isotretinoin (CHEBI:6067)

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ChEBI Name	isotretinoin

ChEBI ID	CHEBI:6067

Definition	A retinoic acid that is all-trans-retinoic acid in which the double bond which is α,β- to the carboxy group is isomerised to Z configuration. A synthetic retinoid, it is used for the treatment of severe cases of acne and other skin diseases.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ZINC000008214733

Download	Molfile XML SDF

Wikipedia	License
Adenosine triphosphate (ATP) is a nucleoside triphosphate that provides energy to drive and support many processes in living cells, such as muscle contraction, nerve impulse propagation, and chemical synthesis. Found in all known forms of life, it is often referred to as the "molecular unit of currency" for intracellular energy transfer. When consumed in a metabolic process, ATP converts either to adenosine diphosphate (ADP) or to adenosine monophosphate (AMP). Other processes regenerate ATP. It is also a precursor to DNA and RNA, and is used as a coenzyme. An average adult human processes around 50 kilograms (about 100 moles) daily. From the perspective of biochemistry, ATP is classified as a nucleoside triphosphate, which indicates that it consists of three components: a nitrogenous base (adenine), the sugar ribose, and the triphosphate.
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Formula

C20H28O2

Net Charge

Average Mass

300.43512

Monoisotopic Mass

300.20893

InChI

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-

InChIKey

SHGAZHPCJJPHSC-XFYACQKRSA-N

SMILES

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

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	teratogenic agent A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via retinoic acid )

Application(s):	keratolytic drug A drug that softens, separates, and causes desquamation of the cornified epithelium or horny layer of skin. Keratolytic drugs are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	isotretinoin (CHEBI:6067) has role antineoplastic agent (CHEBI:35610) isotretinoin (CHEBI:6067) has role keratolytic drug (CHEBI:50176) isotretinoin (CHEBI:6067) has role teratogenic agent (CHEBI:50905) isotretinoin (CHEBI:6067) is a retinoic acid (CHEBI:26536) isotretinoin (CHEBI:6067) is conjugate acid of 13-cis-retinoate (CHEBI:169952)

Incoming	13-cis-retinoate (CHEBI:169952) is conjugate base of isotretinoin (CHEBI:6067)

IUPAC Name

(2Z,4E6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

Citations

Last Modified

22 February 2017