | Value | Source |
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| Lopac-H-0627 | ChEBI | | 6-Oxymelatonin | HMDB | | 6-Hydroxy-N-acetyl-5-methoxytryptamine | HMDB | | 11-beta-Hydroxyetiocholanolone-3-glucuronide | HMDB | | 11beta-Hydroxyandrosterone 3-glucuronide | HMDB | | 11-b-Hydroxyandrosterone-3-glucuronide | Generator | | 11-Β-hydroxyandrosterone-3-glucuronide | Generator |
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| Chemical Formula | C25H38O9 |
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| Average Mass | 482.5638 Da |
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| Monoisotopic Mass | 482.25158 Da |
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| IUPAC Name | (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7S,10S,11S,15S,17S)-17-hydroxy-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}oxane-2-carboxylic acid |
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| Traditional Name | (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7S,10S,11S,15S,17S)-17-hydroxy-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}oxane-2-carboxylic acid |
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| CAS Registry Number | Not Available |
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| SMILES | [H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O |
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| InChI Identifier | InChI=1S/C25H38O9/c1-24-8-7-12(33-23-20(30)18(28)19(29)21(34-23)22(31)32)9-11(24)3-4-13-14-5-6-16(27)25(14,2)10-15(26)17(13)24/h11-15,17-21,23,26,28-30H,3-10H2,1-2H3,(H,31,32)/t11-,12+,13-,14-,15-,17+,18-,19-,20+,21-,23+,24-,25-/m0/s1 |
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| InChI Key | BRPLOVMHAFXVOQ-HUMIJZDLSA-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, 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 | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Indoles and derivatives |
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| Sub Class | Hydroxyindoles |
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| Direct Parent | Hydroxyindoles |
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| Alternative Parents | |
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| Substituents | - Hydroxyindole
- 3-alkylindole
- Indole
- Anisole
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Substituted pyrrole
- Benzenoid
- Pyrrole
- Heteroaromatic compound
- Azacycle
- Ether
- Carboximidic acid derivative
- Carboximidic acid
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic 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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