Np mrd loader

Showing NP-Card for Spermine (NP0000522)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:10 UTC
NP-MRD IDNP0000522
Secondary Accession NumbersNone
Natural Product Identification
Common NameSpermine
DescriptionSpermine, also known as gerontine or musculamine, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. The resultin N-carbamoylputrescine is acted on by a hydrolase to split off urea group, leaving putrescine. The precursor for synthesis of spermine is the amino acid ornithine. The intermediate is spermidine. Spermine is a drug. Spermine exists in all living species, ranging from bacteria to humans. 5'-Methylthioadenosine and spermine can be biosynthesized from S-adenosylmethioninamine and spermidine through its interaction with the enzyme spermine synthase. Another pathway in plants starts with decarboxylation of L-arginine to produce agmatine. In humans, spermine is involved in spermidine and spermine biosynthesis. Outside of the human body, spermine is found, on average, in the highest concentration in oats. Spermine has also been detected, but not quantified in several different foods, such as sapodilla, mexican groundcherries, cloves, sourdocks, and sunflowers. This could make spermine a potential biomarker for the consumption of these foods. This decarboxylation gives putrescine. The name spermin was first used by the German chemists Ladenburg and Abel in 1888, and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling) and Germany (by Wrede et al.). In one pathway L-glutamine is the precursor to L-ornithine, after which the synthesis of spermine from L-ornithine follows the same pathway as in animals. Spermine is a potentially toxic compound.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000522 (Spermine)

127
  Mrv1652309042000202D          

 14 13  0  0  0  0            999 V2000
    4.9504    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5226   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3804   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3793    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0938   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8082    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2371    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9515   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1  9  1  0  0  0  0
  2  8  1  0  0  0  0
  2 10  1  0  0  0  0
  3 13  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
Download

3D MOL for NP0000522 (Spermine)

HMDB0001256
     RDKit          3D
Spermine
 40 39  0  0  0  0  0  0  0  0999 V2000
    5.9451    0.8520    0.3288 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900   -0.0105   -0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1780   -0.7449    1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1242   -1.6107    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.7655   -0.4464 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241    0.0411    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7399    0.9997   -0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3466    1.8923   -0.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695    1.3441    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8915    0.4168    1.0337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3681    0.1930    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8757   -0.5426   -0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3762   -0.7988    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7997   -1.5189   -1.1620 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5867    1.4245    1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7814    0.2866    0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2155   -0.7932   -0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1473    0.6575   -0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8841   -1.3489    1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6974   -0.0456    1.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499   -2.1743    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465   -2.3064   -0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5574   -0.3354   -1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -0.5757    0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8899    0.6924    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    1.6135   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4606    0.3921   -1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5197    2.6142   -1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0198    2.6220    0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3810    2.1972    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    0.8300   -0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -0.5601    0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8867    1.1709    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6279   -0.3448    2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4015   -1.5562   -0.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7267   -0.0206   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6348   -1.4293    0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9315    0.1586    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2527   -0.9311   -1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9495   -1.9846   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
M  END
Download

3D SDF for NP0000522 (Spermine)

127
  Mrv1652309042000202D          

 14 13  0  0  0  0            999 V2000
    4.9504    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5226   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3804   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3793    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0938   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8082    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2371    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9515   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1  9  1  0  0  0  0
  2  8  1  0  0  0  0
  2 10  1  0  0  0  0
  3 13  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000522

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCCNCCCCNCCCN

> <INCHI_IDENTIFIER>
InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2

> <INCHI_KEY>
PFNFFQXMRSDOHW-UHFFFAOYSA-N

> <FORMULA>
C10H26N4

> <MOLECULAR_WEIGHT>
202.3402

> <EXACT_MASS>
202.215746852

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.694691643339382

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine

> <ALOGPS_LOGP>
-0.66

> <JCHEM_LOGP>
-1.4540076160000006

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
4

> <JCHEM_PKA_STRONGEST_BASIC>
10.799251803165692

> <JCHEM_POLAR_SURFACE_AREA>
76.1

> <JCHEM_REFRACTIVITY>
62.558200000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
spermine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000522 (Spermine)

HMDB0001256
     RDKit          3D
Spermine
 40 39  0  0  0  0  0  0  0  0999 V2000
    5.9451    0.8520    0.3288 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900   -0.0105   -0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1780   -0.7449    1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1242   -1.6107    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.7655   -0.4464 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241    0.0411    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7399    0.9997   -0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3466    1.8923   -0.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695    1.3441    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8915    0.4168    1.0337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3681    0.1930    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8757   -0.5426   -0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3762   -0.7988    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7997   -1.5189   -1.1620 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5867    1.4245    1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7814    0.2866    0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2155   -0.7932   -0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1473    0.6575   -0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8841   -1.3489    1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6974   -0.0456    1.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499   -2.1743    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465   -2.3064   -0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5574   -0.3354   -1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -0.5757    0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8899    0.6924    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    1.6135   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4606    0.3921   -1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5197    2.6142   -1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0198    2.6220    0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3810    2.1972    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    0.8300   -0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -0.5601    0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8867    1.1709    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6279   -0.3448    2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4015   -1.5562   -0.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7267   -0.0206   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6348   -1.4293    0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9315    0.1586    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2527   -0.9311   -1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9495   -1.9846   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
M  END
Download

