Record Information |
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Version | 1.0 |
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Created at | 2020-04-17 18:41:22 UTC |
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Updated at | 2020-12-07 19:11:03 UTC |
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CannabisDB ID | CDB004832 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Sphinganine |
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Description | Sphinganine, also known as D18:0 or safingol, belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Thus, sphinganine is considered to be a sphingoid base lipid molecule. Sphinganine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sphinganine exists in all living species, ranging from bacteria to humans. Within humans, sphinganine participates in a number of enzymatic reactions. In particular, sphinganine can be converted into 3-dehydrosphinganine; which is mediated by the enzyme 3-ketodihydrosphingosine reductase. In addition, sphinganine can be converted into sphinganine 1-phosphate; which is catalyzed by the enzyme sphingosine kinase 2. In humans, sphinganine is involved in the metabolic disorder called the fabry disease pathway. Outside of the human body, Sphinganine has been detected, but not quantified in, several different foods, such as beech nuts, docks, citrus, watercress, and brazil nuts. This could make sphinganine a potential biomarker for the consumption of these foods. A Sphinganine having (2S,3R)-configuration. Sphinganine is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | |
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Synonyms | Value | Source |
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(2S,3R)-2-Amino-1,3-octadecanediol | ChEBI | (2S,3R)-2-Aminooctadecane-1,3-diol | ChEBI | (R-(R*,s*))-2-aminooctadecane-1,3-diol | ChEBI | 2-Amino-1,3-dihydroxyoctadecane | ChEBI | C18-Dihydrosphingosine | ChEBI | C18-Sphinganine | ChEBI | D-Erythro-1,3-dihydroxy-2-aminooctadecane | ChEBI | D-Erythro-2-amino-1,3-octadecanediol | ChEBI | D-Erythro-C18-dihydrosphingosine | ChEBI | D18:0 | ChEBI | Dihydrosphingosine | ChEBI | Octadecasphinganine | ChEBI | Safingol | ChEBI | Erythro-D-sphinganine | HMDB | 2-Aminooctadecane-1,3-diol | HMDB | Threo-dihydrosphingosine | HMDB | 2-Amino-D-erythro-1,3-octadecanediol | HMDB | C18-Dihydro-sphingosine | HMDB | D-Erythro-sphinganine | HMDB | Dihydro-C18-sphingosine | HMDB | Erythro-sphinganine | HMDB | [R-(R*,s*)]-2-amino-1,3-octadecanediol | HMDB | (2S,3R)-Sphinganine | HMDB | D-Erythro-dihydrosphingosine | HMDB | SP(D18:0) | HMDB | Sphinganine | HMDB |
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Chemical Formula | C18H39NO2 |
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Average Molecular Weight | 301.51 |
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Monoisotopic Molecular Weight | 301.2981 |
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IUPAC Name | (2S,3R)-2-aminooctadecane-1,3-diol |
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Traditional Name | sphinganine |
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CAS Registry Number | 764-22-7 |
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SMILES | CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO |
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InChI Identifier | InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/m0/s1 |
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InChI Key | OTKJDMGTUTTYMP-ZWKOTPCHSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. |
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Kingdom | Organic compounds |
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Super Class | Organic nitrogen compounds |
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Class | Organonitrogen compounds |
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Sub Class | Amines |
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Direct Parent | 1,2-aminoalcohols |
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Alternative Parents | |
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Substituents | - Secondary alcohol
- 1,2-aminoalcohol
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Primary alcohol
- Organooxygen compound
- Primary aliphatic amine
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental 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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Predicted Properties | [] |
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Spectra |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Sphinganine, 3 TMS, GC-MS Spectrum | splash10-0udi-3980100000-87c0074f611dec416856 | Spectrum | GC-MS | Sphinganine, 3 TMS, GC-MS Spectrum | splash10-0udi-1690000000-8fed2f980c631302b97b | Spectrum | GC-MS | Sphinganine, non-derivatized, GC-MS Spectrum | splash10-0udi-3980100000-87c0074f611dec416856 | Spectrum | GC-MS | Sphinganine, non-derivatized, GC-MS Spectrum | splash10-0udi-1690000000-8fed2f980c631302b97b | Spectrum | Predicted GC-MS | Sphinganine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03di-9120000000-0cfd71520376dffc3c78 | Spectrum | Predicted GC-MS | Sphinganine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0uk9-4490200000-f4c4281643554b83dd43 | Spectrum | Predicted GC-MS | Sphinganine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sphinganine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sphinganine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sphinganine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sphinganine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sphinganine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sphinganine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sphinganine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sphinganine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sphinganine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sphinganine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sphinganine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sphinganine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sphinganine, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0iml-3791000000-013fe5eb404ccb287385 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-03di-9000000000-04469479cb6d83603093 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0bt9-9000000000-4f682b26d6efc1673141 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0udi-0009000000-4d5daf40edf51d7c5ce4 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-0f89-2196000000-86bd4d9593c5a53dfc94 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-01qa-9130000000-819bc3df8d7408799b9f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-03xr-9000000000-0b47410c79f07946095a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-03xr-9000000000-6dd6eb4c242974e7f7cc | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0ab9-3892000000-6d8fa67090a1cebaa6f3 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0159-0092000000-6e15bf1516b938239cb5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0udi-0009000000-4d5daf40edf51d7c5ce4 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0f89-2196000000-86bd4d9593c5a53dfc94 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-01qa-9130000000-819bc3df8d7408799b9f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03xr-9000000000-3157cbca45e3dce158e4 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03xr-9000000000-6dd6eb4c242974e7f7cc | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0udi-2390000000-a002411e49400899cf3c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0gx0-5096000000-ad6ab79ab16fab02d693 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-08fr-9000000000-5afe9071156e7abc48f2 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 25V, Negative | splash10-0159-0092000000-9c001535e8080ffe05e2 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0fsi-0092000000-4cad101913d628c296ba | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0159-2290000000-e693ddcd90fd9234c669 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-06r7-9740000000-808c9a702fe97ec9078e | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-1089000000-00c77e7cc5d9f3475be7 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-115c-5091000000-dc391e96a566caaa0602 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9030000000-a74567f0d047f0915ffc | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | | Spectrum |
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Pathways |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | Sphingolipid Metabolism | | | Gaucher Disease | | Not Available | Globoid Cell Leukodystrophy | | Not Available | Metachromatic Leukodystrophy (MLD) | | Not Available | Fabry disease | | Not Available |
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Protein Targets |
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Enzymes | |
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Transporters | |
Pleckstrin homology domain-containing family A member 8 | PLEKHA8 | 7p21-p11.2 | Q96JA3 | details | Protein PLEKHA9 | PLEKHA9 | 12q | O95397 | details | Glycolipid transfer protein domain-containing protein 2 | GLTPD2 | 17p13.2 | A6NH11 | details | Putative uncharacterized protein PLEKHA8 | PLEKHA8 | 7p21-p11.2 | B5MDU3 | details | Glycolipid transfer protein domain-containing protein 1 | GLTPD1 | 1p36.33 | Q5TA50 | details | Putative uncharacterized protein DKFZp434L0435 | DKFZp434L0435 | | Q9UFH6 | details | Glycolipid transfer protein | GLTP | 12q24.11 | Q9NZD2 | details |
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Metal Bindings | Not Available |
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Receptors | |
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Transcriptional Factors | |
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Concentrations Data |
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| Not Available |
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External Links |
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HMDB ID | HMDB0000269 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB030824 |
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KNApSAcK ID | C00007540 |
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Chemspider ID | 82609 |
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KEGG Compound ID | C00836 |
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BioCyc ID | CPD-13612 |
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BiGG ID | Not Available |
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Wikipedia Link | Safingol |
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METLIN ID | Not Available |
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PubChem Compound | 91486 |
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PDB ID | Not Available |
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ChEBI ID | 16566 |
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References |
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General References | Not Available |
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