Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1018)
Drug Name	Melatonin
Synonyms	Melatonex; Melatonin; Melatonine; Melovine; Circadin; JL5DK93RCL; Melatol; N-Acetyl-5-methoxytryptamine; N-acetyl-5-methoxy-tryptamine; 5-Methoxy-N-acetyltryptamine; 73-31-4; Acetamide, N-(2-(5-methoxyindol-3-yl)ethyl)-; Acetamide, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-; BRN 0205542; CCRIS 3472; CHEMBL45; EINECS 200-797-7; N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide; N-(2-(5-Methoxyindol-3-yl)ethyl)acetamide; N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide; N-[2-(5-methoxyindol-3-yl)ethyl]acetamide; NSC 113928; UNII-JL5DK93RCL
Indication	Foetal growth restriction [ICD11: KA20]			Phase 4	[1]
Structure
Structure	3D MOL		2D MOL
Pharmaceutical Properties	Molecular Weight	232.28	Topological Polar Surface Area		54.1
	Heavy Atom Count	17	Rotatable Bond Count		4
	Hydrogen Bond Donor Count	2	Hydrogen Bond Acceptor Count		2
Cross-matching ID	PubChem CID 896 PubChem SID 2961 ; 4752 ; 105815 ; 410775 ; 798411 ; 841969 ; 893664 ; 3133753 ; 4906256 ; 7636333 ; 7961516 ; 7979886 ; 8144655 ; 8149639 ; 8150851 ; 10321385 ; 10534170 ; 10589869 ; 11111467 ; 11111468 ; 11111469 ; 11221066 ; 11335528 ; 11360767 ; 11363079 ; 11365641 ; 11368203 ; 11372325 ; 11373730 ; 11376365 ; 11408768 ; 11461739 ; 11466486 ; 11467606 ; 11485263 ; 11486211 ; 11489160 ; 11491208 ; 11491881 ; 11493999 ; 11536797 ; 11537588 ; 14773848 ; 17388930 ; 17389536 ; 17405348 ; 24278103 ; 24439254 ; 26612030 ; 26679682 ChEBI ID ChEBI:16796 CAS Number 73-31-4 TTD Drug ID D0AN7B Formula C13H16N2O2 Canonical SMILES CC(=O)NCCC1=CNC2=C1C=C(C=C2)OC InChI 1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16) InChIKey DRLFMBDRBRZALE-UHFFFAOYSA-N

The Metabolic Roadmap of This Drug

The Full List of Drug Metabolites (DM) of This Drug

DM Name	DM ID	PubChem ID	Reaction	DM Level	REF
5-Methoxytryptamine	DM002635	1833	Oxidation - Deacetylation	1	[8]
6-hydroxymelatonin	DM002638	1864	Oxidation - 6-Hydroxylation	1	[8]
Dihydroxy ketobemidone	DM002577	85992903	Oxidation - O-Demethylation	1	[8]
6-hydroxymelatonin sulfate metabolite	DM002639	65096	Other reaction - Sulfonation	2	[8]
Bufotenine	DM002636	10257	Conjugation - Methylation	2	[8]
N-Acetyl-5-hydroxytryptamine glucuronide metabolite	DM002640	154699571	Conjugation - Glucuronidation	2	[8]
N-Acetyl-5-hydroxytryptamine sulfate metabolite	DM002641	45479248	Other reaction - Sulfonation	2	[8]
Pinoline	DM002642	1868	Unclear	2	[8]
N,N-Dimethyltryptamine	DM002637	6089	Unclear	3	[8]

The Full List of Metabolic Reaction (MR) of This Drug

MR ID	Reactant	Product	MR Type	DME	REF
MR003315	Melatonin	Dihydroxy ketobemidone	Oxidation - O-Demethylation	CYP1A2 ...	[8]
MR003316	Melatonin	5-Methoxytryptamine	Oxidation - Deacetylation	Unclear	[8]
MR003317	Melatonin	6-hydroxymelatonin	Oxidation - 6-Hydroxylation	CYP1A1 ...	[8]
MR003311	5-Methoxytryptamine	Bufotenine	Conjugation - Methylation	Unclear	[8]
MR003312	5-Methoxytryptamine	Pinoline	Unclear	Unclear	[8]
MR003314	6-hydroxymelatonin	6-hydroxymelatonin sulfate metabolite	Other reaction - Sulfonation	Unclear	[8]
MR003309	Dihydroxy ketobemidone	N-Acetyl-5-hydroxytryptamine glucuronide metabolite	Conjugation - Glucuronidation	UGT	[8]
MR003310	Dihydroxy ketobemidone	N-Acetyl-5-hydroxytryptamine sulfate metabolite	Other reaction - Sulfonation	Unclear	[8]
MR003313	Bufotenine	N,N-Dimethyltryptamine	Unclear	Unclear	[8]


⏷ Show the Full List of 9 MR(s)

Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug

DME Name	DME Info	Species	Uniprot ID	EC Number	REF
Cytochrome P450 1A1 (CYP1A1)	DME0006	Homo sapiens	CP1A1_HUMAN	1.14.14.1	[2]
Cytochrome P450 1A2 (CYP1A2)	DME0003	Homo sapiens	CP1A2_HUMAN	1.14.14.1	[3]
Cytochrome P450 1B1 (CYP1B1)	DME0023	Homo sapiens	CP1B1_HUMAN	1.14.14.1	[2]
Cytochrome P450 2C9 (CYP2C9)	DME0019	Homo sapiens	CP2C9_HUMAN	1.14.14.1	[4]
Hydroxyindole O-methyltransferase (ASMT)	DME0182	Homo sapiens	ASMT_HUMAN	2.1.1.4	[5]
Indoleamine 2,3-dioxygenase 1 (IDO1)	DME0171	Homo sapiens	I23O1_HUMAN	1.13.11.52	[6]
Mephenytoin 4-hydroxylase (CYP2C19)	DME0021	Homo sapiens	CP2CJ_HUMAN	1.14.14.1	[7]


⏷ Show the Full List of 7 DME(s)

References
1	ClinicalTrials.gov (NCT01695070) Melatonin to Prevent Brain Injury in Unborn Growth Restricted Babies.
2	Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94.
3	Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. Eur J Pharm Sci. 2005 Jan;24(1):123-32.
4	New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126.
5	The pharmacology of the pineal gland. Annu Rev Pharmacol Toxicol. 1976;16:33-51.
6	Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15.
7	The effect of CYP2C19 substrate on the metabolism of melatonin in the elderly: a randomized, double-blind, placebo-controlled study. Methods Find Exp Clin Pharmacol. 2006 Sep;28(7):447-50.
8	Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.

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