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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015408

Secondary Accession Numbers

HMDB15408

Metabolite Identification

Common Name

Bismuth Subsalicylate

Description

Bismuth Subsalicylate, also known as pink bismuth or pepto-bismol, belongs to the class of organic compounds known as benzenoids. These are aromatic compounds containing one or more benzene rings. Bismuth Subsalicylate is a drug which is used to treat nausea, heartburn, indigestion, upset stomach, diarrhea, and other temporary discomforts of the stomach and gastrointestinal tract. Bismuth Subsalicylate is an extremely weak basic (essentially neutral) compound (based on its pKa). A bismuth salt of salicylic acid.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.781  -0.057   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.570  -0.826   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.787   1.472   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.100  -0.826   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.882  -0.064   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.570  -2.369   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.551   2.241   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.113   2.234   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.100  -2.369   0.000  0.00  0.00           C+0
HETATM   10 Bi   UNK     0       1.882   1.472   0.000  0.00  0.00          Bi+0
HETATM   11  C   UNK     0      -0.781  -3.149   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.207   2.241   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   10                                                       
CONECT    8    3                                                            
CONECT    9    4   11                                                       
CONECT   10    5   12    7                                                  
CONECT   11    6    9                                                       
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-benzo[1,3,2]dioxabismin-4-one	ChEBI
Basic bismuth salicylate	ChEBI
Bismuth oxide salicylate	ChEBI
Bismuth oxysalicylate	ChEBI
Pink bismuth	ChEBI
Wismutsubsalicylat	ChEBI
Pepto-bismol	Kegg
Basic bismuth salicylic acid	Generator
Bismuth oxide salicylic acid	Generator
Bismuth oxysalicylic acid	Generator
Bismuth subsalicylic acid	Generator
Bismuth	HMDB
Bismuth(III) subsalicylate	HMDB
Bismuthi subsalicylas	HMDB
Bismutum subsalicylicum	HMDB
Trigastronol	HMDB
Kaopectate	HMDB
Subsalicylate bismuth	HMDB
Helidac	HMDB

Chemical Formula

C₇H₅BiO₄

Average Molecular Weight

362.0926

Monoisotopic Molecular Weight

361.999166889

IUPAC Name

2-hydroxy-2H,4H-benzo[d]1,3-dioxa-2-bismacyclohexan-4-one

Traditional Name

pepto-bismol

CAS Registry Number

14882-18-9

SMILES

O[Bi]1OC(=O)C2=CC=CC=C2O1

InChI Identifier

InChI=1S/C7H6O3.Bi.H2O/c8-6-4-2-1-3-5(6)7(9)10;;/h1-4,8H,(H,9,10);;1H2/q;+3;/p-3

InChI Key

ZREIPSZUJIFJNP-UHFFFAOYSA-K

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenoids. These are aromatic compounds containing one or more benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Not Available

Sub Class

Not Available

Direct Parent

Benzenoids

Alternative Parents

Substituents

Benzenoid
Carboxylic acid salt
Oxacycle
Organic metal salt
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Metalloheterocycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

salicylates (CHEBI:261649 )
bismuth coordination entity (CHEBI:261649 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	59.7 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	59.7 g/L	ALOGPS
logP	0.37	ALOGPS
logP	1.11	ChemAxon
logS	-0.78	ALOGPS
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	35.72 m³·mol⁻¹	ChemAxon
Polarizability	15.67 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
AllCCS	[M+H]+	167.5	32859911
AllCCS	[M+H-H2O]+	164.0	32859911
AllCCS	[M+NH4]+	170.8	32859911
AllCCS	[M+Na]+	171.8	32859911
AllCCS	[M-H]-	152.5	32859911
AllCCS	[M+Na-2H]-	153.6	32859911
AllCCS	[M+HCOO]-	154.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bismuth Subsalicylate	O[Bi]1OC(=O)C2=CC=CC=C2O1	2719.0	Standard polar	33892256
Bismuth Subsalicylate	O[Bi]1OC(=O)C2=CC=CC=C2O1	1446.2	Standard non polar	33892256
Bismuth Subsalicylate	O[Bi]1OC(=O)C2=CC=CC=C2O1	1643.3	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 - Bismuth Subsalicylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0109000000-0b549b564332c3fb7da9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bismuth Subsalicylate 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 - Bismuth Subsalicylate 10V, Positive-QTOF	splash10-014i-0009000000-034d5cac9226ccb84256	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bismuth Subsalicylate 20V, Positive-QTOF	splash10-014i-0009000000-034d5cac9226ccb84256	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bismuth Subsalicylate 40V, Positive-QTOF	splash10-014i-0009000000-034d5cac9226ccb84256	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bismuth Subsalicylate 10V, Negative-QTOF	splash10-014i-0009000000-7fc5ca2161c8644ffae1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bismuth Subsalicylate 20V, Negative-QTOF	splash10-014i-0009000000-7fc5ca2161c8644ffae1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bismuth Subsalicylate 40V, Negative-QTOF	splash10-014i-0009000000-7fc5ca2161c8644ffae1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bismuth Subsalicylate 10V, Positive-QTOF	splash10-03di-0009000000-9827189cbe92c1d01cb7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bismuth Subsalicylate 20V, Positive-QTOF	splash10-03di-0009000000-cf7453f9aff9fc743ca4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bismuth Subsalicylate 40V, Positive-QTOF	splash10-0uxr-9102000000-c4a7cf418f7b1715ec24	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bismuth Subsalicylate 10V, Negative-QTOF	splash10-03di-0009000000-3e960f4ddf60359d410d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bismuth Subsalicylate 20V, Negative-QTOF	splash10-03di-0009000000-0fbec727b56a5dc258c4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bismuth Subsalicylate 40V, Negative-QTOF	splash10-0006-0092000000-f2c3c522dc7825f6f079	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
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 DB01294	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01294	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01294

