Histidine methyl ester

Names
Other names

Methyl L-histidinate, HME

Identifiers

CAS Number

* 1499-46-3 Y
* 7389-87-9 (HCl) N

3D model (JSmol)

* Interactive image

Beilstein Reference

| 957974
ChEBI |

* CHEBI:70961

ChEMBL |

* ChEMBL54664

ChemSpider |

* 83857

EC Number |

* 216-109-3

PubChem CID

* 92893

UNII |

* 9IHZ1723UE Y

InChI

* InChI=1S/C7H11N3O2/c1-12-7(11)6(8)2-5-3-9-4-10-5/h3-4,6H,2,8H2,1H3,(H,9,10)/t6-/m0/s1

Key: BXRMEWOQUXOLDH-LURJTMIESA-N

SMILES

* COC(=O)[C@H](Cc1c[nH]cn1)N

Properties

Chemical formula

| C7H11N3O2
Molar mass | 169.184 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

File:HDC Active Site Diagram.tif Histidine methyl ester (HME) is an irreversible histidine decarboxylase inhibitor.[1][2][3] It is the methyl ester of histidine.

## See also

* Histidine decarboxylase
* Alpha-Fluoromethylhistidine

## References

1. ↑ Lane, Roger S; Manning, James M; Snell, Esmond E (2002). "Histidine decarboxylase of lactobacillus 30a: inactivation and active-site labeling by L-histidine methyl ester". Biochemistry 15 (19): 4180–5. doi:10.1021/bi00664a008. PMID 963031.
2. ↑ Alston, Theodore A; Abeles, Robert H (2002). "Reaction of Lactobacillus histidine decarboxylase with L-histidine methyl ester". Biochemistry 26 (13): 4082–5. doi:10.1021/bi00387a051. PMID 3651438.
3. ↑ Komori, H; Nitta, Y; Ueno, H; Higuchi, Y (2012). "Structural Study Reveals That Ser-354 Determines Substrate Specificity on Human Histidine Decarboxylase". The Journal of Biological Chemistry 287 (34): 29175–83. doi:10.1074/jbc.M112.381897. PMID 22767596.

* v
* t
* e

Monoamine metabolism [[Biology:Enzyme modulator

Non-specific|

| AAAD|

* Substrates→Products: L-DOPA (levodopa)→Dopamine
* 5-HTP→Serotonin
* L-Histidine→Histamine
* [[Chemistry:PhenylPhenylalanine→Phenethylamine|Phenethylamine]]
* L-Tyrosine→Tyramine
* Tryptophan→Tryptamine

* Inhibitors: Benserazide
* Carbidopa
* DFMD
* Genistein
* Methyldopa

|

MAO|

* Substrates→Products (with ALDH/ALR): Epinephrine (adrenaline)→DHMA
* Metanephrine→MHPG/VMA
* Norepinephrine (noradrenaline)→DHMA
* Normetanephrine→MHPG/VMA
* Dopamine→DOPAC
* 3-Methoxytyramine→HVA
* Serotonin→5-HIAA

* Inhibitors: Non-selective: Benmoxin
* Caroxazone
* Echinopsidine
* Furazolidone
* Guineesine
* Hydralazine
* Indantadol
* Iproclozide
* Iproniazid
* Isocarboxazid
* Isoniazid
* Linezolid
* Mebanazine
* Metfendrazine
* Nialamide
* Octamoxin
* Paraxazone
* Phenelzine
* Pheniprazine
* Phenoxypropazine
* Pivhydrazine
* Procarbazine
* Safrazine
* Tranylcypromine

* Inhibitors: MAO-A-selective: Amiflamine
* Bazinaprine
* Befloxatone
* Brofaromine
* Cimoxatone
* Clorgiline
* CX157 (Tyrima)
* Eprobemide
* Esuprone
* Harmala alkaloids (e.g., harmine, harmaline, harman]], norharman, tetrahydroharmine)
* Methylene blue
* Metralindole
* Minaprine
* Moclobemide
* Pirlindole
* Sercloremine
* Tetrindole
* Toloxatone

