| Record Information |
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| Version | 5.0 |
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| Status | Detected but not Quantified |
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| Creation Date | 2021-09-11 20:19:23 UTC |
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| Update Date | 2021-09-26 23:15:44 UTC |
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| HMDB ID | HMDB0258655 |
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| Secondary Accession Numbers | None |
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| Metabolite Identification |
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| Common Name | Syrosingopine |
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| Description | Syrosingopine belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor. Based on a literature review a significant number of articles have been published on Syrosingopine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Syrosingopine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Syrosingopine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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| Structure | CCOC(=O)OC1=C(OC)C=C(C=C1OC)C(=O)OC1CC2CN3CCC4=C(NC5=C4C=CC(OC)=C5)C3CC2C(C1OC)C(=O)OC InChI=1S/C35H42N2O11/c1-7-46-35(40)48-31-26(42-3)12-18(13-27(31)43-4)33(38)47-28-14-19-17-37-11-10-22-21-9-8-20(41-2)15-24(21)36-30(22)25(37)16-23(19)29(32(28)44-5)34(39)45-6/h8-9,12-13,15,19,23,25,28-29,32,36H,7,10-11,14,16-17H2,1-6H3 |
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| Synonyms | | Value | Source |
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| Methyl 17-{4-[(ethoxycarbonyl)oxy]-3,5-dimethoxybenzoyloxy}-6,18-dimethoxy-3,13-diazapentacyclo[11.8.0.0,.0,.0,]henicosa-2(10),4(9),5,7-tetraene-19-carboxylic acid | HMDB |
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| Chemical Formula | C35H42N2O11 |
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| Average Molecular Weight | 666.724 |
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| Monoisotopic Molecular Weight | 666.27886018 |
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| IUPAC Name | methyl 17-{4-[(ethoxycarbonyl)oxy]-3,5-dimethoxybenzoyloxy}-6,18-dimethoxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate |
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| Traditional Name | methyl 17-{4-[(ethoxycarbonyl)oxy]-3,5-dimethoxybenzoyloxy}-6,18-dimethoxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate |
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| CAS Registry Number | Not Available |
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| SMILES | CCOC(=O)OC1=C(OC)C=C(C=C1OC)C(=O)OC1CC2CN3CCC4=C(NC5=C4C=CC(OC)=C5)C3CC2C(C1OC)C(=O)OC |
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| InChI Identifier | InChI=1S/C35H42N2O11/c1-7-46-35(40)48-31-26(42-3)12-18(13-27(31)43-4)33(38)47-28-14-19-17-37-11-10-22-21-9-8-20(41-2)15-24(21)36-30(22)25(37)16-23(19)29(32(28)44-5)34(39)45-6/h8-9,12-13,15,19,23,25,28-29,32,36H,7,10-11,14,16-17H2,1-6H3 |
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| InChI Key | ZCDNRPPFBQDQHR-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Yohimbine alkaloids |
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| Sub Class | Not Available |
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| Direct Parent | Yohimbine alkaloids |
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| Alternative Parents | |
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| Substituents | - Yohimbine
- Corynanthean skeleton
- Yohimbine alkaloid
- Beta-carboline
- Pyridoindole
- Gallic acid or derivatives
- M-methoxybenzoic acid or derivatives
- Benzoate ester
- M-dimethoxybenzene
- Dimethoxybenzene
- 3-alkylindole
- Indole
- Indole or derivatives
- Benzoic acid or derivatives
- Phenoxy compound
- Anisole
- Phenol ether
- Methoxybenzene
- Benzoyl
- Alkyl aryl ether
- Aralkylamine
- Piperidine
- Carbonic acid diester
- Monocyclic benzene moiety
- Dicarboxylic acid or derivatives
- Benzenoid
- Pyrrole
- Heteroaromatic compound
- Methyl ester
- Tertiary amine
- Carboxylic acid ester
- Carbonic acid derivative
- Tertiary aliphatic amine
- Amino acid or derivatives
- Azacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Ether
- Dialkyl ether
- Organooxygen compound
- Amine
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organonitrogen compound
- Carbonyl group
- Organic oxygen compound
- Organopnictogen 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 | |
