(5S,6R)-5-hydroxy-3-methyl-6-phenyl-2,5,6,7-tetrahydro-1H-azocino[5,4-b]indol-4-one

Details

• Internal ID: af0b4dce-be1a-4395-94c0-9f28e8f9c0c4
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indoles > 3-alkylindoles
• IUPAC Name: (5S,6R)-5-hydroxy-3-methyl-6-phenyl-2,5,6,7-tetrahydro-1H-azocino[5,4-b]indol-4-one
• SMILES (Canonical): CN1CCC2=C(C(C(C1=O)O)C3=CC=CC=C3)NC4=CC=CC=C24
• SMILES (Isomeric): CN1CCC2=C([C@H]([C@@H](C1=O)O)C3=CC=CC=C3)NC4=CC=CC=C24
• InChI: InChI=1S/C20H20N2O2/c1-22-12-11-15-14-9-5-6-10-16(14)21-18(15)17(19(23)20(22)24)13-7-3-2-4-8-13/h2-10,17,19,21,23H,11-12H2,1H3/t17-,19+/m1/s1
• InChI Key: LJVOYNUXBXIUNA-MJGOQNOKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀N₂O₂
• Molecular Weight: 320.40 g/mol
• Exact Mass: 320.152477885 g/mol
• Topological Polar Surface Area (TPSA): 56.30 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.68
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9669	96.69%
Caco-2	+	0.8673	86.73%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7464	74.64%
OATP2B1 inhibitior	-	0.8457	84.57%
OATP1B1 inhibitior	+	0.9005	90.05%
OATP1B3 inhibitior	+	0.9367	93.67%
MATE1 inhibitior	-	0.9033	90.33%
OCT2 inhibitior	-	0.6279	62.79%
BSEP inhibitior	+	0.8594	85.94%
P-glycoprotein inhibitior	-	0.5711	57.11%
P-glycoprotein substrate	-	0.7138	71.38%
CYP3A4 substrate	+	0.5825	58.25%
CYP2C9 substrate	-	0.8076	80.76%
CYP2D6 substrate	-	0.7220	72.20%
CYP3A4 inhibition	-	0.5207	52.07%
CYP2C9 inhibition	-	0.7549	75.49%
CYP2C19 inhibition	-	0.7389	73.89%
CYP2D6 inhibition	-	0.7962	79.62%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.8309	83.09%
CYP inhibitory promiscuity	-	0.5307	53.07%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6852	68.52%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9973	99.73%
Skin irritation	-	0.7784	77.84%
Skin corrosion	-	0.9290	92.90%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7885	78.85%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.5052	50.52%
skin sensitisation	-	0.8911	89.11%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.6595	65.95%
Acute Oral Toxicity (c)	III	0.5094	50.94%
Estrogen receptor binding	+	0.5653	56.53%
Androgen receptor binding	+	0.6104	61.04%
Thyroid receptor binding	-	0.5448	54.48%
Glucocorticoid receptor binding	+	0.6625	66.25%
Aromatase binding	+	0.7617	76.17%
PPAR gamma	+	0.6016	60.16%
Honey bee toxicity	-	0.9518	95.18%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	-	0.5338	53.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.80%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.35%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.44%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.20%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.26%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	88.65%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.69%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.57%	85.14%
CHEMBL3310	Q96DB2	Histone deacetylase 11	84.83%	88.56%
CHEMBL255	P29275	Adenosine A2b receptor	83.92%	98.59%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.93%	93.40%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.39%	90.08%
CHEMBL4208	P20618	Proteasome component C5	80.27%	90.00%

Plants that contains it

• Clausena indica

Cross-Links

• PubChem: 23660342
• LOTUS: LTS0113867
• wikiData: Q105152839