(7bR,10aR)-2,3,4,7b,8,9,10,10a-Octahydro-1H-cyclopenta[b][1,4]diazepino[6,7,1-hi]indole

Details

• Internal ID: 08c7e4f5-80d3-433a-b443-a3a867da93e0
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolines > 2,3-Cyclopentanoindolines
• IUPAC Name: (11R,15R)-7,10-diazatetracyclo[8.5.1.05,16.011,15]hexadeca-1,3,5(16)-triene
• SMILES (Canonical): C1CC2C(C1)N3CCNCC4=C3C2=CC=C4
• SMILES (Isomeric): C1C[C@H]2[C@@H](C1)N3CCNCC4=C3C2=CC=C4
• InChI: InChI=1S/C14H18N2/c1-3-10-9-15-7-8-16-13-6-2-4-11(13)12(5-1)14(10)16/h1,3,5,11,13,15H,2,4,6-9H2/t11-,13-/m1/s1
• InChI Key: XOSKJKGKWRIMGV-DGCLKSJQSA-N
• Popularity: 28 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈N₂
• Molecular Weight: 214.31 g/mol
• Exact Mass: 214.146998583 g/mol
• Topological Polar Surface Area (TPSA): 15.30 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.25
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 428868-32-0
• WAY163909
• WAY 163909
• MN9LW8268N
• WAY-163,909
• UNII-MN9LW8268N
• (7bR,10aR)-2,3,4,7b,8,9,10,10a-Octahydro-1H-cyclopenta[b][1,4]diazepino[6,7,1-hi]indole
• CHEMBL1628670
• (11R,15R)-7,10-diazatetracyclo[8.5.1.0^{5,16}.0^{11,15}]hexadeca-1,3,5(16)-triene
• (7bR,10aR)-2,3,4,7b,8,9,10,10a-Octahydro-1H-cyclopenta(b)(1,4)diazepino(6,7,1-hi)indole
• (7bR,10aR)-1,2,3,4,7a,9,10,10a-Octahydro-8H-cyclopenta(4,5)pyrrolo(3,2,1-jk)(1,4)benzodiazepine
• 8H-Cyclopenta(4,5)pyrrolo(3,2,1-jk)(1,4)benzodiazepine, 1,2,3,4,7a,9,10,10a-octahydro-, (7bR,10aR)-
• D0W6RV
• GTPL229
• SCHEMBL4352287
• DTXSID40436021
• BDBM50076245
• AKOS016004084
• HY-15401
• LS-191411
• CS-0006248
• Q27089215
• (11R,15R)-7,10-Diazatetracyclo[8.5.1.05,16.011,15]hexadeca-1,3,5(16)-triene
• (7bR,10aR)-1,2,3,4,7b,9,10,10a-octahydro-8H-cyclopenta[b][1,4]diazepino[6,7,1-hi]indole
• (7bR,10aR)-1,2,3,4,8,9,10,10a-octahydro-7bH-cyclopenta-[b][1,4]diazepino[6,7,1hi]indole

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9946	99.46%
Caco-2	+	0.9503	95.03%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Lysosomes	0.7509	75.09%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.9191	91.91%
OATP1B3 inhibitior	+	0.9485	94.85%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	-	0.8002	80.02%
P-glycoprotein inhibitior	-	0.9697	96.97%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	-	0.5061	50.61%
CYP2C9 substrate	-	0.6131	61.31%
CYP2D6 substrate	+	0.6523	65.23%
CYP3A4 inhibition	-	0.8833	88.33%
CYP2C9 inhibition	-	0.7475	74.75%
CYP2C19 inhibition	-	0.6598	65.98%
CYP2D6 inhibition	+	0.8083	80.83%
CYP1A2 inhibition	+	0.8554	85.54%
CYP2C8 inhibition	-	0.8975	89.75%
CYP inhibitory promiscuity	+	0.5351	53.51%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.7373	73.73%
Eye corrosion	-	0.8558	85.58%
Eye irritation	-	0.7749	77.49%
Skin irritation	-	0.5915	59.15%
Skin corrosion	-	0.6561	65.61%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6622	66.22%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.5856	58.56%
skin sensitisation	-	0.8718	87.18%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6370	63.70%
Acute Oral Toxicity (c)	III	0.5127	51.27%
Estrogen receptor binding	-	0.8248	82.48%
Androgen receptor binding	-	0.5190	51.90%
Thyroid receptor binding	-	0.6287	62.87%
Glucocorticoid receptor binding	-	0.8265	82.65%
Aromatase binding	-	0.7548	75.48%
PPAR gamma	-	0.5928	59.28%
Honey bee toxicity	-	0.9282	92.82%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	-	0.4751	47.51%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	8 nM; 8 nM; 8 nM	EC50; EC50; EC50	PMID: 25633969; via Super-PRED; PMID: 24491146

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL228	P31645	Serotonin transporter	97.13%	95.51%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.52%	97.09%
CHEMBL2581	P07339	Cathepsin D	95.47%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.64%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.61%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.90%	93.99%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.76%	97.25%
CHEMBL1991	O14920	Inhibitor of nuclear factor kappa B kinase beta subunit	88.23%	97.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.27%	95.56%
CHEMBL3310	Q96DB2	Histone deacetylase 11	86.38%	88.56%
CHEMBL238	Q01959	Dopamine transporter	86.28%	95.88%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.46%	95.83%
CHEMBL5203	P33316	dUTP pyrophosphatase	84.23%	99.18%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	83.29%	90.71%
CHEMBL3384	Q16512	Protein kinase N1	83.07%	80.71%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.86%	93.03%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.93%	90.24%
CHEMBL2073	P07947	Tyrosine-protein kinase YES	81.89%	83.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.88%	93.40%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.80%	100.00%
CHEMBL2916	O14746	Telomerase reverse transcriptase	80.91%	90.00%
CHEMBL1902	P62942	FK506-binding protein 1A	80.43%	97.05%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.39%	94.45%

Plants that contains it

• Cannabis sativa
• Piper longum
• Piper nigrum

Cross-Links

• PubChem: 10130594
• NPASS: NPC313673
• ChEMBL: CHEMBL1628670