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5,6-Dihydroxytryptamine; 5-Me ether, Nb-Ac 

AlkaPlorer ID: AK045255

Synonym: 6-Hydroxymelatonin

IUPAC Name: N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide

Structure

SMILES: COC1=CC2=C(C=C1O)NC=C2CCN=C(C)O

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InChI: InChI=1S/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)

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InChIKey: OMYMRCXOJJZYKE-UHFFFAOYSA-N

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Reference

PubChem CID: 1864

CAS: 2208-41-5

LOTUS: LTS0061138

NPASS: NPC316981

COCONUT: CNP0349869

Properties Information

Molecule Weight: 248.28199999999995

TPSA？: 77.84

MolLogP？: 2.401

Number of H-Donors: 3

Number of H-Acceptors: 3

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Equus caballus Ferritin light chain Potency 44668.4 nM None
Gallus gallus Melatonin receptor pRA -1.42 None 10.1021/jm9810093
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 7062.7 nM None
Homo sapiens 15-hydroxyprostaglandin dehydrogenase [NAD+] Potency 39810.7 nM None
Homo sapiens Arachidonate 15-lipoxygenase, type II Potency 12589.3 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 29081.0 nM None
Homo sapiens Cerebroside-sulfatase Potency 37933.0 nM None
Homo sapiens Cytochrome P450 1A2 AC50 31622.78 nM None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2D6 AC50 39810.72 nM None
Homo sapiens Cytochrome P450 2D6 Potency 39810.7 nM None
Homo sapiens Cytochrome P450 3A4 AC50 15848.93 nM None
Homo sapiens Cytochrome P450 3A4 Potency 15848.9 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 39810.7 nM None
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 31622.8 nM None
Homo sapiens Flap endonuclease 1 Potency 8436.8 nM None
Homo sapiens Geminin Potency 112.2 nM None
Homo sapiens Glutaminase kidney isoform, mitochondrial Potency 12589.3 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 22.4 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 19952.6 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 35481.3 nM None
Homo sapiens Melatonin receptor 1A Ki 40.2 nM 10.1016/j.ejmech.2019.111847
Homo sapiens Melatonin receptor 1B Ki 5.5 nM 10.1016/j.ejmech.2019.111847
Homo sapiens M-phase phosphoprotein 8 Potency 125.9 nM None
Homo sapiens Neuropeptide S receptor Potency 10000.0 nM None
Homo sapiens Rac GTPase-activating protein 1 IC50 52260.0 nM None
Homo sapiens Regulator of G-protein signaling 4 Potency 18887.6 nM None
Homo sapiens Serine hydroxymethyltransferase, mitochondrial Inhibition 92.7 % None
Homo sapiens UDP-glucuronosyltransferase 1-10 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 1-7 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B7 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Plasmodium falciparum Plasmodium falciparum Potency 9285.0 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 4228.4 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 31622.8 nM None
None NON-PROTEIN TARGET Potency 10000.0 nM None
None NON-PROTEIN TARGET Potency 17782.8 nM None
None Unchecked IC50 50670.0 nM None
None Unchecked Inhibition nan % 10.1038/nchembio873
None Unchecked Potency 4107.8 nM None
None Unchecked Potency 4466.8 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT011620 COc1cc2c(CCNC(C)=O)c[nH]c2cc1O.O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>COc1cc2c(CCNC(C)=O)c[nH]c2cc1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O enzymemap_34696
AKRT011621 COc1cc2c(CCNC(C)=O)c[nH]c2cc1O>>COc1cc2c(CCNC(C)=O)c[nH]c2cc1OS(=O)(=O)O RXN-11058
AKRT011859 COc1ccc2[nH]cc(CCNC(C)=O)c2c1>>COc1cc2c(CCNC(C)=O)c[nH]c2cc1O RXN-11056