Details of the Drug

General Information of Drug (ID: DMOFCRY)

Drug Name

SEROTONIN

Synonyms

serotonin; 5-HYDROXYTRYPTAMINE; 3-(2-Aminoethyl)-1H-indol-5-ol; 50-67-9; Enteramine; 5-HT; Serotonine; Thrombotonin; Thrombocytin; Antemovis; Ds substance; Hippophain; Antemoqua; Substance DS; Substanz DS; 1H-Indol-5-ol, 3-(2-aminoethyl)-; 5-Hta; Tryptamine, 5-hydroxy-; 3-(2-Aminoethyl)indol-5-ol; Enteramin; UNII-333DO1RDJY; Indol-5-ol, 3-(2-aminoethyl)-; 5-Hydroxy-3-(beta-aminoethyl)indole; 3-(beta-Aminoethyl)-5-hydroxyindole; EINECS 200-058-9; 3-(2-Amino-ethyl)-1H-indol-5-ol; BRN 0143524; 333DO1RDJY; CHEBI:28790

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

176.21

Logarithm of the Partition Coefficient (xlogp)

0.2

Rotatable Bond Count (rotbonds)

2

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

2

Chemical Identifiers

Formula: C10H12N2O
IUPAC Name: 3-(2-aminoethyl)-1H-indol-5-ol
Canonical SMILES: 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
InChIKey: QZAYGJVTTNCVMB-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5202
ChEBI ID: CHEMBL39
CAS Number: 50-67-9
UNII: 333DO1RDJY
DrugBank ID: DB08839
TTD ID: D0F6CD
VARIDT ID: DR00189
INTEDE ID: DR1961

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
5-HT 1A receptor (HTR1A)	TTSQIFT	5HT1A_HUMAN	Inhibitor	[2]
5-HT 1B receptor (HTR1B)	TTK8CXU	5HT1B_HUMAN	Inhibitor	[3]
5-HT 1D receptor (HTR1D)	TT6MSOK	5HT1D_HUMAN	Inhibitor	[4]
5-HT 2A receptor (HTR2A)	TTJQOD7	5HT2A_HUMAN	Inhibitor	[2]
5-HT 2B receptor (HTR2B)	TT0K1SC	5HT2B_HUMAN	Inhibitor	[5]
5-HT 2C receptor (HTR2C)	TTWJBZ5	5HT2C_HUMAN	Inhibitor	[6]
5-HT 3A receptor (HTR3A)	TTPC4TU	5HT3A_HUMAN	Inhibitor	[7]
5-HT 3B receptor (HTR3B)	TTR6K75	5HT3B_HUMAN	Inhibitor	[7]
5-HT 4 receptor (HTR4)	TT07C3Y	5HT4R_HUMAN	Inhibitor	[6]
5-HT 5A receptor (HTR5A)	TTRUFDT	5HT5A_HUMAN	Inhibitor	[8]
5-HT 6 receptor (HTR6)	TTJS8PY	5HT6R_HUMAN	Inhibitor	[9]
5-HT 7 receptor (HTR7)	TTO9X1H	5HT7R_HUMAN	Inhibitor	[8]
Adenosine A3 receptor (ADORA3)	TTJFY5U	AA3R_HUMAN	Inhibitor	[10]

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Sodium-dependent serotonin transporter (SLC6A4)	DTAV4SY	SC6A4_HUMAN	Substrate	[11]
Equilibrative nucleoside transporter 4 (SLC29A4)	DT3EAQP	S29A4_HUMAN	Substrate	[12]
Vesicular amine transporter 2 (SLC18A2)	DTT7VPB	VMAT2_HUMAN	Substrate	[13]
Vesicular amine transporter 1 (SLC18A1)	DTM953D	VMAT1_HUMAN	Substrate	[13]
Organic cation transporter 2 (SLC22A2)	DT9IDPW	S22A2_HUMAN	Substrate	[14]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Monoamine oxidase type A (MAO-A)_{Main DME}	DERE4TU	AOFA_HUMAN	Substrate	[15]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
5-hydroxytryptamine receptor 1D (HTR1D)	OTLS74AF	5HT1D_HUMAN	Regulation of Drug Effects	[16]
5-hydroxytryptamine receptor 2A (HTR2A)	OTWXJX0M	5HT2A_HUMAN	Drug Response	[17]
5-hydroxytryptamine receptor 2B (HTR2B)	OTM1AD9J	5HT2B_HUMAN	Protein Interaction/Cellular Processes	[18]
Acetyl-CoA acetyltransferase, mitochondrial (ACAT1)	OTJC60Q7	THIL_HUMAN	Gene/Protein Processing	[19]
Amyloid-beta precursor protein (APP)	OTKFD7R4	A4_HUMAN	Drug Response	[20]
Chromaffin granule amine transporter (SLC18A1)	OT01OALS	VMAT1_HUMAN	Regulation of Drug Effects	[21]
Equilibrative nucleoside transporter 4 (SLC29A4)	OTWTZXMX	S29A4_HUMAN	Regulation of Drug Effects	[22]
Interleukin-12 subunit beta (IL12B)	OT0JF8A3	IL12B_HUMAN	Protein Interaction/Cellular Processes	[23]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[23]
Mitogen-activated protein kinase 1 (MAPK1)	OTH85PI5	MK01_HUMAN	Post-Translational Modifications	[24]

Molecular Interaction Atlas (MIA)

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Molecular Expression Atlas of This Drug

