MiMeDB: Showing metabocard for N1,N12-Diacetylspermine (MMDBc0000408)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:04 UTC

Update Date

2024-04-30 19:32:16 UTC

Metabolite ID

MMDBc0000408

Metabolite Identification

Common Name

N1,N12-Diacetylspermine

Description

N1,N12-Diacetylspermine is a polyamine commonly occurring in normal human urine (PMID 7775374 ). It has been reported that urinary N1,N12-Diacetylspermine can be used as a marker to efficiently detect colorectal and breast cancers at early stages (PMID 15837752 ). N1,N12-Diacetylspermine has been identified in the human placenta (PMID: 32033212 ).

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>
MMDBc0000408

> <DATABASE_NAME>
MIME

> <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

Synonyms

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

Molecular Formula

C₁₄H₃₀N₄O₂

Average Mass

286.4136

Monoisotopic Mass

286.236876224

IUPAC Name

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

Traditional Name

N(1),N(12)-diacetylspermine

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-4920000000-84c179f5f61cc75a6d58	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-1290000000-204fd298d8648eb559fa	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ufs-5980000000-6a3574952b41f068c5f8	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0596-8900000000-64c9b2e7b01bf25fd8be	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1090000000-59a2a54cb8b30d5401e7	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052u-4190000000-a343244608f9fef3983c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-a6138905f79c3078381e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-6caeb5b4787361992990	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052u-1090000000-dbc8a2e936f1f9f9a108	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9300000000-8fba59d5dec71d28e690	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0590000000-c1446e47bdafc61b1a2e	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uy1-0490000000-07ac0154a9c372d1e40e	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-5900000000-1fb6059d75a9d36f7352	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Placenta
Urine

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191794	Peroxisomal N(1)-acetyl-spermine/spermidine oxidase	Unknown	Q6QHF9	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0003970	Acetyl-CoA	N1,N12-Diacetylspermine	Not Available	RE1240C	VMH	0
MMDBr0004020	N1,N12-Diacetylspermine	Acetamidopropanal	Not Available	RE1538C	VMH	11454677 9359869
MMDBr0004021	N1,N12-Diacetylspermine	Acetamidopropanal	Polyamine oxidase (exo-n4-amino)	RE1538X	VMH	11454677 9359869
MMDBr0010448	N1,N12-Diacetylspermine	Acetyl-CoA	Not Available	HMR_6957	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Leukemia	Increased	Association	Human Urine	HMDB	9464484

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	2	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	0.268	0.166			umol/mmol creatinine	Adult (>18 years old)	Both	Leukemia	HMDB	9464484
Human Urine	Detected and Quantified	0.006	0.006			umol/mmol creatinine	Adult (>18 years old)	Both		HMDB	9464484
Human Urine	Detected and Quantified	0.00679		0.000	0.0260	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	9464484
Human Urine	Detected and Quantified			0.37	3.11	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Urine	Detected and Quantified	1.02	0.51			umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	1.03	0.64			umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	9464484
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0002172

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

References

Synthesis Reference

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. doi: 10.1093/oxfordjournals.jbchem.a124694. [PubMed:7775374 ]
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, 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. doi: 10.1007/s004320050102. [PubMed:9393587 ]
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. doi: 10.1158/1078-0432.CCR-04-2275. [PubMed:15837752 ]
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 ]
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 ]

Showing metabocard for N1,N12-Diacetylspermine (MMDBc0000408)

MOL for #<Metabolite:0x00007fd10a511d40>

3D MOL for #<Metabolite:0x00007fd10a511d40>

3D SDF for #<Metabolite:0x00007fd10a511d40>

3D-SDF for #<Metabolite:0x00007fd10a511d40>

PDB for #<Metabolite:0x00007fd10a511d40>

3D PDB for #<Metabolite:0x00007fd10a511d40>

SMILES for #<Metabolite:0x00007fd10a511d40>

INCHI for #<Metabolite:0x00007fd10a511d40>

Structure for #<Metabolite:0x00007fd10a511d40>

3D Structure for #<Metabolite:0x00007fd10a511d40>