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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H14O5
Molecular Weight 250.2478
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CITRININ

SMILES

C[C@]1([H])[C@@]([H])(C)OC=C2C1=C(C)C(=O)C(=C2O)C(=O)O

InChI

InChIKey=CQIUKKVOEOPUDV-IYSWYEEDSA-N
InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1

HIDE SMILES / InChI

Molecular Formula C13H14O5
Molecular Weight 250.2478
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Citrinin is a mycotoxin produced by several species of the genera Aspergillus, Penicillium and Monascus. It is often found in food. Citrinin is nephrotoxic agent. Inhibition of RNA (predominantly rRNA) and DNA synthesis by citrinin has been reported in different mammalian cell lines including kidney cells. The induction of oxidative stress has also been proposed to account for citrinin toxicity. Citrinin inhibits immune response – it inhibits lipopolysaccharide/interferon-gamma-induced nitric oxide production in glomerular mesangial cells. Citrinin induced apoptosis in human colon cancer and promyelocytic leukemia cell lines.

Originator

Sources: DOI: 10.1098/rstb.1931.0025

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Transport of ochratoxin A by renal multispecific organic anion transporter 1.
1999 Jun
Complementary cell-based high-throughput screens identify novel modulators of the unfolded protein response.
2011 Sep
Evaluation of nephrotoxic effects of mycotoxins, citrinin and patulin, on zebrafish (Danio rerio) embryos.
2012 Dec
Immune modulatory effects of the foodborne contaminant citrinin in mice.
2012 Oct
Citrinin reduces testosterone secretion by inducing apoptosis in rat Leydig cells.
2012 Sep
Cardiotoxicity of mycotoxin citrinin and involvement of microRNA-138 in zebrafish embryos.
2013 Dec
Cell cycle progression, but not genotoxic activity, mainly contributes to citrinin-induced renal carcinogenesis.
2013 Sep 15
Patents

Sample Use Guides

In Vivo Use Guide
Sources: DOI: 10.2903/j.efsa.2012.2605
Curator's Comment:: no-observed-adverse-effect level
Rat: 20 ug/kg body weight per day (90 days study)
Route of Administration: Oral
10–30 uM citrinin directly induced a ∼7–18-fold increase in the intracellular ROS content of ESC-B5 cells, compared with untreated control cells.
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:48:55 UTC 2021
Edited
by admin
on Sat Jun 26 14:48:55 UTC 2021
Record UNII
3S697X6SNZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CITRININ
HSDB   MI  
Common Name English
3H-2-BENZOPYRAN-7-CARBOXYLIC ACID, 4,6-DIHYDRO-8-HYDROXY-3,4,5-TRIMETHYL-6-OXO-, (3R,4S)-
Common Name English
CITRININ [IARC]
Common Name English
NSC-186
Code English
CITRININ [MI]
Common Name English
CITRININ [HSDB]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
208-257-2
Created by admin on Sat Jun 26 14:48:55 UTC 2021 , Edited by admin on Sat Jun 26 14:48:55 UTC 2021
PRIMARY
MERCK INDEX
M3596
Created by admin on Sat Jun 26 14:48:55 UTC 2021 , Edited by admin on Sat Jun 26 14:48:55 UTC 2021
PRIMARY Merck Index
EPA CompTox
518-75-2
Created by admin on Sat Jun 26 14:48:55 UTC 2021 , Edited by admin on Sat Jun 26 14:48:55 UTC 2021
PRIMARY
FDA UNII
3S697X6SNZ
Created by admin on Sat Jun 26 14:48:55 UTC 2021 , Edited by admin on Sat Jun 26 14:48:55 UTC 2021
PRIMARY
HSDB
3473
Created by admin on Sat Jun 26 14:48:55 UTC 2021 , Edited by admin on Sat Jun 26 14:48:55 UTC 2021
PRIMARY
MESH
D002953
Created by admin on Sat Jun 26 14:48:55 UTC 2021 , Edited by admin on Sat Jun 26 14:48:55 UTC 2021
PRIMARY
CAS
518-75-2
Created by admin on Sat Jun 26 14:48:55 UTC 2021 , Edited by admin on Sat Jun 26 14:48:55 UTC 2021
PRIMARY
WIKIPEDIA
CITRININ
Created by admin on Sat Jun 26 14:48:55 UTC 2021 , Edited by admin on Sat Jun 26 14:48:55 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR