HMG-Co A - Ketogenesis Pathway

Ketogenesis Pathway

HMG-CoA lyase breaks it into acetyl CoA and acetoacetate.

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

From Cholesterol (to steroids)

22R-Hydroxycholesterol
20α,22R-Dihydroxycholesterol

Steroid hormones

Corticosteroids
(C21 pregnane)

Mineralocorticoids

Pregnenolone
Progesterone
Cortodoxone
Corticosterone
Aldosterone

Glucocorticoids

Pregnenolone
17-Hydroxypregnenolone
17-Hydroxyprogesterone
Cortisol

Cortisol
Cortisone

Sex steroids

Androgens
(C19 androstane)

DHEA
Androstenedione/5-Androstenediol
Testosterone
Dihydrotestosterone

DHEA sulfate
Epitestosterone

Estrogens
(C18 estrane)

Estetrol
Estrone
Estradiol
Estriol

Nonhuman

Phytosterols	Stigmasterol Brassicasterol

Ergosterols	Ergosterol Ergocalciferol

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

M: END

anat/phys/devp/horm

noco (d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

biochemical families: carbohydrates
- alcohols
- glycoproteins
- glycosides
lipids
- eicosanoids
- fatty acids / intermediates
- phospholipids
- sphingolipids
- steroids
nucleic acids
- constituents / intermediates
proteins
- amino acids / intermediates
tetrapyrroles / intermediates

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→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

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

biochemical families: carbohydrates
- alcohols
- glycoproteins
- glycosides
lipids
- eicosanoids
- fatty acids / intermediates
- phospholipids
- sphingolipids
- steroids
nucleic acids
- constituents / intermediates
proteins
- amino acids / intermediates
tetrapyrroles / intermediates

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