Hmdb loader

Showing metabocard for Erythrityl Tetranitrate (HMDB0015551)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:01 UTC
HMDB IDHMDB0015551
Secondary Accession Numbers
  • HMDB15551
Metabolite Identification
Common NameErythrityl Tetranitrate
DescriptionErythrityl Tetranitrate is only found in individuals that have used or taken this drug. It is a vasodilator with general properties similar to nitroglycerin. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1020)Similar to other nitrites and organic nitrates, erythrityl tetranitrate is converted to an active intermediate compound which activates the enzyme guanylate cyclase. This stimulates the synthesis of cyclic guanosine 3',5'-monophosphate (cGMP) which then activates a series of protein kinase-dependent phosphorylations in the smooth muscle cells, eventually resulting in the dephosphorylation of the myosin light chain of the smooth muscle fiber. The subsequent release of calcium ions results in the relaxation of the smooth muscle cells and vasodilation.
Structure
Data?1582753309
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015551 (Erythrityl Tetranitrate)


  Mrv0541 04191212182D          

 20 19  0  0  1  0            999 V2000
    8.9041  -16.8418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1939  -17.2615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9041  -16.0347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1939  -18.1008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4836  -16.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6466  -17.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3568  -16.8418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7734  -17.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0308  -16.8418    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.3394  -17.2581    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.0241  -16.0168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4836  -18.5205    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.7734  -18.1008    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.4836  -19.3276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6466  -15.6150    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.3568  -16.0347    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.6466  -14.7756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0671  -17.2615    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   11.8023  -16.8565    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   11.0421  -18.0861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  1  0  0  0
  2  1  1  0  0  0  0
  6  1  1  0  0  0  0
  2  4  1  6  0  0  0
  5  2  1  0  0  0  0
 15  3  1  0  0  0  0
 12  4  1  0  0  0  0
  8  5  1  0  0  0  0
  7  6  1  0  0  0  0
 18  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  2  0  0  0  0
 13 12  1  0  0  0  0
 14 12  2  0  0  0  0
 16 15  1  0  0  0  0
 17 15  2  0  0  0  0
 19 18  1  0  0  0  0
 20 18  2  0  0  0  0
M  CHG  8   9   1  10  -1  12   1  13  -1  15   1  16  -1  18   1  19  -1
M  END
Download

3D MOL for HMDB0015551 (Erythrityl Tetranitrate)

HMDB0015551
     RDKit          3D
Erythrityl Tetranitrate
 26 25  0  0  0  0  0  0  0  0999 V2000
    3.0305   -3.5008   -0.1315 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573   -2.2799   -0.3590 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.1470   -1.7747   -1.0196 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.0195   -1.4602    0.0428 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289   -0.3382   -0.7515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5883    0.4447   -0.1901 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8879    0.8976    1.1018 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9579    2.2349    1.4300 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.5636    3.0935    0.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4658    2.5989    2.6522 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.6946   -0.3535   -0.1398 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8222    0.5396    0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6165    1.1040    1.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5807    1.9243    2.0703 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.4577    3.1455    1.9957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6842    1.3850    2.6492 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.0543   -0.8422   -1.4223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2514   -2.1798   -1.6626 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.1944   -2.6375   -2.3369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -3.0681   -1.1293 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.6213    0.3206   -0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5148   -0.6459   -1.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4277    1.3272   -0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6155   -1.1993    0.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9406    1.3508   -0.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7408   -0.0867    0.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 11 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  6
 11 24  1  1
 12 25  1  0
 12 26  1  0
M  CHG  8   2   1   3  -1   8   1  10  -1  14   1  16  -1  18   1  20  -1
M  END
Download

3D SDF for HMDB0015551 (Erythrityl Tetranitrate)


  Mrv0541 04191212182D          

 20 19  0  0  1  0            999 V2000
    8.9041  -16.8418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1939  -17.2615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9041  -16.0347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1939  -18.1008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4836  -16.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6466  -17.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3568  -16.8418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7734  -17.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0308  -16.8418    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.3394  -17.2581    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.0241  -16.0168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4836  -18.5205    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.7734  -18.1008    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.4836  -19.3276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6466  -15.6150    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.3568  -16.0347    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.6466  -14.7756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0671  -17.2615    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   11.8023  -16.8565    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   11.0421  -18.0861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  1  0  0  0
  2  1  1  0  0  0  0
  6  1  1  0  0  0  0
  2  4  1  6  0  0  0
  5  2  1  0  0  0  0
 15  3  1  0  0  0  0
 12  4  1  0  0  0  0
  8  5  1  0  0  0  0
  7  6  1  0  0  0  0
 18  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  2  0  0  0  0
 13 12  1  0  0  0  0
 14 12  2  0  0  0  0
 16 15  1  0  0  0  0
 17 15  2  0  0  0  0
 19 18  1  0  0  0  0
 20 18  2  0  0  0  0
M  CHG  8   9   1  10  -1  12   1  13  -1  15   1  16  -1  18   1  19  -1
M  END
> <DATABASE_ID>
HMDB0015551

