You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2009-01-30 15:03:41 UTC
Update Date2016-02-11 01:21:50 UTC
HMDB IDHMDB11634
Secondary Accession NumbersNone
Metabolite Identification
Common NameNorspermidine
DescriptionNorspermidine is a polyamine of similar structure to the more common spermidine. While norspermidine has been found to occur naturally in some species of plants, bacteria, and algae, it is not known to be a natural product in humans as spermidine is.
Structure
Thumb
Synonyms
ValueSource
1,7-diamino-4-AzaheptaneChEBI
3,3'-Iminobis(propylamine)ChEBI
3,3'-IminobispropylamineChEBI
3,3'-Iminodi(propylamine)ChEBI
3,3-DiaminodipropylamineChEBI
4-Azaheptane-1,7-diamineChEBI
DipropylenetriamineChEBI
N-(3-Aminopropyl)-1,3-propanediamineChEBI
N-(3-Aminopropyl)propane-1,3-diamineChEBI
N-3-Aminopropyl-1,3-diaminopropaneChEBI
-1,3-PropanediamineHMDB
3, 3'-DiaminodipropylamineHMDB
3, {3'-iminobis[propylamine]}HMDB
3,3'-diamino-DipropylamineHMDB
3,3'-DiaminodipropylamineHMDB
3,3'-Iminobis-1-propanamineHMDB
3,3'-Iminobis-propylamineHMDB
3,3'-IminopropylamineHMDB
4-AzaheptamethylenediamineHMDB
Aminobis(propylamine)HMDB
Bis(3-aminopropyl)amineHMDB
CaldineHMDB
Dipropylene triamineHMDB
DipropylentriaminHMDB
imino-Bis(3-propylamine)HMDB
Iminobis(propylamine)HMDB
Initiating explosive iminobispropylamineHMDB
Initiating explosive iminobispropylamine (dot)HMDB
N-(3-Aminopropyl)-1, 3-propanediamineHMDB
N-3-AminopropylHMDB
Chemical FormulaC6H17N3
Average Molecular Weight131.2193
Monoisotopic Molecular Weight131.142247559
IUPAC Namebis(3-aminopropyl)amine
Traditional Namenorspermidine
CAS Registry Number56-18-8
SMILES
NCCCNCCCN
InChI Identifier
InChI=1S/C6H17N3/c7-3-1-5-9-6-2-4-8/h9H,1-8H2
InChI KeyInChIKey=OTBHHUPVCYLGQO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassSecondary amines
Direct ParentDialkylamines
Alternative Parents
Substituents
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-14 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility120.0 mg/mLALOGPS
logP-1.1ALOGPS
logP-1.7ChemAxon
logS-0.04ALOGPS
pKa (Strongest Basic)10.85ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area64.07 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.32 m3·mol-1ChemAxon
Polarizability16.71 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-e76eda3e2b74ed88d7eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-053r-7900000000-d2bbac4e463f15dc4bebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-053r-9800000000-9831b1b2d26ead77bb90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-52e20d6ccbdbbadf204aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00kb-9400000000-e7c781b49abb2c40bff5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0592-9000000000-c236ecd9d64d3e812b77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-05fr-9000000000-a67dcf5d82b9e101ede8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-05mo-9000000000-d86d6a1c51a6868a498fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-2900000000-f2c893d4cbb8db7f04edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0apl-9400000000-1e2b6452d5b9a58dcae6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-26cb076b25b0176b12c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-80d92e7f1d06b41155e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3900000000-1629dea357713b1a5c53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9000000000-652df53898c4bf860731View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028332
KNApSAcK IDNot Available
Chemspider ID5729
KEGG Compound IDC03375
BioCyc IDNORSPERMIDINE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB11634
Metagene LinkHMDB11634
METLIN IDNot Available
PubChem Compound5942
PDB IDNSD
ChEBI ID16841
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in N-acetyltransferase activity
Specific function:
Enzyme which catalyzes the acetylation of polyamines. Substrate specificity: norspermidine = spermidine >> spermine > N(1)-acetylspermine > putrescine. This highly regulated enzyme allows a fine attenuation of the intracellular concentration of polyamines. Also involved in the regulation of polyamine transport out of cells. Acts on 1,3-diaminopropane, 1,5-diaminopentane, putrescine, spermidine (forming N(1)- and N(8)-acetylspermidine), spermine, N(1)-acetylspermidine and N(8)-acetylspermidine.
Gene Name:
SAT1
Uniprot ID:
P21673
Molecular weight:
20023.8
General function:
Involved in oxidoreductase activity, acting on CH-OH group of donors
Specific function:
Not Available
Gene Name:
CHDH
Uniprot ID:
Q8NE62
Molecular weight:
65358.005
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
DMGDH
Uniprot ID:
Q9UI17
Molecular weight:
96810.135
General function:
Involved in spermine synthase activity
Specific function:
Catalyzes the production of spermine from spermidine and decarboxylated S-adenosylmethionine (dcSAM).
