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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields =
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| IUPAC_name = 5,5',6,6',8,8'-Hexahydroxy-2,2',3,3'-tetramethyl-2,2',3,3'-tetrahydro-4H,4'H-9,9'-bibenzo[g]chromene-4,4'-dione
| IUPAC_name = 5,5',6,6',8,8'-Hexahydroxy-2,2',3,3'-tetramethyl-2,2',3,3'-tetrahydro-4H,4'H-9,9'-bibenzo[g]chromene-4,4'-dione
| image = Chaetochromin skeletal.svg
| image = Chaetochromin skeletal.svg
| width =
| width =


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| CAS_number = 75514-37-3
| CAS_number = 75514-37-3
| CAS_supplemental =
| CAS_supplemental =
| UNII_Ref = {{fdacite|correct|FDA}}
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| UNII = YME4GS90I1
| class =
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| ChemSpiderID_Ref =
| ChemSpiderID_Ref =
| ChemSpiderID = 48120
| ChemSpiderID = 48120
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| UNII =
| KEGG =
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| ChEBI =
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'''Chaetochromin''', also known as '''4548-G05''', is an [[oral administration|orally active]], [[small-molecule]], [[binding selectivity|selective]] [[agonist]] of the [[insulin receptor]].<ref name="pmid24651808">{{cite journal | vauthors = Qiang G, Xue S, Yang JJ, Du G, Pang X, Li X, Goswami D, Griffin PR, Ortlund EA, Chan CB, Ye K | title = Identification of a small molecular insulin receptor agonist with potent antidiabetes activity | journal = Diabetes | volume = 63 | issue = 4 | pages = 1394–409 | year = 2014 | pmid = 24651808 | pmc = 3964510 | doi = 10.2337/db13-0334 | url = }}</ref> It has [[potency (pharmacology)|potent]] and long-lasting [[antidiabetic]] activity ''[[in vivo]]'' in mice.<ref name="pmid24651808" /> The drug may represent a novel potential therapeutic agent for the treatment of [[diabetes]] which is more convenient and [[tolerability|tolerable]] to [[drug administration|administer]] than [[injection (medicine)|injected]] [[insulin (medication)|insulin]].<ref name="pmid24651808" /> It was discovered in 1981 in ''[[Chaetomium]] gracile'' fungi.<ref>{{cite journal|pmid=7296410|year=1981|author1=Sekita|first1=S|title=Mycotoxin production by Chaetomium spp. And related fungi|journal=Canadian journal of microbiology|volume=27|issue=8|pages=766–72|last2=Yoshihira|first2=K|last3=Natori|first3=S|last4=Udagawa|first4=S|last5=Muroi|first5=T|last6=Sugiyama|first6=Y|last7=Kurata|first7=H|last8=Umeda|first8=M}}</ref>
'''Chaetochromin''', also known as '''4548-G05''', is an [[oral administration|orally active]], [[small-molecule]], [[binding selectivity|selective]] [[agonist]] of the [[insulin receptor]].<ref name="pmid24651808">{{cite journal | vauthors = Qiang G, Xue S, Yang JJ, Du G, Pang X, Li X, Goswami D, Griffin PR, Ortlund EA, Chan CB, Ye K | display-authors = 6 | title = Identification of a small molecular insulin receptor agonist with potent antidiabetes activity | journal = Diabetes | volume = 63 | issue = 4 | pages = 1394–1409 | date = April 2014 | pmid = 24651808 | pmc = 3964510 | doi = 10.2337/db13-0334 }}</ref> It has [[potency (pharmacology)|potent]] and long-lasting [[antidiabetic]] activity ''[[in vivo]]'' in mice.<ref name="pmid24651808" /> The drug may represent a novel potential therapeutic agent for the treatment of [[diabetes]] which is more convenient and [[tolerability|tolerable]] to [[drug administration|administer]] than [[injection (medicine)|injected]] [[insulin (medication)|insulin]].<ref name="pmid24651808" /> It was discovered in 1981 in ''[[Chaetomium]] gracile'' fungi,<ref>{{cite journal | vauthors = Sekita S, Yoshihira K, Natori S, Udagawa S, Muroi T, Sugiyama Y, Kurata H, Umeda M | display-authors = 6 | title = Mycotoxin production by Chaetomium spp. and related fungi | journal = Canadian Journal of Microbiology | volume = 27 | issue = 8 | pages = 766–772 | date = August 1981 | pmid = 7296410 | doi = 10.1139/m81-119 }}</ref> and its interaction with the insulin receptor was identified in 2014.<ref name="pmid24651808" />


