Citrinin

Details

• Internal ID: f46689d9-f5e3-4650-a639-30c5be297229
• Taxonomy: Organoheterocyclic compounds > Benzopyrans
• IUPAC Name: (3R,4S)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydroisochromene-7-carboxylic acid
• SMILES (Canonical): CC1C(OC=C2C1=C(C(=C(C2=O)C(=O)O)O)C)C
• SMILES (Isomeric): C[C@@H]1[C@H](OC=C2C1=C(C(=C(C2=O)C(=O)O)O)C)C
• InChI: InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,14H,1-3H3,(H,16,17)/t5-,7-/m1/s1
• InChI Key: CBGDIJWINPWWJW-IYSWYEEDSA-N
• Popularity: 1,896 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₄O₅
• Molecular Weight: 250.25 g/mol
• Exact Mass: 250.08412354 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.72
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 518-75-2
• (-)-citrinin
• Citriain
• NSC 186
• (3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
• 4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
• NSC186
• 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R-trans)-
• 3S697X6SNZ
• CHEBI:48707
• NSC-186
• (3R,4S)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydroisochromene-7-carboxylic acid
• (3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
• (3R-trans)-4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
• Citrinin 100 microg/mL in Acetonitrile
• 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R,4S)-
• CCRIS 175
• HSDB 3473
• EINECS 208-257-2
• BRN 0088597
• UNII-3S697X6SNZ
• 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R-trans)-; Citrinin (6CI); (3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid; (-)-Citrinin; 4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid; NSC 186
• MFCD00006912
• Citrinin, 98%
• Spectrum_000451
• CITRININ [HSDB]
• CITRININ [IARC]
• CITRININ [MI]
• Spectrum2_000734
• Spectrum3_000240
• Spectrum4_001804
• Spectrum5_000507
• 3,4-Dihydro-8-hydroxy-3,4,5-trimethyl-6H-6-oxobenzo(c)pyran-7-carboxylic acid
• BSPBio_001919
• KBioGR_002411
• KBioSS_000931
• SPECTRUM210186
• 5-18-09-00061 (Beilstein Handbook Reference)
• DivK1c_000646
• SCHEMBL157775
• SPBio_000688
• DTXSID8020333
• SCHEMBL24312832
• HMS502A08
• KBio1_000646
• KBio2_000931
• KBio2_003499
• KBio2_006067
• KBio3_001419
• CQIUKKVOEOPUDV-IYSWYEEDSA-N
• NINDS_000646
• HMS1923C05
• CCG-39048
• AKOS030254668
• SDCCGMLS-0066537.P001
• IDI1_000646
• NCGC00160164-01
• NCGC00160164-02
• NCGC00160164-03
• NCI60_001544
• E80637
• Q420354
• SR-05000002496
• WLN: T66 CO HV AUT&J D1 E1 G1 IVQ JQ
• SR-05000002496-1
• Citrinin, from Penicillium citrinum, >=98% (HPLC)
• Q63392265
• (3R,4S)-6-hydroxy-3,4,5-trimethyl-8-oxo-4,8-dihydro-3H-2-benzopyran-7-carboxylic acid
• (3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-3,4-dihydroisochromene-7-carboxylic acid
• 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-
• 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid #
• 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-,(3R,4S)-
• 3H-2-Benzopyran-7-carboxylic acid,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R-trans)-
• 4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo, (3R-trans)-3H-2-benzopyran-7-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9466	94.66%
Caco-2	-	0.5606	56.06%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6599	65.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.4895	48.95%
OATP1B3 inhibitior	+	0.9513	95.13%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9573	95.73%
P-glycoprotein inhibitior	-	0.9352	93.52%
P-glycoprotein substrate	-	0.9134	91.34%
CYP3A4 substrate	-	0.5696	56.96%
CYP2C9 substrate	-	0.5868	58.68%
CYP2D6 substrate	-	0.9104	91.04%
CYP3A4 inhibition	-	0.6574	65.74%
CYP2C9 inhibition	-	0.8431	84.31%
CYP2C19 inhibition	-	0.9262	92.62%
CYP2D6 inhibition	-	0.9413	94.13%
CYP1A2 inhibition	-	0.8516	85.16%
CYP2C8 inhibition	-	0.9339	93.39%
CYP inhibitory promiscuity	-	0.7099	70.99%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Danger	0.7668	76.68%
Eye corrosion	-	0.9733	97.33%
Eye irritation	-	0.5603	56.03%
Skin irritation	+	0.7186	71.86%
Skin corrosion	-	0.9366	93.66%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6096	60.96%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.7891	78.91%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5397	53.97%
Acute Oral Toxicity (c)	III	0.3972	39.72%
Estrogen receptor binding	-	0.5256	52.56%
Androgen receptor binding	+	0.5416	54.16%
Thyroid receptor binding	-	0.6127	61.27%
Glucocorticoid receptor binding	-	0.6947	69.47%
Aromatase binding	-	0.6136	61.36%
PPAR gamma	-	0.6315	63.15%
Honey bee toxicity	-	0.9407	94.07%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9153	91.53%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.91%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.93%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.91%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	86.38%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	82.36%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.29%	86.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 54680783
• LOTUS: LTS0143352
• wikiData: Q63392265