The Studied Disease

Discovery agent

ICD Disease Classification

N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Vesicular amine transporter 2 (SLC18A2)	DTP	VMAT2	1.71E-01	-6.86E-01	-8.11E-01
Vesicular amine transporter 1 (SLC18A1)	DTP	VMAT1	3.06E-01	-2.04E-01	-7.90E-01
Sodium-dependent serotonin transporter (SLC6A4)	DTP	SERT	2.81E-02	-2.78E-01	-1.13E+00
Organic cation transporter 2 (SLC22A2)	DTP	SLC22A2	4.95E-01	-1.32E-01	-3.77E-01
Equilibrative nucleoside transporter 4 (SLC29A4)	DTP	ENT4	9.03E-01	1.44E-01	4.54E-01
Monoamine oxidase type A (MAO-A)	DME	MAOA	2.61E-01	-1.87E-01	-8.22E-01

Molecular Expression Atlas (MEA)

MEA Detail

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5).
2	Novel, potent, and selective quinoxaline-based 5-HT(3) receptor ligands. 1. Further structure-activity relationships and pharmacological characteri... J Med Chem. 2009 Nov 12;52(21):6946-50.
3	cis-4-(Piperazin-1-yl)-5,6,7a,8,9,10,11,11a-octahydrobenzofuro[2,3-h]quinazolin-2-amine (A-987306), a new histamine H4R antagonist that blocks pain... J Med Chem. 2008 Nov 27;51(22):7094-8.
4	Designing selective, high affinity ligands of 5-HT1D receptor by covalent dimerization of 5-HT1F ligands derived from 4-fluoro-N-[3-(1-methyl-4-pip... J Med Chem. 2008 Jun 26;51(12):3609-16.
5	Pyrrolo(iso)quinoline derivatives as 5-HT(2C) receptor agonists. Bioorg Med Chem Lett. 2006 Feb;16(3):677-80.
6	Brominated cyclodipeptides from the marine sponge Geodia barretti as selective 5-HT ligands. J Nat Prod. 2006 Oct;69(10):1421-4.
7	Novel potent and selective central 5-HT3 receptor ligands provided with different intrinsic efficacy. 2. Molecular basis of the intrinsic efficacy ... J Med Chem. 1999 May 6;42(9):1556-75.
8	Identification of a potent, selective, and orally active leukotriene a4 hydrolase inhibitor with anti-inflammatory activity. J Med Chem. 2008 Jul 24;51(14):4150-69.
9	5-Cyclic amine-3-arylsulfonylindazoles as novel 5-HT6 receptor antagonists. J Med Chem. 2010 Mar 25;53(6):2521-7.
10	2-n-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine and analogues as A2A adenosine receptor antagonists. Design, synthesis, and pharmacolog... J Med Chem. 2005 Nov 3;48(22):6887-96.
11	Serotonin transporter gene, depressive symptoms, and interleukin-6. Circ Cardiovasc Genet. 2009 Dec;2(6):614-20.
12	Autism spectrum disorder associated with low serotonin in CSF and mutations in the SLC29A4 plasma membrane monoamine transporter (PMAT) gene. Mol Autism. 2014 Aug 13;5:43.
13	SLC18: Vesicular neurotransmitter transporters for monoamines and acetylcholine. Mol Aspects Med. 2013 Apr-Jun;34(2-3):360-72.
14	Differential pharmacological in vitro properties of organic cation transporters and regional distribution in rat brain. Neuropharmacology. 2006 Jun;50(8):941-52.
15	Do monomeric vs dimeric forms of MAO-A make a difference? A direct comparison of the catalytic properties of rat and human MAO-A's. J Neural Transm (Vienna). 2007;114(6):721-4.
16	Evidence for epistasis between SLC6A4 and ITGB3 in autism etiology and in the determination of platelet serotonin levels. Hum Genet. 2007 Apr;121(2):243-56. doi: 10.1007/s00439-006-0301-3. Epub 2007 Jan 3.
17	Pharmacologic analysis of non-synonymous coding h5-HT2A SNPs reveals alterations in atypical antipsychotic and agonist efficacies. Pharmacogenomics J. 2006 Jan-Feb;6(1):42-51. doi: 10.1038/sj.tpj.6500342.
18	A novel (benzodifuranyl)aminoalkane with extremely potent activity at the 5-HT2A receptor. J Med Chem. 1998 Dec 17;41(26):5148-9. doi: 10.1021/jm9803525.
19	Serotonin acts as an up-regulator of acyl-coenzyme A:cholesterol acyltransferase-1 in human monocyte-macrophages. Atherosclerosis. 2006 Jun;186(2):275-81. doi: 10.1016/j.atherosclerosis.2005.08.007. Epub 2005 Sep 12.
20	Rose Essential Oil Delayed Alzheimer's Disease-Like Symptoms by SKN-1 Pathway in C. elegans. J Agric Food Chem. 2017 Oct 11;65(40):8855-8865. doi: 10.1021/acs.jafc.7b03224. Epub 2017 Sep 27.
21	Functional identification and molecular cloning of a human brain vesicle monoamine transporter. J Neurochem. 1993 Dec;61(6):2314-7. doi: 10.1111/j.1471-4159.1993.tb07476.x.
22	Selective transport of monoamine neurotransmitters by human plasma membrane monoamine transporter and organic cation transporter 3. J Pharmacol Exp Ther. 2010 Dec;335(3):743-53. doi: 10.1124/jpet.110.170142. Epub 2010 Sep 21.
23	5-Hydroxytryptamine modulates cytokine and chemokine production in LPS-primed human monocytes via stimulation of different 5-HTR subtypes. Int Immunol. 2005 May;17(5):599-606. doi: 10.1093/intimm/dxh242. Epub 2005 Mar 31.
24	Micromolar concentrations of citalopram or escitalopram inhibit glycoprotein VI-mediated and integrin IIb3-mediated signaling in human platelets. Toxicol Appl Pharmacol. 2019 Feb 1;364:106-113. doi: 10.1016/j.taap.2018.12.016. Epub 2018 Dec 25.