Human Metabolome Database: Showing metabocard for Omeprazole (HMDB0001913)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

enzymes (4) Show 4 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2006-05-17 14:44:52 UTC

Update Date

2018-05-19 21:43:50 UTC

HMDB ID

HMDB0001913

Secondary Accession Numbers

HMDB01913

Metabolite Identification

Common Name

Omeprazole

Description

Omeprazole is a highly effective inhibitor of gastric acid secretion used in the therapy of stomach ulcers, dyspepsia, peptic ulcer disease , gastroesophageal reflux disease and Zollinger-Ellison syndrome. The drug inhibits the H(+)-K(+)-ATPase (H(+)-K(+)-exchanging ATPase) in the proton pump of Gastric Parietal Cells.--Pubchem. Omeprazole is one of the most widely prescribed drugs internationally and is available over the counter in some countries.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Prilosec	Kegg
( -)-Omeprazole	HMDB
(-)-Omeprazole	HMDB
(S)-(-)-Omeprazole	HMDB
(S)-Omeprazole	HMDB
2,3,5-Trimethylpyridine/Omeprazole	HMDB
Antra	HMDB
Antra mups	HMDB
Audazol	HMDB
Aulcer	HMDB
Belmazol	HMDB
Ceprandal	HMDB
Danlox	HMDB
Demeprazol	HMDB
Desec	HMDB
Dizprazol	HMDB
Dudencer	HMDB
Elgam	HMDB
Emeproton	HMDB
Epirazole	HMDB
Erbolin	HMDB
Esomeprazole	HMDB
Esomperazole	HMDB
Exter	HMDB
Gasec	HMDB
Gastrimut	HMDB
Gastroloc	HMDB
Gibancer	HMDB
Indurgan	HMDB
Inhibitron	HMDB
Inhipump	HMDB
Lensor	HMDB
Logastric	HMDB
Lomac	HMDB
Losec	HMDB
Mepral	HMDB
Miol	HMDB
Miracid	HMDB
Mopral	HMDB
Morecon	HMDB
Nexiam	HMDB
Nexium	HMDB
Nexium IV	HMDB
Nilsec	HMDB
Nopramin	HMDB
Nuclosina	HMDB
Ocid	HMDB
Olexin	HMDB
Omapren	HMDB
Omebeta 20	HMDB
Omed	HMDB
Omegast	HMDB
OMEP	HMDB
Omepradex	HMDB
Omepral	HMDB
Omeprazol	HMDB
Omeprazole pellets	HMDB
Omeprazolum	HMDB
Omeprazon	HMDB
Omeprol	HMDB
Omesek	HMDB
Omez	HMDB
Omezol	HMDB
Omezolan	HMDB
Omid	HMDB
Omisec	HMDB
Omizac	HMDB
Ompanyt	HMDB
OMZ	HMDB
Ortanol	HMDB
Osiren	HMDB
Ozoken	HMDB
Paprazol	HMDB
Parizac	HMDB
Pepticum	HMDB
Pepticus	HMDB
Peptilcer	HMDB
Prazentol	HMDB
Prazidec	HMDB
Prazolit	HMDB
Prestwick_808	HMDB
Prilosec otc	HMDB
Procelac	HMDB
Proclor	HMDB
Prysma	HMDB
Ramezol	HMDB
Regulacid	HMDB
Result	HMDB
Sanamidol	HMDB
Secrepina	HMDB
Tedec ulceral	HMDB
Ulceral	HMDB
Ulcesep	HMDB
Ulcometion	HMDB
Ulcozol	HMDB
Ulcsep	HMDB
Ulsen	HMDB
Ultop	HMDB
Ulzol	HMDB
Victrix	HMDB
Zefxon	HMDB
Zegerid	HMDB
Zepral	HMDB
Zimor	HMDB
Zoltum	HMDB
Magnesium, omeprazole	MeSH
Omeprazole magnesium	MeSH
Omeprazole sodium	MeSH
Sodium, omeprazole	MeSH

Chemical Formula

C₁₇H₁₉N₃O₃S

Average Molecular Weight

345.416

Monoisotopic Molecular Weight

345.114712179

IUPAC Name

6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole

Traditional Name

omeprazole

CAS Registry Number

73590-58-6

SMILES

COC1=CC2=C(C=C1)N=C(N2)S(=O)CC1=NC=C(C)C(OC)=C1C

InChI Identifier

InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)

InChI Key

SUBDBMMJDZJVOS-UHFFFAOYSA-N

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

Sulfinylbenzimidazoles

Direct Parent

Sulfinylbenzimidazoles

Alternative Parents

Substituents

Sulfinylbenzimidazole
Anisole
Alkyl aryl ether
Methylpyridine
Pyridine
Benzenoid
Azole
Imidazole
Heteroaromatic compound
Sulfoxide
Azacycle
Ether
Sulfinyl compound
Organic nitrogen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:77260 )
sulfoxide (CHEBI:77260 )
pyridines (CHEBI:77260 )
benzimidazoles (CHEBI:77260 )

Ontology

Blurred vision

Psychiatric disorders:

Confusion

Gastrointestinal disorders:

Nervous system disorders:

Headache

Ingestion

Parenteral:

Intravenous

Biological location:

Biofluid and excreta:

Blood

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Role

Industrial application:

Drug

Pharmaceutical industry:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	156 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.5 mg/mL	Not Available
LogP	2.23	SANGSTER (1994)

Predicted Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
logP	1.66	ALOGPS
logP	2.43	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	4.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.1 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.66 m³·mol⁻¹	ChemAxon
Polarizability	37.45 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udj-0902000000-cfa5184c794ea62ab995	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-014i-1669000000-51f9342d7e4bbd0356b2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-002f-0900000000-412912cbbcdbd1b34699	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0901000000-189e81fb724041d50498	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0f6t-0900000000-db101d248a4e861d4c3b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0uds-0900000000-f579fb74ac97c56dd3eb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-eefbf9686f0313da581e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-363d6954875894f433ba	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0f6t-1900000000-d8c64d496f1d9b3ed465	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-1669000000-51f9342d7e4bbd0356b2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0f6t-0900000000-d21755acc44ff2d29cfa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0f80-2900000000-9989d19c171c612ea3dc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0900000000-f74adb7f41e2d390b602	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0509000000-a35086072388d122723e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0902000000-cf6c80499c6b8e76c5d5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ul9-3900000000-2356754b2ae17bd3bc19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0007-0709000000-1b29375937cfcb406414	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-0900000000-3383df9e4bfd7979d5e5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-4fb7ec8321857498646d	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Omeprazole Action Pathway		Not Available
Omeprazole Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.34 (0.014-7.24) uM	Adult (>18 years old)	Both	Normal	15529418	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00338

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021863

KNApSAcK ID

Not Available

Chemspider ID

4433

KEGG Compound ID

C07324

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

77260

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

2. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

Enzyme Details

3. Potassium-transporting ATPase alpha chain 1

General function:: Involved in ATP binding
Specific function:: Catalyzes the hydrolysis of ATP coupled with the exchange of H(+) and K(+) ions across the plasma membrane. Responsible for acid production in the stomach.
Gene Name:: ATP4A
Uniprot ID:: P20648
Molecular weight:: 114117.74

Enzyme Details

4. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

Showing metabocard for Omeprazole (HMDB0001913)

Structure for HMDB0001913 (Omeprazole)

Enzymes