CHEBI:16113 - cholesterol

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ChEBI Name cholesterol
ChEBI ID CHEBI:16113
Definition A cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3β-hydroxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41564, CHEBI:3659, CHEBI:13982, CHEBI:23204
Supplier Information ChemicalBook:CB6361837, eMolecules:532358, eMolecules:10169597, eMolecules:5753682, eMolecules:1056735, eMolecules:1989215, Selleckchem:Thioguanine, ZINC000006382803
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Tioguanine, also known as thioguanine or 6-thioguanine (6-TG) or tabloid is a medication used to treat acute myeloid leukemia (AML), acute lymphocytic leukemia (ALL), and chronic myeloid leukemia (CML). Long-term use is not recommended. It is given by mouth. Common side effects include bone marrow suppression, liver problems and inflammation of the mouth. It is recommended that liver enzymes be checked weekly when on the medication. People with a genetic deficiency in thiopurine S-methyltransferase are at higher risk of side effects. Avoiding pregnancy when on the medication is recommended. Tioguanine is in the antimetabolite family of medications. It is a purine analogue of guanine and works by disrupting DNA and RNA. Tioguanine was developed between 1949 and 1951. It is on the World Health Organization's List of Essential Medicines.
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Formula C27H46O
Net Charge 0
Average Mass 386.655
Monoisotopic Mass 386.35487
InChI InChI=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
InChIKey HVYWMOMLDIMFJA-DPAQBDIFSA-N
SMILES C1[C@@]2([C@]3(CC[C@]4([C@]([C@@]3(CC=C2C[C@H](C1)O)[H])(CC[C@@]4([C@H](C)CCCC(C)C)[H])[H])C)[H])C
Metabolite of Species Details
Mus musculus (NCBI:txid10090) See: PubMed
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Daphnia galeata (NCBI:txid27404) See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Daphnia galeata metabolite
A Daphnia metabolite produced by the species Daphnia galeata.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cholesterol (CHEBI:16113) has role Daphnia galeata metabolite (CHEBI:83038)
cholesterol (CHEBI:16113) has role algal metabolite (CHEBI:84735)
cholesterol (CHEBI:16113) has role human metabolite (CHEBI:77746)
cholesterol (CHEBI:16113) has role mouse metabolite (CHEBI:75771)
cholesterol (CHEBI:16113) is a 3β-hydroxy-Δ5-steroid (CHEBI:1722)
cholesterol (CHEBI:16113) is a 3β-sterol (CHEBI:35348)
cholesterol (CHEBI:16113) is a C27-steroid (CHEBI:131619)
cholesterol (CHEBI:16113) is a cholestanoid (CHEBI:50401)
Incoming (16S,22S)-dihydroxycholesterol (CHEBI:191938) has functional parent cholesterol (CHEBI:16113)
(20R)-17α,20-dihydroxycholesterol (CHEBI:783) has functional parent cholesterol (CHEBI:16113)
(20S)-17α,20-dihydroxycholesterol (CHEBI:182953) has functional parent cholesterol (CHEBI:16113)
(22R)-22-hydroxycholesterol (CHEBI:67237) has functional parent cholesterol (CHEBI:16113)
(22S)-22-hydroxycholesterol (CHEBI:1301) has functional parent cholesterol (CHEBI:16113)
(24S,25)-dihydroxycholesterol (CHEBI:86074) has functional parent cholesterol (CHEBI:16113)
(24S,26)-dihydroxycholesterol (CHEBI:86075) has functional parent cholesterol (CHEBI:16113)
(25R)-3β,26-dihydroxycholest-5-en-7-one (CHEBI:87653) has functional parent cholesterol (CHEBI:16113)
