Deoxynivalenol

Details

• Internal ID: 9e294a83-2ce9-4a1d-a4a2-861cd17da84d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Trichothecenes
• IUPAC Name: (1R,2R,3S,7R,9R,10R,12S)-3,10-dihydroxy-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one
• SMILES (Canonical): CC1=CC2C(C(C1=O)O)(C3(CC(C(C34CO4)O2)O)C)CO
• SMILES (Isomeric): CC1=C[C@@H]2[C@]([C@@H](C1=O)O)([C@]3(C[C@H]([C@H]([C@@]34CO4)O2)O)C)CO
• InChI: InChI=1S/C15H20O6/c1-7-3-9-14(5-16,11(19)10(7)18)13(2)4-8(17)12(21-9)15(13)6-20-15/h3,8-9,11-12,16-17,19H,4-6H2,1-2H3/t8-,9-,11-,12-,13-,14-,15+/m1/s1
• InChI Key: LINOMUASTDIRTM-QGRHZQQGSA-N
• Popularity: 5,464 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₆
• Molecular Weight: 296.31 g/mol
• Exact Mass: 296.12598835 g/mol
• Topological Polar Surface Area (TPSA): 99.50 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.84
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 51481-10-8
• 4-Deoxynivalenol
• Dehydronivalenol
• 4-Desoxynivalenol
• Desoxynivalenol
• CCRIS 7801
• Rd toxin
• NSC 269144
• JT37HYP23V
• 3alpha,7alpha,15-Trihydroxy-12,13-epoxytrichothec-9-en-8-one
• CHEBI:10022
• 12,13-Epoxy-3-alpha,7-alpha,15-trihydroxy-9-trichothecen-8-one
• NSC-269144
• Trichothec-9-en-8-one, 12,13-epoxy-3,7,15-trihydroxy-, (3-alpha,7-alpha)-
• (1R,2R,3S,7R,9R,10R,12S)-3,10-dihydroxy-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one
• (1R,2R,3S,7R,9R,10R,12S)-3,10-dihydroxy-2-(hydroxymethyl)-1,5-dimethylspiro(8-oxatricyclo(7.2.1.02,7)dodec-5-ene-12,2'-oxirane)-4-one
• 3-epi-DON
• RefChem:131974
• 3 alpha,7 alpha,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one
• 3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro(oxirane-2,12'-tricyclo(7.2.1.02,7)dodecan)-5'-en-4'-one
• 610-668-0
• MFCD09039270
• Trichothec-9-en-8-one, 12,13-epoxy-3,7,15-trihydroxy-, (3a,7a)-
• (3beta,7alpha)-3,7,15-Trihydroxy-12,13-Epoxytrichothec-9-En-8-One
• (3alpha,7alpha)-3,7,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one
• Deoxynivalenol 100 microg/mL in Acetonitrile
• HSDB 7245
• UNII-JT37HYP23V
• DEOXYNIVALENOL?
• VOMITOXIN [MI]
• Epitope ID:910166
• DEOXYNIVALENOL [HSDB]
• CHEMBL513300
• orb1707387
• SCHEMBL2694361
• 4-Deoxynivalenol in acetonitrile
• MSK7213
• Deoxynivalenol, reference material
• EX-A5479
• HY-N6684
• MSK7213-100A
• Maize flour - Deoxynivalenol (blank)
• AKOS024457908
• 20 - Fusarium mycotoxins in maize oil
• CS-W012154
• FD63586
• AC-35348
• AS-75858
• DA-62777
• Wheat flour - Deoxynivalenol (DON) blank
• Deoxynivalenol 100 |Ig/mL in Acetonitrile
• NS00000120
• T15097
• Deoxynivalenol Quality Control Sample,From wheat
• Deoxynivalenol Quality Control Sample ,From wheat
• Q420518
• Deoxynivalenol(DON) Solution in Acetonitrile, 100ug/mL
• 4-Deoxynivalenol Calibration Solution Certified Reference Material
• 3.ALPHA.,7.ALPHA.,15-TRIHYDROXY-12,13-EPOXYTRICHOTHEC-9-EN-8-ONE
• 4-Deoxynivalenol in acetonitrile, IRMM(R) certified Reference Material
• 12,13-EPOXY-3-.ALPHA.,7-.ALPHA.,15-TRIHYDROXY-9-TRICHOTHECEN-8- ONE
• Trichothec-9-en-8-one, 12,13-epoxy-3,7,15-trihydroxy-, (2?,3?,6?,7?,11?,12?)-
• (1'R,2S,2'R,3'S,7'R,9'R,10'R)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0?,?]dodecan]-5'-en-4'-one
• (1R,2R,3S,7R,9R,10R,12S)-3,10-dihydroxy-2-(hydroxymethyl)-1,5-dimethyl-spiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one
• (2R,2'S,3R,5R,5aR,6S,9aR)-3,6-dihydroxy-5a-(hydroxymethyl)-5,8-dimethyl-2,3,4,5,5a,6-hexahydrospiro[2,5-methanobenzo[b]oxepine-10,2'-oxiran]-7(9aH)-one
• (2S,2'R,3'R,5'R,5a'R,6'S,9a'R)-3',6'-dihydroxy-5a'-(hydroxymethyl)-5',8'-dimethyl-2',3',4',5',5a',9a'-hexahydrospiro[oxirane-2,10'-[2,5]methanobenzo[b]oxepin]-7'(6'H)-one
• 3J6
• TRICHOTHEC-9-EN-8-ONE, 12,13-EPOXY-3,7,15-TRIHYDROXY-, (3- .ALPHA.,7-.ALPHA.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9271	92.71%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	+	0.6639	66.39%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5915	59.15%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8867	88.67%
OATP1B3 inhibitior	+	0.9650	96.50%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8366	83.66%
BSEP inhibitior	-	0.8375	83.75%
P-glycoprotein inhibitior	-	0.9235	92.35%
P-glycoprotein substrate	-	0.6889	68.89%
CYP3A4 substrate	+	0.5925	59.25%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8604	86.04%
CYP3A4 inhibition	-	0.9090	90.90%
CYP2C9 inhibition	-	0.8828	88.28%
CYP2C19 inhibition	-	0.8638	86.38%
CYP2D6 inhibition	-	0.9209	92.09%
CYP1A2 inhibition	-	0.8913	89.13%
CYP2C8 inhibition	-	0.9303	93.03%
CYP inhibitory promiscuity	-	0.9220	92.20%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6933	69.33%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9189	91.89%
Skin irritation	-	0.6697	66.97%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	-	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8214	82.14%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5722	57.22%
skin sensitisation	-	0.8399	83.99%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.6757	67.57%
Acute Oral Toxicity (c)	I	0.7287	72.87%
Estrogen receptor binding	+	0.6684	66.84%
Androgen receptor binding	+	0.7330	73.30%
Thyroid receptor binding	+	0.6116	61.16%
Glucocorticoid receptor binding	-	0.4794	47.94%
Aromatase binding	-	0.5126	51.26%
PPAR gamma	+	0.5558	55.58%
Honey bee toxicity	-	0.8920	89.20%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8913	89.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.97%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.22%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.68%	85.14%
CHEMBL2581	P07339	Cathepsin D	93.71%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.65%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.24%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.18%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.49%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	86.26%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.67%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.52%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.06%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.85%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 40024
• LOTUS: LTS0174554
• wikiData: Q420518