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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2021-09-14 15:46:39 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
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
Disposition

Biological location

Source

Route of exposure

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 Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP10(1.68) g/LALOGPS
logP10(1.23) g/LChemAxon
logS10(-3.2) g/LALOGPS
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 Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.04931661259
DarkChem[M-H]-160.72831661259

Predicted Kovats Retention Indices

Not Available
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

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 ]
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 ]