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Showing metabocard for N1-Acetylspermidine (HMDB0001276)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:57 UTC
HMDB IDHMDB0001276
Secondary Accession Numbers
  • HMDB01276
Metabolite Identification
Common NameN1-Acetylspermidine
DescriptionN1-Acetylspermidine is a polyamine. In many organisms, polyamines originate from L-ornithine and methionine. Ornithine decarboxylase (EC 4.1.1.17), a key enzyme in polyamine metabolism, decarboxylates L-ornithine to yield putrescine which is then converted to higher polyamines spermidine and spermine by successive addition of aminopropyl groups derived from decarboxylated S-adenosylmethionine. Aliphatic polyamines occur ubiquitously in organisms and have important functions in the stabilization of cell membranes, biosynthesis of informing molecules, cell growth and differentiation, as well as adaptation to osmotic, ionic, pH and thermal stress. These cationic substances are implicated in multiple functions, therefore it is not surprising that intracellular levels of polyamines are regulated by different mechanisms. The inhibition of polyamine metabolism has important pharmacological and therapeutic implications for the control of physiological processes, reproduction, cancer and parasitic diseases. Recent reports have suggested the idea that parasites with an high turnover of Ornithine Decarboxilase (ODC) are resistant to Difluoromethyl ornithine (DFMO, the irreversible inhibitor of ornithine decarboxylase) because they always contain a fraction of newly synthesized and active enzyme, therefore not DFMO inhibited, sufficient to produce small amounts of putrescine rapidly converted into spermidine, which can support protozoan proliferation. DFMO has proved to be curative in trypanosomiasis, coccidiosis, and certain other protozoan infections. (PMID: 15490259 ).
Structure
Data?1676999734
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001276 (N1-Acetylspermidine)


  Mrv0541 02231219022D          

 13 12  0  0  0  0            999 V2000
    0.0569   -0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9832    0.2126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7706    0.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7007   -0.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4843   -0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4144    0.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660    0.3910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1318   -0.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5798   -0.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8455    0.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2972    0.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5798   -0.8466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5592   -0.2012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  2  0  0  0  0
 10 13  1  0  0  0  0
M  END
Download

3D MOL for HMDB0001276 (N1-Acetylspermidine)

HMDB0001276
     RDKit          3D
N1-Acetylspermidine
 34 33  0  0  0  0  0  0  0  0999 V2000
   -4.9362   -1.7812    0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6543   -0.3718    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5871    0.2724   -0.5430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735    0.1860    0.2686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0268    1.5426   -0.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958    1.8056    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6289    0.8954   -0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011    1.2132    0.1178 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7220    0.4172   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0405    0.7792    0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1951   -0.0019   -0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -1.4951   -0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8988   -1.8519    1.0959 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9386   -2.3105    0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6299   -2.2860   -0.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3152   -1.7375    1.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6688   -0.4271    0.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6948    2.2353    0.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643    1.6534   -1.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498    1.7006    1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3708    2.8790    0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9155   -0.1430   -0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6451    1.1806   -1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7600    1.2408    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536   -0.6712   -0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7533    0.6580   -1.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9674    0.6599    1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2380    1.8516   -0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162    0.3236   -1.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0852    0.2594    0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9311   -1.9680   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -1.8739   -0.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8675   -2.0568    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827   -2.7780    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
M  END
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3D SDF for HMDB0001276 (N1-Acetylspermidine)


  Mrv0541 02231219022D          

 13 12  0  0  0  0            999 V2000
    0.0569   -0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9832    0.2126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7706    0.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7007   -0.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4843   -0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4144    0.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660    0.3910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1318   -0.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5798   -0.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8455    0.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2972    0.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5798   -0.8466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5592   -0.2012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  2  0  0  0  0
 10 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001276

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NCCCNCCCCN

> <INCHI_IDENTIFIER>
InChI=1S/C9H21N3O/c1-9(13)12-8-4-7-11-6-3-2-5-10/h11H,2-8,10H2,1H3,(H,12,13)

> <INCHI_KEY>
MQTAVJHICJWXBR-UHFFFAOYSA-N

> <FORMULA>
C9H21N3O

> <MOLECULAR_WEIGHT>
187.2825

> <EXACT_MASS>
187.168462309

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.110031458857055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{3-[(4-aminobutyl)amino]propyl}acetamide

