Record Information |
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Version | 1.0 |
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Created at | 2020-04-17 18:48:35 UTC |
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Updated at | 2022-12-13 23:36:25 UTC |
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CannabisDB ID | CDB004901 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Spermidine |
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Description | Spermidine, also known as SPD, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Spermidine is a very strong basic compound (based on its pKa). Spermidine exists in all living species, ranging from bacteria to humans. Within humans, spermidine participates in a number of enzymatic reactions. In particular, 5'-methylthioadenosine and spermidine can be biosynthesized from S-adenosylmethioninamine and putrescine; which is mediated by the enzyme spermidine synthase. In addition, S-adenosylmethioninamine and spermidine can be converted into 5'-methylthioadenosine and spermine through the action of the enzyme spermine synthase. In humans, spermidine is involved in spermidine and spermine biosynthesis. Outside of the human body, Spermidine is found, on average, in the highest concentration within milk (cow) and oats. Spermidine has also been detected, but not quantified in, several different foods, such as american cranberries, sour cherries, arctic blackberries, chinese broccoli, and arabica coffee. This could make spermidine a potential biomarker for the consumption of these foods. Spermidine is a potentially toxic compound. A triamine that is the 1,5,10-triaza derivative of decane. Spermidine 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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1,5,10-Triazadecane | ChEBI | 4-Azaoctamethylenediamine | ChEBI | 4-Azaoctane-1,8-diamine | ChEBI | N-(3-Aminopropyl)-1,4-butane-diamine | ChEBI | Spermidin | ChEBI | 1,8-Diamino-4-azaoctane | HMDB | Aminopropylbutandiamine | HMDB | N-(3-Aminopropyl)-1,4-butanediamine | HMDB | N-(3-Aminopropyl)-1,4-diamino-butane | HMDB | N-(3-Aminopropyl)-1,4-diaminobutane | HMDB | N-(3-Aminopropyl)-4-aminobutylamine | HMDB | N-(4-Aminobutyl)-1,3-diaminopropane | HMDB | N-(gamma-Aminopropyl)tetramethylenediamine | HMDB | SPD | HMDB |
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Chemical Formula | C7H19N3 |
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Average Molecular Weight | 145.25 |
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Monoisotopic Molecular Weight | 145.1579 |
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IUPAC Name | (4-aminobutyl)(3-aminopropyl)amine |
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Traditional Name | spermidine |
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CAS Registry Number | 124-20-9 |
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SMILES | NCCCCNCCCN |
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InChI Identifier | InChI=1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2 |
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InChI Key | ATHGHQPFGPMSJY-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. |
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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 | Dialkylamines |
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Alternative Parents | |
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Substituents | - Secondary aliphatic amine
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Primary aliphatic amine
- 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: |
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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 | < 25 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 145 g/L at 20 °C | Wikipedia | logP | 0.0 | Wikipedia |
