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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2019-01-11 19:15:45 UTC |
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HMDB ID | HMDB0001257 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Spermidine |
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Description | Spermidine is a polyamine formed from putrescine. It is found in almost all tissues in association with nucleic acids. It is found as a cation at all pH values, and is thought to help stabilize some membranes and nucleic acid structures. It is a precursor of spermine. |
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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 | 145.2459 |
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Monoisotopic Molecular Weight | 145.157897623 |
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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 | This compound 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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Process | Naturally occurring process: |
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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 | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS) | splash10-00di-5910000000-48794a2dc9d682aab28f | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS) | splash10-066u-1910000000-9fe6c1c8e8f166270be1 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-00rf-1900000000-c88ed717e55f237cf01c | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS) | splash10-00di-6900000000-56396208515d9020bfeb | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-0uki-5920000000-4aac8aba8d9635a96f1c | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (5 TMS) | splash10-00rf-1900000000-f4b7d8b055a8d5025036 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (5 TMS) | splash10-00di-1900000000-1be27daaf9f6d9e03752 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-05tf-0910000000-280a5c2a493fedd0e524 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-5910000000-48794a2dc9d682aab28f | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-066u-1910000000-9fe6c1c8e8f166270be1 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00rf-1900000000-c88ed717e55f237cf01c | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-6900000000-56396208515d9020bfeb | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0uki-5920000000-4aac8aba8d9635a96f1c | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00rf-1900000000-f4b7d8b055a8d5025036 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00di-1900000000-1be27daaf9f6d9e03752 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00rf-1900000000-866eda2dc91354bf795b | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0uki-3920000000-2165a698c4bf674e814b | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-001r-9200000000-e6ccea992bf8aff10122 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00dj-9800000000-02b200749ad6548a5872 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9000000000-c294fdb7876cfc47c089 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00di-9000000000-d3055c2a8763c8034bd2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-052b-0900000000-f08a2a9ba7333f5b725c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00b9-7900000000-062e21e4525351cbd0d4 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-0900000000-31b90f68c9fde4e03f60 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0002-0920000000-28adf399f8ddd0affc22 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0udj-0930000000-3ac88b6d5c40c65f1314 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0006-9000000000-953c054969edecf62533 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00b9-7900000000-8b03c45141b38c718dac | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-004i-0900000000-1e157eec324aa34dd64e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0002-0900000000-f2ca6698501cf6a406df | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-00di-9300000000-2f23967aa87f8e5f5bc1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-00di-9000000000-91aef1c8b5a2507a16e9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-00di-9000000000-18cdaecf173b5d79902a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-00di-9000000000-f0b03de09cb13146e794 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0092-5900000000-4bd537f0811cc264f2cb | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-9200000000-75eacba217a63f3b8847 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-9000000000-8a77bd9436d55b064332 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004j-1900000000-300fe40eb32167464ab8 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0729-9800000000-1a8be3c6776f3924c8b7 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0abc-9000000000-6401e12d220b44018fdf | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-1900000000-79940496e89b73bb1682 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-3900000000-eb4eaf0bb3e88f274a1d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00du-9000000000-fe762fb3fcd81e27f9c7 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Urine
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Tissue Locations | - Brain
- Erythrocyte
- Fibroblasts
- Intestine
- Liver
- Neuron
- Platelet
- Prostate
- Skin
- Testes
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 10.3 +/- 3.78 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 8.47 +/- 2.02 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 0.07 +/- 0.04 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.13-0.40 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.12 +/- 0.04 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Not Specified | Not Specified | Normal | | details | Feces | Detected but not Quantified | | Children (6 - 18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 10 +/- 20 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 1.78 +/- 1.65 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 3.21 +/- 6.80 uM | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 0.05 uM | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 1.27 +/- 1.70 uM | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 1.38 +/- 2.59 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 0.331 +/- 0.265 uM | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 0.402 +/- 0.320 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Not Specified | Normal | | details | Saliva | Detected and Quantified | 0.487 +/- 1.02 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 0.552 +/- 0.329 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.05 (0.01-0.09) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.112 +/- 0.008 umol/mmol creatinine | Adult (>18 years old) | Both | Not Available | | details | Urine | Detected and Quantified | 1.1 +/- 0.2 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | - Geigy Scientific ...
