N-Methylserotonin

Details

• Internal ID: e1fe6860-3b7c-4975-bd6d-5e958868279f
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Tryptamines and derivatives > Serotonins
• IUPAC Name: 3-[2-(methylamino)ethyl]-1H-indol-5-ol
• SMILES (Canonical): CNCCC1=CNC2=C1C=C(C=C2)O
• SMILES (Isomeric): CNCCC1=CNC2=C1C=C(C=C2)O
• InChI: InChI=1S/C11H14N2O/c1-12-5-4-8-7-13-11-3-2-9(14)6-10(8)11/h2-3,6-7,12-14H,4-5H2,1H3
• InChI Key: ASUSBMNYRHGZIG-UHFFFAOYSA-N
• Popularity: 80 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₄N₂O
• Molecular Weight: 190.24 g/mol
• Exact Mass: 190.110613074 g/mol
• Topological Polar Surface Area (TPSA): 48.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.64
• H-Bond Acceptor: 2
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 1134-01-6
• 3-[2-(methylamino)ethyl]-1H-indol-5-ol
• N-Methyl Serotonin
• 1H-Indol-5-ol, 3-[2-(methylamino)ethyl]-
• Lopac-M-1514
• MZ25L5SJ6Z
• CHEMBL277362
• CHEBI:48294
• 3-(2-(methylamino)ethyl)-1H-indol-5-ol
• 1H-Indol-5-ol, 3-(2-(methylamino)ethyl)-
• N-Methyl-5-hydroxytryptamine
• N-Methylserotonine
• Nomega-methylserotonin
• 5-OH-ME-Nw Tryptamine
• UNII-MZ25L5SJ6Z
• 5-Hydroxy-N-methyltryptamine
• Lopac0_000743
• SCHEMBL1127784
• DTXSID40150396
• Nomega-methyl-5-hydroxytryptamine
• BDBM50024202
• PDSP1_001694
• PDSP1_001696
• PDSP2_001677
• PDSP2_001679
• AKOS006227847
• CCG-204828
• SDCCGSBI-0050721.P002
• NCGC00015648-01
• NCGC00015648-02
• NCGC00015648-03
• NCGC00015648-04
• NCGC00015648-06
• NCGC00142416-01
• NCGC00142416-02
• PD034352
• LS-191851
• FT-0672197
• 3-(2-METHYLAMINOETHYL)-1H-INDOL-5-OL
• C06212
• Q855403
• J-002959
• N-Methylserotonin; 3-[2-(methylamino)ethyl]-1H-indol-5-ol; Lopac-M-1514

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.6152	61.52%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.4452	44.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8806	88.06%
OATP1B3 inhibitior	+	0.9489	94.89%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	-	0.9204	92.04%
P-glycoprotein inhibitior	-	0.9833	98.33%
P-glycoprotein substrate	+	0.6792	67.92%
CYP3A4 substrate	-	0.5252	52.52%
CYP2C9 substrate	+	0.5505	55.05%
CYP2D6 substrate	+	0.6397	63.97%
CYP3A4 inhibition	-	0.8835	88.35%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.5154	51.54%
CYP1A2 inhibition	-	0.7993	79.93%
CYP2C8 inhibition	-	0.6776	67.76%
CYP inhibitory promiscuity	-	0.7636	76.36%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7062	70.62%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.5659	56.59%
Skin irritation	-	0.6440	64.40%
Skin corrosion	-	0.8033	80.33%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5242	52.42%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8344	83.44%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8725	87.25%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8548	85.48%
Acute Oral Toxicity (c)	III	0.5022	50.22%
Estrogen receptor binding	-	0.5253	52.53%
Androgen receptor binding	-	0.7436	74.36%
Thyroid receptor binding	+	0.5296	52.96%
Glucocorticoid receptor binding	-	0.5249	52.49%
Aromatase binding	-	0.7391	73.91%
PPAR gamma	-	0.5677	56.77%
Honey bee toxicity	-	0.9459	94.59%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	-	0.8416	84.16%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL289	P10635	Cytochrome P450 2D6	39810.7 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	35481.3 nM	Potency	via CMAUP
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	280 nM	Ki	PMID: 3543362

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.88%	91.11%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	94.31%	90.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	93.58%	89.62%
CHEMBL2581	P07339	Cathepsin D	93.03%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.30%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	91.08%	98.35%
CHEMBL255	P29275	Adenosine A2b receptor	91.00%	98.59%
CHEMBL222	P23975	Norepinephrine transporter	90.86%	96.06%
CHEMBL2996	Q05655	Protein kinase C delta	88.07%	97.79%
CHEMBL2535	P11166	Glucose transporter	87.37%	98.75%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	83.81%	93.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.81%	94.45%
CHEMBL1914	P06276	Butyrylcholinesterase	82.55%	95.00%
CHEMBL1937	Q92769	Histone deacetylase 2	81.27%	94.75%
CHEMBL1952	P04818	Thymidylate synthase	80.25%	93.53%
CHEMBL3401	O75469	Pregnane X receptor	80.19%	94.73%

Plants that contains it

• Aruncus dioicus
• Buxus sempervirens
• Dysoxylum lenticellatum
• Hesperocyparis macrocarpa
• Isocoma veneta
• Kochia trichophylla
• Leuzea carthamoides
• Petchia madagascariensis
• Phyllodium pulchellum
• Piper kadsura
• Potentilla multifida
• Psephellus trinervius
• Saururus cernuus
• Seriphidium oranense
• Strychnos fendleri
• Vicia villosa
• Vitex megapotamica

Cross-Links

• PubChem: 150885
• NPASS: NPC204717
• ChEMBL: CHEMBL277362
• LOTUS: LTS0083699
• wikiData: Q855403