> <DATABASE_NAME>
hmdb

> <SMILES>
[O-][N+](=O)OC[C@@H](O[N+]([O-])=O)[C@H](CO[N+]([O-])=O)O[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6N4O12/c9-5(10)17-1-3(19-7(13)14)4(20-8(15)16)2-18-6(11)12/h3-4H,1-2H2/t3-,4+

> <INCHI_KEY>
SNFOERUNNSHUGP-ZXZARUISSA-N

> <FORMULA>
C4H6N4O12

> <MOLECULAR_WEIGHT>
302.11

> <EXACT_MASS>
301.998221676

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
20.27132447405115

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-1,3,4-tris(nitrooxy)butan-2-yl nitrate

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
1.2304572553333328

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.488791824752245

> <JCHEM_POLAR_SURFACE_AREA>
220.2

> <JCHEM_REFRACTIVITY>
53.2546

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
erythrityl tetranitrate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0015551 (Erythrityl Tetranitrate)

HMDB0015551
     RDKit          3D
Erythrityl Tetranitrate
 26 25  0  0  0  0  0  0  0  0999 V2000
    3.0305   -3.5008   -0.1315 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573   -2.2799   -0.3590 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.1470   -1.7747   -1.0196 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.0195   -1.4602    0.0428 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289   -0.3382   -0.7515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5883    0.4447   -0.1901 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8879    0.8976    1.1018 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9579    2.2349    1.4300 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.5636    3.0935    0.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4658    2.5989    2.6522 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.6946   -0.3535   -0.1398 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8222    0.5396    0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6165    1.1040    1.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5807    1.9243    2.0703 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.4577    3.1455    1.9957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6842    1.3850    2.6492 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.0543   -0.8422   -1.4223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2514   -2.1798   -1.6626 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.1944   -2.6375   -2.3369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -3.0681   -1.1293 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.6213    0.3206   -0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5148   -0.6459   -1.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4277    1.3272   -0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6155   -1.1993    0.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9406    1.3508   -0.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7408   -0.0867    0.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 11 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  6
 11 24  1  1
 12 25  1  0
 12 26  1  0
M  CHG  8   2   1   3  -1   8   1  10  -1  14   1  16  -1  18   1  20  -1
M  END
Download

PDB for HMDB0015551 (Erythrityl Tetranitrate)

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      16.621 -31.438   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.295 -32.221   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      16.621 -29.931   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.295 -33.788   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      13.969 -31.438   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.007 -32.221   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      19.333 -31.438   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      12.644 -32.221   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      11.258 -31.438   0.000  0.00  0.00           N+1
HETATM   10  O   UNK     0       9.967 -32.215   0.000  0.00  0.00           O-1
HETATM   11  O   UNK     0      11.245 -29.898   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      13.969 -34.572   0.000  0.00  0.00           N+1
HETATM   13  O   UNK     0      12.644 -33.788   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0      13.969 -36.078   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      18.007 -29.148   0.000  0.00  0.00           N+1
HETATM   16  O   UNK     0      19.333 -29.931   0.000  0.00  0.00           O-1
HETATM   17  O   UNK     0      18.007 -27.581   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      20.659 -32.221   0.000  0.00  0.00           N+1
HETATM   19  O   UNK     0      22.031 -31.466   0.000  0.00  0.00           O-1
HETATM   20  O   UNK     0      20.612 -33.761   0.000  0.00  0.00           O+0
CONECT    1    3    2    6                                                  
CONECT    2    1    4    5                                                  
CONECT    3    1   15                                                       
CONECT    4    2   12                                                       
CONECT    5    2    8                                                       
CONECT    6    1    7                                                       
CONECT    7    6   18                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    4   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    3   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    7   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END
Download

3D PDB for HMDB0015551 (Erythrityl Tetranitrate)

