Metabolic intermediates refers to molecules which are the precursors or metabolites of biologically significant molecules.

Although these intermediates are of relatively minor direct importance to cellular function, they can play important roles in the allosteric regulation of enzymes.

[edit] Clinical significance

Some can be useful in measuring rates of metabolic processes (for example, Dopac or 3-aminoisobutyrate).

Because they can represent unnatural points of entry into natural metabolic pathways, some (such as AICA ribonucleotide) are of interest to researchers in developing new therapies.

[edit] See also

• metabolism

This chemistry article is a stub. You can help Wikipedia by expanding it. v • d • e

v • d • e Fructose and galactose metabolic intermediates Fructose Fructose-1-phosphate → DHAP/Glyceraldehyde → Glyceraldehyde 3-phosphate Galactose Galactose-1-phosphate → Glucose 1-phosphate → Glucose 6-phosphate → Fructose 6-phosphate Uridine diphosphate galactose · Uridine diphosphate glucose Galactitol · Iditol Mannose Mannose-6-phosphate → Fructose 6-phosphate see also enzymes, disorders

v • d • e Glycogenesis and glycogenolysis metabolic intermediates Glucose Glucose 6-phosphate · Glucose 1-phosphate Uridine Uridine diphosphate glucose · Uridine triphosphate Other Glycogen · Limit dextran see also enzymes, disorders

v • d • e Pentose phosphate pathway metabolic intermediates Oxidative 6-Phosphogluconolactone · 6-Phosphogluconate · Ribulose 5-phosphate · Ribose 5-phosphate Nonoxidative Xylulose 5-phosphate · Sedoheptulose 7-phosphate · Erythrose 4-phosphate see also enzymes, disorders

v • d • e Cholesterol and steroid metabolic intermediates Mevalonate pathway to HMG-CoA Acetyl-CoA · Acetoacetyl-CoA · HMG-CoA Ketone bodies Acetone · Acetoacetic acid · beta-Hydroxybutyric acid to DMAPP Mevalonic acid · Phosphomevalonic acid · 5-Diphosphomevalonic acid · Isopentenyl pyrophosphate · Dimethylallyl pyrophosphate Geranyl- Geranyl pyrophosphate · Geranylgeranyl pyrophosphate Carotenoid Prephytoene diphosphate · Phytoene Non-mevalonate pathway DOXP · MEP · CDP-ME · CDP-MEP · MEcPP · HMB-PP · IPP · DMAPP To Cholesterol Farnesyl pyrophosphate · Squalene · 2,3-Oxidosqualene · Lanosterol Lanosterol · Lathosterol · 7-Dehydrocholesterol · Cholesterol Lanosterol · Zymosterol · 7-Dehydrodesmosterol · Desmosterol · Cholesterol Steroid Corticosteroids (C21 pregnane) Mineralocorticoids Pregnenolone · Progesterone · 11-Deoxycorticosterone · Corticosterone · Aldosterone Glucocorticoids Pregnenolone · 17-Hydroxypregnenolone · 17-Hydroxyprogesterone · 11-Deoxycortisol · Cortisol Cortisol · Cortisone Sex steroids Androgens (C19 andrane) DHEA · Androstenedione/5-Androstenediol · Testosterone · Dihydrotestosterone DHEA sulfate · Epitestosterone Estrogens (C18 estrane) Estrone · Estradiol · Estriol Nonhuman Phytosterols Stigmasterol · Brassicasterol Ergosterols Ergosterol · Ergocalciferol see also enzymes, disorders Major families of biochemicals Saccharides/Carbohydrates/Glycosides · Amino acids/Peptides/Proteins/Glycoproteins · Lipids/Terpenes/Steroids/Carotenoids · Alkaloids/Nucleobases/Nucleic acids · Cofactors/Phenylpropanoids/Polyketides/Tetrapyrroles

