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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:37:09 UTC
Update Date2021-09-26 22:54:06 UTC
HMDB IDHMDB0245557
Secondary Accession NumbersNone
Metabolite Identification
Common Name2',7'-Dichlorofluorescein
Description2',7'-dichlorofluorescein, also known as fluorescein 27, 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 2',7'-dichlorofluorescein. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2',7'-dichlorofluorescein is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2',7'-Dichlorofluorescein is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
Fluorescein 27ChEBI
2',7'-Dichlorofluorescein, disodium saltMeSH
2',7'-DichlorofluorescinMeSH
DichlorofluorescinMeSH
MonohlorofluoresceinMeSH
Chemical FormulaC20H10Cl2O5
Average Molecular Weight401.2
Monoisotopic Molecular Weight399.9905288
IUPAC Name2',7'-dichloro-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one
Traditional Namedichlorofluorescein
CAS Registry NumberNot Available
SMILES
OC1=C(Cl)C=C2C(OC3=CC(O)=C(Cl)C=C3C22OC(=O)C3=CC=CC=C23)=C1
InChI Identifier
InChI=1S/C20H10Cl2O5/c21-13-5-11-17(7-15(13)23)26-18-8-16(24)14(22)6-12(18)20(11)10-4-2-1-3-9(10)19(25)27-20/h1-8,23-24H
InChI KeyVFNKZQNIXUFLBC-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
  • Diaryl ether
  • Benzofuranone
  • Phthalide
  • Isobenzofuranone
  • Isocoumaran
  • Isobenzofuran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aryl chloride
  • Benzenoid
  • Aryl halide
  • Carboxylic acid ester
  • Lactone
  • Oxacycle
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organochloride
  • Organic oxide
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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
logP3.95ALOGPS
logP5.09ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)7.14ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity100.83 m³·mol⁻¹ChemAxon
Polarizability37.64 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-222.4930932474
DeepCCS[M+Na]+197.71930932474
AllCCS[M+H]+185.532859911
AllCCS[M+H-H2O]+182.632859911
AllCCS[M+NH4]+188.132859911
AllCCS[M+Na]+188.932859911
AllCCS[M-H]-173.032859911
AllCCS[M+Na-2H]-171.432859911
AllCCS[M+HCOO]-169.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2',7'-DichlorofluoresceinOC1=C(Cl)C=C2C(OC3=CC(O)=C(Cl)C=C3C22OC(=O)C3=CC=CC=C23)=C15050.6Standard polar33892256
2',7'-DichlorofluoresceinOC1=C(Cl)C=C2C(OC3=CC(O)=C(Cl)C=C3C22OC(=O)C3=CC=CC=C23)=C13232.0Standard non polar33892256
2',7'-DichlorofluoresceinOC1=C(Cl)C=C2C(OC3=CC(O)=C(Cl)C=C3C22OC(=O)C3=CC=CC=C23)=C13275.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2',7'-Dichlorofluorescein GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-1296100000-0cbaa14df3059de65de02021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2',7'-Dichlorofluorescein GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2',7'-Dichlorofluorescein GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2',7'-Dichlorofluorescein GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2',7'-Dichlorofluorescein GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2',7'-Dichlorofluorescein GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',7'-Dichlorofluorescein 10V, Positive-QTOFsplash10-0udi-0000900000-2e03f49f2ecb69b2167c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',7'-Dichlorofluorescein 20V, Positive-QTOFsplash10-0udi-0000900000-2e03f49f2ecb69b2167c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',7'-Dichlorofluorescein 40V, Positive-QTOFsplash10-0udi-0009400000-8b42614ed310f9b7b60e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',7'-Dichlorofluorescein 10V, Negative-QTOFsplash10-0002-0009000000-bd24b3febb60610ee0a52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',7'-Dichlorofluorescein 20V, Negative-QTOFsplash10-0002-0009000000-f6e63683435565b71fb02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',7'-Dichlorofluorescein 40V, Negative-QTOFsplash10-0002-0039000000-9f828a4face5c4a5b1dd2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID58471
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID51596
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]