Showing Compound Acetyldeoxynivalenol (FDB014986)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:35 UTC

Update date

2019-11-26 03:11:04 UTC

Primary ID

FDB014986

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Acetyldeoxynivalenol

Description

Acetyldeoxynivalenol, also known as 3-ADON or acetyldon, belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. Based on a literature review a significant number of articles have been published on Acetyldeoxynivalenol.

CAS Number

50722-38-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
3'-Hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetic acid	Generator
3-Acetyl DON	HMDB
3-Acetyl don	biospider
3-Acetyldeoxynivalenol	MeSH
3-acetyldeoxynivalenol	biospider
3-ADON	MeSH
Acetyldeoxynivalenol	db_source
AcetylDON	MeSH
Dehydronivalenol monoacetate	HMDB
Deoxynivalenol monoacetate	HMDB

Showing 1 to 10 of 10 entries

Predicted Properties

Property	Value	Source
Water Solubility	5.99 g/L	ALOGPS
logP	-0.61	ALOGPS
logP	-0.53	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.75	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.77 m³·mol⁻¹	ChemAxon
Polarizability	33.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C17H22O7

IUPAC name

3'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetate

InChI Identifier

InChI=1S/C17H22O7/c1-8-4-11-16(6-18,13(21)12(8)20)15(3)5-10(23-9(2)19)14(24-11)17(15)7-22-17/h4,10-11,13-14,18,21H,5-7H2,1-3H3

InChI Key

ADFIQZBYNGPCGY-UHFFFAOYSA-N

Isomeric SMILES

CC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)C(=O)C(O)C21CO

Average Molecular Weight

338.3524

Monoisotopic Molecular Weight

338.136553058

Classification

Description

Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Trichothecenes

Alternative Parents

Substituents

Trichothecene skeleton
Oxepane
Cyclohexenone
Oxane
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carbonyl group
Primary alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Weight loss

Health condition:

Shock

Eye disorders:

Blurred vision

Vascular disorders:

Hypotension

General disorders and administration site conditions:

Gastrointestinal disorders:

Ingestion

Biological location:

Cell and elements:

Extracellular

Subcellular:

Source:

Biological:

Animal

Plant:

Poaceae

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 60.35%; H 6.55%; O 33.10%	DFC
Melting Point	Mp 185.5-186°	DFC
Optical Rotation	[a]D +43 (c, 0.2 in MeOH)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Acetyldeoxynivalenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fc0-9685000000-a41157b6d23e342e41c2	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00sl-7319500000-dfc010c08fe50763dc33	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, "Acetyldeoxynivalenol,2TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyldeoxynivalenol, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00g0-0059000000-0575ba57e28e5e6faf89	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00bi-1978000000-05e4adf19bf150ba20af	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-2690000000-00a566c2b765095d32d7	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00g0-0059000000-0575ba57e28e5e6faf89	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00bi-1978000000-05e4adf19bf150ba20af	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-2690000000-00a566c2b765095d32d7	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-2049000000-7fa8366f42fafeaf11df	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aos-3396000000-2a6bc6a3d399b2084c87	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052o-5900000000-1712b7cd5cd0ab353c0f	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-2049000000-7fa8366f42fafeaf11df	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aos-3396000000-2a6bc6a3d399b2084c87	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052o-5900000000-1712b7cd5cd0ab353c0f	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-de819ae41779936fff4d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05n4-0094000000-a3dd225710e5c4f81ee8	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9182000000-26fabb5a5d0a59d67397	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000j-0079000000-640229692c86b9dd9c85	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9083000000-57219594fa23ea18c830	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9252000000-660921396a2be2357e87	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

94569

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

104759

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36137

CRC / DFC (Dictionary of Food Compounds) ID

JXX18-T:JXS02-L

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Acetyldeoxynivalenol (FDB014986)

Structure for FDB014986 (Acetyldeoxynivalenol)