Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2020-02-24 17:48:02 UTC |
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Update Date | 2022-03-07 03:18:20 UTC |
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HMDB ID | HMDB0240640 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | Indolepropionamide |
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Description | Indolepropionamide (IPAM) is a product of tryptophan metabolism formed by symbiotic bacteria in the gastrointestinal tract of mammals. In particular, IPAM is an amide derivatization product of indole-3-propionic acid (IPA). IPAM reduces reactive oxygen species by inhibiting oxidative phosphorylation in complex I of the electron transport chain and acts as a stabilizer of energy metabolism, thereby reducing reactive oxygen species (ROS) production. In contrast to indole-3-propionic acid which bears a polar carboxyl group that is ionized at physiological pH carrying a negative charge, IPAM is non-polar and has sufficient lipophilicity to penetrate through biological membranes. In contrast to melatonin, IPAM is a "reversed amide" lacking the methoxy group as an aromatic substituent. In contrast to IPAM, melatonin is quickly metabolized in the liver by hydroxylation and excreted as the glucuronide or sulfate conjugate of 6-hydroxymelatonin (a pro-oxidant metabolite). IPAM, however, has a long half-life and no pro-oxidant activity (PMID: 20421998 ). |
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Structure | NC(=O)CCC1=CNC2=C1C=CC=C2 InChI=1S/C11H12N2O/c12-11(14)6-5-8-7-13-10-4-2-1-3-9(8)10/h1-4,7,13H,5-6H2,(H2,12,14) |
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Synonyms | Value | Source |
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3-(1H-indol-3-yl)Propanamide | HMDB | 3-(3-Indolyl)propanamide | HMDB | 3-indol-3-Ylpropionamide | HMDB | 3-Indolepropanamide | HMDB | IPAM | HMDB | Indole-3-propionamide | HMDB | Indolepropionamide | HMDB |
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Chemical Formula | C11H12N2O |
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Average Molecular Weight | 188.23 |
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Monoisotopic Molecular Weight | 188.094963014 |
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IUPAC Name | 3-(1H-indol-3-yl)propanamide |
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Traditional Name | 3-(1H-indol-3-yl)propanamide |
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CAS Registry Number | 5814-93-7 |
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SMILES | NC(=O)CCC1=CNC2=C1C=CC=C2 |
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InChI Identifier | InChI=1S/C11H12N2O/c12-11(14)6-5-8-7-13-10-4-2-1-3-9(8)10/h1-4,7,13H,5-6H2,(H2,12,14) |
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InChI Key | OTVHXWFANORBAK-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine. |
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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 | Tryptamines and derivatives |
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Direct Parent | Tryptamines and derivatives |
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Alternative Parents | |
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Substituents | - Triptan
- 3-alkylindole
- Indole
- Fatty amide
- Substituted pyrrole
- Benzenoid
- Fatty acyl
- Pyrrole
- Heteroaromatic compound
- Carboxamide group
- Primary carboxylic acid amide
- Carboxylic acid derivative
- Azacycle
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organic oxide
- 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 | Not Available |
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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 | |
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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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Indolepropionamide,1TMS,isomer #1 | C[Si](C)(C)NC(=O)CCC1=C[NH]C2=CC=CC=C12 | 2144.9 | Semi standard non polar | 33892256 | Indolepropionamide,1TMS,isomer #1 | C[Si](C)(C)NC(=O)CCC1=C[NH]C2=CC=CC=C12 | 2081.1 | Standard non polar | 33892256 | Indolepropionamide,1TMS,isomer #1 | C[Si](C)(C)NC(=O)CCC1=C[NH]C2=CC=CC=C12 | 2697.4 | Standard polar | 33892256 | Indolepropionamide,1TMS,isomer #2 | C[Si](C)(C)N1C=C(CCC(N)=O)C2=CC=CC=C21 | 2134.2 | Semi standard non polar | 33892256 | Indolepropionamide,1TMS,isomer #2 | C[Si](C)(C)N1C=C(CCC(N)=O)C2=CC=CC=C21 | 2034.3 | Standard non polar | 33892256 | Indolepropionamide,1TMS,isomer #2 | C[Si](C)(C)N1C=C(CCC(N)=O)C2=CC=CC=C21 | 2921.8 | Standard polar | 33892256 | Indolepropionamide,2TMS,isomer #1 | C[Si](C)(C)N(C(=O)CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C | 2272.3 | Semi standard non polar | 33892256 | Indolepropionamide,2TMS,isomer #1 | C[Si](C)(C)N(C(=O)CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C | 2243.8 | Standard non polar | 33892256 | Indolepropionamide,2TMS,isomer #1 | C[Si](C)(C)N(C(=O)CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C | 2561.0 | Standard polar | 33892256 | Indolepropionamide,2TMS,isomer #2 | C[Si](C)(C)NC(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12 | 2167.1 | Semi standard non polar | 33892256 | Indolepropionamide,2TMS,isomer #2 | C[Si](C)(C)NC(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12 | 2156.4 | Standard non polar | 33892256 | Indolepropionamide,2TMS,isomer #2 | C[Si](C)(C)NC(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12 | 2433.1 | Standard polar | 33892256 | Indolepropionamide,3TMS,isomer #1 | C[Si](C)(C)N(C(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C | 2313.1 | Semi standard non polar | 33892256 | Indolepropionamide,3TMS,isomer #1 | C[Si](C)(C)N(C(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C | 2281.7 | Standard non polar | 33892256 | Indolepropionamide,3TMS,isomer #1 | C[Si](C)(C)N(C(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C | 2360.7 | Standard polar | 33892256 | Indolepropionamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)CCC1=C[NH]C2=CC=CC=C12 | 2376.0 | Semi standard non polar | 33892256 | Indolepropionamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)CCC1=C[NH]C2=CC=CC=C12 | 2290.0 | Standard non polar | 33892256 | Indolepropionamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)CCC1=C[NH]C2=CC=CC=C12 | 2763.2 | Standard polar | 33892256 | Indolepropionamide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C=C(CCC(N)=O)C2=CC=CC=C21 | 2386.4 | Semi standard non polar | 33892256 | Indolepropionamide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C=C(CCC(N)=O)C2=CC=CC=C21 | 2240.2 | Standard non polar | 33892256 | Indolepropionamide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C=C(CCC(N)=O)C2=CC=CC=C21 | 2982.3 | Standard polar | 33892256 | Indolepropionamide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C(=O)CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C | 2726.1 | Semi standard non polar | 33892256 | Indolepropionamide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C(=O)CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C | 2684.5 | Standard non polar | 33892256 | Indolepropionamide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C(=O)CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C | 2666.0 | Standard polar | 33892256 | Indolepropionamide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 2620.2 | Semi standard non polar | 33892256 | Indolepropionamide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 2578.5 | Standard non polar | 33892256 | Indolepropionamide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 2618.5 | Standard polar | 33892256 | Indolepropionamide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C | 2920.6 | Semi standard non polar | 33892256 | Indolepropionamide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C | 2900.5 | Standard non polar | 33892256 | Indolepropionamide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C | 2636.8 | Standard polar | 33892256 |
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