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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:39 UTC

Update Date

2023-05-30 20:55:57 UTC

HMDB ID

HMDB0002172

Secondary Accession Numbers

HMDB02172

Metabolite Identification

Common Name

N1,N12-Diacetylspermine

Description

N1,N12-Diacetylspermine, also known as daspm, 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). N1,N12-Diacetylspermine exists in all living organisms, ranging from bacteria to humans. N1,N12-Diacetylspermine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make N1,N12-diacetylspermine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on N1,N12-Diacetylspermine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0002172
     RDKit          3D
N1,N12-Diacetylspermine
 50 49  0  0  0  0  0  0  0  0999 V2000
   -7.9366    1.7255   -0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6992    1.6386    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7688    1.4665    1.7344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4244    1.7503   -0.1104 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2346    1.6655    0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0545    0.3519    1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7601    0.4232    2.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725    0.6382    1.3012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3238   -0.4143    0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1198    0.0550   -0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3766   -0.9399   -1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987   -2.2417   -0.7712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8508   -2.1751    0.1874 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418   -1.8075   -0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1067   -1.7971    0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5132   -1.4302    0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176   -0.0941   -0.1587 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7133    0.5131   -0.6253 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7106    1.8550   -1.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8001   -0.1027   -0.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2256    2.7860   -0.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7833    1.1782    0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6834    1.3202   -1.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3361    1.9008   -1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3572    1.7303   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0991    2.5285    1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9180    0.1572    2.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9775   -0.4604    0.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6344   -0.4311    2.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8461    1.3447    2.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5667    1.5847    0.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1854   -0.6364   -0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0881   -1.3446    0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6436    0.3691    0.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239    0.9695   -0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4456   -1.1590   -2.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1700   -0.4503   -1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755   -2.7128   -0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1080   -2.9381   -1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9514   -3.1253    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4840   -2.5758   -1.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1628   -0.8340   -0.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0930   -2.7917    1.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7809   -1.0415    1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8769   -2.1101   -0.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2103   -1.4240    1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6319    0.4402   -0.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0213    1.9197   -2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2730    2.5637   -0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7036    2.1613   -1.5512 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
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
M  END

  Mrv0541 02231219242D          

 20 19  0  0  0  0            999 V2000
   20.3508  -15.8353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0680  -13.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4956  -15.0102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9233  -14.5977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0655  -14.5977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3536  -15.0102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2101  -14.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2087  -15.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6391  -14.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7798  -15.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6378  -15.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7812  -14.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4944  -14.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9246  -15.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3522  -14.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0666  -15.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6364  -14.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7825  -15.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3508  -15.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0680  -14.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  2  0  0  0  0
  2 20  2  0  0  0  0
  3  7  1  0  0  0  0
  3 12  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  1  0  0  0  0
  5 10  1  0  0  0  0
  5 19  1  0  0  0  0
  6  9  1  0  0  0  0
  6 20  1  0  0  0  0
  7 14  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 13  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 15 16  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002172

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NCCCNCCCCNCCCNC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H30N4O2/c1-13(19)17-11-5-9-15-7-3-4-8-16-10-6-12-18-14(2)20/h15-16H,3-12H2,1-2H3,(H,17,19)(H,18,20)

> <INCHI_KEY>
NPDTUDWGJMBVEP-UHFFFAOYSA-N

> <FORMULA>
C14H30N4O2

> <MOLECULAR_WEIGHT>
286.4136

> <EXACT_MASS>
286.236876224

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.39374520029105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.18

