Serotonin

Details

• Internal ID: 62c1fb56-8ded-4f75-a04a-2d2e5b841aaa
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Tryptamines and derivatives > Serotonins
• IUPAC Name: 3-(2-aminoethyl)-1H-indol-5-ol
• SMILES (Canonical): C1=CC2=C(C=C1O)C(=CN2)CCN
• SMILES (Isomeric): C1=CC2=C(C=C1O)C(=CN2)CCN
• InChI: InChI=1S/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2
• InChI Key: QZAYGJVTTNCVMB-UHFFFAOYSA-N
• Popularity: 170,285 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂N₂O
• Molecular Weight: 176.21 g/mol
• Exact Mass: 176.094963011 g/mol
• Topological Polar Surface Area (TPSA): 62.00 Ų
• XlogP: 0.20

Synonyms

• 5-HYDROXYTRYPTAMINE
• 50-67-9
• 3-(2-Aminoethyl)-1H-indol-5-ol
• Enteramine
• Thrombotonin
• Thrombocytin
• 5-HT
• Antemovis
• Serotonine
• Ds substance
• Antemoqua
• Hippophain
• Substance DS
• Substanz DS
• 5-Hta
• 1H-Indol-5-ol, 3-(2-aminoethyl)-
• Tryptamine, 5-hydroxy-
• 3-(2-Aminoethyl)indol-5-ol
• Hippophaine
• Indol-5-ol, 3-(2-aminoethyl)-
• 3-(beta-Aminoethyl)-5-hydroxyindole
• 5-Hydroxy-3-(beta-aminoethyl)indole
• Enteramin
• UNII-333DO1RDJY
• EINECS 200-058-9
• 333DO1RDJY
• BRN 0143524
• Hydroxytryptamine
• CHEBI:28790
• 3-(2-Amino-ethyl)-1H-indol-5-ol
• DTXSID8075330
• 5-22-12-00016 (Beilstein Handbook Reference)
• 3-(.beta.-Aminoethyl)-5-hydroxyindole
• SEROTONIN (MART.)
• SEROTONIN [MART.]
• 5 Hydroxytryptamine
• 5-hydroxytryptamin
• 5-Hydroxytriptamine
• 5-Hydroxyltryptamine
• 5-hydroxy-tryptamine
• 5-hydroxyl tryptamine
• GTPL5
• SEROTONIN [MI]
• CHEMBL39
• Prestwick0_000481
• Prestwick1_000481
• Prestwick2_000481
• Prestwick3_000481
• Lopac-H-9523
• 5-Hydroxytryptamine;5-HT
• Biomol-NT_000083
• bmse000757
• D0F6CD
• SCHEMBL1495
• SEROTONIN [WHO-DD]
• Lopac0_000607
• Oprea1_712368
• BSPBio_000341
• BSPBio_001112
• KBioGR_000452
• KBioGR_002472
• KBioSS_000452
• KBioSS_002479
• Serotonin, analytical standard
• SPBio_002262
• 5-Hydroxytryptamine, free base
• BPBio1_000377
• BPBio1_001079
• DTXCID4040765
• BCBcMAP01_000198
• BDBM10755
• KBio2_000452
• KBio2_002472
• KBio2_003020
• KBio2_005040
• KBio2_005588
• KBio2_007608
• KBio3_000843
• KBio3_000844
• KBio3_002950
• cMAP_000059
• 3-(b-Aminoethyl)-5-hydroxyindole
• 5-Hydroxy-3-(b-aminoethyl)indole
• Bio1_000450
• Bio1_000939
• Bio1_001428
• Bio2_000396
• Bio2_000876
• HMS1362H13
• HMS1792H13
• HMS1990H13
• HMS3403H13
• 3-(2-Aminoethyl)-1H-indol-5-o
• MFCD00055054
• PDSP1_001512
• PDSP2_001496
• STK503758
• AKOS001484724
• 3-(2-Aminoethyl)-1H-indol-5-ol #
• CCG-204696
• DB08839
• SDCCGSBI-0050589.P002
• 5-Hydroxy-3-(.beta.-aminoethyl)indole
• IDI1_002151
• SMP1_000272
• 5-hydroxy tryptamine creatinine disulfate
• NCGC00015525-01
• NCGC00015525-02
• NCGC00015525-03
• NCGC00015525-04
• NCGC00015525-05
• NCGC00015525-06
• NCGC00015525-07
• NCGC00015525-08
• NCGC00015525-09
• NCGC00015525-19
• NCGC00142449-01
• NCGC00142449-02
• NCGC00142449-03
• NCGC00142449-04
• NCGC00142449-05
• AS-75772
• CAS-153-98-0
• LS-83647
• FT-0631212
• 14C-5-hydroxy tryptamine creatinine disulfate
• C00780
• EN300-120141
• H-8000
• A828245
• L000078
• Q167934
• 6F7FD5B4-A558-45F0-A20A-2D068A3EFE6A
• 2-imino-1-methylimidazolidin-4-one; 3-(2-aminoethyl)-1H-indol-5-ol; bis(sulfuric acid)
• 1094000-36-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL256	P0DMS8	Adenosine A3 receptor	79 nM	IC50	PMID: 16250647
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	39810.7 nM	Potency	via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	1995.26 nM; 7943.28 nM	AC50; AC50	via CMAUP; via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	15848.9 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	10000 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	39810.7 nM; 25118.9 nM; 39810.7 nM; 25118.9 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL217	P14416	Dopamine D2 receptor	0.0003 nM	IC50	PMID: 3156993
CHEMBL234	P35462	Dopamine D3 receptor	523 nM	EC50	PMID: 12930145
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	5.2 nM; 5.6 nM; 6 nM; 2 nM; 2 nM; 1.2 nM; 0.5 nM	IC50; IC50; IC50; IC50; IC50; IC50; EC50	PMID: 1447752; PMID: 2918500; PMID: 2918500; PMID: 2918500; PMID: 2918500; PMID: 12954071; via Super-PRED
CHEMBL1898	P28222	Serotonin 1b (5-HT1b) receptor	5 nM; 16 nM; 6.5 nM; 12 nM; 1.1 nM	IC50; IC50; IC50; IC50; Ki	PMID: 1447752; PMID: 18588282; PMID: 23466604; PMID: 23582449; via Super-PRED
