Erythrosin B

Details

• Internal ID: 038b0c36-5bbc-4d4d-96f1-ce741523e129
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthenes
• IUPAC Name: 3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)OC23C4=CC(=C(C(=C4OC5=C(C(=C(C=C35)I)O)I)I)O)I
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)OC23C4=CC(=C(C(=C4OC5=C(C(=C(C=C35)I)O)I)I)O)I
• InChI: InChI=1S/C20H8I4O5/c21-11-5-9-17(13(23)15(11)25)28-18-10(6-12(22)16(26)14(18)24)20(9)8-4-2-1-3-7(8)19(27)29-20/h1-6,25-26H
• InChI Key: OALHHIHQOFIMEF-UHFFFAOYSA-N
• Popularity: 641 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₈I₄O₅
• Molecular Weight: 835.90 g/mol
• Exact Mass: 835.6551 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 6.08
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• Tetraiodofluorescein
• 15905-32-5
• Iodeosin
• Solvent Red 140
• Erythrosine acid
• ERYTHROSINE
• Erythrosine, phenolic
• 2',4',5',7'-Tetraiodofluorescein
• 2,4,5,7-Erythrosin
• E127
• C20H8I4O5
• 3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one
• EINECS 240-046-0
• NSC 328781
• C.I. Solvent Red 140
• BRN 0062817
• UNII-1A878FZQ9B
• 1A878FZQ9B
• DTXSID7044843
• NSC-328781
• Aizen erythrosine
• NCGC00166249-02
• Fluorescein, 2',4',5',7'-tetraiodo-
• Fluorescein, 2',4',5',7'-tetraiodo- (VAN)
• Spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one, 3',6'-dihydroxy-2',4',5',7'-tetraiodo-
• 4-19-00-02923 (Beilstein Handbook Reference)
• DTXCID1024207
• 3',6'-dihydroxy-2',4',5',7'-tetraiodo-3H-spiro[2-benzofuran-1,9'-xanthen]-3-one
• 3',6'-Dihydroxy-2',4',5',7'-tetraiodospiro(isobenzofuran-1(3H),9'-(9H)xanthene)-3-one
• Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-2',4',5',7'-tetraiodo-
• SMR000857151
• CAS-15905-32-5
• Fluoresceins
• Iodoeosine
• Felumin
• Ceplac
• Trace
• Dianthine B
• Iodeosine B
• Pyrosine B
• Tetrajodfluorescein
• 3',6'-DIHYDROXY-2',4',5',7'-TETRAIODO-3H-SPIRO(2-BENZOFURAN-1,9'-XANTHEN)-3-ONE
• 3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-3-one
• Spiro[isobenzofuran-1(3H),9'-[9h]xanthen]-3-one,3',6'-dihydroxy-2',4',5',7'-tetraiodo-
• E127 Erythrosine
• Tetraiodofluoresceuin
• 2,5,7-Erythrosin
• tetra-iodo-fluorescein
• ERYTHROSINE J
• Cogilor orange 211.10
• Cogilor orange 312.42
• 2,5,7-Tetraiodofluorescein
• SCHEMBL25042
• MLS001332405
• MLS001332406
• Red 1427
• CHEMBL1332616
• 2',5',7'-Tetraiodofluorescein
• 2, 4,5,7-Tetraiodofluorescein
• OALHHIHQOFIMEF-UHFFFAOYSA-N
• Fluorescein,4',5',7'-tetraiodo-
• Tox21_113464
• Tox21_301634
• BDBM50542241
• Erythrosin B, Dye content >=95 %
• HB0759
• NSC328781
• STL453505
• AKOS015903873
• Tox21_113464_1
• SMP2_000049
• NCGC00166249-01
• NCGC00166249-03
• NCGC00256240-01
• AS-74205
• LS-69347
• CI 45430:2
• CS-0030748
• T0124
• C.I. 45430:2
• Q420101
• J-009558
• Solvent Red 140; Tetraiodofluoresceuin; Erythrosine
• Spiro[isobenzofuran-1(3H), 3',6'-dihydroxy-2',4',5',7'-tetraiodo-
• 3',6'-Dihydroxy-2',4',5',7'-tetraiodo-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one
• 3',6'-Dihydroxy-2',4',5',7'-tetraiodospiro[isobenzofuran-1(3H),9'(9H)-xanthen]-3-one, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9672	96.72%
Caco-2	-	0.8532	85.32%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6252	62.52%
OATP2B1 inhibitior	-	0.5708	57.08%
OATP1B1 inhibitior	-	0.3620	36.20%
OATP1B3 inhibitior	+	0.8929	89.29%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8166	81.66%
P-glycoprotein inhibitior	-	0.7319	73.19%
P-glycoprotein substrate	-	0.8578	85.78%
CYP3A4 substrate	+	0.5217	52.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8126	81.26%
CYP3A4 inhibition	-	0.5234	52.34%
CYP2C9 inhibition	+	0.7825	78.25%
CYP2C19 inhibition	-	0.7985	79.85%
CYP2D6 inhibition	-	0.8991	89.91%
CYP1A2 inhibition	-	0.7512	75.12%
CYP2C8 inhibition	+	0.4682	46.82%
CYP inhibitory promiscuity	-	0.6449	64.49%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9157	91.57%
Carcinogenicity (trinary)	Danger	0.4422	44.22%
Eye corrosion	-	0.9806	98.06%
Eye irritation	+	0.8974	89.74%
Skin irritation	-	0.5911	59.11%
Skin corrosion	-	0.9653	96.53%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8659	86.59%
Micronuclear	+	0.8074	80.74%
Hepatotoxicity	-	0.6342	63.42%
skin sensitisation	-	0.7639	76.39%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5376	53.76%
Acute Oral Toxicity (c)	III	0.4507	45.07%
Estrogen receptor binding	+	0.8510	85.10%
Androgen receptor binding	+	0.5762	57.62%
Thyroid receptor binding	+	0.7412	74.12%
Glucocorticoid receptor binding	+	0.6846	68.46%
Aromatase binding	+	0.6859	68.59%
PPAR gamma	+	0.7639	76.39%
Honey bee toxicity	-	0.8263	82.63%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9856	98.56%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	28183.8 nM	Potency	via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	22387.2 nM	Potency	via CMAUP
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	3162.3 nM	Potency	via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	14125.4 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	501.2 nM; 501.2 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	11220.2 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.06%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.33%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.32%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.78%	82.69%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.33%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	86.30%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.08%	89.00%
CHEMBL4208	P20618	Proteasome component C5	84.70%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.41%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.85%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	82.07%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.00%	94.00%

Plants that contains it

• Crocus sativus
• Dianthus superbus

Cross-Links

• PubChem: 3259
• NPASS: NPC143402
• ChEMBL: CHEMBL1332616
• LOTUS: LTS0110383
• wikiData: Q420101