cholesterol
Sterol biosynthesized by all animal cells which is an essential structural component of all animal cell membranes
Also known as cholest-5-en-3β-ol · Cholesterin · Hydrocerin · Cholest-5-en-3b-ol · Cordulan · Cholesterine
- Formula
- C₂₇H₄₆O
1
- C₂₇H₄₆O
- Mass
- 386.3549 Da
- Melting point
- 149°C
1
- , 148°C
1
- 149°C
- Boiling point
- 200°C
Overview
Chemistry
All data
764 statements · 87% with external sources · numbers in brackets are citations
- Canonical SMILES
- CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
1
- CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
- Isomeric SMILES
- C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
1
- C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
- Found in taxon
- Homo sapiens
- Eryngium foetidum
- Diplotaxis harra
- Erucaria microcarpa
- Ciona intestinalis
1
- Aloe vera
- Rauvolfia serpentina
- Apostichopus japonicus
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- Acanthaster planci
- Phoenix canariensis
1
- Tamarix gallica
- Citrus unshiu
1
- Dioscorea nelsonii
- Dioscorea bartlettii
- Dioscorea floribunda
- Dioscorea convolvulacea
- Baccharoides anthelmintica
- Leptogorgia piccola
- Ellisella paraplexauroides
- Eunicella labiata
- Leptogorgia ruberrima
- Leptogorgia viminalis
- Leptogorgia violetta
- Cinachyrella alloclada
- Cinachyrella schulzei
- Lolium perenne
- Dioscorea dumetorum
1
- Sweet potato
1
- Saccharomyces cerevisiae
1
- Crassostrea virginica
1
- Dictyuchus monosporus
- Avicennia officinalis
- Acanthus ilicifolius
- Bruguiera gymnorrhiza
- Ceriops decandra
- Derris trifoliata
- Rhizophora mucronata
- Suaeda maritima
- Ulva rigida
1
- Apis mellifera
- Solanum nigrum
- Cliona chilensis
1
- Amaranthus caudatus
- Amaranthus hypochondriacus
1
- Amaranthus leucocarpus
1
- Amaranthus tricolor
2
Sources- 1.Stated in Sterols of amaranthaceae
- 2.Stated in Phytosterols: Wide-Spectrum Antibacterial Agents
- Amaranthus cruentus
1
- Amaranthus retroflexus
1
- Saduria entomon
- Sorghum bicolor
3
Sources- 1.Stated in Varietal similarities and differences in the polycyclic isopentenoid composition of sorghum
- 2.Stated in The biosynthesis, metabolism and translocation of β-amyrin in Sorghum bicolor
- 3.Stated in Varietal similarities and differences in the polycyclic isopentenoid composition of sorghum
- Spongionella gracilis
- Hylocereus undatus
- Pereskia aculeata
- Schlumbergera bridgesii
- Oryza coarctata
- Yucca gloriosa
1
- Clerodendrum scandens
2
Sources- 1.Stated in Sterols of some Clerodendrum species (Verbenaceae): occurrence of the 24 alpha- and 24 beta-epimers of 24-ethylsterols lacking a delta 25-bond
- 2.Stated in (22Z,24S)-Stigmasta-5,22,25-trien-3β-ol and other novel sterols from Clerodendrum scandens: first report of the isolation of a cis-Δ22-unsaturated sterol from a higher plant
- Clerodendrum infortunatum
- Macoma balthica
- Chara australis
1
- Physically interacts with
- RAR related orphan receptor A subject has role: agonist
1
- RAR related orphan receptor A subject has role: agonist
- Subject has role
- precursor applies to part: vitamin D
- primary metabolite
- Part of
- cholesterol binding subject has role: reactant
1
- cholesterol biosynthetic process subject has role: product
1
- cholesterol catabolic process subject has role: reactant
1
- response to cholesterol subject has role: reactant
1
- cellular response to cholesterol subject has role: reactant
1
- intestinal cholesterol absorption subject has role: cargo
1
- cholesterol transport subject has role: cargo
1
- lysosome to ER cholesterol transport subject has role: cargo
1
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- cholesterol transfer activity subject has role: cargo
1
- triglyceride-rich plasma lipoprotein particle
1
- cholesterol efflux subject has role: cargo
1
- cholesterol import subject has role: cargo
1
- cholesterol metabolic process subject has role: participant
1
- cholesterol biosynthetic process via 24,25-dihydrolanosterol subject has role: product
1
- cholesterol biosynthetic process via desmosterol subject has role: product
1
