(3Z)-3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one

Details

• Internal ID: cbaa3447-a6b7-4194-a0a4-9863a353b1dc
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolines
• IUPAC Name: (3Z)-3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one
• SMILES (Canonical): C1=CC=C2C(=C1)C(=C3C(=O)C4=CC=CC=C4N3)C(=O)N2
• SMILES (Isomeric): C1=CC=C2C(=C1)/C(=C/3\C(=O)C4=CC=CC=C4N3)/C(=O)N2
• InChI: InChI=1S/C16H10N2O2/c19-15-10-6-2-4-8-12(10)17-14(15)13-9-5-1-3-7-11(9)18-16(13)20/h1-8,17H,(H,18,20)/b14-13-
• InChI Key: CRDNMYFJWFXOCH-YPKPFQOOSA-N
• Popularity: 1 reference 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): 58.20 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.66
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9958	99.58%
Caco-2	+	0.7622	76.22%
Blood Brain Barrier	+	0.7379	73.79%
Human oral bioavailability	+	0.8714	87.14%
Subcellular localzation	Plasma membrane	0.5536	55.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9443	94.43%
OATP1B3 inhibitior	+	0.9361	93.61%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6521	65.21%
P-glycoprotein inhibitior	-	0.8857	88.57%
P-glycoprotein substrate	-	0.9438	94.38%
CYP3A4 substrate	-	0.5588	55.88%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8482	84.82%
CYP3A4 inhibition	-	0.7701	77.01%
CYP2C9 inhibition	+	0.7922	79.22%
CYP2C19 inhibition	+	0.7526	75.26%
CYP2D6 inhibition	-	0.6903	69.03%
CYP1A2 inhibition	+	0.8837	88.37%
CYP2C8 inhibition	-	0.9532	95.32%
CYP inhibitory promiscuity	+	0.9517	95.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8643	86.43%
Carcinogenicity (trinary)	Non-required	0.4943	49.43%
Eye corrosion	-	0.9896	98.96%
Eye irritation	+	0.7760	77.60%
Skin irritation	-	0.8398	83.98%
Skin corrosion	-	0.9622	96.22%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7080	70.80%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	+	0.8125	81.25%
skin sensitisation	-	0.9176	91.76%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.7890	78.90%
Acute Oral Toxicity (c)	III	0.5903	59.03%
Estrogen receptor binding	+	0.8465	84.65%
Androgen receptor binding	+	0.8689	86.89%
Thyroid receptor binding	+	0.5666	56.66%
Glucocorticoid receptor binding	+	0.8459	84.59%
Aromatase binding	+	0.8674	86.74%
PPAR gamma	+	0.6449	64.49%
Honey bee toxicity	-	0.7865	78.65%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.8819	88.19%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL308	P06493	Cyclin-dependent kinase 1	10000 nM	IC50	PMID: 20810192
CHEMBL301	P24941	Cyclin-dependent kinase 2	2200 nM	IC50	PMID: 12672248
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	4 nM; 4 nM	IC50; IC50	PMID: 26562543; via Super-PRED
CHEMBL4040	P28482	MAP kinase ERK2	31622.8 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	89.1 nM; 251.2 nM; 100 nM; 89.1 nM; 141.3 nM; 199.5 nM	Potency; Potency; Potency; Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	5623.4 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	19952.6 nM	Potency	via CMAUP
CHEMBL267	P12931	Tyrosine-protein kinase SRC	18000 nM	IC50	PMID: 12672248

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.26%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.27%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.53%	82.69%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.80%	93.03%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.42%	92.88%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	87.41%	88.84%
CHEMBL1937	Q92769	Histone deacetylase 2	87.02%	94.75%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.00%	94.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.83%	91.11%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.45%	94.08%
CHEMBL299	P17252	Protein kinase C alpha	84.69%	98.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.15%	99.23%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.01%	96.67%
CHEMBL4237	O75582	Ribosomal protein S6 kinase alpha 5	81.18%	91.00%

Plants that contains it

• Allium macrostemon
• Calanthe discolor
• Crotalaria paniculata
• Geijera parviflora
• Indigofera suffruticosa
• Isatis tinctoria
• Persicaria tinctoria
• Spiraea japonica
• Wrightia tinctoria

Cross-Links

• PubChem: 5318433
• NPASS: NPC300596
• ChEMBL: CHEMBL1276127
• LOTUS: LTS0039100
• wikiData: Q104968482