ChemFOnt: Showing chemical card for all-trans-Retinoic acid (CFc000001227)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:49 UTC

Chemfont ID

CFc000001227

Molecule Identification

Common Name

all-trans-Retinoic acid

Definition

all-trans-Retinoic acid is an isomer of retinoic acid, the oxidized form of vitamin A. Retinoic acid functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID:17495912 ). It is an important regulator of gene expression during growth and development, and in neoplasms. As a drug, all-trans-retinoic acid is known as tretinoin. Tretinoin is derived from maternal vitamin A and is essential for normal growth and embryonic development. An excess of tretinoin can be teratogenic. Tretinoin is used in the treatment of psoriasis, acne vulgaris, and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid	ChEBI
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ecl)	ChEBI
AGN 100335	ChEBI
all-(e)-Retinoic acid	ChEBI
all-trans-beta-Retinoic acid	ChEBI
all-trans-Tretinoin	ChEBI
all-trans-Vitamin a acid	ChEBI
all-trans-Vitamin a1 acid	ChEBI
beta-Retinoic acid	ChEBI
Eudyna	ChEBI
Renova	ChEBI
Retin-a	ChEBI
Retinoic acid	ChEBI
Retisol-a	ChEBI
Ro 1-5488	ChEBI
Solage	ChEBI
Stieva-a	ChEBI
trans-Retinoic acid	ChEBI
Tretin m	ChEBI
Tretinoin	ChEBI
Vesanoid	ChEBI
Vitamin a acid	ChEBI
Vitinoin	ChEBI
all-trans-Retinoate	Kegg
Avita	Kegg
Retin a	Kegg
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate	Generator
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoate (ecl)	Generator
all-(e)-Retinoate	Generator
all-trans-b-Retinoate	Generator
all-trans-b-Retinoic acid	Generator
all-trans-beta-Retinoate	Generator
all-trans-Β-retinoate	Generator
all-trans-Β-retinoic acid	Generator
b-Retinoate	Generator
b-Retinoic acid	Generator
beta-Retinoate	Generator
Β-retinoate	Generator
Β-retinoic acid	Generator
Retinoate	Generator
trans-Retinoate	Generator
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate	HMDB
Tretinoin zinc salt	HMDB
trans Retinoic acid	HMDB
Acid, all-trans-retinoic	HMDB
Salt, tretinoin sodium	HMDB
beta all trans Retinoic acid	HMDB
beta-all-trans-Retinoic acid	HMDB
Acid, vitamin a	HMDB
Potassium salt, tretinoin	HMDB
Sodium salt, tretinoin	HMDB
Acid, beta-all-trans-retinoic	HMDB
Tretinoin potassium salt	HMDB
Zinc salt, tretinoin	HMDB
Acid, retinoic	HMDB
Acid, trans-retinoic	HMDB
Salt, tretinoin potassium	HMDB
Salt, tretinoin zinc	HMDB
Tretinoin sodium salt	HMDB
all trans Retinoic acid	HMDB
Retin-a micro	HMDB
Atralin	HMDB
Tretin-X	HMDB
all-trans-Retinoic acid	MeSH

Chemical Formula

C₂₀H₂₈O₂

Average Molecular Weight

300.442

Monoisotopic Molecular Weight

300.208930142

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

Traditional Name

tretinoin

CAS Registry Number

302-79-4

SMILES

C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O

InChI Identifier

InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+

InChI Key

SHGAZHPCJJPHSC-YCNIQYBTSA-N

Chemical Taxonomy

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
Diterpenoid
Retinoid skeleton
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Unsaturated fatty acid
Fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinoic acid (CHEBI:15367 )
Retinoids (C00777 )
Retinoids (LMPR01090019 )

Functional Ontology

Not Available

Adipose tissue (HMDB: HMDB0001852)

Epithelium

Epidermis (HMDB: HMDB0001852)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2756924)

Organ substructure

Adrenal cortex (HMDB: HMDB0001852)

Organ

Gland

Adrenal Gland (HMDB: HMDB0001852)

Cell

Fibroblasts (HMDB: HMDB0001852)
Neuron (HMDB: HMDB0001852)

Hematocyte

Platelet (HMDB: HMDB0001852)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0001852)
Nucleus (HMDB: HMDB0001852)

Source

Exogenous

Exogenous (HMDB: HMDB0001852)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0001852)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Retinol Metabolism (HMDB: HMDB0001852)

Disease pathway

Vitamin A Deficiency (PathBank: SMP0120500)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0048 g/L	ALOGPS
logP	5.66	ALOGPS
logP	5.01	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.79 m³·mol⁻¹	ChemAxon
Polarizability	36.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001852

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022710

KNApSAcK ID

Not Available

Chemspider ID

392618

KEGG Compound ID

C00777

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tretinoin

METLIN ID

Not Available

PubChem Compound

444795

PDB ID

Not Available

ChEBI ID

15367

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Solladie, Guy; Girardin, Andre. Highly stereoselective synthesis of vitamin A and all-trans retinoic acid by low-valent titanium induced reductive elimination. Tetrahedron Letters (1988), 29(2), 213-16.

Showing chemical card for all-trans-Retinoic acid (CFc000001227)

MOL for CFc000001227 (all-trans-Retinoic acid)

3D MOL for CFc000001227 (all-trans-Retinoic acid)

3D SDF for CFc000001227 (all-trans-Retinoic acid)

3D-SDF for CFc000001227 (all-trans-Retinoic acid)

PDB for CFc000001227 (all-trans-Retinoic acid)

3D PDB for CFc000001227 (all-trans-Retinoic acid)

SMILES for CFc000001227 (all-trans-Retinoic acid)

INCHI for CFc000001227 (all-trans-Retinoic acid)

Structure for CFc000001227 (all-trans-Retinoic acid)

3D Structure for CFc000001227 (all-trans-Retinoic acid)