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 07:55:08 UTC |
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Update Date | 2021-09-26 23:02:29 UTC |
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HMDB ID | HMDB0250810 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | D,L-Stepholidine |
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Description | 4,10-dimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene-3,11-diol belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. 4,10-dimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene-3,11-diol is a strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). D,l-stepholidine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically D,L-Stepholidine 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 | COC1=CC2=C(C=C1O)C1CC3=C(CN1CC2)C(OC)=C(O)C=C3 InChI=1S/C19H21NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3 |
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Synonyms | Value | Source |
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Stepholidine | MeSH | (-)-Stepholidine | MeSH | L-Stepholidine | MeSH |
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Chemical Formula | C19H21NO4 |
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Average Molecular Weight | 327.38 |
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Monoisotopic Molecular Weight | 327.14705816 |
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IUPAC Name | 4,10-dimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene-3,11-diol |
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Traditional Name | stepholidine |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC2=C(C=C1O)C1CC3=C(CN1CC2)C(OC)=C(O)C=C3 |
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InChI Identifier | InChI=1S/C19H21NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3 |
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InChI Key | JKPISQIIWUONPB-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Protoberberine alkaloids and derivatives |
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Sub Class | Not Available |
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Direct Parent | Protoberberine alkaloids and derivatives |
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Alternative Parents | |
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Substituents | - Protoberberine skeleton
- Tetrahydroprotoberberine skeleton
- Tetrahydroisoquinoline
- Anisole
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Aralkylamine
- Benzenoid
- Tertiary amine
- Tertiary aliphatic amine
- Ether
- Azacycle
- Organoheterocyclic compound
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Amine
- Organic oxygen 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 IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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D,L-Stepholidine,1TMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C)C1CC3=CC=C(O)C(OC)=C3CN1CC2 | 2945.1 | Semi standard non polar | 33892256 | D,L-Stepholidine,1TMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C)C1CC3=CC=C(O)C(OC)=C3CN1CC2 | 2857.4 | Standard non polar | 33892256 | D,L-Stepholidine,1TMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C)C1CC3=CC=C(O)C(OC)=C3CN1CC2 | 3838.0 | Standard polar | 33892256 | D,L-Stepholidine,1TMS,isomer #2 | COC1=CC2=C(C=C1O)C1CC3=CC=C(O[Si](C)(C)C)C(OC)=C3CN1CC2 | 2955.4 | Semi standard non polar | 33892256 | D,L-Stepholidine,1TMS,isomer #2 | COC1=CC2=C(C=C1O)C1CC3=CC=C(O[Si](C)(C)C)C(OC)=C3CN1CC2 | 2866.8 | Standard non polar | 33892256 | D,L-Stepholidine,1TMS,isomer #2 | COC1=CC2=C(C=C1O)C1CC3=CC=C(O[Si](C)(C)C)C(OC)=C3CN1CC2 | 3830.5 | Standard polar | 33892256 | D,L-Stepholidine,2TMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C)C1CC3=CC=C(O[Si](C)(C)C)C(OC)=C3CN1CC2 | 2903.1 | Semi standard non polar | 33892256 | D,L-Stepholidine,2TMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C)C1CC3=CC=C(O[Si](C)(C)C)C(OC)=C3CN1CC2 | 2927.0 | Standard non polar | 33892256 | D,L-Stepholidine,2TMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C)C1CC3=CC=C(O[Si](C)(C)C)C(OC)=C3CN1CC2 | 3612.0 | Standard polar | 33892256 | D,L-Stepholidine,1TBDMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1CC3=CC=C(O)C(OC)=C3CN1CC2 | 3194.4 | Semi standard non polar | 33892256 | D,L-Stepholidine,1TBDMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1CC3=CC=C(O)C(OC)=C3CN1CC2 | 3102.5 | Standard non polar | 33892256 | D,L-Stepholidine,1TBDMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1CC3=CC=C(O)C(OC)=C3CN1CC2 | 3964.1 | Standard polar | 33892256 | D,L-Stepholidine,1TBDMS,isomer #2 | COC1=CC2=C(C=C1O)C1CC3=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3CN1CC2 | 3216.1 | Semi standard non polar | 33892256 | D,L-Stepholidine,1TBDMS,isomer #2 | COC1=CC2=C(C=C1O)C1CC3=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3CN1CC2 | 3110.2 | Standard non polar | 33892256 | D,L-Stepholidine,1TBDMS,isomer #2 | COC1=CC2=C(C=C1O)C1CC3=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3CN1CC2 | 3958.7 | Standard polar | 33892256 | D,L-Stepholidine,2TBDMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1CC3=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3CN1CC2 | 3352.1 | Semi standard non polar | 33892256 | D,L-Stepholidine,2TBDMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1CC3=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3CN1CC2 | 3368.3 | Standard non polar | 33892256 | D,L-Stepholidine,2TBDMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1CC3=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3CN1CC2 | 3808.4 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - D,L-Stepholidine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0gvp-0952000000-c69727ff619b6fb43b22 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D,L-Stepholidine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D,L-Stepholidine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D,L-Stepholidine 10V, Positive-QTOF | splash10-004i-0009000000-354160c39518aa1987e3 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D,L-Stepholidine 20V, Positive-QTOF | splash10-004i-0019000000-e0392c5d3977f667476c | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D,L-Stepholidine 40V, Positive-QTOF | splash10-052f-0891000000-abdf40f53d943cd0cc4b | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D,L-Stepholidine 10V, Negative-QTOF | splash10-004i-0009000000-82e8b7e0c70cdc0f9fe6 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D,L-Stepholidine 20V, Negative-QTOF | splash10-004i-0039000000-5e748b51ea1d79634775 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D,L-Stepholidine 40V, Negative-QTOF | splash10-0uyi-0090000000-202b5637e2f556c806fb | 2021-10-12 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 5290 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]
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