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17215772

KEGG Compound ID

C07870

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bismuth subsalicylate

METLIN ID

Not Available

PubChem Compound

53629521

PDB ID

Not Available

ChEBI ID

261649

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)

Download (PDF)

General References

Goldenberg MM, Honkomp LJ, Burrous SE, Castellion AW: Protective effect of Pepto-Bismol liquid on the gastric mucosa of rats. Gastroenterology. 1975 Sep;69(3):636-40. [PubMed:1158081 ]

Enzymes

Enzyme Details

1. Xanthine dehydrogenase/oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:: XDH
Uniprot ID:: P47989
Molecular weight:: 146422.99

References

Lewis RW, Olivier G: In vitro oxidation of 6-MP and its metallo complexes by xanthine oxidase. Res Commun Chem Pathol Pharmacol. 1977 Oct;18(2):377-80. [PubMed:918354 ]

Enzyme Details

2. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Graham GG, Scott KF: Mechanisms of action of paracetamol and related analgesics. Inflammopharmacology. 2003;11(4):401-13. [PubMed:15035793 ]
Fiebich BL, Chrubasik S: Effects of an ethanolic salix extract on the release of selected inflammatory mediators in vitro. Phytomedicine. 2004 Feb;11(2-3):135-8. [PubMed:15070163 ]
Chae HJ, Chae SW, Reed JC, Kim HR: Salicylate regulates COX-2 expression through ERK and subsequent NF-kappaB activation in osteoblasts. Immunopharmacol Immunotoxicol. 2004 Feb;26(1):75-91. [PubMed:15106733 ]
Wu KK: Aspirin and other cyclooxygenase inhibitors: new therapeutic insights. Semin Vasc Med. 2003 May;3(2):107-12. [PubMed:15199473 ]
Elvira C, Gallardo A, Lacroix N, Schacht E, San Roman J: Incorporation of salicylic acid derivatives to hydrophilic copolymer systems with biomedical applications. J Mater Sci Mater Med. 2001 Jun;12(6):535-42. [PubMed:15348270 ]
Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5. [PubMed:5284360 ]

Enzyme Details

3. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Moon C, Ahn M, Jee Y, Heo S, Kim S, Kim H, Sim KB, Koh CS, Shin YG, Shin T: Sodium salicylate-induced amelioration of experimental autoimmune encephalomyelitis in Lewis rats is associated with the suppression of inducible nitric oxide synthase and cyclooxygenases. Neurosci Lett. 2004 Feb 12;356(2):123-6. [PubMed:14746879 ]
Graham GG, Scott KF: Mechanisms of action of paracetamol and related analgesics. Inflammopharmacology. 2003;11(4):401-13. [PubMed:15035793 ]
Sun R, Carlson NG, Hemmert AC, Kishore BK: P2Y2 receptor-mediated release of prostaglandin E2 by IMCD is altered in hydrated and dehydrated rats: relevance to AVP-independent regulation of IMCD function. Am J Physiol Renal Physiol. 2005 Sep;289(3):F585-92. Epub 2005 Apr 19. [PubMed:15840771 ]
Celik G, Pasaoglu G, Bavbek S, Abadoglu O, Dursun B, Mungan D, Misirligil Z: Tolerability of selective cyclooxygenase inhibitor, celecoxib, in patients with analgesic intolerance. J Asthma. 2005 Mar;42(2):127-31. [PubMed:15871445 ]
Liu X, Lee TL, Wong PT: Cyclooxygenase-1 inhibition shortens the duration of diazepam-induced loss of righting reflex in mice. Anesth Analg. 2006 Jan;102(1):135-40. [PubMed:16368818 ]
Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5. [PubMed:5284360 ]
Goldenberg MM, Honkomp LJ, Burrous SE, Castellion AW: Protective effect of Pepto-Bismol liquid on the gastric mucosa of rats. Gastroenterology. 1975 Sep;69(3):636-40. [PubMed:1158081 ]

Showing metabocard for Bismuth Subsalicylate (HMDB0015408)

MOL for HMDB0015408 (Bismuth Subsalicylate)

3D MOL for HMDB0015408 (Bismuth Subsalicylate)

3D SDF for HMDB0015408 (Bismuth Subsalicylate)

3D-SDF for HMDB0015408 (Bismuth Subsalicylate)

PDB for HMDB0015408 (Bismuth Subsalicylate)

3D PDB for HMDB0015408 (Bismuth Subsalicylate)

SMILES for HMDB0015408 (Bismuth Subsalicylate)

INCHI for HMDB0015408 (Bismuth Subsalicylate)

Structure for HMDB0015408 (Bismuth Subsalicylate)

3D Structure for HMDB0015408 (Bismuth Subsalicylate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References