Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:36:07 UTC |
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Update Date | 2022-03-07 02:52:30 UTC |
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HMDB ID | HMDB0030323 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Paxilline |
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Description | Paxilline belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Paxilline is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Paxilline. |
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Structure | [H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H](C(=O)C=C3[C@]1(O)CC2)C(C)(C)O InChI=1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3/t15-,21-,23-,25+,26+,27+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C27H33NO4 |
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Average Molecular Weight | 435.5552 |
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Monoisotopic Molecular Weight | 435.240958549 |
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IUPAC Name | (1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one |
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Traditional Name | paxilline |
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CAS Registry Number | 57186-25-1 |
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SMILES | [H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H](C(=O)C=C3[C@]1(O)CC2)C(C)(C)O |
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InChI Identifier | InChI=1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3/t15-,21-,23-,25+,26+,27+/m0/s1 |
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InChI Key | ACNHBCIZLNNLRS-UBGQALKQSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Naphthopyrans |
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Sub Class | Not Available |
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Direct Parent | Naphthopyrans |
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Alternative Parents | |
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Substituents | - Naphthopyran
- Naphthalene
- 3-alkylindole
- Indole
- Indole or derivatives
- Dihydropyranone
- Pyran
- Benzenoid
- Heteroaromatic compound
- Tertiary alcohol
- Pyrrole
- Cyclic alcohol
- Cyclic ketone
- Ketone
- Oxacycle
- Azacycle
- Dialkyl ether
- Ether
- Alcohol
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Carbonyl group
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 252 °C | 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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Paxilline,1TMS,isomer #1 | CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O[Si](C)(C)C)(CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 3898.9 | Semi standard non polar | 33892256 | Paxilline,1TMS,isomer #2 | CC(C)(O[Si](C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 3923.9 | Semi standard non polar | 33892256 | Paxilline,1TMS,isomer #3 | CC(C)(O)C1=C(O[Si](C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O)CC[C@H]2CC4=C([NH]C5=CC=CC=C45)[C@@]23C)O1 | 3882.7 | Semi standard non polar | 33892256 | Paxilline,1TMS,isomer #4 | CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4CC5=C(N([Si](C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 3919.7 | Semi standard non polar | 33892256 | Paxilline,2TMS,isomer #1 | CC(C)(O[Si](C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O[Si](C)(C)C)(CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 3823.7 | Semi standard non polar | 33892256 | Paxilline,2TMS,isomer #2 | CC(C)(O)C1=C(O[Si](C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O[Si](C)(C)C)CC[C@H]2CC4=C([NH]C5=CC=CC=C45)[C@@]23C)O1 | 3836.2 | Semi standard non polar | 33892256 | Paxilline,2TMS,isomer #3 | CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O[Si](C)(C)C)(CC[C@H]4CC5=C(N([Si](C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 3831.2 | Semi standard non polar | 33892256 | Paxilline,2TMS,isomer #4 | CC(C)(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O)CC[C@H]2CC4=C([NH]C5=CC=CC=C45)[C@@]23C)O1 | 3874.6 | Semi standard non polar | 33892256 | Paxilline,2TMS,isomer #5 | CC(C)(O[Si](C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4CC5=C(N([Si](C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 3854.9 | Semi standard non polar | 33892256 | Paxilline,2TMS,isomer #6 | CC(C)(O)C1=C(O[Si](C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O)CC[C@H]2CC4=C(N([Si](C)(C)C)C5=CC=CC=C45)[C@@]23C)O1 | 3841.7 | Semi standard non polar | 33892256 | Paxilline,3TMS,isomer #1 | CC(C)(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O[Si](C)(C)C)CC[C@H]2CC4=C([NH]C5=CC=CC=C45)[C@@]23C)O1 | 3791.9 | Semi standard non polar | 33892256 | Paxilline,3TMS,isomer #1 | CC(C)(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O[Si](C)(C)C)CC[C@H]2CC4=C([NH]C5=CC=CC=C45)[C@@]23C)O1 | 3556.5 | Standard non polar | 33892256 | Paxilline,3TMS,isomer #2 | CC(C)(O[Si](C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O[Si](C)(C)C)(CC[C@H]4CC5=C(N([Si](C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 3783.4 | Semi standard non polar | 33892256 | Paxilline,3TMS,isomer #2 | CC(C)(O[Si](C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O[Si](C)(C)C)(CC[C@H]4CC5=C(N([Si](C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 3618.9 | Standard non polar | 33892256 | Paxilline,3TMS,isomer #3 | CC(C)(O)C1=C(O[Si](C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O[Si](C)(C)C)CC[C@H]2CC4=C(N([Si](C)(C)C)C5=CC=CC=C45)[C@@]23C)O1 | 3759.9 | Semi standard non polar | 33892256 | Paxilline,3TMS,isomer #3 | CC(C)(O)C1=C(O[Si](C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O[Si](C)(C)C)CC[C@H]2CC4=C(N([Si](C)(C)C)C5=CC=CC=C45)[C@@]23C)O1 | 3535.5 | Standard non polar | 33892256 | Paxilline,3TMS,isomer #4 | CC(C)(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O)CC[C@H]2CC4=C(N([Si](C)(C)C)C5=CC=CC=C45)[C@@]23C)O1 | 3794.2 | Semi standard non polar | 33892256 | Paxilline,3TMS,isomer #4 | CC(C)(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O)CC[C@H]2CC4=C(N([Si](C)(C)C)C5=CC=CC=C45)[C@@]23C)O1 | 3673.2 | Standard non polar | 33892256 | Paxilline,4TMS,isomer #1 | CC(C)(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O[Si](C)(C)C)CC[C@H]2CC4=C(N([Si](C)(C)C)C5=CC=CC=C45)[C@@]23C)O1 | 3726.8 | Semi standard non polar | 33892256 | Paxilline,4TMS,isomer #1 | CC(C)(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O[Si](C)(C)C)CC[C@H]2CC4=C(N([Si](C)(C)C)C5=CC=CC=C45)[C@@]23C)O1 | 3593.9 | Standard non polar | 33892256 | Paxilline,1TBDMS,isomer #1 | CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O[Si](C)(C)C(C)(C)C)(CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 4112.6 | Semi standard non polar | 33892256 | Paxilline,1TBDMS,isomer #2 | CC(C)(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 4165.9 | Semi standard non polar | 33892256 | Paxilline,1TBDMS,isomer #3 | CC(C)(O)C1=C(O[Si](C)(C)C(C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O)CC[C@H]2CC4=C([NH]C5=CC=CC=C45)[C@@]23C)O1 | 4110.8 | Semi standard non polar | 33892256 | Paxilline,1TBDMS,isomer #4 | CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4CC5=C(N([Si](C)(C)C(C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 4116.4 | Semi standard non polar | 33892256 | Paxilline,2TBDMS,isomer #1 | CC(C)(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O[Si](C)(C)C(C)(C)C)(CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 4257.9 | Semi standard non polar | 33892256 | Paxilline,2TBDMS,isomer #2 | CC(C)(O)C1=C(O[Si](C)(C)C(C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O[Si](C)(C)C(C)(C)C)CC[C@H]2CC4=C([NH]C5=CC=CC=C45)[C@@]23C)O1 | 4261.9 | Semi standard non polar | 33892256 | Paxilline,2TBDMS,isomer #3 | CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O[Si](C)(C)C(C)(C)C)(CC[C@H]4CC5=C(N([Si](C)(C)C(C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 4207.1 | Semi standard non polar | 33892256 | Paxilline,2TBDMS,isomer #4 | CC(C)(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O)CC[C@H]2CC4=C([NH]C5=CC=CC=C45)[C@@]23C)O1 | 4312.9 | Semi standard non polar | 33892256 | Paxilline,2TBDMS,isomer #5 | CC(C)(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4CC5=C(N([Si](C)(C)C(C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 4271.6 | Semi standard non polar | 33892256 | Paxilline,2TBDMS,isomer #6 | CC(C)(O)C1=C(O[Si](C)(C)C(C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O)CC[C@H]2CC4=C(N([Si](C)(C)C(C)(C)C)C5=CC=CC=C45)[C@@]23C)O1 | 4234.5 | Semi standard non polar | 33892256 | Paxilline,3TBDMS,isomer #1 | CC(C)(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O[Si](C)(C)C(C)(C)C)CC[C@H]2CC4=C([NH]C5=CC=CC=C45)[C@@]23C)O1 | 4393.8 | Semi standard non polar | 33892256 | Paxilline,3TBDMS,isomer #1 | CC(C)(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O[Si](C)(C)C(C)(C)C)CC[C@H]2CC4=C([NH]C5=CC=CC=C45)[C@@]23C)O1 | 4175.6 | Standard non polar | 33892256 | Paxilline,3TBDMS,isomer #2 | CC(C)(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O[Si](C)(C)C(C)(C)C)(CC[C@H]4CC5=C(N([Si](C)(C)C(C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 4368.8 | Semi standard non polar | 33892256 | Paxilline,3TBDMS,isomer #2 | CC(C)(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O[Si](C)(C)C(C)(C)C)(CC[C@H]4CC5=C(N([Si](C)(C)C(C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O | 4236.5 | Standard non polar | 33892256 | Paxilline,3TBDMS,isomer #3 | CC(C)(O)C1=C(O[Si](C)(C)C(C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O[Si](C)(C)C(C)(C)C)CC[C@H]2CC4=C(N([Si](C)(C)C(C)(C)C)C5=CC=CC=C45)[C@@]23C)O1 | 4312.8 | Semi standard non polar | 33892256 | Paxilline,3TBDMS,isomer #3 | CC(C)(O)C1=C(O[Si](C)(C)C(C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O[Si](C)(C)C(C)(C)C)CC[C@H]2CC4=C(N([Si](C)(C)C(C)(C)C)C5=CC=CC=C45)[C@@]23C)O1 | 4138.3 | Standard non polar | 33892256 | Paxilline,3TBDMS,isomer #4 | CC(C)(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O)CC[C@H]2CC4=C(N([Si](C)(C)C(C)(C)C)C5=CC=CC=C45)[C@@]23C)O1 | 4393.0 | Semi standard non polar | 33892256 | Paxilline,3TBDMS,isomer #4 | CC(C)(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O)CC[C@H]2CC4=C(N([Si](C)(C)C(C)(C)C)C5=CC=CC=C45)[C@@]23C)O1 | 4306.9 | Standard non polar | 33892256 | Paxilline,4TBDMS,isomer #1 | CC(C)(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O[Si](C)(C)C(C)(C)C)CC[C@H]2CC4=C(N([Si](C)(C)C(C)(C)C)C5=CC=CC=C45)[C@@]23C)O1 | 4457.2 | Semi standard non polar | 33892256 | Paxilline,4TBDMS,isomer #1 | CC(C)(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2[C@H](CC[C@@]3(C)[C@@]2(O[Si](C)(C)C(C)(C)C)CC[C@H]2CC4=C(N([Si](C)(C)C(C)(C)C)C5=CC=CC=C45)[C@@]23C)O1 | 4362.6 | Standard non polar | 33892256 |
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