Gene Name:
SMS
Uniprot ID:
P52788
Molecular weight:
35278.2
General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
General function:
Involved in iron ion binding
Specific function:
Catalyzes the formation of L-carnitine from gamma-butyrobetaine.
Gene Name:
BBOX1
Uniprot ID:
O75936
Molecular weight:
44714.6
General function:
Involved in transferase activity, transferring pentosyl groups
Specific function:
Catalyzes the reversible phosphorylation of S-methyl-5'-thioadenosine (MTA) to adenine and 5-methylthioribose-1-phosphate. Involved in the breakdown of MTA, a major by-product of polyamine biosynthesis. Responsible for the first step in the methionine salvage pathway after MTA has been generated from S-adenosylmethionine. Has broad substrate specificity with 6-aminopurine nucleosides as preferred substrates.
Gene Name:
MTAP
Uniprot ID:
Q13126
Molecular weight:
31235.76
General function:
Involved in adenosylmethionine decarboxylase activity
Specific function:
Not Available
Gene Name:
AMD1
Uniprot ID:
P17707
Molecular weight:
21301.015
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the biosynthesis of guanidinoacetate, the immediate precursor of creatine. Creatine plays a vital role in energy metabolism in muscle tissues. May play a role in embryonic and central nervous system development. May be involved in the response to heart failure by elevating local creatine synthesis.
Gene Name:
GATM
Uniprot ID:
P50440
Molecular weight:
48455.01
General function:
Involved in zinc ion binding
Specific function:
Involved in the regulation of homocysteine metabolism. Converts betaine and homocysteine to dimethylglycine and methionine, respectively. This reaction is also required for the irreversible oxidation of choline.
Gene Name:
BHMT
Uniprot ID:
Q93088
Molecular weight:
44998.205
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
SARDH
Uniprot ID:
Q9UL12
Molecular weight:
101035.985
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the biosynthesis of histamine from histidine.
Gene Name:
HDC
Uniprot ID:
P19113
Molecular weight:
74139.825
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ODC1
Uniprot ID:
P11926
Molecular weight:
51147.73
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Flavoenzyme which catalyzes the oxidation of spermine to spermidine. Can also use N(1)-acetylspermine and spermidine as substrates, with different affinity depending on the isoform (isozyme) and on the experimental conditions. Plays an important role in the regulation of polyamine intracellular concentration and has the potential to act as a determinant of cellular sensitivity to the antitumor polyamine analogs. May contribute to beta-alanine production via aldehyde dehydrogenase conversion of 3-amino-propanal.
Gene Name:
SMOX
Uniprot ID:
Q9NWM0
Molecular weight:
65006.29
General function:
Involved in agmatinase activity
Specific function:
Not Available
Gene Name:
AGMAT
Uniprot ID:
Q9BSE5
Molecular weight:
37660.065
General function:
Involved in oxidation reduction
Specific function:
Converts trimethyllysine (TML) into hydroxytrimethyllysine (HTML).
Gene Name:
TMLHE
Uniprot ID:
Q9NVH6
Molecular weight:
44048.895
General function:
Involved in zinc ion binding
Specific function:
Involved in the regulation of homocysteine metabolism. Converts homocysteine to methionine using S-methylmethionine (SMM) as a methyl donor.
Gene Name:
BHMT2
Uniprot ID:
Q9H2M3
Molecular weight:
33166.69
General function:
Involved in oxidoreductase activity
Specific function:
Decreases the sensitivity of PDP1 to magnesium ions, and this inhibition is reversed by the polyamine spermine
Gene Name:
PDPR
Uniprot ID:
Q8NCN5
Molecular weight:
99363.7
General function:
Involved in enzyme inhibitor activity
Specific function:
Binds to, and destabilizes, ornithine decarboxylase which is then degraded. Also inhibits cellular uptake of polyamines by inactivating the polyamine uptake transporter. SMAD1/OAZ1/PSMB4 complex mediates the degradation of the CREBBP/EP300 repressor SNIP1
Gene Name:
OAZ1
Uniprot ID:
P54368
Molecular weight:
25405.3
General function:
Involved in leucine zipper domain binding
Specific function:
Part of the MIS12 complex which is required for normal chromosome alignment and segregation and kinetochore formation during mitosis. May act as a cotranscription partner of NFE2L2 involved in regulation of polyamine-induced transcription of SSAT
Gene Name:
PMF1
Uniprot ID:
Q6P1K2
Molecular weight:
23339.2