Cholesterol metabolism with Bloch and Kandutsch-Russell pathways (WP4346)

Mus musculus

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This pathway is inspired by the Lipidmaps>Sterol lipids expended pathway display [https://lipidmaps.org/pathway/pathways_maps] and extended with Scheme 1 from Acimovic et al (2013 [https://www.ncbi.nlm.nih.gov/pubmed/23558541]). Literature suggests that cholesterol synthesis preferentially starts with the Bloch pathway, however there is a shift to the Kandutsch-Russell part via lathosterol (Bae et al, 1997[https://www.ncbi.nlm.nih.gov/pubmed/9291139]). Dashed lines indicate that multiple steps are involved to create the final product. Several regulatory effects concerning the metabolites of cholesterol have been indicated as well. The content from the Bloch and Kandutsch-Russel pathways have been checked against literature, and differences compared to the original LipidMaps pathway have been coloured turquoise.

Authors

Eoin Fahy , Ryan Miller , Denise Slenter , Egon Willighagen , Conroy lipids , and Eric Weitz

Activity

last edited

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Organisms

Mus musculus

Communities

Lipids and LIPID MAPS

Annotations

Pathway Ontology

lipid signaling pathway cholesterol biosynthetic pathway cholesterol metabolic pathway

Participants

Label Type Compact URI Comment
9Z-palmitoleic acid Metabolite lipidmaps:LMFA01030056 Assuming this is omega 7-type
7alpha-hydroxycholesterol Metabolite lipidmaps:LMST01010013
3beta-hydroxylanost-8-en-32-al Metabolite lipidmaps:LMST01010223
Zymosterone Metabolite lipidmaps:LMST01010168
Acetyl-CoA Metabolite lipidmaps:LMFA07050281
4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol Metabolite lipidmaps:LMST01010229
Zymostenone Metabolite lipidmaps:LMST01010239
32-Oxolanosterol Metabolite lipidmaps:LMST01010222
4α-formyl-5α-cholesta-8-en-3β-ol Metabolite lipidmaps:LMST01010231
lanost-8-en-3beta,30-diol Metabolite lipidmaps:LMST01010224
4α-formyl-5α-cholesta-8,24-dien-3β-ol Metabolite lipidmaps:LMST01010226
4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol Metabolite lipidmaps:LMST01010233
4α-carboxy-5α-cholesta-8-en-3β-ol Metabolite lipidmaps:LMST01010228
CE(16:1) Metabolite wikidata:Q412366 Assuming this is omega-7 type
4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol Metabolite lipidmaps:LMST01010232
3-keto-4alpha-methyl-zymosterol Metabolite lipidmaps:LMST01010237
4α-hydroxymethyl-5α-cholesta-8-en-3β-ol Metabolite lipidmaps:LMST01010235
4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol Metabolite lipidmaps:LMST01010234
IPP Metabolite lipidmaps:LMPR01010008
4α-carboxyzymosterol Metabolite lipidmaps:LMST01010522
4α-formyl-4β-methyl-5α-cholesta-8-en-3β-ol Metabolite lipidmaps:LMST01010230
Acetoacetyl-CoA Metabolite lipidmaps:LMFA07050030
HMG-CoA Metabolite lipidmaps:LMFA07050116
Mevalonic acid Metabolite lipidmaps:LMFA01050352
Mevalonate-5-P Metabolite lipidmaps:LMFA01050415
Mevalonate-5-PP Metabolite lipidmaps:LMFA01050416
Isopentenyl-PP Metabolite lipidmaps:LMPR01010008
Dimethylallyl-PP Metabolite lipidmaps:LMPR01010001
Geranyl-PP Metabolite lipidmaps:LMPR0102010001
Farnesyl-PP Metabolite lipidmaps:LMPR0103010002
Squalene Metabolite lipidmaps:LMPR0106010002
Squalene-2,3-epoxide Metabolite lipidmaps:LMPR0106010010
Diepoxy-squalene Metabolite lipidmaps:LMPR0106010038
Lanosterol Metabolite lipidmaps:LMST01010017
24,25-epoxycholesterol Metabolite lipidmaps:LMST01010012
24,25-dihydrolanosterol Metabolite lipidmaps:LMST01010087
32-hydroxylanosterol Metabolite lipidmaps:LMST01010124
4,4-dimethylcholesta-8,11,24-trienol Metabolite lipidmaps:LMST01010149
4,4-dimethylcholest-8-enol Metabolite lipidmaps:LMST01010225
14-demethyl-lanosterol Metabolite lipidmaps:LMST01010176
Zymosterol Metabolite lipidmaps:LMST01010066
4-alpha-methyl-cholest-8-enone Metabolite lipidmaps:LMST01010236
Zymostenol Metabolite lipidmaps:LMST01010096
Lathosterol Metabolite lipidmaps:LMST01010089
