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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:29 UTC
HMDB IDHMDB0014865
Secondary Accession Numbers
  • HMDB14865
Metabolite Identification
Common NameNitroglycerin
DescriptionNitroglycerin is only found in individuals that have used or taken this drug. It is a volatile vasodilator which relieves angina pectoris by stimulating guanylate cyclase and lowering cytosolic calcium. [PubChem]Similar to other nitrites and organic nitrates, nitroglycerin is converted to nitric oxide (NO), 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?1582753229
Synonyms
ValueSource
1,2,3-PropanetrioltrinitrateChEBI
1,2,3-Propanetriyl nitrateChEBI
Glycerin trinitrateChEBI
Glycerol trinitrateChEBI
Glycerol, nitric acid triesterChEBI
Glyceryl trinitrateChEBI
MinitranChEBI
NatisprayChEBI
NGChEBI
Nitro-durChEBI
NitroglycerineChEBI
NitroglycerolChEBI
NitrolingualChEBI
NitromistChEBI
NitrostatChEBI
Propane-1,2,3-triyl trinitrateChEBI
RectogesicChEBI
Transderm nitroChEBI
TrinitroglycerinChEBI
TrinitroglycerolChEBI
Nitro-bidKegg
Transderm-nitroKegg
1,2,3-Propanetrioltrinitric acidGenerator
1,2,3-Propanetriyl nitric acidGenerator
Glycerin trinitric acidGenerator
Glycerol trinitric acidGenerator
Glycerol, nitrate triesterGenerator
Glyceryl trinitric acidGenerator
Propane-1,2,3-triyl trinitric acidGenerator
Nitroglycerin ointmentHMDB
NTGHMDB
TNGHMDB
NitroBidHMDB
NitroDurHMDB
NitrocardHMDB
NitrodermHMDB
NitroglynHMDB
SustakHMDB
GilustenonHMDB
Nitro bidHMDB
TridilHMDB
DynamiteHMDB
NitranginHMDB
Nitroderm TTSHMDB
NitrolanHMDB
NitrongHMDB
NitrospanHMDB
SustonitHMDB
Trinitrate, glycerylHMDB
TrinitrinHMDB
TrinitrolongHMDB
AnginineHMDB
Nitro durHMDB
NitrolHMDB
PerlinganitHMDB
SusadrinHMDB
SustacHMDB
Chemical FormulaC3H5N3O9
Average Molecular Weight227.0865
Monoisotopic Molecular Weight227.002578773
IUPAC Name1,3-bis(nitrooxy)propan-2-yl nitrate
Traditional Namenitroglycerin
CAS Registry Number55-63-0
SMILES
[O-][N+](=O)OCC(CO[N+]([O-])=O)O[N+]([O-])=O
InChI Identifier
InChI=1S/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2
InChI KeySNIOPGDIGTZGOP-UHFFFAOYSA-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:

Role

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point13.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 g/LNot Available
LogP1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP1.25ALOGPS
logP0.94ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area165.15 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity40.6 m³·mol⁻¹ChemAxon
Polarizability15.56 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2910000000-7e0a7efb140cbfba7482Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-7b8724b54d55339884e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0490000000-eccb5cfa311360a6d1cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-7900000000-dfa7cd8533d95e3908a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-3644f8d65b1b573fa474Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2390000000-d5a66ecca766d2de99bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v09-2920000000-fe3db65c7d301a910f03Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00727 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00727 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00727
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4354
KEGG Compound IDC07455
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNitroglycerin
METLIN IDNot Available
PubChem Compound4510
PDB IDNot Available
ChEBI ID28787
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
References
  1. Badejo AM Jr, Hodnette C, Dhaliwal JS, Casey DB, Pankey E, Murthy SN, Nossaman BD, Hyman AL, Kadowitz PJ: Mitochondrial aldehyde dehydrogenase mediates vasodilator responses of glyceryl trinitrate and sodium nitrite in the pulmonary vascular bed of the rat. Am J Physiol Heart Circ Physiol. 2010 Sep;299(3):H819-26. doi: 10.1152/ajpheart.00959.2009. Epub 2010 Jun 11. [PubMed:20543077 ]
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. Madhani M, Scotland RS, MacAllister RJ, Hobbs AJ: Vascular natriuretic peptide receptor-linked particulate guanylate cyclases are modulated by nitric oxide-cyclic GMP signalling. Br J Pharmacol. 2003 Aug;139(7):1289-96. [PubMed:12890708 ]
  2. Bauersachs J: Aminoethyl nitrate--the novel super nitrate? Br J Pharmacol. 2009 Sep;158(2):507-9. doi: 10.1111/j.1476-5381.2009.00414.x. [PubMed:19732062 ]