> <JCHEM_LOGP>
-1.8163144100000002

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
16.596204131932776

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.994141360609714

> <JCHEM_PKA_STRONGEST_BASIC>
10.782353310644947

> <JCHEM_POLAR_SURFACE_AREA>
82.26

> <JCHEM_REFRACTIVITY>
81.44580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N(1),N(12)-diacetylspermine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002172
     RDKit          3D
N1,N12-Diacetylspermine
 50 49  0  0  0  0  0  0  0  0999 V2000
   -7.9366    1.7255   -0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6992    1.6386    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7688    1.4665    1.7344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4244    1.7503   -0.1104 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2346    1.6655    0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0545    0.3519    1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7601    0.4232    2.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725    0.6382    1.3012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3238   -0.4143    0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1198    0.0550   -0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3766   -0.9399   -1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987   -2.2417   -0.7712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8508   -2.1751    0.1874 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418   -1.8075   -0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1067   -1.7971    0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5132   -1.4302    0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176   -0.0941   -0.1587 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7133    0.5131   -0.6253 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7106    1.8550   -1.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8001   -0.1027   -0.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2256    2.7860   -0.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7833    1.1782    0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6834    1.3202   -1.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3361    1.9008   -1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3572    1.7303   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0991    2.5285    1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9180    0.1572    2.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9775   -0.4604    0.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6344   -0.4311    2.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8461    1.3447    2.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5667    1.5847    0.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1854   -0.6364   -0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0881   -1.3446    0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6436    0.3691    0.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239    0.9695   -0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4456   -1.1590   -2.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1700   -0.4503   -1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755   -2.7128   -0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1080   -2.9381   -1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9514   -3.1253    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4840   -2.5758   -1.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1628   -0.8340   -0.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0930   -2.7917    1.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7809   -1.0415    1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8769   -2.1101   -0.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2103   -1.4240    1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6319    0.4402   -0.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0213    1.9197   -2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2730    2.5637   -0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7036    2.1613   -1.5512 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
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
M  END

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  O   UNK     0      37.988 -29.559   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      57.994 -25.709   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      51.325 -28.019   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      44.657 -27.249   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      39.322 -27.249   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      56.660 -28.019   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      52.659 -27.249   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      43.323 -28.019   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      55.326 -27.249   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      40.656 -28.019   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      45.991 -28.019   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      49.992 -27.249   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      41.990 -27.249   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      53.993 -28.019   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      47.324 -27.249   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      48.658 -28.019   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      36.655 -27.249   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      59.327 -28.019   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.988 -28.019   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      57.994 -27.249   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    7   12                                                       
CONECT    4    8   11                                                       
CONECT    5   10   19                                                       
CONECT    6    9   20                                                       
CONECT    7    3   14                                                       
CONECT    8    4   13                                                       
CONECT    9    6   14                                                       
CONECT   10    5   13                                                       
CONECT   11    4   15                                                       
CONECT   12    3   16                                                       
CONECT   13    8   10                                                       
CONECT   14    7    9                                                       
CONECT   15   11   16                                                       
CONECT   16   12   15                                                       
CONECT   17   19                                                            
CONECT   18   20                                                            
CONECT   19    1    5   17                                                  
CONECT   20    2    6   18                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0002172
HETATM    1  C1  UNL     1      -7.937   1.726  -0.322  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.699   1.639   0.499  1.00  0.00           C  
HETATM    3  O1  UNL     1      -6.769   1.467   1.734  1.00  0.00           O  
HETATM    4  N1  UNL     1      -5.424   1.750  -0.110  1.00  0.00           N  
HETATM    5  C3  UNL     1      -4.235   1.666   0.672  1.00  0.00           C  
HETATM    6  C4  UNL     1      -4.054   0.352   1.404  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.760   0.423   2.180  1.00  0.00           C  
HETATM    8  N2  UNL     1      -1.673   0.638   1.301  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.324  -0.414   0.411  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.120   0.055  -0.379  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.377  -0.940  -1.366  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.799  -2.242  -0.771  1.00  0.00           C  
HETATM   13  N3  UNL     1       1.851  -2.175   0.187  1.00  0.00           N  
HETATM   14  C10 UNL     1       3.142  -1.808  -0.333  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.107  -1.797   0.824  1.00  0.00           C  
HETATM   16  C12 UNL     1       5.513  -1.430   0.425  1.00  0.00           C  
HETATM   17  N4  UNL     1       5.518  -0.094  -0.159  1.00  0.00           N  
HETATM   18  C13 UNL     1       6.713   0.513  -0.625  1.00  0.00           C  
HETATM   19  C14 UNL     1       6.711   1.855  -1.210  1.00  0.00           C  
HETATM   20  O2  UNL     1       7.800  -0.103  -0.540  1.00  0.00           O  
HETATM   21  H1  UNL     1      -8.226   2.786  -0.356  1.00  0.00           H  
HETATM   22  H2  UNL     1      -8.783   1.178   0.153  1.00  0.00           H  
HETATM   23  H3  UNL     1      -7.683   1.320  -1.317  1.00  0.00           H  
HETATM   24  H4  UNL     1      -5.336   1.901  -1.163  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.357   1.730  -0.024  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.099   2.529   1.361  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.918   0.157   2.097  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.977  -0.460   0.652  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.634  -0.431   2.872  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.846   1.345   2.830  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.567   1.585   0.935  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.185  -0.636  -0.244  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.088  -1.345   0.945  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.644   0.369   0.350  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.424   0.970  -0.928  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.446  -1.159  -2.089  1.00  0.00           H  
HETATM   37  H17 UNL     1       1.170  -0.450  -1.968  1.00  0.00           H  
HETATM   38  H18 UNL     1      -0.075  -2.713  -0.287  1.00  0.00           H  
HETATM   39  H19 UNL     1       1.108  -2.938  -1.583  1.00  0.00           H  
HETATM   40  H20 UNL     1       1.951  -3.125   0.609  1.00  0.00           H  
HETATM   41  H21 UNL     1       3.484  -2.576  -1.062  1.00  0.00           H  
HETATM   42  H22 UNL     1       3.163  -0.834  -0.817  1.00  0.00           H  
HETATM   43  H23 UNL     1       4.093  -2.792   1.314  1.00  0.00           H  
HETATM   44  H24 UNL     1       3.781  -1.041   1.588  1.00  0.00           H  
HETATM   45  H25 UNL     1       5.877  -2.110  -0.372  1.00  0.00           H  
HETATM   46  H26 UNL     1       6.210  -1.424   1.273  1.00  0.00           H  
HETATM   47  H27 UNL     1       4.632   0.440  -0.240  1.00  0.00           H  
HETATM   48  H28 UNL     1       6.021   1.920  -2.082  1.00  0.00           H  
HETATM   49  H29 UNL     1       6.273   2.564  -0.447  1.00  0.00           H  
HETATM   50  H30 UNL     1       7.704   2.161  -1.551  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3    4
CONECT    4    5   24
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8   29   30
CONECT    8    9   31
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   36   37
CONECT   12   13   38   39
CONECT   13   14   40
CONECT   14   15   41   42
CONECT   15   16   43   44
CONECT   16   17   45   46
CONECT   17   18   47
CONECT   18   19   20   20
CONECT   19   48   49   50
END