> <ALOGPS_LOGP>
-0.47

> <JCHEM_LOGP>
-1.3307173369999998

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.528018704992306

> <JCHEM_PKA_STRONGEST_BASIC>
10.665494107139267

> <JCHEM_POLAR_SURFACE_AREA>
67.14999999999999

> <JCHEM_REFRACTIVITY>
54.412200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N1-acetylspermidine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001276 (N1-Acetylspermidine)

HMDB0001276
     RDKit          3D
N1-Acetylspermidine
 34 33  0  0  0  0  0  0  0  0999 V2000
   -4.9362   -1.7812    0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6543   -0.3718    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5871    0.2724   -0.5430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735    0.1860    0.2686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0268    1.5426   -0.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958    1.8056    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6289    0.8954   -0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011    1.2132    0.1178 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7220    0.4172   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0405    0.7792    0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1951   -0.0019   -0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -1.4951   -0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8988   -1.8519    1.0959 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9386   -2.3105    0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6299   -2.2860   -0.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3152   -1.7375    1.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6688   -0.4271    0.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6948    2.2353    0.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643    1.6534   -1.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498    1.7006    1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3708    2.8790    0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9155   -0.1430   -0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6451    1.1806   -1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7600    1.2408    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536   -0.6712   -0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7533    0.6580   -1.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9674    0.6599    1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2380    1.8516   -0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162    0.3236   -1.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0852    0.2594    0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9311   -1.9680   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -1.8739   -0.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8675   -2.0568    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827   -2.7780    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
M  END
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PDB for HMDB0001276 (N1-Acetylspermidine)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.106  -0.220   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.835   0.397   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.438   0.553   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.175  -0.376   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.771  -0.220   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.507   0.397   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.350   0.730   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -5.846  -0.376   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.682  -0.043   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.178   0.397   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.021   0.730   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.682  -1.580   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      -8.511  -0.376   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11   12                                                  
CONECT   10    8   13                                                       
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for HMDB0001276 (N1-Acetylspermidine)

COMPND    HMDB0001276
HETATM    1  C1  UNL     1      -4.936  -1.781   0.375  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.654  -0.372   0.002  1.00  0.00           C  
HETATM    3  O1  UNL     1      -5.587   0.272  -0.543  1.00  0.00           O  
HETATM    4  N1  UNL     1      -3.373   0.186   0.269  1.00  0.00           N  
HETATM    5  C3  UNL     1      -3.027   1.543  -0.065  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.596   1.806   0.350  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.629   0.895  -0.368  1.00  0.00           C  
HETATM    8  N2  UNL     1       0.701   1.213   0.118  1.00  0.00           N  
HETATM    9  C6  UNL     1       1.722   0.417  -0.507  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.040   0.779   0.144  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.195  -0.002  -0.446  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.008  -1.495  -0.297  1.00  0.00           C  
HETATM   13  N3  UNL     1       3.899  -1.852   1.096  1.00  0.00           N  
HETATM   14  H1  UNL     1      -3.939  -2.311   0.415  1.00  0.00           H  
HETATM   15  H2  UNL     1      -5.630  -2.286  -0.313  1.00  0.00           H  
HETATM   16  H3  UNL     1      -5.315  -1.738   1.427  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.669  -0.427   0.728  1.00  0.00           H  
HETATM   18  H5  UNL     1      -3.695   2.235   0.488  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.164   1.653  -1.159  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.550   1.701   1.456  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.371   2.879   0.133  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.916  -0.143  -0.198  1.00  0.00           H  
HETATM   23  H10 UNL     1      -0.645   1.181  -1.440  1.00  0.00           H  
HETATM   24  H11 UNL     1       0.760   1.241   1.163  1.00  0.00           H  
HETATM   25  H12 UNL     1       1.554  -0.671  -0.409  1.00  0.00           H  
HETATM   26  H13 UNL     1       1.753   0.658  -1.589  1.00  0.00           H  
HETATM   27  H14 UNL     1       2.967   0.660   1.241  1.00  0.00           H  
HETATM   28  H15 UNL     1       3.238   1.852  -0.071  1.00  0.00           H  
HETATM   29  H16 UNL     1       4.416   0.324  -1.461  1.00  0.00           H  
HETATM   30  H17 UNL     1       5.085   0.259   0.203  1.00  0.00           H  
HETATM   31  H18 UNL     1       4.931  -1.968  -0.690  1.00  0.00           H  
HETATM   32  H19 UNL     1       3.175  -1.874  -0.921  1.00  0.00           H  
HETATM   33  H20 UNL     1       2.867  -2.057   1.256  1.00  0.00           H  
HETATM   34  H21 UNL     1       4.383  -2.778   1.248  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3    4
CONECT    4    5   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8   22   23
CONECT    8    9   24
CONECT    9   10   25   26
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   33   34
END
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SMILES for HMDB0001276 (N1-Acetylspermidine)

