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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015551

Secondary Accession Numbers

HMDB15551

Metabolite Identification

Common Name

Erythrityl Tetranitrate

Description

Erythrityl 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

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


  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

$$$$

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2R*,3S)-rel-1,2,3,4-butanetetroltetranitrate	ChEBI
1,2,3,4-Butanetetralyl tetranitrate	ChEBI
Eritrityl tetranitrate	ChEBI
Eritrityli tetranitras	ChEBI
Erythritol tetranitrate	ChEBI
Erythrol tetranitrate	ChEBI
ETN	ChEBI
Meso-erythritol tetranitrate	ChEBI
Tetranitrate d'eritrityle	ChEBI
Tetranitrato de eritritilo	ChEBI
Tetranitrin	ChEBI
Tetranitrol	ChEBI
Cardilate	Kegg
(2R*,3S)-rel-1,2,3,4-butanetetroltetranitric acid	Generator
1,2,3,4-Butanetetralyl tetranitric acid	Generator
Eritrityl tetranitric acid	Generator
Erythritol tetranitric acid	Generator
Erythrol tetranitric acid	Generator
Meso-erythritol tetranitric acid	Generator
Tetranitric acid d'eritrityle	Generator
Cardilic acid	Generator
Erythrityl tetranitric acid	Generator
Eritritile tetranitrato	HMDB
Nitroerythrit	HMDB
Nitroerythrite	HMDB
Nitroerythrol	HMDB
Tetranitrate, erythrityl	HMDB

Chemical Formula

C₄H₆N₄O₁₂

Average Molecular Weight

302.11

Monoisotopic Molecular Weight

301.998221676

IUPAC Name

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

Traditional Name

erythrityl tetranitrate

CAS Registry Number

7297-25-8

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 Key

SNFOERUNNSHUGP-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organic oxoanionic compounds

Sub Class

Organic nitrates

Direct Parent

Alkyl 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 Framework

Aliphatic acyclic compounds

External Descriptors

nitrate ester (CHEBI:60072 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015551)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	61 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.2 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.2 g/L	ALOGPS
logP	1.68	ALOGPS
logP	1.23	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	220.2 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	53.25 m³·mol⁻¹	ChemAxon
Polarizability	20.27 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	167.049	31661259
DarkChem	[M-H]-	160.728	31661259
DeepCCS	[M+H]+	134.401	30932474
DeepCCS	[M-H]-	130.724	30932474
DeepCCS	[M-2H]-	166.8	30932474
DeepCCS	[M+Na]+	142.796	30932474
AllCCS	[M+H]+	159.7	32859911
AllCCS	[M+H-H2O]+	156.5	32859911
AllCCS	[M+NH4]+	162.5	32859911
AllCCS	[M+Na]+	163.4	32859911
AllCCS	[M-H]-	150.2	32859911
AllCCS	[M+Na-2H]-	149.9	32859911
AllCCS	[M+HCOO]-	149.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Erythrityl Tetranitrate	[O-][N+](=O)OC[C@@H](O[N+]([O-])=O)[C@H](CO[N+]([O-])=O)O[N+]([O-])=O	2946.0	Standard polar	33892256
Erythrityl Tetranitrate	[O-][N+](=O)OC[C@@H](O[N+]([O-])=O)[C@H](CO[N+]([O-])=O)O[N+]([O-])=O	1840.4	Standard non polar	33892256
Erythrityl Tetranitrate	[O-][N+](=O)OC[C@@H](O[N+]([O-])=O)[C@H](CO[N+]([O-])=O)O[N+]([O-])=O	1686.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrityl Tetranitrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-2921000000-e0ca780b2d08f29e85af	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrityl Tetranitrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrityl Tetranitrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrityl Tetranitrate 10V, Positive-QTOF	splash10-0udi-0019000000-bce7384e677be314b4b8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrityl Tetranitrate 20V, Positive-QTOF	splash10-0udi-0169000000-e089d6d2f520d2e8d2fa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrityl Tetranitrate 40V, Positive-QTOF	splash10-0006-9410000000-2c9da2a32b0819ca6195	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrityl Tetranitrate 10V, Negative-QTOF	splash10-0udi-0019000000-5bfde0569140cca60c9e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrityl Tetranitrate 20V, Negative-QTOF	splash10-0udi-2139000000-e3bfe7181e1ca1634c6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrityl Tetranitrate 40V, Negative-QTOF	splash10-0udi-1940000000-1ea1e96041b909cbe142	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01613	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01613	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01613

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4447608

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Erythritol_tetranitrate

METLIN ID

Not Available

PubChem Compound

5284553

PDB ID

Not Available

ChEBI ID

60072

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not 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

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 ]
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 ]
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

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 ]
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 ]
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 ]

Showing metabocard for Erythrityl Tetranitrate (HMDB0015551)

MOL for HMDB0015551 (Erythrityl Tetranitrate)

3D MOL for HMDB0015551 (Erythrityl Tetranitrate)

3D SDF for HMDB0015551 (Erythrityl Tetranitrate)

3D-SDF for HMDB0015551 (Erythrityl Tetranitrate)

PDB for HMDB0015551 (Erythrityl Tetranitrate)

3D PDB for HMDB0015551 (Erythrityl Tetranitrate)

SMILES for HMDB0015551 (Erythrityl Tetranitrate)

INCHI for HMDB0015551 (Erythrityl Tetranitrate)

Structure for HMDB0015551 (Erythrityl Tetranitrate)

3D Structure for HMDB0015551 (Erythrityl Tetranitrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References