HMDB0002172
     RDKit          3D
N1,N12-Diacetylspermine
 50 49  0  0  0  0  0  0  0  0999 V2000
   -7.9366    1.7255   -0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6992    1.6386    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7688    1.4665    1.7344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4244    1.7503   -0.1104 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2346    1.6655    0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0545    0.3519    1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7601    0.4232    2.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725    0.6382    1.3012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3238   -0.4143    0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1198    0.0550   -0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3766   -0.9399   -1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987   -2.2417   -0.7712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8508   -2.1751    0.1874 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418   -1.8075   -0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1067   -1.7971    0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5132   -1.4302    0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176   -0.0941   -0.1587 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7133    0.5131   -0.6253 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7106    1.8550   -1.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8001   -0.1027   -0.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2256    2.7860   -0.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7833    1.1782    0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6834    1.3202   -1.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3361    1.9008   -1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3572    1.7303   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0991    2.5285    1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9180    0.1572    2.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9775   -0.4604    0.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6344   -0.4311    2.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8461    1.3447    2.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5667    1.5847    0.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1854   -0.6364   -0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0881   -1.3446    0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6436    0.3691    0.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239    0.9695   -0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4456   -1.1590   -2.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1700   -0.4503   -1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755   -2.7128   -0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1080   -2.9381   -1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9514   -3.1253    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4840   -2.5758   -1.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1628   -0.8340   -0.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0930   -2.7917    1.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7809   -1.0415    1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8769   -2.1101   -0.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2103   -1.4240    1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6319    0.4402   -0.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0213    1.9197   -2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2730    2.5637   -0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7036    2.1613   -1.5512 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
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
DASpm	ChEBI
N',n''-diacetylspermine	MeSH, HMDB
Diacetylspermine	MeSH, HMDB
N1,N12-Diacetylspermine	ChEBI

Chemical Formula

C₁₄H₃₀N₄O₂

Average Molecular Weight

286.4136

Monoisotopic Molecular Weight

286.236876224

IUPAC Name

N-[3-({4-[(3-acetamidopropyl)amino]butyl}amino)propyl]acetamide

Traditional Name

N(1),N(12)-diacetylspermine

CAS Registry Number

61345-83-3

SMILES

CC(=O)NCCCNCCCCNCCCNC(C)=O

InChI Identifier

InChI=1S/C14H30N4O2/c1-13(19)17-11-5-9-15-7-3-4-8-16-10-6-12-18-14(2)20/h15-16H,3-12H2,1-2H3,(H,17,19)(H,18,20)