7-dehdrocholesterol Metabolite lipidmaps:LMST01010069
Cholestadienol Metabolite lipidmaps:LMST01010206 aka 24-dehydrolathosterol
7-dehydodesmosterol Metabolite lipidmaps:LMST01010121
Desmosterol Metabolite lipidmaps:LMST01010016
Cholesterol Metabolite lipidmaps:LMST01010001
7-oxocholesterol Metabolite lipidmaps:LMST01010049
Cholestenone Metabolite lipidmaps:LMST01010015
4beta-hydroxycholesterol Metabolite lipidmaps:LMST01010014
24S-hydroxycholesterol Metabolite lipidmaps:LMST01010019
25-hydroxycholesterol Metabolite lipidmaps:LMST01010018
27-hydroxycholesterol Metabolite lipidmaps:LMST01010057
Cholesteryl esters (CE) Metabolite lipidmaps:LMST01020000
Acyl-CoA Metabolite lipidmaps:LMFA07050000
PreSqualene-PP Metabolite lipidmaps:LMPR0106010003 Annotated while assuming this compound is actually presqualene-diphosphate
CE(18:1) Metabolite wikidata:Q27116670 Assuming this is omega-7 type
Oleic acid Metabolite lipidmaps:LMFA01030002 Aka C18:1 (omega 9)
4alpha-methylcholest-8-en-3beta-ol Metabolite lipidmaps:LMST01010197
4-methyl-4-carboxyzymostenone Metabolite lipidmaps:LMST01010227 C12CC[C@@]3([H])C(C)(COOH)[C@@H](O)CC[C@]3(C)C=1CC[C@]1(C)[C@@]([H])([C@@](C)([H])CC/CC(\C)/C)CC[C]21H
4,4-dimethylcholesta-8,14-dienol Metabolite lipidmaps:LMST01010277 C12CC[C@@]3([H])C(C)(C)[C@@H](O)CC[C@]3(C)C=1CC[C@]1(C)[C@@]([H])([C@@](C)([H])CC/CC(\C)/C)CC=[C@@]21C
IPP Metabolite lipidmaps:LMPR01010008
Acetyl-CoA Metabolite lipidmaps:LMFA07050281
4-methyl-4-carboxyzymosterone Metabolite lipidmaps:LMST01010388 C12CC[C@@]3([H])C(C)(COOH)[C@@H](O)CC[C@]3(C)C=1CC[C@]1(C)[C@@]([H])([C@@](C)([H])CC/C=C(\C)/C)CC[C]21H
4alpha-methyl zymosterol Metabolite lipidmaps:LMST01010202 C12CC[C@@]3([H])C(C)[C@@H](O)CC[C@]3(C)C=1CC[C@]1(C)[C@@]([H])([C@@](C)([H])CC/C=C(\C)/C)CC[C]21H
Srebf1 GeneProduct ensembl:ENSMUSG00000020538
Acat1 GeneProduct uniprot:Q8QZT1
Abca1 GeneProduct ensembl:ENSMUSG00000015243
Ch25h GeneProduct ncbigene:12642
Hmgcr GeneProduct ncbigene:15357
Cyp7a1 GeneProduct uniprot:Q64505
Nr1h3 GeneProduct ensembl:ENSMUSG00000002108
Soat1 GeneProduct ncbigene:20652
Fasn GeneProduct ensembl:ENSMUSG00000025153
Dhcr7 GeneProduct ncbigene:13360
Sc5d GeneProduct ncbigene:235293
Ebp GeneProduct ncbigene:13595
Tm7fs2 GeneProduct ncbigene:73166
Cyp46a1 GeneProduct ncbigene:13116
Cyp27a1 GeneProduct ncbigene:104086
Soat2 GeneProduct ncbigene:223920
Acat2 GeneProduct uniprot:Q8CAY6
Hmgcs1 GeneProduct ncbigene:208715
Hmgcs2 GeneProduct ncbigene:15360
Mvk GeneProduct ncbigene:17855
Pmvk GeneProduct ncbigene:68603
Mvd GeneProduct ncbigene:192156
Sqle GeneProduct ncbigene:20775
Idi1 GeneProduct ncbigene:319554
Idi2 GeneProduct ncbigene:320581
Fdft1 GeneProduct ncbigene:14137
Ggps1 GeneProduct ncbigene:14593
Fdps GeneProduct ncbigene:110196
Lss GeneProduct ncbigene:16987
Dhcr7 GeneProduct ncbigene:13360
Dhcr24 GeneProduct ncbigene:74754
Nr1h2 GeneProduct ensembl:ENSMUSG00000060601
Abcg1 GeneProduct ensembl:ENSMUSG00000024030
Mylip (IDOL) GeneProduct ensembl:ENSMUSG00000038175
Srebf2 GeneProduct ensembl:ENSMUSG00000022463
Acsl1 GeneProduct ensembl:ENSMUSG00000018796
Acsl3 GeneProduct ensembl:ENSMUSG00000032883
Acsl4 GeneProduct ensembl:ENSMUSG00000031278
Acot1 GeneProduct ensembl:ENSMUSG00000072949
Acot2 GeneProduct ensembl:ENSMUSG00000021226
Nsdhl GeneProduct uniprot:Q9R1J0
Dhcr24 Protein uniprot:Q8VCH6
Elovl2 Protein ensembl:ENSMUSG00000021364
Elovl3 Protein ensembl:ENSMUSG00000038754
Elovl4 Protein ensembl:ENSMUSG00000032262
Elovl5 Protein ensembl:ENSMUSG00000032349
Fads1 Protein ensembl:ENSMUSG00000010663
Fads2 Protein ensembl:ENSMUSG00000024665
Scd1 Protein ensembl:ENSMUSG00000037071
Scd2 Protein uniprot:P13011
Cyp51A1 Protein uniprot:Q8K0C4
Tm7sf2 Protein uniprot:Q71KT5
Msmo1 Protein uniprot:Q9CRA4
Lbr Protein uniprot:Q3U9G9
Cyp51A1 Protein uniprot:Q8K0C4
Hsd17b7 Protein ncbigene:15490
Nsdhl Protein uniprot:Q9R1J0
Msmo1 Protein uniprot:Q9CRA4
Hsd17b7 Protein ncbigene:15490
Cyp51A1 Protein uniprot:Q8K0C4

