Rhetsinine

Details

• Internal ID: f8b038ed-69ac-4cc4-aa70-ea3ef850a764
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
• IUPAC Name: 2-[2-(methylamino)benzoyl]-4,9-dihydro-3H-pyrido[3,4-b]indol-1-one
• SMILES (Canonical): CNC1=CC=CC=C1C(=O)N2CCC3=C(C2=O)NC4=CC=CC=C34
• SMILES (Isomeric): CNC1=CC=CC=C1C(=O)N2CCC3=C(C2=O)NC4=CC=CC=C34
• InChI: InChI=1S/C19H17N3O2/c1-20-15-8-4-3-7-14(15)18(23)22-11-10-13-12-6-2-5-9-16(12)21-17(13)19(22)24/h2-9,20-21H,10-11H2,1H3
• InChI Key: RAEOYMOPVHBBKE-UHFFFAOYSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₇N₃O₂
• Molecular Weight: 319.40 g/mol
• Exact Mass: 319.132076794 g/mol
• Topological Polar Surface Area (TPSA): 65.20 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.05
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 526-43-2
• 2-[2-(methylamino)benzoyl]-4,9-dihydro-3H-pyrido[3,4-b]indol-1-one
• YQ7LSR9JJA
• CHEMBL508030
• 1H-Pyrido(3,4-b)indol-1-one, 2,3,4,9-tetrahydro-2-(2-(methyamino)benzoyl)-
• NSC 258315
• NSC-258315
• 2-[2-(Methylamino)benzoyl]-3,4-dihydro-beta-carboline-1(2H)-one
• 2-(2-(Methylamino)benzoyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one
• NSC258315
• Spectrum_001552
• SpecPlus_000722
• UNII-YQ7LSR9JJA
• Spectrum2_001661
• Spectrum3_001649
• Spectrum4_001894
• Spectrum5_000548
• BSPBio_003377
• KBioGR_002453
• KBioSS_002032
• DivK1c_006818
• SPECTRUM1504176
• SPBio_001841
• SCHEMBL14478778
• KBio1_001762
• KBio2_002032
• KBio2_004600
• KBio2_007168
• KBio3_002597
• DTXSID30200576
• BDBM50292374
• CCG-38771
• 2,3,4,9-Tetrahydro-2-[2-(methylamino)benzoyl]-1H-pyrido[3,4-b]indol-1-one
• NCGC00095696-01
• NCGC00095696-02
• SR-05000002580
• SR-05000002580-1
• BRD-K08814982-001-02-9
• 1H-Pyrido[3, 2,3,4,9-tetrahydro-2-[2-(methylamino)benzoyl]-
• 2-[2-(Methylamino)benzoyl]-2,3,4,9-tetrahydro-1H- pyrido[3,4-b]indol-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9538	95.38%
Caco-2	+	0.8122	81.22%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6418	64.18%
OATP2B1 inhibitior	-	0.7012	70.12%
OATP1B1 inhibitior	+	0.9297	92.97%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	+	0.5175	51.75%
BSEP inhibitior	+	0.7192	71.92%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.6591	65.91%
CYP3A4 substrate	+	0.5482	54.82%
CYP2C9 substrate	-	0.5616	56.16%
CYP2D6 substrate	-	0.7500	75.00%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	-	0.8815	88.15%
CYP2C19 inhibition	-	0.7797	77.97%
CYP2D6 inhibition	-	0.8044	80.44%
CYP1A2 inhibition	-	0.5861	58.61%
CYP2C8 inhibition	-	0.7347	73.47%
CYP inhibitory promiscuity	+	0.5454	54.54%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6481	64.81%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9882	98.82%
Skin irritation	-	0.8295	82.95%
Skin corrosion	-	0.9552	95.52%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7035	70.35%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.9307	93.07%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6577	65.77%
Acute Oral Toxicity (c)	III	0.5742	57.42%
Estrogen receptor binding	+	0.8886	88.86%
Androgen receptor binding	+	0.5699	56.99%
Thyroid receptor binding	+	0.6290	62.90%
Glucocorticoid receptor binding	+	0.5753	57.53%
Aromatase binding	+	0.6186	61.86%
PPAR gamma	+	0.5859	58.59%
Honey bee toxicity	-	0.9378	93.78%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	-	0.5906	59.06%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	31622.8 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	14125.4 nM	Potency	via CMAUP
CHEMBL4801	P29466	Caspase-1	15848.9 nM	Potency	via CMAUP
CHEMBL3468	P55210	Caspase-7	15848.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	1000 nM; 1000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	19952.6 nM	Potency	via CMAUP
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	32000 nM	Ki	DOI: 10.1021/np960678l

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.48%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.08%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.83%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.66%	95.56%
CHEMBL2535	P11166	Glucose transporter	93.91%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.28%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.23%	94.45%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	89.91%	96.00%
CHEMBL3310	Q96DB2	Histone deacetylase 11	85.64%	88.56%
CHEMBL255	P29275	Adenosine A2b receptor	85.51%	98.59%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.32%	85.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.25%	93.03%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	83.90%	96.47%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.89%	89.00%
CHEMBL4302	P08183	P-glycoprotein 1	83.83%	92.98%
CHEMBL4208	P20618	Proteasome component C5	82.85%	90.00%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	80.86%	92.67%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.56%	96.67%
CHEMBL221	P23219	Cyclooxygenase-1	80.45%	90.17%
CHEMBL5028	O14672	ADAM10	80.38%	97.50%

Plants that contains it

• Tetradium ruticarpum

Cross-Links

• PubChem: 99652
• NPASS: NPC133003
• ChEMBL: CHEMBL508030
• LOTUS: LTS0072207
• wikiData: Q72506086