CAS 2321-07-5|fluorescein|Solvent Yellow 94|Fluorescein|3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one|Acid Yellow 73|Deoxyribonucleic acid|Fluorescein Low Range DNA standard|3',6'-Fluor...

General Information

Structure

Molecular Formula

C₂₀H₁₂O₅

Molecular Mass

332.30628

Exact Mass

332.06847348

Charge

InChI

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

InChIKey

GNBHRKFJIUUOQI-UHFFFAOYSA-N

Canonic Smiles

Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3cccc2)ccc(c1)O

Isomeric Smiles

O1C2(c3c(C1=O)cccc3)c1c(Oc3c2ccc(O)c3)cc(O)cc1

Calculated Properties

JChem

LogD (pH = 7.4)

3.86

LogD (pH = 5.5)

3.88

Log P

3.88

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

8.72

Polar Surface Area

75.99

Polarizability

33.12

Molar Refractivity

91.22

LOG S

-4.95

Data Source

Names and Identifiers

Synonyms

Solvent Yellow 94FluoresceinAcid Yellow 73Deoxyribonucleic acidFluorescein Low Range DNA standardC.I. Solvent Yellow 943',6'-Dihydroxyspiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one3',6'-FluorandiolC.I. 45350, solvent yellow 94, D & C yellow no. 7, angiofluonFluoresceinD and C Yellow No. 73',6'-Dihydroxyfluoran3,6-Dihydroxyspiro[xanthene-9,3'-phthalide]Japan Yellow 201Japan yellow 201, soap yellowFluorescein9-(o-Carboxyphenyl)-6-hydroxy-3-isoxanthenone2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic AcidNSC 667256C.I. 45350.1Fluorescein AcidC.I. 45350:1Yellow Fluorescein荧光素resorcinolphthaleinD&C Yellow No. 7Japan Yellow No. 201Fluorescein (free acid)3',6'-Dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one酸性黄 73fluoresceineYellow fluoresceinfluorescein lactoneresorcinolphthaleinSolvent Yellow 94C.I. Solvent Yellow 949-(o-carboxyphenyl)-6-hydroxy-3-isoxanthenone9-(o-carboxyphenyl)-6-hydroxy-3H-xanthen-3-onefluorescein (lactone form)C.I. 453503,6-fluorandiolJapan Yellow 201D and C Yellow No. 7Fluoreszein3',6'-dihydroxyfluoranD&C Yellow No. 7

IUPAC name

3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one 3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthen]-3-one

IUPAC Traditional name

fluorescein

Brand Name

Fluorescein Sodium saltFluoresciteAcid Yellow 73EosinUranineFluorescein disodium saltUraninFluorescein acidFunduscein-25Fluorescein sodiumFluorescein disodium salt dihydrateFluorescein, Disodium Salt, Fluorescein, disodium salt

Names and Identifiers

Registration numbers

Color Index Number

4535045350:1

EC Number

219-031-8

PubChem SID

2485956616096403824894822248704834650470324398110

CAS Number

Beilstein Number

MDL Number

PubChem CID

Merck Index

MeSH Name

KEGG ID

Unique Ingredient Identifier

TPY09G7XIR

Chemspider ID

1596815,968

CHEBI ID

31624CHEBI:606590CHEBI:31624

CHEMBL

DrugBank ID

Wikipedia Title

BKMS React Database

Patent number

US2002110691US2002015961US2003044830US2005038105US2005214807US2005255475US2006105410US2006141530US2004175726US2004171572US2007020681WO2007102149WO2005068483US2006269958

PubMed Citation Links

9294871284908622645783933661250163074752470979915836438267563941294505578735552906582328781922786891229237120237376588637844

UniProt Database

Q80UJ1O88909Q8IWN7Q8LAS8P49446Q47910

ACToR Database

518-45-6126605-73-02321-07-5

Protein Data Bank

4FAB

Golm Database

8acde29d-dd92-4e33-9ebc-4ed7b21a28d2fbd892f0-4776-4b65-992e-e7dcbef8529b

MetaboLights Database

MTBLS3750MTBLS1918MTBLS2633

BRENDA Database

2.5.1.181.11.1.191.1.1.413.2.1.233.1.1.13.2.1.965.3.99.2

BRENDA Ligand Database

HMDB Database

SureChEMBL Database

Gmelin ID

CompTox Database

BindingDB Database

KEGG DRUG Database

Reaxys Registry

NMRShiftDB Database

Registration numbers

Properties

Safety Information

LM5075000

S:26

S26 36

26-60

Pharmacology Properties

human ... PTPN1(5770), PTPRF(5792)

Properties

Related Proteins

PDB Bank

4FAB

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00693

Drug Groups

approved

Description

A phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium, such as the aqueous humor, and is used therapeutically as a diagnostic aid in corneal injuries and corneal trauma. It has been approved by FDA for use in externally applied drugs and cosmetics. (From Merck Index, 12th ed; American Medical Association Drug Evaluations; 1995, p2275)

Indication

For diagnostic imaging. Primarily indicated in diagnostic fluorescein angiography or angioscopy of the fundus and of the iris vasculature.

Affected Organisms

Humans and other mammals

Absorption

Rapidly distributed

Protein Binding

85%

Elimination

Fluorescein and its metabolites are mainly eliminated via renal excretion.

Distribution

* 0.5 L/kg

Clearance

* renal cl=1.75 mL/min/kg [After IV administration]
* hepatic cl=1.50 mL/min/kg [After IV administration]

References

• 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]

External Links

• [Wikipedia]

• [RxList]

MP Biomedicals

02151155

C.I. 45350.1
Free Acid
Crystalline
Purity: ~96%

Wikipedia

Fluorescein

Sigma Aldrich

F2456

Packaging
2.5, 100, 500 g in glass bottle

46978

Components
1 vial pBR 322 Hin F1 digest in 10 mM TRIS, pH 8.0, 1 mM EDTA (50 fmol/μl each fragment; 0.14 μg/μl), 200 μl1 vial 5× loading buffer (12.5% Ficoll, 0.05% bromophenol blue, 50 mM TRIS, pH 8.0, 5 mM EDTA), 500 μl
General description
pBR 322 Hin F1 digest, 10 Fluorescein end-labeled fragments: 75, 154, 220/221, 296, 334, 396, 504, 517, 1632 bpdetection: Exc.: 302 nm, Em.: 521 nm

32615

General description
Visit our Titration Center to learn more.

TRC

F485250

A fluorescent tracer used for many applications. It is used in ophthalmology as a tool in the diagnosis of corneal abrasions, corneal ulcers and herpetic corneal infections. It can attach to certain biologically active molecules, thus allowing biologists

ChEBI

CHEBI:31624

A xanthene dye that is highly fluorescent, detectable even when present in minute quantities. Used forensically to detect traces of blood, in analytical chemistry as an indicator in silver nitrate titrations and in microscopy.

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Can. Med. Assoc. J., 80, 997 (1996)

• Drees, B.L. et al.: J. Biol. Chem., 271, 32168 (1996)

• Taki, M. et al.: Prot. Eng. Des. Select., 17, 119 (1996)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one 3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthen]-3-one

IUPAC Traditional name

fluorescein

Brand Name

Related Proteins

PDB Bank

4FAB

Molecule Details

DrugBank

DB00693

Drug Groups

approved

Description

Indication

For diagnostic imaging. Primarily indicated in diagnostic fluorescein angiography or angioscopy of the fundus and of the iris vasculature.

Affected Organisms

Humans and other mammals

Absorption

Rapidly distributed

Protein Binding

85%

Elimination

Fluorescein and its metabolites are mainly eliminated via renal excretion.

Distribution

* 0.5 L/kg

Clearance

* renal cl=1.75 mL/min/kg [After IV administration]
* hepatic cl=1.50 mL/min/kg [After IV administration]

References

• 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]

External Links

• [Wikipedia]

• [RxList]

MP Biomedicals

02151155

C.I. 45350.1
Free Acid
Crystalline
Purity: ~96%

Wikipedia

Fluorescein

Sigma Aldrich

F2456

Packaging
2.5, 100, 500 g in glass bottle

46978

32615

General description
Visit our Titration Center to learn more.

TRC

F485250

ChEBI

CHEBI:31624

References

PubChem Literature

From Data Sources

• 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

• Can. Med. Assoc. J., 80, 997 (1996)

• Drees, B.L. et al.: J. Biol. Chem., 271, 32168 (1996)

• Taki, M. et al.: Prot. Eng. Des. Select., 17, 119 (1996)

Bioactivity

PubChem BioAssay