References

  1. Cholesterol biosynthesis from lanosterol: development of a novel assay method and characterization of rat liver microsomal lanosterol delta 24-reductase. Bae SH, Paik YK. Biochem J. 1997 Sep 1;326 ( Pt 2)(Pt 2):609–16. PubMed Europe PMC Scholia
  2. A mouse macrophage lipidome. Dennis EA, Deems RA, Harkewicz R, Quehenberger O, Brown HA, Milne SB, et al. J Biol Chem. 2010 Dec 17;285(51):39976–85. PubMed Europe PMC Scholia
  3. Liver x receptor modulation of gene expression leading to proluteolytic effects in primate luteal cells. Bogan RL, Debarber AE, Hennebold JD. Biol Reprod. 2012 Mar 30;86(3):89. PubMed Europe PMC Scholia
  4. Steroidal triterpenes of cholesterol synthesis. Ačimovič J, Rozman D. Molecules. 2013 Apr 4;18(4):4002–17. PubMed Europe PMC Scholia
  5. A comprehensive machine-readable view of the mammalian cholesterol biosynthesis pathway. Mazein A, Watterson S, Hsieh WY, Griffiths WJ, Ghazal P. Biochem Pharmacol. 2013 Jul 1;86(1):56–66. PubMed Europe PMC Scholia