| 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 17:35:53 UTC |
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| Update Date | 2022-03-07 02:52:29 UTC |
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| HMDB ID | HMDB0030280 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | (-)-Chimonanthine |
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| Description | (-)-Chimonanthine belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Based on a literature review very few articles have been published on (-)-Chimonanthine. |
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| Structure | CN1CCC2(C1NC1=C2C=CC=C1)C12CCN(C)C1NC1=C2C=CC=C1 InChI=1S/C22H26N4/c1-25-13-11-21(15-7-3-5-9-17(15)23-19(21)25)22-12-14-26(2)20(22)24-18-10-6-4-8-16(18)22/h3-10,19-20,23-24H,11-14H2,1-2H3 |
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| Synonyms | | Value | Source |
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| 1-Demethyl-calycanthidine | HMDB | | 1-Demethylcalycanthidine | HMDB | | Chimonanthin | HMDB | | Chimonanthine | HMDB | | L-Chimonanthine | HMDB |
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| Chemical Formula | C22H26N4 |
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| Average Molecular Weight | 346.4686 |
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| Monoisotopic Molecular Weight | 346.215746852 |
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| IUPAC Name | 1-methyl-3a-{1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl}-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indole |
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| Traditional Name | chimonanthine |
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| CAS Registry Number | 5545-89-1 |
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| SMILES | CN1CCC2(C1NC1=C2C=CC=C1)C12CCN(C)C1NC1=C2C=CC=C1 |
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| InChI Identifier | InChI=1S/C22H26N4/c1-25-13-11-21(15-7-3-5-9-17(15)23-19(21)25)22-12-14-26(2)20(22)24-18-10-6-4-8-16(18)22/h3-10,19-20,23-24H,11-14H2,1-2H3 |
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| InChI Key | HOYXPMHLHJOGHD-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. |
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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 | Pyrroloindoles |
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| Direct Parent | Pyrroloindoles |
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| Alternative Parents | |
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| Substituents | - Pyrroloindole
- Indole
- Dihydroindole
- Secondary aliphatic/aromatic amine
- Benzenoid
- N-alkylpyrrolidine
- Pyrrole
- Pyrrolidine
- Azacycle
- Secondary amine
- Hydrocarbon derivative
- Organonitrogen compound
- Organopnictogen compound
- Organic nitrogen compound
- Amine
- 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 | Not Available |
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| Role | Not Available |
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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 | 188 - 189 °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 Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022. | 3.3 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 10.5167 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 3.85 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 186.9 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 655.2 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 208.1 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 151.7 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 188.5 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 67.0 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 273.1 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 360.0 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 1000.1 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 735.3 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 60.2 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 928.7 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 230.0 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 261.7 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 590.6 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 682.3 seconds | 40023050 | | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 55.3 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| (-)-Chimonanthine,1TMS,isomer #1 | CN1CCC2(C34CCN(C)C3N([Si](C)(C)C)C3=CC=CC=C34)C3=CC=CC=C3NC12 | 2950.8 | Semi standard non polar | 33892256 | | (-)-Chimonanthine,1TMS,isomer #1 | CN1CCC2(C34CCN(C)C3N([Si](C)(C)C)C3=CC=CC=C34)C3=CC=CC=C3NC12 | 3009.8 | Standard non polar | 33892256 | | (-)-Chimonanthine,2TMS,isomer #1 | CN1CCC2(C34CCN(C)C3N([Si](C)(C)C)C3=CC=CC=C34)C3=CC=CC=C3N([Si](C)(C)C)C12 | 2929.7 | Semi standard non polar | 33892256 | | (-)-Chimonanthine,2TMS,isomer #1 | CN1CCC2(C34CCN(C)C3N([Si](C)(C)C)C3=CC=CC=C34)C3=CC=CC=C3N([Si](C)(C)C)C12 | 3008.9 | Standard non polar | 33892256 | | (-)-Chimonanthine,1TBDMS,isomer #1 | CN1CCC2(C34CCN(C)C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C34)C3=CC=CC=C3NC12 | 3160.9 | Semi standard non polar | 33892256 | | (-)-Chimonanthine,1TBDMS,isomer #1 | CN1CCC2(C34CCN(C)C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C34)C3=CC=CC=C3NC12 | 3338.9 | Standard non polar | 33892256 | | (-)-Chimonanthine,2TBDMS,isomer #1 | CN1CCC2(C34CCN(C)C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C34)C3=CC=CC=C3N([Si](C)(C)C(C)(C)C)C12 | 3324.9 | Semi standard non polar | 33892256 | | (-)-Chimonanthine,2TBDMS,isomer #1 | CN1CCC2(C34CCN(C)C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C34)C3=CC=CC=C3N([Si](C)(C)C(C)(C)C)C12 | 3578.6 | Standard non polar | 33892256 |
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| GC-MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - (-)-Chimonanthine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fz9-0839000000-e6dc51fe7686225cb76e | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - (-)-Chimonanthine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - (-)-Chimonanthine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Chimonanthine 10V, Positive-QTOF | splash10-0002-0009000000-ede6dda140966de044ba | 2016-08-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Chimonanthine 20V, Positive-QTOF | splash10-0002-1009000000-5fc4e48dea2309927723 | 2016-08-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Chimonanthine 40V, Positive-QTOF | splash10-001r-6094000000-72a46e04248bd284193c | 2016-08-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Chimonanthine 10V, Negative-QTOF | splash10-0002-0209000000-f04b1a47b3ee880c297d | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Chimonanthine 20V, Negative-QTOF | splash10-0002-1109000000-036750f7127d1ff0f027 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Chimonanthine 40V, Negative-QTOF | splash10-0avi-2934000000-45e537f8de9ae517804d | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Chimonanthine 10V, Positive-QTOF | splash10-0002-0009000000-37c95b847a9e45a22589 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Chimonanthine 20V, Positive-QTOF | splash10-0002-0019000000-5f6508ee1c8e805d7483 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Chimonanthine 40V, Positive-QTOF | splash10-0fdx-2695000000-2bc392ec5723c1849154 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Chimonanthine 10V, Negative-QTOF | splash10-0002-0009000000-a5ed12fd7e24b3ac19f5 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Chimonanthine 20V, Negative-QTOF | splash10-0002-0009000000-a5ed12fd7e24b3ac19f5 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Chimonanthine 40V, Negative-QTOF | splash10-00di-0902000000-eaebb7fc5a7a7f5c48bf | 2021-09-24 | Wishart Lab | View Spectrum |
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