CC(=O)NCCCNCCCCN
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INCHI for HMDB0001276 (N1-Acetylspermidine)

InChI=1S/C9H21N3O/c1-9(13)12-8-4-7-11-6-3-2-5-10/h11H,2-8,10H2,1H3,(H,12,13)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-N-AcetylspermidineChEBI
An N-acetylspermidineHMDB
N(1)-AcetylspermidineHMDB
N-(3-((4-Aminobutyl)amino)propyl)-acetamideHMDB
N-(3-((4-Aminobutyl)amino)propyl)acetamideHMDB
N-AcetylspermidineHMDB
N1-AcetylspermidineChEBI
Chemical FormulaC9H21N3O
Average Molecular Weight187.2825
Monoisotopic Molecular Weight187.168462309
IUPAC NameN-{3-[(4-aminobutyl)amino]propyl}acetamide
Traditional NameN1-acetylspermidine
CAS Registry Number14278-49-0
SMILES
CC(=O)NCCCNCCCCN
InChI Identifier
InChI=1S/C9H21N3O/c1-9(13)12-8-4-7-11-6-3-2-5-10/h11H,2-8,10H2,1H3,(H,12,13)
InChI KeyMQTAVJHICJWXBR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
Sub ClassCarboximidic acids
Direct ParentCarboximidic acids
Alternative Parents
Substituents
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.72 g/LALOGPS
logP-0.47ALOGPS
logP-1.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)16.53ChemAxon
pKa (Strongest Basic)10.67ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area67.15 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity54.41 m³·mol⁻¹ChemAxon
Polarizability23.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+142.73331661259
DarkChem[M-H]-140.36331661259
AllCCS[M+H]+142.90832859911
AllCCS[M-H]-146.84832859911
DeepCCS[M+H]+145.08330932474
DeepCCS[M-H]-142.15730932474
DeepCCS[M-2H]-178.61930932474
DeepCCS[M+Na]+154.15630932474
AllCCS[M+H]+142.932859911
AllCCS[M+H-H2O]+139.432859911
AllCCS[M+NH4]+146.232859911
AllCCS[M+Na]+147.132859911
AllCCS[M-H]-146.832859911
AllCCS[M+Na-2H]-148.432859911
AllCCS[M+HCOO]-150.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.55 minutes32390414
Predicted by Siyang on May 30, 20228.4514 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20228.03 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid389.0 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid315.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid229.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid75.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid162.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid52.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid266.5 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid237.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)943.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid543.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid38.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid543.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid179.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid209.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate1027.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA686.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water316.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N1-AcetylspermidineCC(=O)NCCCNCCCCN2610.3Standard polar33892256
N1-AcetylspermidineCC(=O)NCCCNCCCCN1905.4Standard non polar33892256
N1-AcetylspermidineCC(=O)NCCCNCCCCN1800.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N1-Acetylspermidine,1TMS,isomer #1CC(=O)NCCCNCCCCN[Si](C)(C)C2003.8Semi standard non polar33892256
N1-Acetylspermidine,1TMS,isomer #1CC(=O)NCCCNCCCCN[Si](C)(C)C2012.9Standard non polar33892256
N1-Acetylspermidine,1TMS,isomer #1CC(=O)NCCCNCCCCN[Si](C)(C)C2705.0Standard polar33892256
N1-Acetylspermidine,1TMS,isomer #2CC(=O)N(CCCNCCCCN)[Si](C)(C)C1850.2Semi standard non polar33892256
N1-Acetylspermidine,1TMS,isomer #2CC(=O)N(CCCNCCCCN)[Si](C)(C)C1941.1Standard non polar33892256
N1-Acetylspermidine,1TMS,isomer #2CC(=O)N(CCCNCCCCN)[Si](C)(C)C2936.1Standard polar33892256
N1-Acetylspermidine,1TMS,isomer #3CC(=O)NCCCN(CCCCN)[Si](C)(C)C1972.7Semi standard non polar33892256