v • d • e Amino acid metabolism metabolic intermediates K→acetyl-CoA lysine→ Saccharopine · Allysine · α-Aminoadipic acid · α-Aminoadipate · Glutaryl-CoA · Glutaconyl-CoA · Crotonyl-CoA · β-Hydroxybutyryl-CoA leucine→ α-Ketoisocaproic acid · Isovaleryl-CoA · 3-Methylcrotonyl-CoA · 3-Methylglutaconyl-CoA · HMG-CoA tryptophan→alanine→ N'-Formylkynurenine · Kynurenine · Anthranilic acid · 3-Hydroxykynurenine · 3-Hydroxyanthranilic acid · 2-Amino-3-carboxymuconic semialdehyde · 2-Aminomuconic semialdehyde · 2-Aminomuconic acid · Glutaryl-CoA G G→pyruvate→citrate glycine→serine→ 3-Phosphoglyceric acid glycine→creatine: Glycocyamine · Phosphocreatine · Creatinine G→glutamate→ α-ketoglutarate histidine→ Urocanic acid · Imidazol-4-one-5-propionic acid · Formiminoglutamic acid · Glutamate-1-semialdehyde proline→ 1-Pyrroline-5-carboxylic acid arginine→ Ornithine · Putrescine · Agmatine other cysteine+glutamate→glutathione: γ-Glutamylcysteine G→propionyl-CoA→ succinyl-CoA valine→ α-Ketoisovaleric acid · Isobutyryl-CoA · Methacrylyl-CoA · 3-Hydroxyisobutyryl-CoA · 3-Hydroxyisobutyric acid · 2-Methyl-3-oxopropanoic acid isoleucine→ 2,3-Dihydroxy-3-methylpentanoic acid · 2-Methylbutyryl-CoA · Tiglyl-CoA · 2-Methylacetoacetyl-CoA methionine→ generation of homocysteine: S-Adenosyl methionine · S-Adenosyl-L-homocysteine · Homocysteine conversion to cysteine: Cystathionine · alpha-Ketobutyric acid+Cysteine threonine→ α-Ketobutyric acid propionyl-CoA→ Methylmalonyl-CoA G→fumarate phenylalanine→tyrosine→ 4-Hydroxyphenylpyruvic acid · Homogentisic acid · 4-Maleylacetoacetate G→oxaloacetate see urea cycle Other Cysteine metabolism Cysteine sulfinic acid see also enzymes, disorders

v • d • e Nucleotide metabolic intermediates Purine metabolism Anabolism R5P→IMP: R5P · PRPP · PRA · GAR · FGAR · FGAM · AIR · CAIR · SAICAR · AICAR · FAICAR IMP→AMP: Adenylosuccinate IMP→GMP: Xanthosine monophosphate Catabolism Hypoxanthine · Xanthine · Uric acid · 5-Hydroxyisourate Pyrimidine metabolism Anabolism Carbamoyl phosphate · Carbamoyl aspartic acid · 4,5-Dihydroorotic acid · Orotic acid · Orotidine 5'-monophosphate · Uridine monophosphate Catabolism uracil: Dihydrouracil · 3-Ureidopropionic acid · β-Alanine thymine: Dihydrothymine · β-Ureidoisobutyric acid · 3-Aminoisobutyric acid see also enzymes, disorders

v • d • e Neurotransmitter metabolic intermediates catecholamines Anabolism (tyrosine→epinephrine) Tyrosine → Levodopa → Dopamine → Norepinephrine → Epinephrine Catabolism/ metabolites dopamine: DOPAL · DOPAC · MOPET · Hydroxytyrosol · 3-Methoxytyramine · Homovanillic acid norepinephrine: 3,4-Dihydroxymandelic acid · Normetanephrine · Vanillylmandelic acid · 3-Methoxy-4-hydroxyphenylglycol · Dihydroxyphenylethylene glycol epinephrine: Metanephrine tryptophan→serotonin anabolism: 5-Hydroxytryptophan catabolism: 5-Hydroxyindoleacetic acid serotonin→melatonin Normelatonin see also enzymes

v • d • e Heme metabolic intermediates Porphyrin biosynthesis early mitochondrial: D-Aminolevulinic acid cytosolic: Porphobilinogen · Hydroxymethylbilane · Uroporphyrinogen III · Coproporphyrinogen III late mitochondrial: Protoporphyrinogen IX · Protoporphyrin IX Heme degradation and excretion Breakdown of heme spleen: Heme → Biliverdin → Bilirubin blood: Bilirubin+Albumin liver: Bilirubin diglucuronide Intestine, excretion in feces Stercobilinogen · Stercobilin · Urobilinogen Kidney, excretion in urine Urobilin see also disorders, enzymes

v • d • e Thyroid hormone metabolic intermediates Tyrosine / iodotyrosine Monoiodotyrosine · Diiodotyrosine Thyronine / iodothyronine 3'-Monoiodothyronine · 3,3'-Diiodothyronine · 3,3',5-Triiodothyronine (T3) · 3,3',5'-Triiodothyronine (Reverse T3) · 3,5,3',5'-Tetra­iodothyronine (Thyroxine, T4) Thyronamine / iodothyronamine 3-Iodothyronamine · 3,3',5-Triiodothyronamine see also enzymes