(4Z)-4-(2-amino-4-oxo-1H-imidazol-5-ylidene)-1,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8-one

Details

• Internal ID: 1a59966d-2c41-4155-97a4-168873a18d92
• Taxonomy: Organoheterocyclic compounds > Pyrroloazepines
• IUPAC Name: (4Z)-4-(2-amino-4-oxo-1H-imidazol-5-ylidene)-1,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8-one
• SMILES (Canonical): C1CNC(=O)C2=C(C1=C3C(=O)N=C(N3)N)C=CN2
• SMILES (Isomeric): C\1CNC(=O)C2=C(/C1=C\3/C(=O)N=C(N3)N)C=CN2
• InChI: InChI=1S/C11H11N5O2/c12-11-15-8(10(18)16-11)6-2-4-14-9(17)7-5(6)1-3-13-7/h1,3,13H,2,4H2,(H,14,17)(H3,12,15,16,18)/b8-6-
• InChI Key: JYRJOQGKGMHTOO-VURMDHGXSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₁N₅O₂
• Molecular Weight: 245.24 g/mol
• Exact Mass: 245.09127461 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -0.70
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9888	98.88%
Caco-2	-	0.6552	65.52%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.4890	48.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9575	95.75%
OATP1B3 inhibitior	+	0.9406	94.06%
MATE1 inhibitior	-	0.6000	60.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.7847	78.47%
P-glycoprotein inhibitior	-	0.9485	94.85%
P-glycoprotein substrate	-	0.7216	72.16%
CYP3A4 substrate	-	0.5344	53.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8333	83.33%
CYP3A4 inhibition	-	0.7111	71.11%
CYP2C9 inhibition	-	0.7686	76.86%
CYP2C19 inhibition	-	0.6786	67.86%
CYP2D6 inhibition	-	0.8350	83.50%
CYP1A2 inhibition	-	0.5413	54.13%
CYP2C8 inhibition	-	0.8918	89.18%
CYP inhibitory promiscuity	-	0.9007	90.07%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5931	59.31%
Eye corrosion	-	0.9823	98.23%
Eye irritation	-	0.9924	99.24%
Skin irritation	-	0.7726	77.26%
Skin corrosion	-	0.9214	92.14%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6624	66.24%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8411	84.11%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6602	66.02%
Acute Oral Toxicity (c)	III	0.5682	56.82%
Estrogen receptor binding	-	0.4816	48.16%
Androgen receptor binding	+	0.5604	56.04%
Thyroid receptor binding	+	0.6465	64.65%
Glucocorticoid receptor binding	+	0.6784	67.84%
Aromatase binding	+	0.7463	74.63%
PPAR gamma	-	0.5559	55.59%
Honey bee toxicity	-	0.8094	80.94%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	-	0.7550	75.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3587	Q02750	Dual specificity mitogen-activated protein kinase kinase 1	2500 nM	IC50	PMID: 11784156
CHEMBL4040	P28482	MAP kinase ERK2	824 nM; 824 nM	IC50; IC50	PMID: 11784156; PMID: 15261294
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	725 nM; 330 nM; 725 nM	IC50; IC50; IC50	PMID: 22285028; PMID: 19111462; PMID: 15261294
CHEMBL2527	O96017	Serine/threonine-protein kinase Chk2	183 nM; 183 nM	IC50; IC50	PMID: 22285028; PMID: 15261294

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.36%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.17%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.14%	94.45%
CHEMBL3384	Q16512	Protein kinase N1	90.93%	80.71%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	90.15%	85.30%
CHEMBL2581	P07339	Cathepsin D	88.54%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.32%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.97%	97.09%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	86.12%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.93%	94.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	84.44%	80.96%
CHEMBL4208	P20618	Proteasome component C5	83.76%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.22%	86.33%
CHEMBL255	P29275	Adenosine A2b receptor	81.83%	98.59%
CHEMBL2996	Q05655	Protein kinase C delta	81.68%	97.79%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.37%	96.67%
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	80.82%	95.72%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.72%	95.64%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	80.57%	88.84%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.52%	83.10%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.30%	92.88%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	80.26%	82.86%
CHEMBL226	P30542	Adenosine A1 receptor	80.25%	95.93%
CHEMBL299	P17252	Protein kinase C alpha	80.08%	98.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.02%	95.89%

Plants that contains it

• Leiboldia serrata
• Marah fabacea

Cross-Links

• PubChem: 5288032
• NPASS: NPC162268
• ChEMBL: CHEMBL255465
• LOTUS: LTS0076073
• wikiData: Q105192744