Showing Metabocard for D-erythro-1-(imidazol-4-yl)glycerol 3-phosphate (BASm0003339)

Common Name	D-erythro-1-(imidazol-4-yl)glycerol 3-phosphate
Description	D-Erythro-imidazole-glycerol-phosphate belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. D-Erythro-imidazole-glycerol-phosphate is a very strong basic compound (based on its pKa). Outside of the human body, D-erythro-imidazole-glycerol-phosphate has been detected, but not quantified in, several different foods, such as mammee apples, scarlet beans, grass pea, olives, and bog bilberries. This could make D-erythro-imidazole-glycerol-phosphate a potential biomarker for the consumption of these foods. D-Erythro-imidazole-glycerol-phosphate is an intermediate in histidine metabolism. It is a substrate for imidazoleglycerol-phosphate dehydratase (hisB) and can be generated from phosphoribulosylformimino-AICAR-P.
Structure
Molecular Formula	C₆H₁₁N₂O₆P
Average Mass	238.13510
Monoisotopic Mass	238.03547
IUPAC Name	[(2R,3S)-2,3-dihydroxy-3-(1H-imidazol-4-yl)propoxy]phosphonic acid
Traditional Name	(2r,3s)-2,3-dihydroxy-3-(1h-imidazol-4-yl)propoxyphosphonic acid
CAS Registry Number	36244-87-8
SMILES	O=P([O-])([O-])OC[C@@H](O)[C@@H](O)c1c[nH]cn1
InChI Identifier	InChI=1S/C6H11N2O6P/c9-5(2-14-15(11,12)13)6(10)4-1-7-3-8-4/h1,3,5-6,9-10H,2H2,(H,7,8)(H2,11,12,13)/t5-,6+/m1/s1
InChI Key	HFYBTHCYPKEDQQ-RITPCOANSA-N
CHEBI ID	CHEBI:58278
HMDB ID	HMDB0012208
State	Solid
Water Solubility	2.22e+01 g/l
logP	-1.59
logS	-1.03
pKa (Strongest Acidic)	1.48
pKa (Strongest Basic)	5.79
Hydrogen Acceptor Count	6
Hydrogen Donor Count	5
Polar Surface Area	135.9 Å²
Rotatable Bond Count	5
Physiological Charge	-2
Formal Charge	0
Refractivity	48.18 m³·mol⁻¹
Polarizability	19.79

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