Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:46:25 UTC
Update Date2019-07-23 06:21:37 UTC
HMDB IDHMDB0036613
Secondary Accession Numbers
  • HMDB36613
Metabolite Identification
Common NameRose bengal
DescriptionRose bengal belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring. Based on a literature review very few articles have been published on Rose bengal.
Structure
Data?1563862897
Synonyms
ValueSource
2',4',5',7'-Tetrabromo-2,3,4,5-tetraiodofluoresceinChEBI
3,4,5,6-tetrachloro-2',4',5',7'-Tetraiodofluorescein, 8ciHMDB
4,5,6,7-tetrachloro-3',6'-Dihydroxy-2',4',5',7'-tetraiodospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 9ciHMDB
Ak-rose liq 1%HMDB
C.I. 45440HMDB
C.I. solvent red 141HMDB
Bengal, roseMeSH
Rose bengalMeSH
Rose bengal sodium I 125MeSH
Rose bengal sodium I 131MeSH
Chemical FormulaC20H4Cl4I4O5
Average Molecular Weight973.673
Monoisotopic Molecular Weight971.499157746
IUPAC Name2,3,4,5-tetrachloro-6-(6-hydroxy-2,4,5,7-tetraiodo-3-oxo-3H-xanthen-9-yl)benzoic acid
Traditional Namerose bengal
CAS Registry Number4159-77-7
SMILES
OC(=O)C1=C(C(Cl)=C(Cl)C(Cl)=C1Cl)C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C(O)=C(I)C=C12
InChI Identifier
InChI=1S/C20H4Cl4I4O5/c21-10-8(9(20(31)32)11(22)13(24)12(10)23)7-3-1-5(25)16(29)14(27)18(3)33-19-4(7)2-6(26)17(30)15(19)28/h1-2,29H,(H,31,32)
InChI KeyVDNLFJGJEQUWRB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentXanthenes
Alternative Parents
Substituents
  • Xanthene
  • 2-halobenzoic acid or derivatives
  • 3-halobenzoic acid or derivatives
  • 4-halobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • 2-halobenzoic acid
  • 3-halobenzoic acid
  • 4-halobenzoic acid
  • Halobenzoic acid
  • Benzoic acid
  • Benzoic acid or derivatives
  • Benzoyl
  • 2-iodophenol
  • 1-carboxy-2-haloaromatic compound
  • Chlorobenzene
  • Halobenzene
  • Monocyclic benzene moiety
  • Aryl iodide
  • Aryl halide
  • Benzenoid
  • Aryl chloride
  • Vinylogous halide
  • Heteroaromatic compound
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organochloride
  • Organoiodide
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00068 g/LALOGPS
logP10(6.02) g/LALOGPS
logP10(9.26) g/LChemAxon
logS10(-6.2) g/LALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)1.81ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity176.05 m³·mol⁻¹ChemAxon
Polarizability63.8 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose bengal 10V, Positive-QTOFsplash10-00di-0000000009-f3bf8c5a3e0f0a0853fc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose bengal 20V, Positive-QTOFsplash10-00di-0000000009-66093dd459c6362a7d972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose bengal 40V, Positive-QTOFsplash10-00b9-1000000009-2e8b9a120af7568843302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose bengal 10V, Negative-QTOFsplash10-00di-0000000009-db1a74d9f739e534146d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose bengal 20V, Negative-QTOFsplash10-00fr-0000000009-29def3b73f15b66f75612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose bengal 40V, Negative-QTOFsplash10-00b9-0000000019-a195e1189bd1f1119c6b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose bengal 10V, Negative-QTOFsplash10-00di-0000000009-4d514593d08da0819fba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose bengal 20V, Negative-QTOFsplash10-00di-0000000009-cb8d88946ddbbd8b9e9b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose bengal 40V, Negative-QTOFsplash10-004i-0000000119-bd361297dc21f404f3852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose bengal 10V, Positive-QTOFsplash10-00di-0000000009-f3e6775ccbb7efabbbe22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose bengal 20V, Positive-QTOFsplash10-00di-0000000009-6240466616fe0b78d3a92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose bengal 40V, Positive-QTOFsplash10-0v4l-0000000019-0a9443190bf8c294261b2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015529
KNApSAcK IDNot Available
Chemspider ID23774
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRose bengal
METLIN IDNot Available
PubChem Compound25474
PDB IDNot Available
ChEBI ID87202
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. Roat MI, Romanowski E, Araullo-Cruz T, Gordon YJ: The antiviral effects of rose bengal and fluorescein. Arch Ophthalmol. 1987 Oct;105(10):1415-7. [PubMed:2821977 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .