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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H14O5
Molecular Weight 250.2473
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CITRININ

SMILES

C[C@H]1OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@@H]1C

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 250.2473
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Hetherington, A.C.|Raistrick, H.
1
Sources: DOI: 10.1098/rstb.1931.0025

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1447
Inhibitor
8504
Oxidative Stress
162
Target ID: WP408
Sources: DOI: 10.2903/j.efsa.2012.2605
Activator
1447
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Cardiotoxicity of mycotoxin citrinin and involvement of microRNA-138 in zebrafish embryos.
2013-12
Cell cycle progression, but not genotoxic activity, mainly contributes to citrinin-induced renal carcinogenesis.
2013-09-15
Evaluation of nephrotoxic effects of mycotoxins, citrinin and patulin, on zebrafish (Danio rerio) embryos.
2012-12
Immune modulatory effects of the foodborne contaminant citrinin in mice.
2012-10
Citrinin reduces testosterone secretion by inducing apoptosis in rat Leydig cells.
2012-09
Complementary cell-based high-throughput screens identify novel modulators of the unfolded protein response.
2011-09
Citrinin-generated reactive oxygen species cause cell cycle arrest leading to apoptosis via the intrinsic mitochondrial pathway in mouse skin.
2011-08
Mycotoxin citrinin induced cell cycle G2/M arrest and numerical chromosomal aberration associated with disruption of microtubule formation in human cells.
2011-01
Activation of JNK and PAK2 is essential for citrinin-induced apoptosis in a human osteoblast cell line.
2009-08
Activation of ERK and JNK signaling pathways by mycotoxin citrinin in human cells.
2009-06-15
The mycotoxins citrinin, gliotoxin, and patulin affect interferon-gamma rather than interleukin-4 production in human blood cells.
2002
Transport of ochratoxin A by renal multispecific organic anion transporter 1.
1999-06
Patents

Patents

JP2002142761A
1
JP2003507474A
1
JP2004073199A
1
JP2004321176A
1
JP2005507754A
21
JP2008048680A
1
JP2008048681A
1
JPH049332A
1
JPH05336872A
1
JPH07196489A
1
JPH07274978A
1

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
In Vitro Use Guide
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 Mon Mar 31 19:52:59 GMT 2025
Edited
by admin
on Mon Mar 31 19:52:59 GMT 2025
Record UNII
3S697X6SNZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CITRININ
HSDB   MI  
Common Name English
NSC-186
Preferred 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
CITRININ [MI]
Common Name English
CITRININ [HSDB]
Common Name English
Code System Code Type Description
NSC
186
Created by admin on Mon Mar 31 19:52:59 GMT 2025 , Edited by admin on Mon Mar 31 19:52:59 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-257-2
Created by admin on Mon Mar 31 19:52:59 GMT 2025 , Edited by admin on Mon Mar 31 19:52:59 GMT 2025
PRIMARY
MERCK INDEX
m3596
Created by admin on Mon Mar 31 19:52:59 GMT 2025 , Edited by admin on Mon Mar 31 19:52:59 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID8020333
Created by admin on Mon Mar 31 19:52:59 GMT 2025 , Edited by admin on Mon Mar 31 19:52:59 GMT 2025
PRIMARY
FDA UNII
3S697X6SNZ
Created by admin on Mon Mar 31 19:52:59 GMT 2025 , Edited by admin on Mon Mar 31 19:52:59 GMT 2025
PRIMARY
HSDB
3473
Created by admin on Mon Mar 31 19:52:59 GMT 2025 , Edited by admin on Mon Mar 31 19:52:59 GMT 2025
PRIMARY
MESH
D002953
Created by admin on Mon Mar 31 19:52:59 GMT 2025 , Edited by admin on Mon Mar 31 19:52:59 GMT 2025
PRIMARY
CAS
518-75-2
Created by admin on Mon Mar 31 19:52:59 GMT 2025 , Edited by admin on Mon Mar 31 19:52:59 GMT 2025
PRIMARY
CHEBI
48707
Created by admin on Mon Mar 31 19:52:59 GMT 2025 , Edited by admin on Mon Mar 31 19:52:59 GMT 2025
PRIMARY
WIKIPEDIA
CITRININ
Created by admin on Mon Mar 31 19:52:59 GMT 2025 , Edited by admin on Mon Mar 31 19:52:59 GMT 2025
PRIMARY
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