PDB for NP0000522 (Spermine)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 127                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  N   UNK     0       9.241   0.385   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0      15.909  -0.385   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       3.907   0.385   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      21.243  -0.385   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      11.908   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.242  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.575  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.575   0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.907  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.243   0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574   0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.576  -0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.240  -0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.909   0.385   0.000  0.00  0.00           C+0
CONECT    1    7    9                                                       
CONECT    2    8   10                                                       
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    1    5                                                       
CONECT    8    2    6                                                       
CONECT    9    1   11                                                       
CONECT   10    2   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13    3   11                                                       
CONECT   14    4   12                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END
Download

3D PDB for NP0000522 (Spermine)

COMPND    HMDB0001256
HETATM    1  N1  UNL     1       5.945   0.852   0.329  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.890  -0.010  -0.134  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.178  -0.745   1.003  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.124  -1.611   0.272  1.00  0.00           C  
HETATM    5  N2  UNL     1       2.272  -0.766  -0.446  1.00  0.00           N  
HETATM    6  C4  UNL     1       1.324   0.041   0.259  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.740   1.000  -0.728  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.347   1.892  -0.308  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.670   1.344   0.009  1.00  0.00           C  
HETATM   10  N3  UNL     1      -1.892   0.417   1.034  1.00  0.00           N  
HETATM   11  C8  UNL     1      -3.368   0.193   1.112  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.876  -0.543  -0.081  1.00  0.00           C  
HETATM   13  C10 UNL     1      -5.376  -0.799   0.026  1.00  0.00           C  
HETATM   14  N4  UNL     1      -5.800  -1.519  -1.162  1.00  0.00           N  
HETATM   15  H1  UNL     1       5.587   1.425   1.114  1.00  0.00           H  
HETATM   16  H2  UNL     1       6.781   0.287   0.567  1.00  0.00           H  
HETATM   17  H3  UNL     1       5.216  -0.793  -0.848  1.00  0.00           H  
HETATM   18  H4  UNL     1       4.147   0.657  -0.639  1.00  0.00           H  
HETATM   19  H5  UNL     1       4.884  -1.349   1.571  1.00  0.00           H  
HETATM   20  H6  UNL     1       3.697  -0.046   1.698  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.550  -2.174   1.039  1.00  0.00           H  
HETATM   22  H8  UNL     1       3.647  -2.306  -0.413  1.00  0.00           H  
HETATM   23  H9  UNL     1       2.557  -0.335  -1.312  1.00  0.00           H  
HETATM   24  H10 UNL     1       0.591  -0.576   0.750  1.00  0.00           H  
HETATM   25  H11 UNL     1       1.890   0.692   1.002  1.00  0.00           H  
HETATM   26  H12 UNL     1       1.650   1.614  -1.082  1.00  0.00           H  
HETATM   27  H13 UNL     1       0.461   0.392  -1.653  1.00  0.00           H  
HETATM   28  H14 UNL     1      -0.520   2.614  -1.186  1.00  0.00           H  
HETATM   29  H15 UNL     1       0.020   2.622   0.487  1.00  0.00           H  
HETATM   30  H16 UNL     1      -2.381   2.197   0.179  1.00  0.00           H  
HETATM   31  H17 UNL     1      -2.006   0.830  -0.969  1.00  0.00           H  
HETATM   32  H18 UNL     1      -1.505  -0.560   0.809  1.00  0.00           H  
HETATM   33  H19 UNL     1      -3.887   1.171   1.157  1.00  0.00           H  
HETATM   34  H20 UNL     1      -3.628  -0.345   2.032  1.00  0.00           H  
HETATM   35  H21 UNL     1      -3.402  -1.556  -0.100  1.00  0.00           H  
HETATM   36  H22 UNL     1      -3.727  -0.021  -1.050  1.00  0.00           H  
HETATM   37  H23 UNL     1      -5.635  -1.429   0.899  1.00  0.00           H  
HETATM   38  H24 UNL     1      -5.932   0.159   0.127  1.00  0.00           H  
HETATM   39  H25 UNL     1      -6.253  -0.931  -1.875  1.00  0.00           H  
HETATM   40  H26 UNL     1      -4.949  -1.985  -1.573  1.00  0.00           H  
CONECT    1    2   15   16
CONECT    2    3   17   18
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6   23
CONECT    6    7   24   25
CONECT    7    8   26   27
CONECT    8    9   28   29
CONECT    9   10   30   31
CONECT   10   11   32
CONECT   11   12   33   34
CONECT   12   13   35   36
CONECT   13   14   37   38
CONECT   14   39   40
END
Download

SMILES for NP0000522 (Spermine)

NCCCNCCCCNCCCN
Download

INCHI for NP0000522 (Spermine)

InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
Download
View in JSmol
Synonyms
ValueSource
4,9-Diaza-1,12-dodecanediamineChEBI
4,9-Diazadodecane-1,12-diamineChEBI
N,N'-bis(3-aminopropyl)-1,4-butanediamineChEBI
1,5,10,14-TetraazatetradecaneHMDB
4,9-DiazadodecamethylenediamineHMDB
Diaminopropyl-tetramethylenediamineHMDB
DiaminopropyltetramethylenediamineHMDB
GerontineHMDB
MusculamineHMDB
N,N'-bis(3-aminopropyl)-1,4-tetramethylenediamineHMDB
N,N'-bis(3-aminopropyl)butane-1,4-diamineHMDB
N1,N4-Bis(3-aminopropyl)-1,4-butanediamineHMDB
NeuridineHMDB
SperminHMDB
Spermine dihydrateHMDB
Spermine purissHMDB
SPMHMDB
Chemical FormulaC10H26N4
Average Mass202.3402 Da
Monoisotopic Mass202.21575 Da
IUPAC Name(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine
Traditional Namespermine
CAS Registry Number71-44-3
SMILES
NCCCNCCCCNCCCN
InChI Identifier
InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
InChI KeyPFNFFQXMRSDOHW-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apis ceranaLOTUS Database
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaKNApSAcK Database
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativaKNApSAcK Database
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Brugmansia arboreaLOTUS Database
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Canavalia bonariensisKNApSAcK Database
Canavalia ensiformisKNApSAcK Database
Canavalia gladiataLOTUS Database
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cyanidium caldariumLOTUS Database
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daphnia magnaLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Galleria mellonellaLOTUS Database
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusKNApSAcK Database
Heliotropium indicumLOTUS Database
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Homo sapiensLOTUS Database
Hordeum vulgareKNApSAcK Database
Hydrilla verticillataLOTUS Database
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusKNApSAcK Database
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusKNApSAcK Database
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lotus corniculatusLOTUS Database
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
Lyallia kerguelensisKNApSAcK Database
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus domesticaLOTUS Database
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Nicotiana alataLOTUS Database
Nicotiana tabacumLOTUS Database
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengKNApSAcK Database
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Peucedanum palustreLOTUS Database
Phaseolus coccineusKNApSAcK Database
Phaseolus lunatusKNApSAcK Database
Phaseolus vulgarisKNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Picea glaucaLOTUS Database
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusKNApSAcK Database
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trifolium subterraneumKNApSAcK Database
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
Utricularia intermediaLOTUS Database
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaKNApSAcK Database
Vicia sativaKNApSAcK Database
Vigna aconitifoliaFooDB
Vigna angularisKNApSAcK Database
Vigna mungoKNApSAcK Database
Vigna radiataKNApSAcK Database
Vigna umbellataFooDB
Vigna unguiculataKNApSAcK Database
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Wisteria floribundaKNApSAcK Database
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentDialkylamines
Alternative Parents
Substituents
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point29 °CNot Available
Boiling Point308.38 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.543 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility2.19 g/LALOGPS
logP-0.66ALOGPS
logP-1.5ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)10.8ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area76.1 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity62.56 m³·mol⁻¹ChemAxon
Polarizability26.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001256
DrugBank IDDB00127
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003225
KNApSAcK IDC00001432
Chemspider ID1072
KEGG Compound IDC00750
BioCyc IDSPERMINE
BiGG ID35875
Wikipedia LinkSpermine
METLIN ID255
PubChem Compound1103
PDB IDNot Available
ChEBI ID15746
Good Scents IDrw1284281
References
General References
  1. Mollica F, Li Volti S, Rapisarda A, Longo G, Pavone L, Vanella A: Increased erythrocytic spermine in Duchenne muscular dystrophy. Pediatr Res. 1980 Nov;14(11):1196-8. [PubMed:7454431 ]
  2. Swift TA, Dias JA: Effects of the polyamine spermine on binding of follicle-stimulating hormone to membrane-bound immature bovine testis receptors. Biochim Biophys Acta. 1986 Feb 21;885(2):221-30. [PubMed:3004602 ]
  3. Cipolla BG, Ziade J, Bansard JY, Moulinoux JP, Staerman F, Quemener V, Lobel B, Guille F: Pretherapeutic erythrocyte polyamine spermine levels discriminate high risk relapsing patients with M1 prostate carcinoma. Cancer. 1996 Sep 1;78(5):1055-65. [PubMed:8780544 ]
  4. Venza M, Visalli M, Cicciu D, Teti D: Determination of polyamines in human saliva by high-performance liquid chromatography with fluorescence detection. J Chromatogr B Biomed Sci Appl. 2001 Jun 5;757(1):111-7. [PubMed:11419735 ]
  5. Uehara N, Shirakawa S, Uchino H, Saeki Y: Elevated contents of spermidine and spermine in the erythrocytes of cancer patients. Cancer. 1980 Jan 1;45(1):108-11. [PubMed:7350997 ]
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