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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:45 UTC
HMDB IDHMDB0014831
Secondary Accession Numbers
  • HMDB14831
Metabolite Identification
Common NameFluorescein
DescriptionFluorescein, also known as 3,6-fluorandiol or c.i. 45350, 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. Fluorescein is a drug which is used for diagnostic imaging. primarily indicated in diagnostic fluorescein angiography or angioscopy of the fundus and of the iris vasculature. Fluorescein is an extremely weak basic (essentially neutral) compound (based on its pKa). Fluorescein is a potentially toxic compound. A xanthene dye that is highly fluorescent, detectable even when present in minute quantities.
Structure
Data?1582753225
Synonyms
ValueSource
3',6'-DihydroxyfluoranChEBI
3,6-FluorandiolChEBI
9-(O-Carboxyphenyl)-6-hydroxy-3-isoxanthenoneChEBI
9-(O-Carboxyphenyl)-6-hydroxy-3H-xanthen-3-oneChEBI
C.I. 45350ChEBI
C.I. solvent yellow 94ChEBI
D And C yellow no. 7ChEBI
D&C yellow no. 7ChEBI
FluoresceineChEBI
FluoreszeinChEBI
Japan yellow 201ChEBI
ResorcinolphthaleinChEBI
Solvent yellow 94ChEBI
Yellow fluoresceinChEBI
FluoresciteKegg
2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acidHMDB
D And C yellow no. 8HMDB
Fluor I strip a.t.HMDB
Fluorescein, disodiumHMDB
Disodium fluoresceinHMDB
Disodium salt, fluoresceinHMDB
Fluorescein monosodium saltHMDB
Fluorescein sodium, minimsHMDB
Fluoresceine, minimsHMDB
Ful gloHMDB
FundusceinHMDB
Optifluor dibaHMDB
UranineHMDB
Colircusi fluoresceinaHMDB
Fluor-I-strip a.t.HMDB
Fluorescéine sodique faureHMDB
Ful-gloHMDB
Minims fluorescein sodiumHMDB
Minims stainsHMDB
Fluorescein, sodiumHMDB
Fluoresceina, colircusiHMDB
FluoretsHMDB
Monosodium salt, fluoresceinHMDB
Sodium fluoresceinHMDB
DiofluorHMDB
Dipotassium salt, fluoresceinHMDB
Fluorescein dipotassium saltHMDB
Fluorescein disodium saltHMDB
Fluorescein sodiumHMDB
Minims fluoresceineHMDB
Sodium, fluoresceinHMDB
Chemical FormulaC20H12O5
Average Molecular Weight332.3063
Monoisotopic Molecular Weight332.068473494
IUPAC Name3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one
Traditional Namefluorescein
CAS Registry Number2321-07-5
SMILES
OC1=CC2=C(C=C1)C1(OC(=O)C3=CC=CC=C13)C1=C(O2)C=C(O)C=C1
InChI Identifier
InChI=1S/C20H12O5/c21-11-5-7-15-17(9-11)24-18-10-12(22)6-8-16(18)20(15)14-4-2-1-3-13(14)19(23)25-20/h1-10,21-22H
InChI KeyGNBHRKFJIUUOQI-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
  • Isobenzofuran
  • Isocoumaran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point315 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.026 g/LNot Available
LogP3.4Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available172.336http://allccs.zhulab.cn/database/detail?ID=AllCCS00000950
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP2.64ALOGPS
logP3.88ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)8.72ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity91.22 m³·mol⁻¹ChemAxon
Polarizability33.14 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.48431661259
DarkChem[M-H]-173.00731661259
DeepCCS[M-2H]-212.77330932474
DeepCCS[M+Na]+188.00230932474
AllCCS[M+H]+176.632859911
AllCCS[M+H-H2O]+173.232859911
AllCCS[M+NH4]+179.732859911
AllCCS[M+Na]+180.632859911
AllCCS[M-H]-178.332859911
AllCCS[M+Na-2H]-177.032859911
AllCCS[M+HCOO]-175.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FluoresceinOC1=CC2=C(C=C1)C1(OC(=O)C3=CC=CC=C13)C1=C(O2)C=C(O)C=C14582.1Standard polar33892256
FluoresceinOC1=CC2=C(C=C1)C1(OC(=O)C3=CC=CC=C13)C1=C(O2)C=C(O)C=C13018.5Standard non polar33892256
FluoresceinOC1=CC2=C(C=C1)C1(OC(=O)C3=CC=CC=C13)C1=C(O2)C=C(O)C=C13437.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fluorescein,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OC1=CC(O)=CC=C1C21OC(=O)C2=CC=CC=C213184.1Semi standard non polar33892256
Fluorescein,2TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OC1=CC(O[Si](C)(C)C)=CC=C1C21OC(=O)C2=CC=CC=C213250.2Semi standard non polar33892256
Fluorescein,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=CC(O)=CC=C1C21OC(=O)C2=CC=CC=C213460.6Semi standard non polar33892256