InChI Key

NPDTUDWGJMBVEP-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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboximidic acids and derivatives

Sub Class

Carboximidic acids

Direct Parent

Carboximidic 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
Organooxygen compound
Organonitrogen compound
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

acetylspermine (CHEBI:28101 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0002172)

Organ

Placenta (HMDB: HMDB0002172)

Excreta

Biofluid or Excreta

Urine (PMID: 9464484)
Feces (PMID: 27543620)

Source

Endogenous

Endogenous (HMDB: HMDB0002172)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	-0.18	ALOGPS
logP	-1.8	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	15.99	ChemAxon
pKa (Strongest Basic)	10.78	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	82.26 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	81.45 m³·mol⁻¹	ChemAxon
Polarizability	35.39 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	168.281	31661259
DarkChem	[M-H]-	163.664	31661259
DeepCCS	[M+H]+	165.148	30932474
DeepCCS	[M-H]-	162.358	30932474
DeepCCS	[M-2H]-	198.106	30932474
DeepCCS	[M+Na]+	173.752	30932474
AllCCS	[M+H]+	170.7	32859911
AllCCS	[M+H-H2O]+	168.0	32859911
AllCCS	[M+NH4]+	173.2	32859911
AllCCS	[M+Na]+	173.9	32859911
AllCCS	[M-H]-	174.2	32859911
AllCCS	[M+Na-2H]-	175.2	32859911
AllCCS	[M+HCOO]-	176.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N1,N12-Diacetylspermine	CC(=O)NCCCNCCCCNCCCNC(C)=O	3515.2	Standard polar	33892256
N1,N12-Diacetylspermine	CC(=O)NCCCNCCCCNCCCNC(C)=O	2692.7	Standard non polar	33892256
N1,N12-Diacetylspermine	CC(=O)NCCCNCCCCNCCCNC(C)=O	2757.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N1,N12-Diacetylspermine,1TMS,isomer #1	CC(=O)NCCCNCCCCNCCCN(C(C)=O)[Si](C)(C)C	2726.7	Semi standard non polar	33892256
N1,N12-Diacetylspermine,1TMS,isomer #1	CC(=O)NCCCNCCCCNCCCN(C(C)=O)[Si](C)(C)C	2801.6	Standard non polar	33892256
N1,N12-Diacetylspermine,1TMS,isomer #1	CC(=O)NCCCNCCCCNCCCN(C(C)=O)[Si](C)(C)C	3637.4	Standard polar	33892256
N1,N12-Diacetylspermine,1TMS,isomer #2	CC(=O)NCCCNCCCCN(CCCNC(C)=O)[Si](C)(C)C	2821.5	Semi standard non polar	33892256
N1,N12-Diacetylspermine,1TMS,isomer #2	CC(=O)NCCCNCCCCN(CCCNC(C)=O)[Si](C)(C)C	2720.6	Standard non polar	33892256
N1,N12-Diacetylspermine,1TMS,isomer #2	CC(=O)NCCCNCCCCN(CCCNC(C)=O)[Si](C)(C)C	3804.8	Standard polar	33892256
N1,N12-Diacetylspermine,2TMS,isomer #1	CC(=O)N(CCCNCCCCNCCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2621.5	Semi standard non polar	33892256
N1,N12-Diacetylspermine,2TMS,isomer #1	CC(=O)N(CCCNCCCCNCCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2875.8	Standard non polar	33892256
N1,N12-Diacetylspermine,2TMS,isomer #1	CC(=O)N(CCCNCCCCNCCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	3134.2	Standard polar	33892256
N1,N12-Diacetylspermine,2TMS,isomer #2	CC(=O)NCCCN(CCCCNCCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2760.0	Semi standard non polar	33892256
N1,N12-Diacetylspermine,2TMS,isomer #2	CC(=O)NCCCN(CCCCNCCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2819.6	Standard non polar	33892256
N1,N12-Diacetylspermine,2TMS,isomer #2	CC(=O)NCCCN(CCCCNCCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	3324.8	Standard polar	33892256
N1,N12-Diacetylspermine,2TMS,isomer #3	CC(=O)NCCCNCCCCN(CCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2795.9	Semi standard non polar	33892256
N1,N12-Diacetylspermine,2TMS,isomer #3	CC(=O)NCCCNCCCCN(CCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2824.5	Standard non polar	33892256
N1,N12-Diacetylspermine,2TMS,isomer #3	CC(=O)NCCCNCCCCN(CCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	3333.3	Standard polar	33892256
N1,N12-Diacetylspermine,2TMS,isomer #4	CC(=O)NCCCN(CCCCN(CCCNC(C)=O)[Si](C)(C)C)[Si](C)(C)C	2907.8	Semi standard non polar	33892256
N1,N12-Diacetylspermine,2TMS,isomer #4	CC(=O)NCCCN(CCCCN(CCCNC(C)=O)[Si](C)(C)C)[Si](C)(C)C	2792.0	Standard non polar	33892256