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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 | Spermidine, 5 TMS, GC-MS Spectrum | splash10-00di-5910000000-48794a2dc9d682aab28f | Spectrum | GC-MS | Spermidine, 5 TMS, GC-MS Spectrum | splash10-066u-1910000000-9fe6c1c8e8f166270be1 | Spectrum | GC-MS | Spermidine, non-derivatized, GC-MS Spectrum | splash10-00rf-1900000000-c88ed717e55f237cf01c | Spectrum | GC-MS | Spermidine, 5 TMS, GC-MS Spectrum | splash10-00di-6900000000-56396208515d9020bfeb | Spectrum | GC-MS | Spermidine, 4 TMS, GC-MS Spectrum | splash10-0uki-5920000000-4aac8aba8d9635a96f1c | Spectrum | GC-MS | Spermidine, 5 TMS, GC-MS Spectrum | splash10-00rf-1900000000-f4b7d8b055a8d5025036 | Spectrum | GC-MS | Spermidine, 5 TMS, GC-MS Spectrum | splash10-00di-1900000000-1be27daaf9f6d9e03752 | Spectrum | GC-MS | Spermidine, non-derivatized, GC-MS Spectrum | splash10-05tf-0910000000-280a5c2a493fedd0e524 | Spectrum | GC-MS | Spermidine, non-derivatized, GC-MS Spectrum | splash10-00di-5910000000-48794a2dc9d682aab28f | Spectrum | GC-MS | Spermidine, non-derivatized, GC-MS Spectrum | splash10-066u-1910000000-9fe6c1c8e8f166270be1 | Spectrum | GC-MS | Spermidine, non-derivatized, GC-MS Spectrum | splash10-00rf-1900000000-c88ed717e55f237cf01c | Spectrum | GC-MS | Spermidine, non-derivatized, GC-MS Spectrum | splash10-00di-6900000000-56396208515d9020bfeb | Spectrum | GC-MS | Spermidine, non-derivatized, GC-MS Spectrum | splash10-0uki-5920000000-4aac8aba8d9635a96f1c | Spectrum | GC-MS | Spermidine, non-derivatized, GC-MS Spectrum | splash10-00rf-1900000000-f4b7d8b055a8d5025036 | Spectrum | GC-MS | Spermidine, non-derivatized, GC-MS Spectrum | splash10-00di-1900000000-1be27daaf9f6d9e03752 | Spectrum | GC-MS | Spermidine, non-derivatized, GC-MS Spectrum | splash10-00rf-1900000000-866eda2dc91354bf795b | Spectrum | GC-MS | Spermidine, non-derivatized, GC-MS Spectrum | splash10-0uki-3920000000-2165a698c4bf674e814b | Spectrum | Predicted GC-MS | Spermidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001r-9200000000-e6ccea992bf8aff10122 | Spectrum | Predicted GC-MS | Spermidine, non-derivatized, 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) | splash10-00dj-9800000000-02b200749ad6548a5872 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9000000000-c294fdb7876cfc47c089 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00di-9000000000-d3055c2a8763c8034bd2 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-052b-0900000000-f08a2a9ba7333f5b725c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00b9-7900000000-062e21e4525351cbd0d4 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-0900000000-31b90f68c9fde4e03f60 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0002-0920000000-28adf399f8ddd0affc22 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0udj-0930000000-3ac88b6d5c40c65f1314 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0006-9000000000-953c054969edecf62533 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00b9-7900000000-8b03c45141b38c718dac | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-004i-0900000000-1e157eec324aa34dd64e | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0002-0900000000-f2ca6698501cf6a406df | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-00di-9300000000-2f23967aa87f8e5f5bc1 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-00di-9000000000-91aef1c8b5a2507a16e9 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-00di-9000000000-18cdaecf173b5d79902a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-00di-9000000000-f0b03de09cb13146e794 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0092-5900000000-4bd537f0811cc264f2cb | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-9200000000-75eacba217a63f3b8847 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-9000000000-8a77bd9436d55b064332 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004j-1900000000-300fe40eb32167464ab8 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0729-9800000000-1a8be3c6776f3924c8b7 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0abc-9000000000-6401e12d220b44018fdf | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-1900000000-79940496e89b73bb1682 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-3900000000-eb4eaf0bb3e88f274a1d | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00du-9000000000-fe762fb3fcd81e27f9c7 | 2015-05-27 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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Pathways |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | Methionine Metabolism | | | Spermidine and Spermine Biosynthesis | | Not Available | Cystathionine Beta-Synthase Deficiency | | Not Available | Hypermethioninemia | | Not Available | S-Adenosylhomocysteine (SAH) Hydrolase Deficiency | | Not Available |
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Protein Targets |
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Enzymes | |