Fluorescein,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C21OC(=O)C2=CC=CC=C213738.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Fluorescein GC-MS (2 TMS)splash10-001i-1353900000-611445d6ab5246bd851e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fluorescein EI-B (Non-derivatized)splash10-000i-2290000000-eaff9e9aba714ba94d702017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fluorescein EI-B (Non-derivatized)splash10-000i-0090000000-074ba8ce3e0f48eac1d42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fluorescein GC-MS (Non-derivatized)splash10-001i-1353900000-611445d6ab5246bd851e2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluorescein GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0293000000-5c35ecc919b17d5620ee2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluorescein GC-MS (2 TMS) - 70eV, Positivesplash10-00di-6209500000-ab23980f2cb4a151abfd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluorescein GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluorescein GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorescein 75V, Positive-QTOFsplash10-0f80-0190000000-96c116d14e45c092e3f62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorescein 90V, Positive-QTOFsplash10-0udi-0290000000-944ad92942eac5b0f55f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorescein 30V, Negative-QTOFsplash10-000i-0090000000-204c801c10d3ba0033ed2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorescein 15V, Negative-QTOFsplash10-001i-0039000000-d0fed4e679a1e2dc78c92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorescein 45V, Positive-QTOFsplash10-001i-0009000000-672d3730ba6ae79ee5462021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorescein 60V, Positive-QTOFsplash10-001r-0097000000-67a600d065bee725a05f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorescein 30V, Positive-QTOFsplash10-001i-0009000000-6567ba7d3ba05b9d01d32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorescein 15V, Positive-QTOFsplash10-001i-0009000000-c316a18c3fdc7e099efa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorescein 90V, Negative-QTOFsplash10-000i-0090000000-84665b22751248226f522021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorescein 75V, Negative-QTOFsplash10-000i-0090000000-a6509aa14ca1771543632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorescein 45V, Negative-QTOFsplash10-000i-0090000000-c3e2a008fb7411e3a84a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorescein 60V, Negative-QTOFsplash10-000i-0090000000-cd13dbf3066c7e4ffcd72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorescein 10V, Positive-QTOFsplash10-001i-0009000000-410e3782a3377a4627312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorescein 20V, Positive-QTOFsplash10-001i-0019000000-1289e7fde734685fd3a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorescein 40V, Positive-QTOFsplash10-000i-3091000000-652abda58542de8219382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorescein 10V, Negative-QTOFsplash10-001i-0019000000-9f41afc4f708c3e148c12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorescein 20V, Negative-QTOFsplash10-0019-0098000000-53c4786408b95271c9e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorescein 40V, Negative-QTOFsplash10-000i-0090000000-40b0e641661193aac8a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorescein 10V, Positive-QTOFsplash10-001i-0009000000-f4f678f3c48d6f43d1c32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorescein 20V, Positive-QTOFsplash10-001i-0009000000-f4f678f3c48d6f43d1c32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorescein 40V, Positive-QTOFsplash10-001i-0094000000-ce67e0891aa59a25f4c82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorescein 10V, Negative-QTOFsplash10-001i-0009000000-69a3ee786a10c930b4432021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorescein 20V, Negative-QTOFsplash10-001i-0029000000-7b8b5113b7dd9ac05ef22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorescein 40V, Negative-QTOFsplash10-0059-5396000000-4bc93173d30ee8ba9c962021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00693 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00693 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00693
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID15968
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFluorescein
METLIN IDNot Available
PubChem Compound16850
PDB IDNot Available
ChEBI ID31624
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. Noga EJ, Udomkusonsri P: Fluorescein: a rapid, sensitive, nonlethal method for detecting skin ulceration in fish. Vet Pathol. 2002 Nov;39(6):726-31. [PubMed:12450204 ]

Enzymes

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.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular weight:
58164.815
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular weight:
171589.5
References
  1. Sun H, Johnson DR, Finch RA, Sartorelli AC, Miller DW, Elmquist WF: Transport of fluorescein in MDCKII-MRP1 transfected cells and mrp1-knockout mice. Biochem Biophys Res Commun. 2001 Jun 22;284(4):863-9. [PubMed:11409873 ]
General function:
Involved in ATP binding
Specific function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular weight:
146405.8
References
  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Lu R, Chan BS, Schuster VL: Cloning of the human kidney PAH transporter: narrow substrate specificity and regulation by protein kinase C. Am J Physiol. 1999 Feb;276(2 Pt 2):F295-303. [PubMed:9950961 ]