N1,N12-Diacetylspermine,2TMS,isomer #4	CC(=O)NCCCN(CCCCN(CCCNC(C)=O)[Si](C)(C)C)[Si](C)(C)C	3506.5	Standard polar	33892256
N1,N12-Diacetylspermine,3TMS,isomer #1	CC(=O)N(CCCNCCCCN(CCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2720.1	Semi standard non polar	33892256
N1,N12-Diacetylspermine,3TMS,isomer #1	CC(=O)N(CCCNCCCCN(CCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2894.9	Standard non polar	33892256
N1,N12-Diacetylspermine,3TMS,isomer #1	CC(=O)N(CCCNCCCCN(CCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2990.0	Standard polar	33892256
N1,N12-Diacetylspermine,3TMS,isomer #2	CC(=O)NCCCN(CCCCN(CCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2879.7	Semi standard non polar	33892256
N1,N12-Diacetylspermine,3TMS,isomer #2	CC(=O)NCCCN(CCCCN(CCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2896.0	Standard non polar	33892256
N1,N12-Diacetylspermine,3TMS,isomer #2	CC(=O)NCCCN(CCCCN(CCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	3144.2	Standard polar	33892256
N1,N12-Diacetylspermine,4TMS,isomer #1	CC(=O)N(CCCN(CCCCN(CCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2851.4	Semi standard non polar	33892256
N1,N12-Diacetylspermine,4TMS,isomer #1	CC(=O)N(CCCN(CCCCN(CCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2936.7	Standard non polar	33892256
N1,N12-Diacetylspermine,4TMS,isomer #1	CC(=O)N(CCCN(CCCCN(CCCN(C(C)=O)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2897.6	Standard polar	33892256
N1,N12-Diacetylspermine,1TBDMS,isomer #1	CC(=O)NCCCNCCCCNCCCN(C(C)=O)[Si](C)(C)C(C)(C)C	2948.7	Semi standard non polar	33892256
N1,N12-Diacetylspermine,1TBDMS,isomer #1	CC(=O)NCCCNCCCCNCCCN(C(C)=O)[Si](C)(C)C(C)(C)C	3010.5	Standard non polar	33892256
N1,N12-Diacetylspermine,1TBDMS,isomer #1	CC(=O)NCCCNCCCCNCCCN(C(C)=O)[Si](C)(C)C(C)(C)C	3553.6	Standard polar	33892256
N1,N12-Diacetylspermine,1TBDMS,isomer #2	CC(=O)NCCCNCCCCN(CCCNC(C)=O)[Si](C)(C)C(C)(C)C	3076.6	Semi standard non polar	33892256
N1,N12-Diacetylspermine,1TBDMS,isomer #2	CC(=O)NCCCNCCCCN(CCCNC(C)=O)[Si](C)(C)C(C)(C)C	2943.0	Standard non polar	33892256
N1,N12-Diacetylspermine,1TBDMS,isomer #2	CC(=O)NCCCNCCCCN(CCCNC(C)=O)[Si](C)(C)C(C)(C)C	3728.3	Standard polar	33892256
N1,N12-Diacetylspermine,2TBDMS,isomer #1	CC(=O)N(CCCNCCCCNCCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3091.2	Semi standard non polar	33892256
N1,N12-Diacetylspermine,2TBDMS,isomer #1	CC(=O)N(CCCNCCCCNCCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3244.1	Standard non polar	33892256
N1,N12-Diacetylspermine,2TBDMS,isomer #1	CC(=O)N(CCCNCCCCNCCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3185.2	Standard polar	33892256
N1,N12-Diacetylspermine,2TBDMS,isomer #2	CC(=O)NCCCN(CCCCNCCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3243.8	Semi standard non polar	33892256
N1,N12-Diacetylspermine,2TBDMS,isomer #2	CC(=O)NCCCN(CCCCNCCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3190.4	Standard non polar	33892256
N1,N12-Diacetylspermine,2TBDMS,isomer #2	CC(=O)NCCCN(CCCCNCCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3313.1	Standard polar	33892256
N1,N12-Diacetylspermine,2TBDMS,isomer #3	CC(=O)NCCCNCCCCN(CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3277.8	Semi standard non polar	33892256
N1,N12-Diacetylspermine,2TBDMS,isomer #3	CC(=O)NCCCNCCCCN(CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3197.7	Standard non polar	33892256
N1,N12-Diacetylspermine,2TBDMS,isomer #3	CC(=O)NCCCNCCCCN(CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3319.3	Standard polar	33892256
N1,N12-Diacetylspermine,2TBDMS,isomer #4	CC(=O)NCCCN(CCCCN(CCCNC(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3405.0	Semi standard non polar	33892256
N1,N12-Diacetylspermine,2TBDMS,isomer #4	CC(=O)NCCCN(CCCCN(CCCNC(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3158.3	Standard non polar	33892256
N1,N12-Diacetylspermine,2TBDMS,isomer #4	CC(=O)NCCCN(CCCCN(CCCNC(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3451.9	Standard polar	33892256
