(4,4-Dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en-2-yl)(1H-indol-3-yl)methanone

Details

• Internal ID: eccf09d0-ac15-42f7-a2e0-f161f2e295a6
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indoles
• IUPAC Name: (4,4-dimethyl-8-methylidene-3-azabicyclo[3.3.1]non-2-en-2-yl)-(1H-indol-3-yl)methanone
• SMILES (Canonical): CC1(C2CCC(=C)C(C2)C(=N1)C(=O)C3=CNC4=CC=CC=C43)C
• SMILES (Isomeric): CC1(C2CCC(=C)C(C2)C(=N1)C(=O)C3=CNC4=CC=CC=C43)C
• InChI: InChI=1S/C20H22N2O/c1-12-8-9-13-10-15(12)18(22-20(13,2)3)19(23)16-11-21-17-7-5-4-6-14(16)17/h4-7,11,13,15,21H,1,8-10H2,2-3H3
• InChI Key: JASABNKRQAFMNO-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂N₂O
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.173213330 g/mol
• Topological Polar Surface Area (TPSA): 45.20 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 4.56
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• Makomakine, 9-dehydro- 8-oxo-
• (4,4-Dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en-2-yl)(1H-indol-3-yl)methanone
• CHEMBL1967651
• NSC-640738
• NCI60_013625
• (2,2-dimethyl-6-methylene-3-azabicyclo[3.3.1]non-3-en-4-yl)-(1H-indol-3-yl)methanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9915	99.15%
Caco-2	+	0.5421	54.21%
Blood Brain Barrier	+	0.8379	83.79%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6630	66.30%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9054	90.54%
OATP1B3 inhibitior	+	0.9340	93.40%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6824	68.24%
P-glycoprotein inhibitior	-	0.4356	43.56%
P-glycoprotein substrate	-	0.6571	65.71%
CYP3A4 substrate	+	0.6513	65.13%
CYP2C9 substrate	+	0.6409	64.09%
CYP2D6 substrate	-	0.8309	83.09%
CYP3A4 inhibition	+	0.6114	61.14%
CYP2C9 inhibition	-	0.5446	54.46%
CYP2C19 inhibition	+	0.5317	53.17%
CYP2D6 inhibition	-	0.7270	72.70%
CYP1A2 inhibition	+	0.5799	57.99%
CYP2C8 inhibition	+	0.6975	69.75%
CYP inhibitory promiscuity	+	0.7712	77.12%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.6246	62.46%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.9580	95.80%
Skin irritation	-	0.7277	72.77%
Skin corrosion	-	0.9130	91.30%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7818	78.18%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.7254	72.54%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.7417	74.17%
Acute Oral Toxicity (c)	III	0.6007	60.07%
Estrogen receptor binding	+	0.8295	82.95%
Androgen receptor binding	+	0.7027	70.27%
Thyroid receptor binding	+	0.7193	71.93%
Glucocorticoid receptor binding	+	0.8239	82.39%
Aromatase binding	+	0.8541	85.41%
PPAR gamma	+	0.6954	69.54%
Honey bee toxicity	-	0.8760	87.60%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9634	96.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.30%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.18%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.08%	94.62%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.60%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.46%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.24%	97.09%
CHEMBL3310	Q96DB2	Histone deacetylase 11	89.73%	88.56%
CHEMBL4040	P28482	MAP kinase ERK2	88.02%	83.82%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.10%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.97%	93.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.92%	94.45%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.20%	94.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.41%	92.62%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	83.72%	92.67%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	83.61%	96.39%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.17%	95.50%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	82.76%	90.71%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.65%	94.08%
CHEMBL213	P08588	Beta-1 adrenergic receptor	82.61%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.47%	94.00%
CHEMBL221	P23219	Cyclooxygenase-1	80.47%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.41%	89.00%
CHEMBL2535	P11166	Glucose transporter	80.26%	98.75%

Plants that contains it

• Aristotelia chilensis

Cross-Links

• PubChem: 369151
• LOTUS: LTS0028809
• wikiData: Q105123982