* Inhibitors: MAO-B selective: Adarigiline
* Almoxatone
* D-Deprenyl
* Ethanol
* Ladostigil
* Lazabemide
* Milacemide
* Mofegiline
* Nicotine
* Pargyline‡
* Rasagiline
* Safinamide
* Selegiline (L-Deprenyl)
* Sembragiline

Phenethylamines
(dopamine, epinephrine]],
norepinephrine)</small>|

| PAH|

* Substrates→Products: [[Chemistry:PhenylPhenylalanine]]→Tyrosine

* Inhibitors: 3,4-Dihydroxystyrene

|

TH|

* Substrates→Products: Tyrosine→L-DOPA (levodopa)

* Inhibitors: 2-Hydroxyestradiol
* 2-Hydroxyestrone
* 3-Iodotyrosine
* Aquayamycin
* Bulbocapnine
* Metirosine
* Oudenone

DBH|

* Substrates→Products: Dopamine→Norepinephrine (Noradrenaline)

* Inhibitors: Bupicomide
* Disulfiram
* Dopastin
* Fusaric acid
* Nepicastat
* Phenopicolinic acid
* Tropolone

PNMT|

* Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine (adrenaline)

* Inhibitors: CGS-19281A
* SKF-64139
* SKF-7698

COMT|

* Substrates→Products: Dopamine→3-Methoxytyramine
* DOPAC→Homovanillic acid
* Norepinephrine→Normetanephrine
* Epinephrine→Metanephrine
* DOPEG→MOPEG
* DOMA→VMA
* 2-Hydroxyestradiol→2-Methoxyestradiol
* [[Chemistry:2-Hydroxy2-Hydroxyestrone]]→2-Methoxyestrone
* 4-Hydroxyestradiol→4-Methoxyestradiol
* [[Chemistry:4-Hydroxy4-Hydroxyestrone]]→4-Methoxyestrone

* Inhibitors: 2-Hydroxyestradiol
* 2-Hydroxyestrone
* Entacapone
* Neluxicapone
* Nitecapone
* Opicapone
* Tolcapone

Tryptamines
(serotonin, melatonin)|

| TPH|

* Substrates→Products: Tryptophan→5-HTP

* Inhibitors: AGN-2979
* Fenclonine (PCPA)
* Telotristat ethyl

|

AANAT|

* Substrates→Products: Serotonin→N-Acetylserotonin

ASMT|

* Substrates→Products: N-Acetylserotonin→Melatonin

Histamine|

| HDC|

* Substrates→Products: L-Histidine→Histamine

* Inhibitors: Catechin
* Alpha-Fluoromethylhistidine
* Histidine methyl ester
* Meciadanol
* Naringenin
* Tritoqualine

|

HNMT|

* Substrates→Products: Histamine→N-Methylhistamine

* Inhibitors: Amodiaquine
* Diphenhydramine
* Harmaline
* Metoprine
* Quinacrine
* SKF-91488
* Tacrine

DAO|

* Substrates→Products: Histamine→Imidazole acetic acid

* Inhibitors: Pimagedine (aminoguanidine)

See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Histidine methyl ester. Read more

|

Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Histidine_methyl_ester&oldid=494374"
*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[AAAD]: Aromatic L-amino acid decarboxylase
*[MAO]: Monoamine oxidase
*[ALDH]: Aldehyde dehydrogenase
*[ALR]: Aldehyde reductase
*[PAH]: Phenylalanine hydroxylase
*[TH]: Tyrosine hydroxylase
*[DBH]: Dopamine beta-monooxygenase
*[PNMT]: Phenylethanolamine N-methyltransferase
*[COMT]: Catechol-O-methyl transferase
*[TPH]: Tryptophan hydroxylase
*[AANAT]: Serotonin N-acetyl transferase
*[ASMT]: Acetylserotonin O-methyltransferase
*[HDC]: Histidine decarboxylase
*[HNMT]: Histamine N-methyltransferase
*[DAO]: Diamine oxidase