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Compound Detail

CHEMBL1057

FLUORESCEIN
💊 Approved Drug
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💊 Approved Drug
O=C1OC2(c3ccc(O)cc3Oc3cc(O)ccc32)c2ccccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1057
Name FLUORESCEIN
Phase Approved
Structure Type MOL
InChI Key GNBHRKFJIUUOQI-UHFFFAOYSA-N

Known Names

Acid yellow 73 CI 45350:1 D & c yellow no. 7 k7133 Fluorescein Ki201 NSC-667256 NSC-759114 Yellow 7
8
Targets
14
Activities
3
Assay Types
7
PK Parameters
20
Publications
8
Known Names
4
Indications

Molecular Properties

332.3
MW (Da)
3.67
ALogP
5
HBA
2
HBD
76.0
PSA (Ų)
0.61
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1976
Availability Prescription
Chirality Achiral

Routes of Administration

Parenteral Topical

Flags

Natural Product

Extended Properties

Molecular Formula C20H12O5
MW 332.31
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness 0.60

Indications

Hyperemia Brain Neoplasms Breast Neoplasms Neoplasms

ATC Classification

S01JA01
fluorescein
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S01JA51
fluorescein, combinations
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 9 meas. best 6.17
Ki 4 meas. best 5.53
EC50 1 meas. best 4.71

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
SARS-CoV-2
CHEMBL4303835
 IC50 6.17 6.17 670.0 2
Cytochrome P450 2C19
CHEMBL3622
 IC50 6.04 6.04 907.4 1
Solute carrier family 22 member 6
CHEMBL5653
 Ki 5.53 5.525 2951.2 2
Alpha-ketoglutarate-dependent dioxygenase FTO
CHEMBL2331065
 IC50 5.49 5.49 3230.0 1
Mothers against decapentaplegic homolog 3
CHEMBL1293258
 IC50 5.31 5.31 4890.0 1
Angiotensin-converting enzyme 2
CHEMBL3736
 EC50 4.71 4.71 19500.0 1
Protein arginine N-methyltransferase 1
CHEMBL5524
 IC50 4.12 4.12 75000.0 1
Solute carrier family 22 member 20
CHEMBL5269
 Ki 4.0 4.0 99000.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 1.3 mL.min-1.kg-1 Homo sapiens
F 99.0 % Homo sapiens
Fu 0.11 - Homo sapiens
Fu 0.42 - Rattus norvegicus
MRT 1.8 hr Homo sapiens
T1/2 1.6 hr Homo sapiens
Vd 1.8 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
SARS-CoV-2 IC50 = 670.0 nM 6.17 Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity o... -
SARS-CoV-2 IC50 = 670.0 nM 6.17 Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity o... -
Cytochrome P450 2C19 IC50 = 907.4 nM 6.04 DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Solute carrier family 22 member 6 Ki = 2951.21 nM 5.53 Inhibition of mouse Oat1-mediated [3H]PAH uptake in Xenopus oocytes after 1 hr 17553798
Solute carrier family 22 member 6 Ki = 3000.0 nM 5.52 Inhibition of mouse Oat1-mediated [3H]PAH uptake in Xenopus oocytes after 1 hr 17553798
Alpha-ketoglutarate-dependent dioxygenase FTO IC50 = 3230.0 nM 5.49 Inhibition of N-terminal 31 residues truncated FTO (unknown origin) demethylase ... 34792334
Mothers against decapentaplegic homolog 3 IC50 = 4890.0 nM 5.31 PUBCHEM_BIOASSAY: SMAD Transcription Factor Inhibitors Secondary Dose Response C... -
Angiotensin-converting enzyme 2 EC50 = 19500.0 nM 4.71 Activation of recombinant human ACE2 using McaAPK(Dnp)-OH as substrate preincuba... 37974956
Protein arginine N-methyltransferase 1 IC50 = 75000.0 nM 4.12 Inhibition of human recombinant GST-PRMT1 expressed in BL21 cells 17323938
Solute carrier family 22 member 20 Ki = 100000.0 nM 4.0 Inhibition of mouse Oat6-mediated [3H]ES uptake in Xenopus oocytes after 1 hr 17553798
Solute carrier family 22 member 20 Ki = 99000.0 nM 4.0 Inhibition of mouse Oat6-mediated [3H]ES uptake in Xenopus oocytes after 1 hr 17553798

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
18426954 10.1124/dmd.108.020479 ADMET 4
12482432 10.1016/s0960-894x(02)00885-5 DU-145 3
21149540 10.1124/dmd.110.035998 Brain 3
12482432 10.1016/s0960-894x(02)00885-5 HCT-15 3
16759101 10.1021/jm050617x Transcription factor p65 2
- 10.6019/CHEMBL4495565 Vero C1008 2
17553798 10.1074/jbc.m703467200 Solute carrier family 22 member 6 2
17553798 10.1074/jbc.m703467200 Solute carrier family 22 member 20 2
- 10.6019/CHEMBL4495565 ADMET 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4651402 Vero C1008 2
38442261 10.1021/acs.jmedchem.4c00058 No relevant target 1
15050628 10.1016/j.bmcl.2004.01.079 Tyrosine-protein phosphatase 1 1
17553798 10.1074/jbc.m703467200 Unchecked 1
18457386 10.1021/jm7015683 ATP-binding cassette sub-family C member 2 1
20373811 10.1021/jm901846t MDCK 1

Data from ChEMBL 36 via Core Engine