CHEMBL1983	P28221	Serotonin 1d (5-HT1d) receptor	3 nM; 3 nM; 0.5 nM	IC50; IC50; Ki	PMID: 2374139; DOI: 10.1016/0960-894X(95)00417-R; via Super-PRED
CHEMBL2182	P28566	Serotonin 1e (5-HT1e) receptor	10.72 nM; 11 nM; 10.72 nM	Ki; Ki; Ki	PMID: 24365159; PMID: 24365159; via Super-PRED
CHEMBL1805	P30939	Serotonin 1f (5-HT1f) receptor	7.9 nM	EC50	PMID: 11708905
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	510 nM; 320 nM; 8.2 nM; 398.11 nM; 14 nM; 14 nM; 8.2 nM; 120 nM; 160 nM; 130 nM; 150 nM; 323.59 nM; 320 nM; 0.51 nM	Ki; Ki; Ki; Ki; Ki; Ki; Ki; Ki; Ki; Ki; Ki; Ki; Ki; EC50	PMID: 8071931; PMID: 11975483; PMID: 12954071; PMID: 14613313; PMID: 15081042; PMID: 16257207; PMID: 16392816; PMID: 18468904; PMID: 18468904; PMID: 18468904; PMID: 18468904; PMID: 23301527; PMID: 23301527; via Super-PRED
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	1.5 nM; 1.5 nM; 0.5 nM; 0.86 nM; 1.1 nM; 1.072 nM; 0.92 nM; 0.5 nM	EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50	PMID: 15081042; PMID: 16257207; PMID: 19284718; PMID: 22778800; PMID: 23602445; PMID: 23602445; PMID: 25633969; via Super-PRED
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81 nM; 0.09 nM	IC50; EC50	PMID: 2374139; via Super-PRED
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	500 nM; 457.09 nM; 178 nM; 141 nM; 141 nM	EC50; EC50; EC50; EC50; EC50	PMID: 17722904; PMID: 17722904; PMID: 21146988; PMID: 21146988; via Super-PRED
CHEMBL1875	Q13639	Serotonin 4 (5-HT4) receptor	500 nM; 29.51 nM; 109.65 nM; 12 nM	Ki; Ki; Ki; EC50	PMID: 17067154; PMID: 19223092; PMID: 19223092; via Super-PRED
CHEMBL3426	P47898	Serotonin 5a (5-HT5a) receptor	184 nM; 180 nM; 180 nM; 79 nM	IC50; IC50; IC50; IC50	PMID: 18588282; PMID: 18983139; PMID: 26988801; via Super-PRED
CHEMBL3371	P50406	Serotonin 6 (5-HT6) receptor	262 nM; 200 nM; 27.5 nM; 100 nM; 180 nM; 120 nM; 27.5 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 18588282; PMID: 18983139; PMID: 20170099; PMID: 23466604; PMID: 23582449; PMID: 26988801; via Super-PRED
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	0.61 nM; 0.29 nM; 0.49 nM; 0.25 nM; 0.11 nM	IC50; IC50; IC50; IC50; Ki	PMID: 18983139; PMID: 23466604; PMID: 23582449; PMID: 26988801; via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.42%	91.11%
CHEMBL242	Q92731	Estrogen receptor beta	93.98%	98.35%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.20%	96.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	91.69%	91.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.20%	94.45%
CHEMBL4581	P52732	Kinesin-like protein 1	89.70%	93.18%
CHEMBL213	P08588	Beta-1 adrenergic receptor	88.64%	95.56%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	88.55%	82.86%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	86.72%	94.01%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	84.89%	95.48%
CHEMBL2535	P11166	Glucose transporter	84.22%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.13%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	83.33%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.18%	95.56%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	82.62%	83.10%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.89%	92.94%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	81.87%	93.24%
CHEMBL1952	P04818	Thymidylate synthase	81.47%	93.53%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.06%	99.17%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	80.92%	97.23%
CHEMBL3038469	P24941	CDK2/Cyclin A	80.16%	91.38%

Plants that contains it

• Amorphophallus konjac
• Ananas comosus
• Arabidopsis thaliana
• Araujia sericifera
• Aruncus dioicus
• Buxus sempervirens
• Cnidoscolus texanus
• Dysoxylum lenticellatum
• Hesperocyparis macrocarpa
• Hyacinthoides non-scripta
• Hypericum perforatum
• Isocoma veneta
• Juglans regia
• Kochia trichophylla
• Lemna aequinoctialis
• Leuzea carthamoides
• Mimosa somnians
• Nitraria schoberi
• Peganum harmala
• Petchia madagascariensis
• Piper kadsura
• Potentilla multifida
• Psephellus trinervius
• Ranunculus sceleratus
• Rheum officinale
• Saururus cernuus
• Seriphidium oranense
• Strychnos fendleri
• Theobroma cacao
• Tovaria pendula
• Urtica dioica
• Vicia villosa
• Vitex megapotamica

Cross-Links

• PubChem: 5202
• NPASS: NPC220765
• ChEMBL: CHEMBL39
• LOTUS: LTS0141462
• wikiData: Q167934