- West Cadwell, N.J...
- Basel, Switzerlan...
| details | Urine | Detected and Quantified | 0.026 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.069 +/- 0.053 uM | Adult (>18 years old) | Both | uremia | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | | Children (6 - 18 years old) | Not Specified | Crohns disease | | details | Feces | Detected but not Quantified | | Children (6 - 18 years old) | Not Specified | Ulcerative colitis | | details | Feces | Detected but not Quantified | | Children (6 - 18 years old) | Not Specified | Unclassified IBD | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal Cancer | | details | Saliva | Detected and Quantified | 0.46 +/- 0.14 uM | Adult (>18 years old) | Male | Alzheimer's disease | | details | Saliva | Detected and Quantified | 0.72 +/- 0.39 uM | Adult (>18 years old) | Male | Frontotemporal lobe dementia | | details | Saliva | Detected and Quantified | 1.19 +/- 1.70 uM | Adult (>18 years old) | Both | Lewy body disease | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Leukemia | | details | Urine | Detected and Quantified | 0.347 +/- 0.147 umol/mmol creatinine | Adult (>18 years old) | Both | Leukemia | | details |
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Associated Disorders and Diseases |
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Disease References | Uremia |
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- Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
| Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Crohn's disease |
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- Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
| Ulcerative colitis |
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- Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
| Alzheimer's disease |
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- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| Frontotemporal dementia |
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- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| Lewy body disease |
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- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| Leukemia |
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- Lee SH, Suh JW, Chung BC, Kim SO: Polyamine profiles in the urine of patients with leukemia. Cancer Lett. 1998 Jan 9;122(1-2):1-8. [PubMed:9464484 ]
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Associated OMIM IDs | |
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External Links |
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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 | SPD |
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ChEBI ID | 16610 |
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References |
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Synthesis Reference | Bergeron, Raymond J., Jr. Preparation and formulation spermidine analogues for pharmaceutical use as tumor growth inhibitors. U.S. (2001), 31 pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Venza M, Visalli M, Cicciu D, Teti D: Determination of polyamines in human saliva by high-performance liquid chromatography with fluorescence detection. J Chromatogr B Biomed Sci Appl. 2001 Jun 5;757(1):111-7. [PubMed:11419735 ]
- Uehara N, Shirakawa S, Uchino H, Saeki Y: Elevated contents of spermidine and spermine in the erythrocytes of cancer patients. Cancer. 1980 Jan 1;45(1):108-11. [PubMed:7350997 ]
- Proctor MS, Fletcher HV Jr, Shukla JB, Rennert OM: Elevated spermidine and spermine levels in the blood of psoriasis patients. J Invest Dermatol. 1975 Oct;65(4):409-11. [PubMed:1176793 ]
- El Baze P, Milano G, Verrando P, Renee N, Ortonne JP: Polyamine levels in normal human skin. A comparative study of pure epidermis, pure dermis, and suction blister fluid. Arch Dermatol Res. 1983;275(4):218-21. [PubMed:6625645 ]
- Mirzoian PA, Promyslov MSh: [Contents of putrescine, spermidine and spermine in tissue of the human brain glial tumors]. Ukr Biokhim Zh (1978). 1979 Sep-Oct;51(5):474-6. [PubMed:516181 ]
- Chaisiri P, Harper ME, Blamey RW, Peeling WB, Griffiths K: Plasma spermidine concentrations in patients with tumours of the breast or prostate or testis. Clin Chim Acta. 1980 Jul 1;104(3):367-75. [PubMed:6156039 ]
- Martinet N, Beninati S, Nigra TP, Folk JE: N1N8-bis(gamma-glutamyl)spermidine cross-linking in epidermal-cell envelopes. Comparison of cross-link levels in normal and psoriatic cell envelopes. Biochem J. 1990 Oct 15;271(2):305-8. [PubMed:2241917 ]
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