N1,N12-Diacetylspermine,3TBDMS,isomer #1	CC(=O)N(CCCNCCCCN(CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3419.3	Semi standard non polar	33892256
N1,N12-Diacetylspermine,3TBDMS,isomer #1	CC(=O)N(CCCNCCCCN(CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3403.9	Standard non polar	33892256
N1,N12-Diacetylspermine,3TBDMS,isomer #1	CC(=O)N(CCCNCCCCN(CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3209.6	Standard polar	33892256
N1,N12-Diacetylspermine,3TBDMS,isomer #2	CC(=O)NCCCN(CCCCN(CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3585.7	Semi standard non polar	33892256
N1,N12-Diacetylspermine,3TBDMS,isomer #2	CC(=O)NCCCN(CCCCN(CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3384.0	Standard non polar	33892256
N1,N12-Diacetylspermine,3TBDMS,isomer #2	CC(=O)NCCCN(CCCCN(CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3302.6	Standard polar	33892256
N1,N12-Diacetylspermine,4TBDMS,isomer #1	CC(=O)N(CCCN(CCCCN(CCCN(C(C)=O)[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)C	3750.2	Semi standard non polar	33892256
N1,N12-Diacetylspermine,4TBDMS,isomer #1	CC(=O)N(CCCN(CCCCN(CCCN(C(C)=O)[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)C	3554.3	Standard non polar	33892256
N1,N12-Diacetylspermine,4TBDMS,isomer #1	CC(=O)N(CCCN(CCCCN(CCCN(C(C)=O)[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)C	3213.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N1,N12-Diacetylspermine GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-4920000000-84c179f5f61cc75a6d58	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N1,N12-Diacetylspermine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1,N12-Diacetylspermine 10V, Positive-QTOF	splash10-000j-1290000000-204fd298d8648eb559fa	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1,N12-Diacetylspermine 20V, Positive-QTOF	splash10-0ufs-5980000000-6a3574952b41f068c5f8	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1,N12-Diacetylspermine 40V, Positive-QTOF	splash10-0596-8900000000-64c9b2e7b01bf25fd8be	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1,N12-Diacetylspermine 10V, Negative-QTOF	splash10-000i-1090000000-59a2a54cb8b30d5401e7	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1,N12-Diacetylspermine 20V, Negative-QTOF	splash10-052u-4190000000-a343244608f9fef3983c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1,N12-Diacetylspermine 40V, Negative-QTOF	splash10-0a4l-9000000000-a6138905f79c3078381e	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1,N12-Diacetylspermine 10V, Negative-QTOF	splash10-000i-0090000000-6caeb5b4787361992990	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1,N12-Diacetylspermine 20V, Negative-QTOF	splash10-052u-1090000000-dbc8a2e936f1f9f9a108	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1,N12-Diacetylspermine 40V, Negative-QTOF	splash10-052f-9300000000-8fba59d5dec71d28e690	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1,N12-Diacetylspermine 10V, Positive-QTOF	splash10-0079-0590000000-c1446e47bdafc61b1a2e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1,N12-Diacetylspermine 20V, Positive-QTOF	splash10-0uy1-0490000000-07ac0154a9c372d1e40e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N1,N12-Diacetylspermine 40V, Positive-QTOF	splash10-0udi-5900000000-1fb6059d75a9d36f7352	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	9464484	details
Urine	Detected and Quantified	0.006 +/- 0.006 umol/mmol creatinine	Adult (>18 years old)	Both	Not Available	9464484	details
Urine	Detected and Quantified	0.37-3.11 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	1.02 +/- 0.51 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	1.03 +/- 0.64 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	2.29 (1.16-3.10) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	0.00679 (0.000 -0.0260) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9464484	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Leukemia	9464484	details
Urine	Detected and Quantified	0.268 +/- 0.166 umol/mmol creatinine	Adult (>18 years old)	Both	Leukemia	9464484	details