COMPND    HMDB0015551
HETATM    1  O1  UNL     1       3.031  -3.501  -0.131  1.00  0.00           O  
HETATM    2  N1  UNL     1       3.057  -2.280  -0.359  1.00  0.00           N1+
HETATM    3  O2  UNL     1       4.147  -1.775  -1.020  1.00  0.00           O1-
HETATM    4  O3  UNL     1       2.019  -1.460   0.043  1.00  0.00           O  
HETATM    5  C1  UNL     1       1.729  -0.338  -0.752  1.00  0.00           C  
HETATM    6  C2  UNL     1       0.588   0.445  -0.190  1.00  0.00           C  
HETATM    7  O4  UNL     1       0.888   0.898   1.102  1.00  0.00           O  
HETATM    8  N2  UNL     1       0.958   2.235   1.430  1.00  0.00           N1+
HETATM    9  O5  UNL     1       0.564   3.094   0.623  1.00  0.00           O  
HETATM   10  O6  UNL     1       1.466   2.599   2.652  1.00  0.00           O1-
HETATM   11  C3  UNL     1      -0.695  -0.353  -0.140  1.00  0.00           C  
HETATM   12  C4  UNL     1      -1.822   0.540   0.316  1.00  0.00           C  
HETATM   13  O7  UNL     1      -1.617   1.104   1.576  1.00  0.00           O  
HETATM   14  N3  UNL     1      -2.581   1.924   2.070  1.00  0.00           N1+
HETATM   15  O8  UNL     1      -2.458   3.146   1.996  1.00  0.00           O  
HETATM   16  O9  UNL     1      -3.684   1.385   2.649  1.00  0.00           O1-
HETATM   17  O10 UNL     1      -1.054  -0.842  -1.422  1.00  0.00           O  
HETATM   18  N4  UNL     1      -1.251  -2.180  -1.663  1.00  0.00           N1+
HETATM   19  O11 UNL     1      -2.194  -2.638  -2.337  1.00  0.00           O  
HETATM   20  O12 UNL     1      -0.357  -3.068  -1.129  1.00  0.00           O1-
HETATM   21  H1  UNL     1       2.621   0.321  -0.758  1.00  0.00           H  
HETATM   22  H2  UNL     1       1.515  -0.646  -1.798  1.00  0.00           H  
HETATM   23  H3  UNL     1       0.428   1.327  -0.859  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.616  -1.199   0.551  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.941   1.351  -0.412  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.741  -0.087   0.354  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5
CONECT    5    6   21   22
CONECT    6    7   11   23
CONECT    7    8
CONECT    8    9    9   10
CONECT   11   12   17   24
CONECT   12   13   25   26
CONECT   13   14
CONECT   14   15   15   16
CONECT   17   18
CONECT   18   19   19   20
END
Download

SMILES for HMDB0015551 (Erythrityl Tetranitrate)

[O-][N+](=O)OC[C@@H](O[N+]([O-])=O)[C@H](CO[N+]([O-])=O)O[N+]([O-])=O
Download

INCHI for HMDB0015551 (Erythrityl Tetranitrate)