N1-Acetylspermidine,1TMS,isomer #3CC(=O)NCCCN(CCCCN)[Si](C)(C)C1892.6Standard non polar33892256
N1-Acetylspermidine,1TMS,isomer #3CC(=O)NCCCN(CCCCN)[Si](C)(C)C3012.0Standard polar33892256
N1-Acetylspermidine,2TMS,isomer #1CC(=O)N(CCCNCCCCN[Si](C)(C)C)[Si](C)(C)C1960.1Semi standard non polar33892256
N1-Acetylspermidine,2TMS,isomer #1CC(=O)N(CCCNCCCCN[Si](C)(C)C)[Si](C)(C)C2167.4Standard non polar33892256
N1-Acetylspermidine,2TMS,isomer #1CC(=O)N(CCCNCCCCN[Si](C)(C)C)[Si](C)(C)C2281.0Standard polar33892256
N1-Acetylspermidine,2TMS,isomer #2CC(=O)NCCCN(CCCCN[Si](C)(C)C)[Si](C)(C)C2124.0Semi standard non polar33892256
N1-Acetylspermidine,2TMS,isomer #2CC(=O)NCCCN(CCCCN[Si](C)(C)C)[Si](C)(C)C2109.7Standard non polar33892256
N1-Acetylspermidine,2TMS,isomer #2CC(=O)NCCCN(CCCCN[Si](C)(C)C)[Si](C)(C)C2466.1Standard polar33892256
N1-Acetylspermidine,2TMS,isomer #3CC(=O)NCCCNCCCCN([Si](C)(C)C)[Si](C)(C)C2206.5Semi standard non polar33892256
N1-Acetylspermidine,2TMS,isomer #3CC(=O)NCCCNCCCCN([Si](C)(C)C)[Si](C)(C)C2158.9Standard non polar33892256
N1-Acetylspermidine,2TMS,isomer #3CC(=O)NCCCNCCCCN([Si](C)(C)C)[Si](C)(C)C2512.6Standard polar33892256
N1-Acetylspermidine,2TMS,isomer #4CC(=O)N(CCCN(CCCCN)[Si](C)(C)C)[Si](C)(C)C1922.7Semi standard non polar33892256
N1-Acetylspermidine,2TMS,isomer #4CC(=O)N(CCCN(CCCCN)[Si](C)(C)C)[Si](C)(C)C2088.3Standard non polar33892256
N1-Acetylspermidine,2TMS,isomer #4CC(=O)N(CCCN(CCCCN)[Si](C)(C)C)[Si](C)(C)C2720.8Standard polar33892256
N1-Acetylspermidine,3TMS,isomer #1CC(=O)N(CCCN(CCCCN[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2037.2Semi standard non polar33892256
N1-Acetylspermidine,3TMS,isomer #1CC(=O)N(CCCN(CCCCN[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2268.0Standard non polar33892256
N1-Acetylspermidine,3TMS,isomer #1CC(=O)N(CCCN(CCCCN[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2211.6Standard polar33892256
N1-Acetylspermidine,3TMS,isomer #2CC(=O)N(CCCNCCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2152.3Semi standard non polar33892256
N1-Acetylspermidine,3TMS,isomer #2CC(=O)N(CCCNCCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2273.6Standard non polar33892256
N1-Acetylspermidine,3TMS,isomer #2CC(=O)N(CCCNCCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2192.0Standard polar33892256
N1-Acetylspermidine,3TMS,isomer #3CC(=O)NCCCN(CCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2302.8Semi standard non polar33892256
N1-Acetylspermidine,3TMS,isomer #3CC(=O)NCCCN(CCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2268.8Standard non polar33892256
N1-Acetylspermidine,3TMS,isomer #3CC(=O)NCCCN(CCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2340.8Standard polar33892256
N1-Acetylspermidine,4TMS,isomer #1CC(=O)N(CCCN(CCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2282.3Semi standard non polar33892256
N1-Acetylspermidine,4TMS,isomer #1CC(=O)N(CCCN(CCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2388.7Standard non polar33892256
N1-Acetylspermidine,4TMS,isomer #1CC(=O)N(CCCN(CCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2157.2Standard polar33892256
N1-Acetylspermidine,1TBDMS,isomer #1CC(=O)NCCCNCCCCN[Si](C)(C)C(C)(C)C2255.3Semi standard non polar33892256
N1-Acetylspermidine,1TBDMS,isomer #1CC(=O)NCCCNCCCCN[Si](C)(C)C(C)(C)C2211.3Standard non polar33892256
N1-Acetylspermidine,1TBDMS,isomer #1CC(=O)NCCCNCCCCN[Si](C)(C)C(C)(C)C2679.5Standard polar33892256
N1-Acetylspermidine,1TBDMS,isomer #2CC(=O)N(CCCNCCCCN)[Si](C)(C)C(C)(C)C2068.4Semi standard non polar33892256
N1-Acetylspermidine,1TBDMS,isomer #2CC(=O)N(CCCNCCCCN)[Si](C)(C)C(C)(C)C2146.1Standard non polar33892256
N1-Acetylspermidine,1TBDMS,isomer #2CC(=O)N(CCCNCCCCN)[Si](C)(C)C(C)(C)C2909.2Standard polar33892256
N1-Acetylspermidine,1TBDMS,isomer #3CC(=O)NCCCN(CCCCN)[Si](C)(C)C(C)(C)C2215.5Semi standard non polar33892256
