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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:22 UTC
HMDB IDHMDB15551
Secondary Accession NumbersNone
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
Thumb
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
(2R*,3S)-rel-1,2,3,4-butanetetroltetranitric acidGenerator
Erythrityl tetranitric 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
Eritritile tetranitratoHMDB
NitroerythritHMDB
NitroerythriteHMDB
NitroerythrolHMDB
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 KeyInChIKey=SNFOERUNNSHUGP-ZXZARUISSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitrate esters. These are compounds containing a nitrate ester functional group, with the general structure RON+(=O)O, (R cannot be a hydrogen).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic nitric acids and derivatives
Sub ClassNitrate esters
Direct ParentNitrate esters
Alternative Parents
Substituents
  • Alkyl nitrate
  • Organic nitrate
  • Nitrate ester
  • Organic nitro compound
  • Organic 1,3-dipolar compound
  • Allyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organic zwitterion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Nitrates and Nitrites
  • Vasodilator Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point61 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.95e-01 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.2 mg/mLALOGPS
logP1.68ALOGPS
logP1.23ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area220.2 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity53.25 m3·mol-1ChemAxon
Polarizability20.27 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01613
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01613
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01613
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4447608
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB15551
Metagene LinkHMDB15551
METLIN IDNot Available
PubChem Compound5284553
PDB IDNot Available
ChEBI ID60072
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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. [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. [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. Epub 2008 Apr 26. [19406636 ]
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. [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. [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. [2895614 ]