Showing Compound Isoacitretin (FDB023099)

Record Information

Version

1.0

Creation date

2011-09-21 00:24:39 UTC

Update date

2015-07-21 06:57:31 UTC

Primary ID

FDB023099

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Isoacitretin

Description

Acitretin, also known as soriatane or neotigason, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Acitretin is an extremely weak basic (essentially neutral) compound (based on its pKa).

CAS Number

69427-46-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid	HMDB
(all-e)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate	Generator
(all-e)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid	ChEBI
13-cis-Acitretin	HMDB
13-cis-Etretin	hmdb
Acetretin	HMDB
Acitretin	HMDB
Acitretin andreu brand	HMDB
Acitretin roche brand	HMDB
Acitretin, (Z,e,e,e)-isomer	HMDB

Showing 1 to 10 of 26 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.00048 g/L	ALOGPS
logP	5.2	ALOGPS
logP	5.59	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	5.01	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	104.17 m³·mol⁻¹	ChemAxon
Polarizability	38.58 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H26O3

IUPAC name

(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

InChI Identifier

InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+

InChI Key

IHUNBGSDBOWDMA-AQFIFDHZSA-N

Isomeric SMILES

COC1=C(C)C(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O)C(C)=C1

Average Molecular Weight

326.4293

Monoisotopic Molecular Weight

326.188194698

Classification

Description

Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents

Substituents

Retinoic acid
Retinoid skeleton
Sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Medium-chain fatty acid
Styrene
Alkyl aryl ether
Branched fatty acid
Methyl-branched fatty acid
Monocyclic benzene moiety
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

retinoid (CHEBI:50173 )
alpha,beta-unsaturated monocarboxylic acid (CHEBI:50173 )
acitretin (CHEBI:50173 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

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	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Isoacitretin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03di-1279000000-d74bbc0348cfdb3b3732	Spectrum
Predicted GC-MS	Isoacitretin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-4139000000-85e857f30a345651bb66	Spectrum
Predicted GC-MS	Isoacitretin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-01t9-0592000000-92a48c620c961fdb430f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-056r-1943000000-77c18bcac662a9f6bdcb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-056r-2942000000-57cdf186555912258599	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05r0-0389000000-28f8ff224c8fd7ac1606	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02t9-0690000000-11440b22373ebd567609	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-114j-4920000000-bf257c11adfb644686f4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0059000000-2338c505b394d676d7a4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-0097000000-d73443e0cee4f07fd0d9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066r-3391000000-8adb8a7f90aecb16b198	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001j-0092000000-da6b1640ed88e8dd0629	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-017j-1291000000-8d03b8e6cfa817060924	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dj-1494000000-45aa9916567486569a90	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ke9-0395000000-2d28d3c86a8a16a5adac	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0940000000-2f4d9396336fd697861e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00tf-1900000000-f5a87d3a7b17af3487e6	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4942363

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

6437841

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB03039

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

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

Soriatane

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 Isoacitretin (FDB023099)

Structure for FDB023099 (Isoacitretin)