(25R)-3β-hydroxycholest-5-en-7-one-26-al (CHEBI:87677) has functional parent cholesterol (CHEBI:16113)
(25R)-3β-hydroxycholest-5-en-7-one-26-oic acid (CHEBI:87783) has functional parent cholesterol (CHEBI:16113)
(25R)-cholest-5-ene-3β,26-diol (CHEBI:76591) has functional parent cholesterol (CHEBI:16113)
24-hydroxycholesterol (CHEBI:50515) has functional parent cholesterol (CHEBI:16113)
24-methylenecholesterol (CHEBI:19812) has functional parent cholesterol (CHEBI:16113)
25-hydroxycholesterol (CHEBI:42977) has functional parent cholesterol (CHEBI:16113)
26-hydroxycholesterol (CHEBI:17703) has functional parent cholesterol (CHEBI:16113)
3β-hydroxycholest-5-en-26-al (CHEBI:84145) has functional parent cholesterol (CHEBI:16113)
3β-hydroxycholest-5-en-26-oic acid (CHEBI:81014) has functional parent cholesterol (CHEBI:16113)
4β-hydroxycholesterol (CHEBI:85778) has functional parent cholesterol (CHEBI:16113)
7α,24-dihydroxycholesterol (CHEBI:50517) has functional parent cholesterol (CHEBI:16113)
7α,25-dihydroxycholesterol (CHEBI:37623) has functional parent cholesterol (CHEBI:16113)
7α,26-dihydroxycholesterol (CHEBI:18431) has functional parent cholesterol (CHEBI:16113)
7α-hydroxycholesterol (CHEBI:17500) has functional parent cholesterol (CHEBI:16113)
7β-hydroxycholesterol (CHEBI:42989) has functional parent cholesterol (CHEBI:16113)
7-aminocholesterol (CHEBI:77845) has functional parent cholesterol (CHEBI:16113)
7-ketocholesterol (CHEBI:64294) has functional parent cholesterol (CHEBI:16113)
cholesterol sulfate (CHEBI:41321) has functional parent cholesterol (CHEBI:16113)
cholesteryl β-D-glucoside (CHEBI:17495) has functional parent cholesterol (CHEBI:16113)
cholesteryl ester (CHEBI:17002) has functional parent cholesterol (CHEBI:16113)
cholesteryl glycoside (CHEBI:61656) has functional parent cholesterol (CHEBI:16113)
cholesteryl hemisuccinate (CHEBI:138742) has functional parent cholesterol (CHEBI:16113)
Glycino 3β-cholesterol ester group (CHEBI:143135) has functional parent cholesterol (CHEBI:16113)
oxysterol (CHEBI:53030) has functional parent cholesterol (CHEBI:16113)
cholesteryl β-D-galactoside (CHEBI:189066) has part cholesterol (CHEBI:16113)
cholesteryl β-D-xyloside (CHEBI:189067) has part cholesterol (CHEBI:16113)
IUPAC Name
cholest-5-en-3β-ol
Synonyms Sources
(3β,14β,17α)-cholest-5-en-3-ol IUPAC
Cholest-5-en-3beta-ol KEGG COMPOUND
Cholesterin NIST Chemistry WebBook
Cholesterol KEGG COMPOUND
CHOLESTEROL PDBeChem
cholesterol UniProt
Manual Xrefs Databases
C00003648 KNApSAcK
C00187 KEGG COMPOUND
Cholesterol Wikipedia
CHOLESTEROL MetaCyc
CLR PDBeChem
D00040 KEGG DRUG
DB04540 DrugBank
HMDB0000067 HMDB
LMST01010001 LIPID MAPS
View more database links
Registry Numbers Types Sources
2060565 Reaxys Registry Number Reaxys
550297 Gmelin Registry Number Gmelin
57-88-5 CAS Registry Number KEGG COMPOUND
57-88-5 CAS Registry Number ChemIDplus
57-88-5 CAS Registry Number NIST Chemistry WebBook
Citations Types Sources
10901445 PubMed citation Europe PMC
11412894 PubMed citation Europe PMC
16341241 PubMed citation Europe PMC
24287311 PubMed citation Europe PMC
25308664 PubMed citation Europe PMC
25451949 PubMed citation Europe PMC
25522988 PubMed citation Europe PMC
25658343 PubMed citation Europe PMC
25977713 PubMed citation Europe PMC
4696527 PubMed citation Europe PMC
8838010 PubMed citation Europe PMC
Last Modified
11 February 2022