N1-Acetylspermidine,1TBDMS,isomer #3CC(=O)NCCCN(CCCCN)[Si](C)(C)C(C)(C)C2109.6Standard non polar33892256
N1-Acetylspermidine,1TBDMS,isomer #3CC(=O)NCCCN(CCCCN)[Si](C)(C)C(C)(C)C3005.1Standard polar33892256
N1-Acetylspermidine,2TBDMS,isomer #1CC(=O)N(CCCNCCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2437.8Semi standard non polar33892256
N1-Acetylspermidine,2TBDMS,isomer #1CC(=O)N(CCCNCCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2545.1Standard non polar33892256
N1-Acetylspermidine,2TBDMS,isomer #1CC(=O)N(CCCNCCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2417.3Standard polar33892256
N1-Acetylspermidine,2TBDMS,isomer #2CC(=O)NCCCN(CCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2619.6Semi standard non polar33892256
N1-Acetylspermidine,2TBDMS,isomer #2CC(=O)NCCCN(CCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2511.0Standard non polar33892256
N1-Acetylspermidine,2TBDMS,isomer #2CC(=O)NCCCN(CCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2540.4Standard polar33892256
N1-Acetylspermidine,2TBDMS,isomer #3CC(=O)NCCCNCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2641.5Semi standard non polar33892256
N1-Acetylspermidine,2TBDMS,isomer #3CC(=O)NCCCNCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2547.6Standard non polar33892256
N1-Acetylspermidine,2TBDMS,isomer #3CC(=O)NCCCNCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2531.6Standard polar33892256
N1-Acetylspermidine,2TBDMS,isomer #4CC(=O)N(CCCN(CCCCN)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2422.4Semi standard non polar33892256
N1-Acetylspermidine,2TBDMS,isomer #4CC(=O)N(CCCN(CCCCN)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2492.4Standard non polar33892256
N1-Acetylspermidine,2TBDMS,isomer #4CC(=O)N(CCCN(CCCCN)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2706.5Standard polar33892256
N1-Acetylspermidine,3TBDMS,isomer #1CC(=O)N(CCCN(CCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2776.7Semi standard non polar33892256
N1-Acetylspermidine,3TBDMS,isomer #1CC(=O)N(CCCN(CCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2800.3Standard non polar33892256
N1-Acetylspermidine,3TBDMS,isomer #1CC(=O)N(CCCN(CCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2516.1Standard polar33892256
N1-Acetylspermidine,3TBDMS,isomer #2CC(=O)N(CCCNCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2811.3Semi standard non polar33892256
N1-Acetylspermidine,3TBDMS,isomer #2CC(=O)N(CCCNCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2824.9Standard non polar33892256
N1-Acetylspermidine,3TBDMS,isomer #2CC(=O)N(CCCNCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2475.6Standard polar33892256
N1-Acetylspermidine,3TBDMS,isomer #3CC(=O)NCCCN(CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2973.7Semi standard non polar33892256
N1-Acetylspermidine,3TBDMS,isomer #3CC(=O)NCCCN(CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2801.8Standard non polar33892256
N1-Acetylspermidine,3TBDMS,isomer #3CC(=O)NCCCN(CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2564.0Standard polar33892256
N1-Acetylspermidine,4TBDMS,isomer #1CC(=O)N(CCCN(CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3139.9Semi standard non polar33892256
N1-Acetylspermidine,4TBDMS,isomer #1CC(=O)N(CCCN(CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3055.7Standard non polar33892256
N1-Acetylspermidine,4TBDMS,isomer #1CC(=O)N(CCCN(CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2550.9Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.007 +/- 0.002 uMAdult (>18 years old)FemaleNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0045 +/- 0.005 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.39 (0.12-0.72) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.38 +/- 0.033 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.199 +/- 0.142 umol/mmol creatinineAdult (>18 years old)BothNot Available details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.06 (1.74-3.53) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0056 +/- 0.0027 uMAdult (>18 years old)FemaleBreast cancer details
