(3aS,8bS)-4-[3-[2-(dimethylamino)ethyl]-5-hydroxy-1H-indol-4-yl]-3-methyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-8b-ol

Details

• Internal ID: c0944523-cfa7-4f52-b643-eea5cc5778a8
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Tryptamines and derivatives > Serotonins
• IUPAC Name: (3aS,8bS)-4-[3-[2-(dimethylamino)ethyl]-5-hydroxy-1H-indol-4-yl]-3-methyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-8b-ol
• SMILES (Canonical): CN1CCC2(C1N(C3=CC=CC=C32)C4=C(C=CC5=C4C(=CN5)CCN(C)C)O)O
• SMILES (Isomeric): CN1CC[C@]2([C@@H]1N(C3=CC=CC=C32)C4=C(C=CC5=C4C(=CN5)CCN(C)C)O)O
• InChI: InChI=1S/C23H28N4O2/c1-25(2)12-10-15-14-24-17-8-9-19(28)21(20(15)17)27-18-7-5-4-6-16(18)23(29)11-13-26(3)22(23)27/h4-9,14,22,24,28-29H,10-13H2,1-3H3/t22-,23-/m0/s1
• InChI Key: LJSAOKIBMQABTP-GOTSBHOMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈N₄O₂
• Molecular Weight: 392.50 g/mol
• Exact Mass: 392.22122615 g/mol
• Topological Polar Surface Area (TPSA): 66.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.98
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9900	99.00%
Caco-2	+	0.5636	56.36%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5203	52.03%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.8973	89.73%
OATP1B3 inhibitior	+	0.9357	93.57%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6529	65.29%
BSEP inhibitior	+	0.8616	86.16%
P-glycoprotein inhibitior	+	0.7828	78.28%
P-glycoprotein substrate	+	0.7019	70.19%
CYP3A4 substrate	+	0.7203	72.03%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	+	0.5084	50.84%
CYP3A4 inhibition	+	0.5321	53.21%
CYP2C9 inhibition	-	0.7685	76.85%
CYP2C19 inhibition	-	0.5719	57.19%
CYP2D6 inhibition	-	0.5787	57.87%
CYP1A2 inhibition	-	0.6214	62.14%
CYP2C8 inhibition	-	0.8281	82.81%
CYP inhibitory promiscuity	+	0.6462	64.62%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5726	57.26%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9734	97.34%
Skin irritation	-	0.7971	79.71%
Skin corrosion	-	0.9279	92.79%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6629	66.29%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.7457	74.57%
skin sensitisation	-	0.8516	85.16%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.9095	90.95%
Acute Oral Toxicity (c)	III	0.6159	61.59%
Estrogen receptor binding	+	0.6495	64.95%
Androgen receptor binding	+	0.7311	73.11%
Thyroid receptor binding	+	0.7675	76.75%
Glucocorticoid receptor binding	-	0.4762	47.62%
Aromatase binding	+	0.6214	62.14%
PPAR gamma	+	0.6874	68.74%
Honey bee toxicity	-	0.8551	85.51%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.6666	66.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3192	Q9BY41	Histone deacetylase 8	99.24%	93.99%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.90%	96.09%
CHEMBL240	Q12809	HERG	98.35%	89.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.24%	91.11%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	94.95%	90.71%
CHEMBL2581	P07339	Cathepsin D	94.25%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.69%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	92.63%	94.75%
CHEMBL3310	Q96DB2	Histone deacetylase 11	90.77%	88.56%
CHEMBL1914	P06276	Butyrylcholinesterase	90.64%	95.00%
CHEMBL228	P31645	Serotonin transporter	90.36%	95.51%
CHEMBL4208	P20618	Proteasome component C5	89.72%	90.00%
CHEMBL233	P35372	Mu opioid receptor	89.64%	97.93%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.27%	82.69%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	86.81%	95.17%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	86.21%	85.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.03%	89.00%
CHEMBL5805	Q9NR97	Toll-like receptor 8	84.01%	96.25%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.76%	90.08%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.35%	95.89%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.95%	96.67%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.60%	96.39%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.71%	93.04%
CHEMBL2535	P11166	Glucose transporter	80.69%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.58%	89.62%

Plants that contains it

• Arundo donax

Cross-Links

• PubChem: 163195278
• LOTUS: LTS0144193
• wikiData: Q105152749