Isoindigotin

Details

• Internal ID: 1609356a-bc90-4fa6-b93a-5a3c4ea19ea3
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Hydroxyindoles
• IUPAC Name: 3-(2-hydroxy-1H-indol-3-yl)indol-2-one
• SMILES (Canonical): C1=CC=C2C(=C1)C(=C(N2)O)C3=C4C=CC=CC4=NC3=O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=C(N2)O)C3=C4C=CC=CC4=NC3=O
• InChI: InChI=1S/C16H10N2O2/c19-15-13(9-5-1-3-7-11(9)17-15)14-10-6-2-4-8-12(10)18-16(14)20/h1-8,17,19H
• InChI Key: VBMISAYWIMDRCV-UHFFFAOYSA-N
• Popularity: 88 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₀N₂O₂
• Molecular Weight: 262.26 g/mol
• Exact Mass: 262.074227566 g/mol
• Topological Polar Surface Area (TPSA): 65.50 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 1.23
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• Isoindigo
• 476-34-6
• (E)-[3,3'-Biindolinylidene]-2,2'-dione
• 180479-95-2
• [3,3'-Biindolinylidene]-2,2'-dione
• 6UE33XXJ1Y
• CHEMBL515155
• 2H-Indol-2-one, 3-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-
• 3-(2-hydroxy-1H-indol-3-yl)indol-2-one
• UNII-6UE33XXJ1Y
• Oprea1_712169
• SCHEMBL9899736
• SCHEMBL9899740
• (3E)-3-(2-oxo-1H-indol-3-ylidene)-1H-indol-2-one
• SCHEMBL12386233
• .DELTA.3,3'-BIOXINDOLE
• MLCPSWPIYHDOKG-BUHFOSPRSA-N
• BCP32739
• BDBM50342561
• NSC717810
• AKOS001588195
• AKOS032947324
• NSC-717810
• (2-oxoindolin-3-ylidene)indolin-2-one
• 3,3'-biindole 2,2'(1h,1'h)-dione
• AS-82948
• NCI60_040614
• HY-107869
• CS-0030758
• (E)-[3,3''-biindolinylidene]-2,2''-dione
• (.DELTA.3,3'-BIINDOLINE)-2,2'-DIONE
• (3E)-3-(2-oxoindolin-3-ylidene)indolin-2-one
• SR-01000390554
• Isoindigo;(E)-[3,3'-biindolinylidene]-2,2'-dione
• SR-01000390554-1
• Q27265545
• 3-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)-2,3-dihydro-1H-indol-2-one
• 3-(1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE)-1,3-DIHYDRO-2H-INDOL-2-ONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9971	99.71%
Caco-2	+	0.4948	49.48%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Plasma membrane	0.5370	53.70%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.8587	85.87%
OATP1B3 inhibitior	+	0.9339	93.39%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.4812	48.12%
P-glycoprotein inhibitior	-	0.8383	83.83%
P-glycoprotein substrate	-	0.8995	89.95%
CYP3A4 substrate	+	0.5157	51.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8324	83.24%
CYP3A4 inhibition	+	0.5575	55.75%
CYP2C9 inhibition	+	0.7819	78.19%
CYP2C19 inhibition	-	0.5541	55.41%
CYP2D6 inhibition	-	0.6404	64.04%
CYP1A2 inhibition	+	0.8873	88.73%
CYP2C8 inhibition	-	0.6217	62.17%
CYP inhibitory promiscuity	+	0.7173	71.73%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7500	75.00%
Carcinogenicity (trinary)	Non-required	0.5733	57.33%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.6174	61.74%
Skin irritation	-	0.8109	81.09%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8631	86.31%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.5198	51.98%
skin sensitisation	-	0.8321	83.21%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6888	68.88%
Acute Oral Toxicity (c)	III	0.4212	42.12%
Estrogen receptor binding	+	0.7143	71.43%
Androgen receptor binding	+	0.6572	65.72%
Thyroid receptor binding	+	0.6844	68.44%
Glucocorticoid receptor binding	+	0.9151	91.51%
Aromatase binding	+	0.9069	90.69%
PPAR gamma	+	0.9331	93.31%
Honey bee toxicity	-	0.9294	92.94%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9539	95.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.97%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.21%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.48%	94.62%
CHEMBL2535	P11166	Glucose transporter	91.82%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.19%	99.23%
CHEMBL2581	P07339	Cathepsin D	90.49%	98.95%
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	88.85%	95.72%
CHEMBL1951	P21397	Monoamine oxidase A	87.57%	91.49%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	86.41%	94.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.95%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.94%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	83.64%	94.75%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.97%	96.00%
CHEMBL1781	P11387	DNA topoisomerase I	80.67%	97.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.22%	96.67%
CHEMBL3310	Q96DB2	Histone deacetylase 11	80.13%	88.56%

Plants that contains it

• Isatis tinctoria

Cross-Links

• PubChem: 164610
• LOTUS: LTS0236544
• wikiData: Q104389762