UrineDetected and Quantified0.0011 +/- 0.003 umol/mmol creatinineAdult (>18 years old)FemaleBreast cancer details
UrineDetected and Quantified1.9 +/- 0.35 umol/mmol creatinineAdult (>18 years old)BothPancreatic cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothLeukemia details
UrineDetected and Quantified1.03 +/- 0.693 umol/mmol creatinineAdult (>18 years old)BothLeukemia details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Byun JA, Lee SH, Jung BH, Choi MH, Moon MH, Chung BC: Analysis of polyamines as carbamoyl derivatives in urine and serum by liquid chromatography-tandem mass spectrometry. Biomed Chromatogr. 2008 Jan;22(1):73-80. [PubMed:17668437 ]
Thyroid cancer
  1. Loser C, Folsch UR, Paprotny C, Creutzfeldt W: Polyamine concentrations in pancreatic tissue, serum, and urine of patients with pancreatic cancer. Pancreas. 1990 Mar;5(2):119-27. [PubMed:2315288 ]
Leukemia
  1. 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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022530
KNApSAcK IDNot Available
Chemspider ID482
KEGG Compound IDC00612
BioCyc IDCPD-568
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3323
PubChem Compound496
PDB IDNot Available
ChEBI ID17927
Food Biomarker OntologyNot Available
VMH IDN1ASPMD
MarkerDB IDMDB00000313
Good Scents IDNot Available
References
Synthesis ReferenceLurdes M; Almeida S; Grehn L; Ragnarsson U Facile synthesis of monoacetylated spermidines, illustrating selective deacetylation and application of a common precursor. Acta chemica Scandinavica (Copenhagen, Denmark : 1989) (1989), 43(10), 990-4.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hrushesky WJ, Merdink J, Abdel-Monem MM: Circadian rhythmicity of polyamine urinary excretion. Cancer Res. 1983 Aug;43(8):3944-7. [PubMed:6861156 ]
  2. Seiler N, Graham A, Bartholeyns J: Enhanced urinary excretion of N1-acetylspermidine and the presence of tumors. Cancer Res. 1981 Apr;41(4):1572-3. [PubMed:6897929 ]
  3. Abdel-Monem MM, Merdink JL, Theologides A: Urinary excretion of monoacetyl polyamines in patients with non-Hodgkin's lymphoma. Cancer Res. 1982 May;42(5):2097-8. [PubMed:7066912 ]
  4. Smith RG, Bartos D, Bartos F, Grettie DP, Frick W, Campbell RA, Daves GD Jr: 1-N-Acetylspermidine: occurrence in normal human serum. Biomed Mass Spectrom. 1978 Sep;5(9):515-7. [PubMed:708851 ]
  5. Ruggeri P, Lagana G, Bellocco E, Fabiano C, Leonaldi R, Forino D: Polyamines biosynthesis and oxidation in free-living amoebae. Amino Acids. 2004 Dec;27(3-4):367-72. Epub 2004 Oct 15. [PubMed:15490259 ]

Enzymes

Enzyme Details
1. Diamine acetyltransferase 2
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.
Gene Name:
SAT2
Uniprot ID:
Q96F10
Molecular weight:
19154.905
Enzyme Details
2. Diamine acetyltransferase 1
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
Enzyme Details
3. Peroxisomal N(1)-acetyl-spermine/spermidine oxidase
General function:
Amino acid transport and metabolism
Specific function:
Flavoenzyme which catalyzes the oxidation of N(1)-acetylspermine to spermidine and is thus involved in the polyamine back-conversion. Can also oxidize N(1)-acetylspermidine to putrescine. Substrate specificity: N(1)-acetylspermine = N(1)-acetylspermidine > N(1),N(12)-diacylspermine >> spermine. Does not oxidize spermidine. 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.
Gene Name:
PAOX
Uniprot ID:
Q6QHF9
Molecular weight:
55512.64
Reactions
N1-Acetylspermidine + Oxygen + Water → Putrescine + Acetamidopropanal + Hydrogen peroxidedetails
N1,N12-Diacetylspermine + Oxygen + Water → N1-Acetylspermidine + 3-Acetamidobutanal + Hydrogen peroxidedetails