Indolo[2,1-b]quinazoline-6,12-dione

Details

• Internal ID: 13826629-6e8c-42fc-96c8-58343a7a27b9
• Taxonomy: Organoheterocyclic compounds > Diazanaphthalenes > Benzodiazines > Quinazolines > Indoloquinazolines
• IUPAC Name: indolo[2,1-b]quinazoline-6,12-dione
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)N3C4=CC=CC=C4C(=O)C3=N2
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)N3C4=CC=CC=C4C(=O)C3=N2
• InChI: InChI=1S/C15H8N2O2/c18-13-10-6-2-4-8-12(10)17-14(13)16-11-7-3-1-5-9(11)15(17)19/h1-8H
• InChI Key: VQQVWGVXDIPORV-UHFFFAOYSA-N
• Popularity: 310 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₈N₂O₂
• Molecular Weight: 248.24 g/mol
• Exact Mass: 248.058577502 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.93
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Indolo[2,1-b]quinazoline-6,12-dione
• 13220-57-0
• Tryptanthrine
• Couroupitine a
• TCMDC-125859
• GNF-PF-2691
• Indolo(2,1-b)quinazoline-6,12-dione
• C15H8N2O2
• MFCD00012073
• NSC 349447
• CHEBI:9768
• CHEMBL306946
• 4Y6E3F2U66
• NSC349447
• NSC-349447
• SR-01000521538
• Tryptantherin
• Trypthanthrine
• TRIPTANTRIN
• Indolo[2,12-dione
• D0I9AT
• Oprea1_754264
• 6,12-dihydro-6,12-dioxoindole(2,1-b)quinazoline
• MLS001049121
• UNII-4Y6E3F2U66
• GTPL8224
• SCHEMBL2426211
• DTXSID90157431
• Tryptanthrin, >=98% (HPLC)
• HMS2271H05
• AMY31414
• HY-N6607
• BDBM50240612
• C15-H8-N2-O2
• s5686
• STK078931
• AKOS000671350
• CCG-208326
• NCGC00160337-01
• NCGC00160337-02
• DS-15687
• NCI60_003113
• SMR000386951
• SY017117
• NCGC00160337-01!TRYPTANTHRINE
• CS-0034349
• FT-0733127
• J-006143
• SR-01000521538-1
• SR-01000521538-4
• Q27089028

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9959	99.59%
Caco-2	+	0.8229	82.29%
Blood Brain Barrier	+	0.9879	98.79%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7689	76.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9217	92.17%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8816	88.16%
BSEP inhibitior	-	0.6346	63.46%
P-glycoprotein inhibitior	-	0.8486	84.86%
P-glycoprotein substrate	-	0.9669	96.69%
CYP3A4 substrate	+	0.5184	51.84%
CYP2C9 substrate	+	0.5905	59.05%
CYP2D6 substrate	-	0.8620	86.20%
CYP3A4 inhibition	-	0.9060	90.60%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	+	0.7013	70.13%
CYP2D6 inhibition	-	0.8495	84.95%
CYP1A2 inhibition	+	0.8783	87.83%
CYP2C8 inhibition	-	0.7190	71.90%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5017	50.17%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.5536	55.36%
Skin irritation	-	0.8496	84.96%
Skin corrosion	-	0.9710	97.10%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8486	84.86%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.6580	65.80%
Acute Oral Toxicity (c)	II	0.5756	57.56%
Estrogen receptor binding	+	0.7432	74.32%
Androgen receptor binding	-	0.6563	65.63%
Thyroid receptor binding	+	0.6688	66.88%
Glucocorticoid receptor binding	+	0.9079	90.79%
Aromatase binding	+	0.8489	84.89%
PPAR gamma	+	0.7643	76.43%
Honey bee toxicity	-	0.9100	91.00%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	-	0.7002	70.02%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	150 nM	IC50	PMID: 22819942
CHEMBL230	P35354	Cyclooxygenase-2	64 nM; 64 nM; 64 nM; 64 nM	IC50; IC50; IC50; IC50	PMID: 22819942; via Super-PRED; PMID: 16038536; PMID: 23146282
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	31622.8 nM	Potency	via CMAUP
CHEMBL5514	P42858	Huntingtin	11220.2 nM	Potency	via CMAUP
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	7150 nM; 53.7 nM	IC50; IC50	PMID: 24099220; PMID: 24099220
CHEMBL1293224	P10636	Microtubule-associated protein tau	17782.8 nM	Potency	via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	2818.4 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	354.8 nM; 354.8 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	3162.3 nM	Potency	via CMAUP
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	140 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.20%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	96.09%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.10%	99.23%
CHEMBL2581	P07339	Cathepsin D	94.88%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.18%	85.14%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	90.18%	96.67%
CHEMBL5805	Q9NR97	Toll-like receptor 8	89.44%	96.25%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	88.65%	96.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.25%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.73%	99.15%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.48%	80.78%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.20%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.12%	94.00%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	83.05%	92.67%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.90%	93.40%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.61%	96.00%

Plants that contains it

• Agathosma mundtii
• Calanthe discolor
• Cotoneaster simonsii
• Couroupita guianensis
• Hordeum vulgare
• Isatis tinctoria
• Nicotiana tabacum
• Persicaria tinctoria
• Phaius mishmensis
• Solanum lycopersicum
• Solanum tuberosum
• Strobilanthes cusia
• Viburnum orientale
• Zea mays

Cross-Links

• PubChem: 73549
• NPASS: NPC207554
• ChEMBL: CHEMBL306946
• LOTUS: LTS0210698
• wikiData: Q27089028