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Showing metabocard for Bismuth Subsalicylate (HMDB0015408)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:58 UTC
HMDB IDHMDB0015408
Secondary Accession Numbers
  • HMDB15408
Metabolite Identification
Common NameBismuth Subsalicylate
DescriptionBismuth 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
Data?1582753293
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015408 (Bismuth Subsalicylate)

  Mrv0541 02231215222D          

 12 13  0  0  0  0            999 V2000
   -0.4184   -0.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052   -0.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4218    0.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1248   -0.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0083   -0.0343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052   -1.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2950    1.2003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1317    1.1968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1248   -1.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0083    0.7888    0.0000 Bi  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4184   -1.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7182    1.2003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
 10 12  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
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3D MOL for HMDB0015408 (Bismuth Subsalicylate)

HMDB0015408
     RDKit          3D
Bismuth Subsalicylate
 17 18  0  0  0  0  0  0  0  0999 V2000
    0.3524    2.9288    0.7607 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7747    1.7067    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1367    1.6465    0.8121 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -0.3628    0.9303 Bi  0  0  0  0  0  3  0  0  0  0  0  0
    4.6123   -0.5584   -0.3588 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2331   -1.4000    0.0509 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0510   -0.6685   -0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0345   -1.5031   -0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3189   -1.0313   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5368    0.3050   -0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841    1.1042    0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1488    0.6574    0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673   -1.4956   -0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834   -2.5548   -0.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1498   -1.6728   -0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495    0.7368   -0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7496    2.1617    0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  2  1  0
 12  7  1  0
  5 13  1  0
  8 14  1  0
  9 15  1  0
 10 16  1  0
 11 17  1  0
M  END
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3D SDF for HMDB0015408 (Bismuth Subsalicylate)

  Mrv0541 02231215222D          

 12 13  0  0  0  0            999 V2000
   -0.4184   -0.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052   -0.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4218    0.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1248   -0.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0083   -0.0343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052   -1.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2950    1.2003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1317    1.1968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1248   -1.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0083    0.7888    0.0000 Bi  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4184   -1.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7182    1.2003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
 10 12  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015408

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C7H5BiO4

> <MOLECULAR_WEIGHT>
362.0926

> <EXACT_MASS>
361.999166889

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
15.668776506424715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.37

> <JCHEM_LOGP>
1.1142999999999998

> <ALOGPS_LOGS>
-0.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.301070756672548

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1045116510314266

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
35.7177

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.97e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pepto-bismol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0015408 (Bismuth Subsalicylate)

HMDB0015408
     RDKit          3D
Bismuth Subsalicylate
 17 18  0  0  0  0  0  0  0  0999 V2000
    0.3524    2.9288    0.7607 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7747    1.7067    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1367    1.6465    0.8121 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -0.3628    0.9303 Bi  0  0  0  0  0  3  0  0  0  0  0  0
    4.6123   -0.5584   -0.3588 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2331   -1.4000    0.0509 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0510   -0.6685   -0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0345   -1.5031   -0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3189   -1.0313   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5368    0.3050   -0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841    1.1042    0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1488    0.6574    0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673   -1.4956   -0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834   -2.5548   -0.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1498   -1.6728   -0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495    0.7368   -0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7496    2.1617    0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  2  1  0
 12  7  1  0
  5 13  1  0
  8 14  1  0
  9 15  1  0
 10 16  1  0
 11 17  1  0
M  END
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PDB for HMDB0015408 (Bismuth Subsalicylate)

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
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3D PDB for HMDB0015408 (Bismuth Subsalicylate)

COMPND    HMDB0015408
HETATM    1  O1  UNL     1       0.352   2.929   0.761  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.775   1.707   0.590  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.137   1.647   0.812  1.00  0.00           O  
HETATM    4 BI1  UNL     1       2.928  -0.363   0.930  1.00  0.00          BI  
HETATM    5  O3  UNL     1       4.612  -0.558  -0.359  1.00  0.00           O  
HETATM    6  O4  UNL     1       1.233  -1.400   0.051  1.00  0.00           O  
HETATM    7  C2  UNL     1       0.051  -0.668  -0.007  1.00  0.00           C  
HETATM    8  C3  UNL     1      -1.034  -1.503  -0.359  1.00  0.00           C  
HETATM    9  C4  UNL     1      -2.319  -1.031  -0.486  1.00  0.00           C  
HETATM   10  C5  UNL     1      -2.537   0.305  -0.257  1.00  0.00           C  
HETATM   11  C6  UNL     1      -1.484   1.104   0.083  1.00  0.00           C  
HETATM   12  C7  UNL     1      -0.149   0.657   0.223  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.767  -1.496  -0.586  1.00  0.00           H  
HETATM   14  H2  UNL     1      -0.883  -2.555  -0.543  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.150  -1.673  -0.756  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.550   0.737  -0.345  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.750   2.162   0.248  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4
CONECT    4    5    6
CONECT    5   13
CONECT    6    7
CONECT    7    8    8   12
CONECT    8    9   14
CONECT    9   10   10   15
CONECT   10   11   16
CONECT   11   12   12   17
END
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SMILES for HMDB0015408 (Bismuth Subsalicylate)

O[Bi]1OC(=O)C2=CC=CC=C2O1
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INCHI for HMDB0015408 (Bismuth Subsalicylate)

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
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC7H5BiO4
Average Molecular Weight362.0926
Monoisotopic Molecular Weight361.999166889
IUPAC Name2-hydroxy-2H,4H-benzo[d]1,3-dioxa-2-bismacyclohexan-4-one
Traditional Namepepto-bismol
CAS Registry Number14882-18-9
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 KeyZREIPSZUJIFJNP-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNot Available
Sub ClassNot Available
Direct ParentBenzenoids
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility59.7 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01294 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01294 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01294
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID17215772
KEGG Compound IDC07870
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBismuth subsalicylate
METLIN IDNot Available
PubChem Compound53629521
PDB IDNot Available
ChEBI ID261649
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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
  1. 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
  1. Graham GG, Scott KF: Mechanisms of action of paracetamol and related analgesics. Inflammopharmacology. 2003;11(4):401-13. [PubMed:15035793 ]
  2. 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 ]
  3. 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 ]
  4. Wu KK: Aspirin and other cyclooxygenase inhibitors: new therapeutic insights. Semin Vasc Med. 2003 May;3(2):107-12. [PubMed:15199473 ]
  5. 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 ]
  6. 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
  1. 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 ]
  2. Graham GG, Scott KF: Mechanisms of action of paracetamol and related analgesics. Inflammopharmacology. 2003;11(4):401-13. [PubMed:15035793 ]
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