InChI=1S/C4H6N4O12/c9-5(10)17-1-3(19-7(13)14)4(20-8(15)16)2-18-6(11)12/h3-4H,1-2H2/t3-,4+
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
(2R*,3S)-rel-1,2,3,4-butanetetroltetranitrateChEBI
1,2,3,4-Butanetetralyl tetranitrateChEBI
Eritrityl tetranitrateChEBI
Eritrityli tetranitrasChEBI
Erythritol tetranitrateChEBI
Erythrol tetranitrateChEBI
ETNChEBI
Meso-erythritol tetranitrateChEBI
Tetranitrate d'eritrityleChEBI
Tetranitrato de eritritiloChEBI
TetranitrinChEBI
TetranitrolChEBI
CardilateKegg
(2R*,3S)-rel-1,2,3,4-butanetetroltetranitric acidGenerator
1,2,3,4-Butanetetralyl tetranitric acidGenerator
Eritrityl tetranitric acidGenerator
Erythritol tetranitric acidGenerator
Erythrol tetranitric acidGenerator
Meso-erythritol tetranitric acidGenerator
Tetranitric acid d'eritrityleGenerator
Cardilic acidGenerator
Erythrityl tetranitric acidGenerator
Eritritile tetranitratoHMDB
NitroerythritHMDB
NitroerythriteHMDB
NitroerythrolHMDB
Tetranitrate, erythritylHMDB
Chemical FormulaC4H6N4O12
Average Molecular Weight302.11
Monoisotopic Molecular Weight301.998221676
IUPAC Name(2S,3R)-1,3,4-tris(nitrooxy)butan-2-yl nitrate
Traditional Nameerythrityl tetranitrate
CAS Registry Number7297-25-8
SMILES
[O-][N+](=O)OC[C@@H](O[N+]([O-])=O)[C@H](CO[N+]([O-])=O)O[N+]([O-])=O
InChI Identifier
InChI=1S/C4H6N4O12/c9-5(10)17-1-3(19-7(13)14)4(20-8(15)16)2-18-6(11)12/h3-4H,1-2H2/t3-,4+
InChI KeySNFOERUNNSHUGP-ZXZARUISSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl nitrates. These are organic compounds containing a nitrate that is O-linked to an alkyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganic oxoanionic compounds
Sub ClassOrganic nitrates
Direct ParentAlkyl nitrates
Alternative Parents
Substituents
  • Alkyl nitrate
  • Organic nitro compound
  • Organic nitric acid or derivatives
  • Organic 1,3-dipolar compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point61 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP1.68ALOGPS
logP1.23ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area220.2 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity53.25 m³·mol⁻¹ChemAxon
Polarizability20.27 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.04931661259
DarkChem[M-H]-160.72831661259
DeepCCS[M+H]+134.40130932474
DeepCCS[M-H]-130.72430932474
DeepCCS[M-2H]-166.830932474
DeepCCS[M+Na]+142.79630932474
AllCCS[M+H]+159.732859911
AllCCS[M+H-H2O]+156.532859911
AllCCS[M+NH4]+162.532859911
AllCCS[M+Na]+163.432859911
AllCCS[M-H]-150.232859911
AllCCS[M+Na-2H]-149.932859911
AllCCS[M+HCOO]-149.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.81 minutes32390414
Predicted by Siyang on May 30, 202213.2342 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.01 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid39.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1188.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid305.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid81.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid173.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid42.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid291.0 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid427.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)359.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid707.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid123.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1187.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid204.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid223.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate632.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA289.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water250.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Erythrityl Tetranitrate[O-][N+](=O)OC[C@@H](O[N+]([O-])=O)[C@H](CO[N+]([O-])=O)O[N+]([O-])=O2946.0Standard polar33892256
Erythrityl Tetranitrate[O-][N+](=O)OC[C@@H](O[N+]([O-])=O)[C@H](CO[N+]([O-])=O)O[N+]([O-])=O1840.4Standard non polar33892256
Erythrityl Tetranitrate[O-][N+](=O)OC[C@@H](O[N+]([O-])=O)[C@H](CO[N+]([O-])=O)O[N+]([O-])=O1686.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Erythrityl Tetranitrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2921000000-e0ca780b2d08f29e85af2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erythrityl Tetranitrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erythrityl Tetranitrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrityl Tetranitrate 10V, Positive-QTOFsplash10-0udi-0019000000-bce7384e677be314b4b82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrityl Tetranitrate 20V, Positive-QTOFsplash10-0udi-0169000000-e089d6d2f520d2e8d2fa2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrityl Tetranitrate 40V, Positive-QTOFsplash10-0006-9410000000-2c9da2a32b0819ca61952016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrityl Tetranitrate 10V, Negative-QTOFsplash10-0udi-0019000000-5bfde0569140cca60c9e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrityl Tetranitrate 20V, Negative-QTOFsplash10-0udi-2139000000-e3bfe7181e1ca1634c6f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrityl Tetranitrate 40V, Negative-QTOFsplash10-0udi-1940000000-1ea1e96041b909cbe1422016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01613 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01613 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01613
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4447608
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkErythritol_tetranitrate
METLIN IDNot Available
PubChem Compound5284553
PDB IDNot Available
ChEBI ID60072
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Atrial natriuretic peptide receptor 2
General function:
Involved in phosphorus-oxygen lyase activity
Specific function:
Receptor for the C-type natriuretic peptide NPPC/CNP hormone. Has guanylate cyclase activity upon binding of its ligand. May play a role in the regulation of skeletal growth.
Gene Name:
NPR2
Uniprot ID:
P20594
Molecular weight:
117020.97
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Lange K, Koenig A, Roegler C, Seeling A, Lehmann J: NO donors. Part 18: Bioactive metabolites of GTN and PETN--synthesis and vasorelaxant properties. Bioorg Med Chem Lett. 2009 Jun 1;19(11):3141-4. doi: 10.1016/j.bmcl.2008.04.057. Epub 2008 Apr 26. [PubMed:19406636 ]
Enzyme Details
2. Atrial natriuretic peptide receptor 1
General function:
Involved in phosphorus-oxygen lyase activity
Specific function:
Receptor for the atrial natriuretic peptide NPPA/ANP and the brain natriuretic peptide NPPB/BNP which are potent vasoactive hormones playing a key role in cardiovascular homeostasis. Has guanylate cyclase activity upon binding of the ligand.
Gene Name:
NPR1
Uniprot ID:
P16066
Molecular weight:
118918.11
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Schroder H, Noack E: Structure-activity relationship of organic nitrates for activation of guanylate cyclase. Arch Int Pharmacodyn Ther. 1987 Dec;290(2):235-46. [PubMed:2895614 ]