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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. | 6.54 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 15.0541 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 2.63 minutes | 32390414 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 3287.7 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 178.2 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 244.2 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 169.8 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 141.7 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 695.3 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 | 607.2 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 424.5 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 1213.8 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 633.7 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 | 2019.7 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 419.9 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 452.7 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 283.4 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 178.1 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 | 12.3 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| Syrosingopine,1TMS,isomer #1 | CCOC(=O)OC1=C(OC)C=C(C(=O)OC2CC3CN4CCC5=C(C4CC3C(C(=O)OC)C2OC)N([Si](C)(C)C)C2=CC(OC)=CC=C52)C=C1OC | 4956.9 | Semi standard non polar | 33892256 | | Syrosingopine,1TMS,isomer #1 | CCOC(=O)OC1=C(OC)C=C(C(=O)OC2CC3CN4CCC5=C(C4CC3C(C(=O)OC)C2OC)N([Si](C)(C)C)C2=CC(OC)=CC=C52)C=C1OC | 4553.5 | Standard non polar | 33892256 | | Syrosingopine,1TMS,isomer #1 | CCOC(=O)OC1=C(OC)C=C(C(=O)OC2CC3CN4CCC5=C(C4CC3C(C(=O)OC)C2OC)N([Si](C)(C)C)C2=CC(OC)=CC=C52)C=C1OC | 6781.9 | Standard polar | 33892256 | | Syrosingopine,1TBDMS,isomer #1 | CCOC(=O)OC1=C(OC)C=C(C(=O)OC2CC3CN4CCC5=C(C4CC3C(C(=O)OC)C2OC)N([Si](C)(C)C(C)(C)C)C2=CC(OC)=CC=C52)C=C1OC | 5063.7 | Semi standard non polar | 33892256 | | Syrosingopine,1TBDMS,isomer #1 | CCOC(=O)OC1=C(OC)C=C(C(=O)OC2CC3CN4CCC5=C(C4CC3C(C(=O)OC)C2OC)N([Si](C)(C)C(C)(C)C)C2=CC(OC)=CC=C52)C=C1OC | 4676.3 | Standard non polar | 33892256 | | Syrosingopine,1TBDMS,isomer #1 | CCOC(=O)OC1=C(OC)C=C(C(=O)OC2CC3CN4CCC5=C(C4CC3C(C(=O)OC)C2OC)N([Si](C)(C)C(C)(C)C)C2=CC(OC)=CC=C52)C=C1OC | 6737.2 | Standard polar | 33892256 |
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| MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Negative-QTOF | splash10-014i-0010019000-7fcde86a9944ec40fa60 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014i-0000009000-94be94a76eac46eadbd6 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-004i-0891000000-bd01e1654c8d6b6c06f7 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014i-0000009000-9cb2af563f1a3b63f2cc | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-00e9-0920000000-3e71f9d81714ecd653d5 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014i-0000009000-ad63bcfc9f6a53d46deb | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014i-0101009000-08a683d9f7694d308b87 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014i-0010019000-96e4c968017538bfeeb1 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014j-0428149000-043b11fe6e71f47b7e2f | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014i-0000009000-7b8fcc8bc8f0a15f651c | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014l-0571097000-345a4298db27ac960814 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014l-0561098000-22364e96cec7c2ca45df | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014i-0000009000-a8575e8d3d75592e59e3 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-0fr6-0461096000-6fd2915804ae3ccd6d45 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014i-0000009000-d47079b17a2086c867f5 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014i-0000009000-c2b599badcc44eb57592 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014j-0327149000-be073b2ea45030a3bbfe | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014i-0101009000-d9d371e8401c3714e8e3 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-004i-0591000000-6bffe3f305092fe13905 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014i-0100019000-8fdd61b01e56d31d9e57 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-00e9-0910000000-6d819b182ab053ff366a | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-014j-0428149000-77afccdf556a6aee84c0 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOF | splash10-004i-0691000000-2b9734bc04e33b22f0f5 | 2021-09-20 | HMDB team, MONA | View Spectrum |
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