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cholesterol |
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CHEBI:16113 |
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A cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3β-hydroxy group. |
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This entity has been manually annotated by the ChEBI Team.
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CHEBI:41564, CHEBI:3659, CHEBI:13982, CHEBI:23204
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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. |
Read full article at Wikipedia
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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 |
HVYWMOMLDIMFJA-DPAQBDIFSA-N |
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 |
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Mus musculus
(NCBI:txid10090)
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See:
PubMed
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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Daphnia galeata
(NCBI:txid27404)
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See:
PubMed
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Chlamydomonas reinhardtii
(NCBI:txid3055)
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See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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See:
DOI
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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.
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View more via ChEBI Ontology
Outgoing
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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)
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Incoming
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(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)
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(3β,14β,17α)-cholest-5-en-3-ol
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IUPAC
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Cholest-5-en-3beta-ol
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KEGG COMPOUND
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Cholesterin
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NIST Chemistry WebBook
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Cholesterol
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KEGG COMPOUND
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CHOLESTEROL
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PDBeChem
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cholesterol
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UniProt
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2060565
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Reaxys Registry Number
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Reaxys
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550297
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Gmelin Registry Number
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Gmelin
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57-88-5
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CAS Registry Number
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KEGG COMPOUND
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57-88-5
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CAS Registry Number
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ChemIDplus
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57-88-5
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CAS Registry Number
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NIST Chemistry WebBook
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10901445
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PubMed citation
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Europe PMC
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11412894
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PubMed citation
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Europe PMC
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16341241
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PubMed citation
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Europe PMC
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24287311
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PubMed citation
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Europe PMC
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25308664
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PubMed citation
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Europe PMC
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25451949
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PubMed citation
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Europe PMC
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25522988
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PubMed citation
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Europe PMC
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25658343
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PubMed citation
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Europe PMC
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25977713
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PubMed citation
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Europe PMC
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4696527
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PubMed citation
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Europe PMC
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8838010
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PubMed citation
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Europe PMC
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