Associated Disorders and Diseases

Disease References

Leukemia
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 IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022884

KNApSAcK ID

Not Available

Chemspider ID

117134

KEGG Compound ID

C03413

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6525

PubChem Compound

132680

PDB ID

Not Available

ChEBI ID

28101

Food Biomarker Ontology

Not Available

VMH ID

C03413

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

van den Berg GA, Muskiet FA, Kingma AW, van der Slik W, Halie MR: Simultaneous gas-chromatographic determination of free and acetyl-conjugated polyamines in urine. Clin Chem. 1986 Oct;32(10):1930-7. [PubMed:3757213 ]
Hiramatsu K, Sugimoto M, Kamei S, Hoshino M, Kinoshita K, Iwasaki K, Kawakita M: Determination of amounts of polyamines excreted in urine: demonstration of N1,N8-diacetylspermidine and N1,N12-diacetylspermine as components commonly occurring in normal human urine. J Biochem. 1995 Jan;117(1):107-12. [PubMed:7775374 ]
Enjoji M, Kotoh K, Nakamuta M: [Factors affecting the increase of urinary diacetylspermine levels : a study in patients with liver diseases]. Rinsho Byori. 2006 Feb;54(2):126-31. [PubMed:16548232 ]
Shimpo K, Chihara T, Hibiya M, Ito S, Nagatsu T: [Amines and pteridines]. Nihon Rinsho. 1996 Jun;54(6):1515-20. [PubMed:8691603 ]
Hiramatsu K, Takahashi K, Yamaguchi T, Matsumoto H, Miyamoto H, Tanaka S, Tanaka C, Tamamori Y, Imajo M, Kawaguchi M, Toi M, Mori T, Kawakita M: N(1),N(12)-Diacetylspermine as a sensitive and specific novel marker for early- and late-stage colorectal and breast cancers. Clin Cancer Res. 2005 Apr 15;11(8):2986-90. [PubMed:15837752 ]
Hiramatsu K, Sugimoto M, Kamei S, Hoshino M, Kinoshita K, Iwasaki K, Kawakita M: Diagnostic and prognostic usefulness of N1,N8-diacetylspermidine and N1,N12-diacetylspermine in urine as novel markers of malignancy. J Cancer Res Clin Oncol. 1997;123(10):539-45. [PubMed:9393587 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. 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,N12-Diacetylspermine + Oxygen + Water → N1-Acetylspermidine + 3-Acetamidobutanal + Hydrogen peroxide	details

Showing metabocard for N1,N12-Diacetylspermine (HMDB0002172)

MOL for HMDB0002172 (N1,N12-Diacetylspermine)

3D MOL for HMDB0002172 (N1,N12-Diacetylspermine)

3D SDF for HMDB0002172 (N1,N12-Diacetylspermine)

3D-SDF for HMDB0002172 (N1,N12-Diacetylspermine)

PDB for HMDB0002172 (N1,N12-Diacetylspermine)

3D PDB for HMDB0002172 (N1,N12-Diacetylspermine)

SMILES for HMDB0002172 (N1,N12-Diacetylspermine)

INCHI for HMDB0002172 (N1,N12-Diacetylspermine)

Structure for HMDB0002172 (N1,N12-Diacetylspermine)

3D Structure for HMDB0002172 (N1,N12-Diacetylspermine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions