6-[(2Z)-3-Oxo-2,3-dihydro-1H-indole-2-ylidene]indolo[2,1-b]quinazoline-12-one

Details

• Internal ID: 14e17ac6-6121-4d42-afc3-3c5e8a7a0b5f
• Taxonomy: Organoheterocyclic compounds > Diazanaphthalenes > Benzodiazines > Quinazolines > Indoloquinazolines
• IUPAC Name: (6Z)-6-(3-oxo-1H-indol-2-ylidene)indolo[2,1-b]quinazolin-12-one
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)C(=C3C4=CC=CC=C4N5C3=NC6=CC=CC=C6C5=O)N2
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)/C(=C/3\C4=CC=CC=C4N5C3=NC6=CC=CC=C6C5=O)/N2
• InChI: InChI=1S/C23H13N3O2/c27-21-13-7-1-4-10-16(13)24-20(21)19-15-9-3-6-12-18(15)26-22(19)25-17-11-5-2-8-14(17)23(26)28/h1-12,24H/b20-19-
• InChI Key: DXENDDMPDZMHSQ-VXPUYCOJSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₁₃N₃O₂
• Molecular Weight: 363.40 g/mol
• Exact Mass: 363.100776666 g/mol
• Topological Polar Surface Area (TPSA): 61.80 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.14
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• NSC-600586
• Cadinine
• CHEMBL503442
• SCHEMBL12290061
• Indolo[2, 6-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-
• 6-[(2Z)-3-Oxo-2,3-dihydro-1H-indole-2-ylidene]indolo[2,1-b]quinazoline-12-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5823	58.23%
Blood Brain Barrier	+	0.8629	86.29%
Human oral bioavailability	+	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6899	68.99%
OATP2B1 inhibitior	-	0.8637	86.37%
OATP1B1 inhibitior	+	0.9332	93.32%
OATP1B3 inhibitior	+	0.9421	94.21%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7816	78.16%
BSEP inhibitior	+	0.5931	59.31%
P-glycoprotein inhibitior	-	0.7458	74.58%
P-glycoprotein substrate	-	0.8047	80.47%
CYP3A4 substrate	+	0.5815	58.15%
CYP2C9 substrate	+	0.6000	60.00%
CYP2D6 substrate	-	0.8584	85.84%
CYP3A4 inhibition	-	0.8593	85.93%
CYP2C9 inhibition	+	0.8792	87.92%
CYP2C19 inhibition	+	0.8416	84.16%
CYP2D6 inhibition	-	0.7775	77.75%
CYP1A2 inhibition	+	0.8515	85.15%
CYP2C8 inhibition	+	0.4703	47.03%
CYP inhibitory promiscuity	+	0.7912	79.12%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5082	50.82%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9181	91.81%
Skin irritation	-	0.8424	84.24%
Skin corrosion	-	0.9576	95.76%
Ames mutagenesis	+	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5488	54.88%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.9135	91.35%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7881	78.81%
Acute Oral Toxicity (c)	II	0.5313	53.13%
Estrogen receptor binding	+	0.7688	76.88%
Androgen receptor binding	+	0.6988	69.88%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7510	75.10%
Aromatase binding	+	0.6545	65.45%
PPAR gamma	+	0.8269	82.69%
Honey bee toxicity	-	0.8639	86.39%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.7828	78.28%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3623	P15559	Quinone reductase 1)	25000 nM	IC50	PMID: 17011189

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.81%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	96.64%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.86%	99.23%
CHEMBL2581	P07339	Cathepsin D	95.46%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.86%	85.14%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.57%	94.62%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	92.04%	89.44%
CHEMBL255	P29275	Adenosine A2b receptor	91.94%	98.59%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	91.05%	85.49%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	89.07%	96.67%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	88.42%	80.78%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.50%	89.00%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	87.41%	92.67%
CHEMBL1781	P11387	DNA topoisomerase I	86.62%	97.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.39%	86.33%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	86.03%	96.47%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.69%	94.00%
CHEMBL3524	P56524	Histone deacetylase 4	85.30%	92.97%
CHEMBL4237	O75582	Ribosomal protein S6 kinase alpha 5	84.95%	91.00%
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	84.48%	95.72%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.03%	95.83%
CHEMBL5805	Q9NR97	Toll-like receptor 8	83.32%	96.25%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.71%	96.39%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.59%	96.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.30%	94.08%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.05%	93.03%
CHEMBL2094121	P14867	GABA-A receptor; alpha-1/beta-3/gamma-2	80.89%	95.50%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.47%	89.67%

Plants that contains it

• Isatis tinctoria
• Kitagawia praeruptora
• Persicaria tinctoria
• Phaius mishmensis
• Strobilanthes cusia

Cross-Links

• PubChem: 5320815
• NPASS: NPC295021
• ChEMBL: CHEMBL503442
• LOTUS: LTS0045216
• wikiData: Q104990975