Diamine acetyltransferase 1 | SAT1 | Xp22.1 | P21673 | details | 3-ketoacyl-CoA thiolase, mitochondrial | ACAA2 | 18q21.1 | P42765 | details | Peroxisomal N(1)-acetyl-spermine/spermidine oxidase | PAOX | 10q26.3 | Q6QHF9 | details | Thioredoxin reductase 1, cytoplasmic | TXNRD1 | 12q23-q24.1 | Q16881 | details | Choline dehydrogenase, mitochondrial | CHDH | 3p21.1 | Q8NE62 | details | Dimethylglycine dehydrogenase, mitochondrial | DMGDH | 5q14.1 | Q9UI17 | details | Spermine synthase | SMS | Xp22.1 | P52788 | details | Spermidine synthase | SRM | 1p36-p22 | P19623 | details | Deoxyhypusine synthase | DHPS | 19p13.2 | P49366 | details | Propionyl-CoA carboxylase alpha chain, mitochondrial | PCCA | 13q32 | P05165 | details | 4-trimethylaminobutyraldehyde dehydrogenase | ALDH9A1 | 1q23.1 | P49189 | details | Gamma-butyrobetaine dioxygenase | BBOX1 | 11p14.2 | O75936 | details | S-methyl-5'-thioadenosine phosphorylase | MTAP | 9p21 | Q13126 | details | S-adenosylmethionine decarboxylase proenzyme | AMD1 | 6q21 | P17707 | details | Glycine amidinotransferase, mitochondrial | GATM | 15q21.1 | P50440 | details | Betaine--homocysteine S-methyltransferase 1 | BHMT | 5q14.1 | Q93088 | details | Sarcosine dehydrogenase, mitochondrial | SARDH | 9q33-q34 | Q9UL12 | details | Histidine decarboxylase | HDC | 15q21-q22 | P19113 | details | Ornithine decarboxylase | ODC1 | 2p25 | P11926 | details | Spermine oxidase | SMOX | 20p13 | Q9NWM0 | details | Agmatinase, mitochondrial | AGMAT | 1p36.21 | Q9BSE5 | details | Trimethyllysine dioxygenase, mitochondrial | TMLHE | Xq28 | Q9NVH6 | details | S-methylmethionine--homocysteine S-methyltransferase BHMT2 | BHMT2 | 5q13 | Q9H2M3 | details | Pyruvate dehydrogenase phosphatase regulatory subunit, mitochondrial | PDPR | 16q22.1 | Q8NCN5 | details | Ornithine decarboxylase antizyme 1 | OAZ1 | 19p13.3 | P54368 | details |
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Transporters | |
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Metal Bindings | |
Propionyl-CoA carboxylase alpha chain, mitochondrial | PCCA | 13q32 | P05165 | details | Gamma-butyrobetaine dioxygenase | BBOX1 | 11p14.2 | O75936 | details | Betaine--homocysteine S-methyltransferase 1 | BHMT | 5q14.1 | Q93088 | details | Agmatinase, mitochondrial | AGMAT | 1p36.21 | Q9BSE5 | details | Trimethyllysine dioxygenase, mitochondrial | TMLHE | Xq28 | Q9NVH6 | details | S-methylmethionine--homocysteine S-methyltransferase BHMT2 | BHMT2 | 5q13 | Q9H2M3 | details |
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Receptors | Not Available |
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Transcriptional Factors | Not Available |
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Concentrations Data |
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Alien Dawg | Detected and Quantified | 0.00153 mg/g dry wt | | details | Gabriola | Detected and Quantified | 0.00115 mg/g dry wt | | details | Island Honey | Detected and Quantified | 0.00810 mg/g dry wt | | details | Quadra | Detected and Quantified | 0.00458 mg/g dry wt | | details | Sensi Star | Detected and Quantified | 0.00136 mg/g dry wt | | details | Tangerine Dream | Detected and Quantified | 0.00208 mg/g dry wt | | details |
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External Links |
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HMDB ID | HMDB0001257 |
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DrugBank ID | DB03566 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB012039 |
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KNApSAcK ID | C00001431 |
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Chemspider ID | 1071 |
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KEGG Compound ID | C00315 |
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BioCyc ID | SPERMIDINE |
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BiGG ID | 34593 |
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Wikipedia Link | Spermidine |
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METLIN ID | 254 |
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PubChem Compound | 1102 |
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PDB ID | Not Available |
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ChEBI ID | 16610 |
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References |
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General References | Not Available |
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