- cholesterol biosynthetic process via lathosterol subject has role: product
1
- cholesterol homeostasis subject has role: process variable
1
- cholesterol O-acyltransferase activity
1
- cholesterol 25-hydroxylase activity
1
- cholesterol 7-alpha-monooxygenase activity
1
- cholesterol oxidase activity
1
- cholesterol 24-hydroxylase activity
1
- 7-dehydrocholesterol reductase activity
1
- steryl-beta-glucosidase activity
1
- cholesterol alpha-glucosyltransferase activity
1
- steroid hydroxylase activity
1
- cholesterol monooxygenase (side-chain-cleaving) activity
1
- sterol transporter activity
1
- cholesterol sulfotransferase activity
1
- cholesterol binding subject has role: reactant
- Stereoisomer of
- (20S)-Cholesta-5-ene-3beta-ol
- (3S,8S,9R,10R,13S,14S,17S)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
- (3R,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
- (3S,8R,9R,10R,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
- (3S,8R,9S,10R,13R,14R,17S)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
- epicholesterol
- (3S)-10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
On other databases
94 identifiers linking cholesterol across the web's reference databases
- BabelNet ID00018696n
- BBC News topic IDcq77k03q084t
- BBC Things IDfdb792c5-0755-4d3a-a6fc-418b3161c766
- Bibliothèque nationale de France ID11931193t
- BNCF Thesaurus ID20899
- Cannabis Database ID004794
- CAS Registry Number57-88-5
- CCDC Number1124462
- ChEBI ID16113
- ChEMBL IDCHEMBL112570
- ChemSpider ID5775
- CosIng number74991
- CSD RefcodeCHOEST20
- Cultureel Woordenboek IDlevenswetenschappen-en-geneeskunde/cholesterol
- Daum Encyclopedia IDb21k3635a
- Dewey Decimal Classification572.579 5
- DrugBank IDDB04540
- DSSTOX compound identifierDTXCID402401
- DSSTox substance IDDTXSID3022401
- EC number200-353-2
- ECHA Substance Infocard ID100.000.321
- Encyclopædia Universalis IDcholesterol
- Encyclopedia of China (Third Edition) ID (2026)1WlSuq
- Encyclopedia of China (Third Edition) old ID (2021)538603
- Freebase ID/m/01w_3
- Gmelin number550297
- GND ID4010034-0
- Golden ID (archived)Cholesterol-VPP9
- Gran Enciclopèdia Catalana IDcolesterol
- Gran Enciclopèdia Catalana ID (former scheme)0091738
- Great Norwegian Encyclopedia IDkolesterol
- Great Russian Encyclopedia portal IDkholesterin-04e677
- Guide to Pharmacology Ligand ID2718
- Harper's tagcholesterol
- HSDB ID7106
- Human Metabolome Database IDHMDB0000067
- IEDB Epitope ID150761
- InChIInChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
- InChIKeyHVYWMOMLDIMFJA-DPAQBDIFSA-N
- J9U entity ID987007285757605171
- JSTOR topic ID (archived)serum-cholesterol
- KBpedia IDCholesterol
- KEGG IDD00040
- Krugosvet article (archived)nauka_i_tehnika/biologiya/HOLESTERIN.html
- Lex IDkolesterol
- Library of Congress Authorities IDsh85024654
- LIPID MAPS IDLMST01010001
- MassBank accession IDMSBNK-Fac_Eng_Univ_Tokyo-JP002693
- MeSH descriptor IDD002784
- MeSH tree codeD04.210.500.247.222.284
- Microsoft Academic ID (discontinued)2778163477
- NALT ID18135
- Naver Encyclopedia ID (pre-August 2026)5646864
- NDF-RT IDN0000146961
- NDL Authority ID00566626
- NE.se IDkolesterol
- NicoNicoPedia word article IDコレステロール
- Nikkaji IDJ2.804E
- NL CR AUT IDph119190
- NSC number8798
- OmegaWiki Defined Meaning438873
- OpenAlex IDC2909484148
- PDB ligand IDCLR
- PDB structure ID4NC3
- Pixiv Encyclopedia IDコレステロール
- Probes And Drugs IDPD011961
- PSH ID6134
- PubChem CID5997
- Quora topic IDCholesterol
- Reaxys registry number2060565
- RTECS numberFZ8400000
- RxNorm CUI2438
- ScienceDirect topic IDfood-science/cholesterol
- SPLASHsplash10-000l-9527000000-5529a262047f5369c9c1
- Store medisinske leksikon IDkolesterol
- SureChEMBL ID2156
- SVKKL authority IDh0009235-cholesterol
- SwissLipids IDSLM:000000287
- Treccani IDcolesterolo
- UK Parliament thesaurus ID9158
- UMLS CUIC0008377
- UniChem compound ID93507
- UNII97C5T2UQ7J
- Vikidia article IDfr:Cholestérol
- WikiKids IDCholesterol
- WikiProjectMed IDCholesterol
- WikiSkripta article ID8323
- WordNet 3.1 Synset ID15083111-n
- Yale LUX IDconcept/1ef2630c-8ffb-4480-9cef-76c12ac1dfcc
- Yle topic ID18-207391