Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-22 19:50:11 UTC |
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Update Date | 2019-07-23 07:15:50 UTC |
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HMDB ID | HMDB0061136 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | di-Hydroxymelatonin |
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Description | di-Hydroxymelatonin belongs to the class of organic compounds known as n-acetyl-2-arylethylamines. N-acetyl-2-arylethylamines are compounds containing an acetamide group that is N-linked to an arylethylamine. di-Hydroxymelatonin is an extremely weak basic (essentially neutral) compound (based on its pKa). di-Hydroxymelatonin is a metabolite of melatonin. In animals, circulating levels of the hormone melatonin vary in a daily cycle, thereby allowing the entrainment of the circadian rhythms of several biological functions. Melatonin Listen/ˌmɛləˈtoʊnɪn/, also known chemically as N-acetyl-5-methoxytryptamine, is a naturally occurring compound found in animals, plants, and microbes. |
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Structure | COC1=C(O)C2=C(NC=C2CCNC(C)=O)C=C1O InChI=1S/C13H16N2O4/c1-7(16)14-4-3-8-6-15-9-5-10(17)13(19-2)12(18)11(8)9/h5-6,15,17-18H,3-4H2,1-2H3,(H,14,16) |
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Synonyms | Not Available |
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Chemical Formula | C13H16N2O4 |
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Average Molecular Weight | 264.2771 |
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Monoisotopic Molecular Weight | 264.11100701 |
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IUPAC Name | N-[2-(4,6-dihydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide |
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Traditional Name | N-[2-(4,6-dihydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide |
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CAS Registry Number | Not Available |
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SMILES | COC1=C(O)C2=C(NC=C2CCNC(C)=O)C=C1O |
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InChI Identifier | InChI=1S/C13H16N2O4/c1-7(16)14-4-3-8-6-15-9-5-10(17)13(19-2)12(18)11(8)9/h5-6,15,17-18H,3-4H2,1-2H3,(H,14,16) |
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InChI Key | UEZDFVJSDBULCI-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as n-acetyl-2-arylethylamines. N-acetyl-2-arylethylamines are compounds containing an acetamide group that is N-linked to an arylethylamine. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Carboxylic acid derivatives |
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Direct Parent | N-acetyl-2-arylethylamines |
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Alternative Parents | |
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Substituents | - N-acetyl-2-arylethylamine
- 3-alkylindole
- Hydroxyindole
- Indole
- Indole or derivatives
- Anisole
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Substituted pyrrole
- Benzenoid
- Heteroaromatic compound
- Pyrrole
- Secondary carboxylic acid amide
- Organoheterocyclic compound
- Azacycle
- Ether
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organopnictogen compound
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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di-Hydroxymelatonin,1TMS,isomer #1 | COC1=C(O)C=C2[NH]C=C(CCNC(C)=O)C2=C1O[Si](C)(C)C | 2718.0 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,1TMS,isomer #2 | COC1=C(O[Si](C)(C)C)C=C2[NH]C=C(CCNC(C)=O)C2=C1O | 2710.7 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,1TMS,isomer #3 | COC1=C(O)C=C2C(=C1O)C(CCNC(C)=O)=CN2[Si](C)(C)C | 2758.3 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,1TMS,isomer #4 | COC1=C(O)C=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C)C2=C1O | 2655.4 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,2TMS,isomer #1 | COC1=C(O[Si](C)(C)C)C=C2[NH]C=C(CCNC(C)=O)C2=C1O[Si](C)(C)C | 2703.0 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,2TMS,isomer #2 | COC1=C(O)C=C2C(=C1O[Si](C)(C)C)C(CCNC(C)=O)=CN2[Si](C)(C)C | 2754.1 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,2TMS,isomer #3 | COC1=C(O)C=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C)C2=C1O[Si](C)(C)C | 2605.1 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,2TMS,isomer #4 | COC1=C(O[Si](C)(C)C)C=C2C(=C1O)C(CCNC(C)=O)=CN2[Si](C)(C)C | 2731.1 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,2TMS,isomer #5 | COC1=C(O[Si](C)(C)C)C=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C)C2=C1O | 2619.4 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,2TMS,isomer #6 | COC1=C(O)C=C2C(=C1O)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C | 2661.7 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,3TMS,isomer #1 | COC1=C(O[Si](C)(C)C)C=C2C(=C1O[Si](C)(C)C)C(CCNC(C)=O)=CN2[Si](C)(C)C | 2741.8 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,3TMS,isomer #1 | COC1=C(O[Si](C)(C)C)C=C2C(=C1O[Si](C)(C)C)C(CCNC(C)=O)=CN2[Si](C)(C)C | 2632.2 | Standard non polar | 33892256 | di-Hydroxymelatonin,3TMS,isomer #1 | COC1=C(O[Si](C)(C)C)C=C2C(=C1O[Si](C)(C)C)C(CCNC(C)=O)=CN2[Si](C)(C)C | 2885.3 | Standard polar | 33892256 | di-Hydroxymelatonin,3TMS,isomer #2 | COC1=C(O[Si](C)(C)C)C=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C)C2=C1O[Si](C)(C)C | 2639.2 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,3TMS,isomer #2 | COC1=C(O[Si](C)(C)C)C=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C)C2=C1O[Si](C)(C)C | 2740.7 | Standard non polar | 33892256 | di-Hydroxymelatonin,3TMS,isomer #2 | COC1=C(O[Si](C)(C)C)C=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C)C2=C1O[Si](C)(C)C | 2835.0 | Standard polar | 33892256 | di-Hydroxymelatonin,3TMS,isomer #3 | COC1=C(O)C=C2C(=C1O[Si](C)(C)C)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C | 2656.5 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,3TMS,isomer #3 | COC1=C(O)C=C2C(=C1O[Si](C)(C)C)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C | 2769.5 | Standard non polar | 33892256 | di-Hydroxymelatonin,3TMS,isomer #3 | COC1=C(O)C=C2C(=C1O[Si](C)(C)C)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C | 2959.6 | Standard polar | 33892256 | di-Hydroxymelatonin,3TMS,isomer #4 | COC1=C(O[Si](C)(C)C)C=C2C(=C1O)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C | 2661.9 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,3TMS,isomer #4 | COC1=C(O[Si](C)(C)C)C=C2C(=C1O)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C | 2791.8 | Standard non polar | 33892256 | di-Hydroxymelatonin,3TMS,isomer #4 | COC1=C(O[Si](C)(C)C)C=C2C(=C1O)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C | 2920.3 | Standard polar | 33892256 | di-Hydroxymelatonin,4TMS,isomer #1 | COC1=C(O[Si](C)(C)C)C=C2C(=C1O[Si](C)(C)C)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C | 2702.9 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,4TMS,isomer #1 | COC1=C(O[Si](C)(C)C)C=C2C(=C1O[Si](C)(C)C)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C | 2721.7 | Standard non polar | 33892256 | di-Hydroxymelatonin,4TMS,isomer #1 | COC1=C(O[Si](C)(C)C)C=C2C(=C1O[Si](C)(C)C)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C | 2732.9 | Standard polar | 33892256 | di-Hydroxymelatonin,1TBDMS,isomer #1 | COC1=C(O)C=C2[NH]C=C(CCNC(C)=O)C2=C1O[Si](C)(C)C(C)(C)C | 2954.9 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,1TBDMS,isomer #2 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2[NH]C=C(CCNC(C)=O)C2=C1O | 2950.4 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,1TBDMS,isomer #3 | COC1=C(O)C=C2C(=C1O)C(CCNC(C)=O)=CN2[Si](C)(C)C(C)(C)C | 3004.2 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,1TBDMS,isomer #4 | COC1=C(O)C=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1O | 2890.2 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,2TBDMS,isomer #1 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2[NH]C=C(CCNC(C)=O)C2=C1O[Si](C)(C)C(C)(C)C | 3171.5 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,2TBDMS,isomer #2 | COC1=C(O)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(CCNC(C)=O)=CN2[Si](C)(C)C(C)(C)C | 3202.7 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,2TBDMS,isomer #3 | COC1=C(O)C=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1O[Si](C)(C)C(C)(C)C | 3068.8 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,2TBDMS,isomer #4 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=C1O)C(CCNC(C)=O)=CN2[Si](C)(C)C(C)(C)C | 3210.6 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,2TBDMS,isomer #5 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1O | 3084.4 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,2TBDMS,isomer #6 | COC1=C(O)C=C2C(=C1O)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C | 3100.5 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,3TBDMS,isomer #1 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(CCNC(C)=O)=CN2[Si](C)(C)C(C)(C)C | 3379.2 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,3TBDMS,isomer #1 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(CCNC(C)=O)=CN2[Si](C)(C)C(C)(C)C | 3210.0 | Standard non polar | 33892256 | di-Hydroxymelatonin,3TBDMS,isomer #1 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(CCNC(C)=O)=CN2[Si](C)(C)C(C)(C)C | 3150.9 | Standard polar | 33892256 | di-Hydroxymelatonin,3TBDMS,isomer #2 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1O[Si](C)(C)C(C)(C)C | 3268.2 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,3TBDMS,isomer #2 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1O[Si](C)(C)C(C)(C)C | 3333.5 | Standard non polar | 33892256 | di-Hydroxymelatonin,3TBDMS,isomer #2 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1O[Si](C)(C)C(C)(C)C | 3148.1 | Standard polar | 33892256 | di-Hydroxymelatonin,3TBDMS,isomer #3 | COC1=C(O)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C | 3282.8 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,3TBDMS,isomer #3 | COC1=C(O)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C | 3346.1 | Standard non polar | 33892256 | di-Hydroxymelatonin,3TBDMS,isomer #3 | COC1=C(O)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C | 3205.1 | Standard polar | 33892256 | di-Hydroxymelatonin,3TBDMS,isomer #4 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=C1O)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C | 3291.7 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,3TBDMS,isomer #4 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=C1O)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C | 3355.0 | Standard non polar | 33892256 | di-Hydroxymelatonin,3TBDMS,isomer #4 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=C1O)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C | 3180.8 | Standard polar | 33892256 | di-Hydroxymelatonin,4TBDMS,isomer #1 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C | 3471.8 | Semi standard non polar | 33892256 | di-Hydroxymelatonin,4TBDMS,isomer #1 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C | 3414.7 | Standard non polar | 33892256 | di-Hydroxymelatonin,4TBDMS,isomer #1 | COC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C | 3120.9 | Standard polar | 33892256 |
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