==Stereochemistry==
==Stereochemistry==
Chaetochromin A and B are [[stereoisomer]]s of this structure, while chaetochromin C and D are related but different compounds.<ref>''Pubchem'': [https://www.ncbi.nlm.nih.gov/pccompound?term=chaetochromin Chaetochromin].</ref> It is not known whether the insulin mimetic effect was found in chaetochromin A or B, or in a mixture.
Chaetochromin A and B are [[stereoisomer]]s of this structure, while chaetochromin C and D are related but different compounds.<ref>{{cite web | url = https://www.ncbi.nlm.nih.gov/pccompound?term=chaetochromin | title = Chaetochromin | work = PubChem | publisher = U.S. National Library of Medicine }}</ref> It is not known whether the insulin mimetic effect was found in chaetochromin A or B, or in a mixture.<ref name="pmid24651808" />


==See also==
== See also ==
* [[Anti-diabetic medication]]
* [[Anti-diabetic medication]]


==References==
== References ==
{{Reflist|2}}
{{Reflist}}


⚫
[[Category:Polyphenols]]

{{Signaling peptide/protein receptor modulators}}

⚫
[[Category:Alcohols]]
⚫
[[Category:Anti-diabetic drugs]]
[[Category:Benzochromenes]]
[[Category:Benzochromenes]]
[[Category:Diketones]]
[[Category:Diketones]]
[[Category:Heterocyclic compounds with 3 rings]]
[[Category:Insulin receptor agonists]]
⚫
[[Category:3-Hydroxypropenals]]
[[Category:Resorcinols]]
[[Category:Biphenyls]]

Latest revision as of 20:23, 1 December 2023

Chaetochromin
Clinical data
Other names4548-G05
Identifiers
  • 5,5',6,6',8,8'-Hexahydroxy-2,2',3,3'-tetramethyl-2,2',3,3'-tetrahydro-4H,4'H-9,9'-bibenzo[g]chromene-4,4'-dione
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC30H26O10
Molar mass546.528 g·mol−1
3D model (JSmol)
  • CC1C(Oc2cc3c(c(cc(c3c4c5cc6c(c(c5c(cc4O)O)O)C(=O)C(C(O6)C)C)O)O)c(c2C1=O)O)C
  • InChI=1S/C30H26O10/c1-9-11(3)39-19-5-13-21(15(31)7-17(33)23(13)29(37)25(19)27(9)35)22-14-6-20-26(28(36)10(2)12(4)40-20)30(38)24(14)18(34)8-16(22)32/h5-12,31-34,37-38H,1-4H3
  • Key:RHNVLFNWDGWACV-UHFFFAOYSA-N

Chaetochromin, also known as 4548-G05, is an orally active, small-molecule, selective agonist of the insulin receptor.[1] It has potent and long-lasting antidiabetic activity in vivo in mice.[1] The drug may represent a novel potential therapeutic agent for the treatment of diabetes which is more convenient and tolerable to administer than injected insulin.[1] It was discovered in 1981 in Chaetomium gracile fungi,[2] and its interaction with the insulin receptor was identified in 2014.[1]

Stereochemistry

[edit]

Chaetochromin A and B are stereoisomers of this structure, while chaetochromin C and D are related but different compounds.[3] It is not known whether the insulin mimetic effect was found in chaetochromin A or B, or in a mixture.[1]

See also

[edit]

References

[edit]
  1. ^ a b c d e Qiang G, Xue S, Yang JJ, Du G, Pang X, Li X, et al. (April 2014). "Identification of a small molecular insulin receptor agonist with potent antidiabetes activity". Diabetes. 63 (4): 1394–1409. doi:10.2337/db13-0334. PMC 3964510. PMID 24651808.
  2. ^ Sekita S, Yoshihira K, Natori S, Udagawa S, Muroi T, Sugiyama Y, et al. (August 1981). "Mycotoxin production by Chaetomium spp. and related fungi". Canadian Journal of Microbiology. 27 (8): 766–772. doi:10.1139/m81-119. PMID 7296410.
  3. ^ "Chaetochromin". PubChem. U.S. National Library of Medicine.
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