9CR

(9cis)-retinoic acid

Created:	2012-12-18
Last modified:	2012-12-21

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24 entries where 9CR is found as a standalone ligand1 entries where 9CR is covalently linked to polymer or other heterogen groups

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Chemical Details
Formal Charge	0
Atom Count	50
Chiral Atom Count	0
Bond Count	50
Aromatic Bond Count	0

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Chemical Component Summary
Name	(9cis)-retinoic acid
Systematic Name (OpenEye OEToolkits)	(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
Formula	C₂₀ H₂₈ O₂
Molecular Weight	300.435
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C(O)\C=C(\C=C\C=C(/C=C/C1=C(C)CCCC1(C)C)C)C
SMILES	CACTVS	3.370	CC1=C(C=CC(C)=CC=CC(C)=CC(O)=O)C(C)(C)CCC1
SMILES	OpenEye OEToolkits	1.7.6	CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
Canonical SMILES	CACTVS	3.370	CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C(O)=O)C(C)(C)CCC1
Canonical SMILES	OpenEye OEToolkits	1.7.6	CC1=C(C(CCC1)(C)C)/C=C/C(=C\C=C\C(=C\C(=O)O)\C)/C
InChI	InChI	1.03	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	InChI	1.03	SHGAZHPCJJPHSC-ZVCIMWCZSA-N

Drug Info: DrugBank

DrugBank ID	DB00523
Name	Alitretinoin
Groups	approved investigational
Description	An important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth; and embryonic development. An excess of tretinoin can be teratogenic. It 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).
Synonyms	(7E,9Z,11E,13E)-retinoic acid Alitretinoinum 9-cis-retinoic acid 9-cis-Tretinoin Alitretinoína 9(Z)-Retinoic acid Alitretinoin Alitrétinoïne (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
Brand Names	Toctino Hanzema Clindamycin 1% / Niacinamide 4% / Tretinoin 0.05% Panretin
Indication	For topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma.
Categories	Agents for Dermatitis, Excluding Corticosteroids Alkenes Antineoplastic Agents Antineoplastic and Immunomodulating Agents Biological Factors Carotenoids Cyclohexanes Cyclohexenes Cycloparaffins Dermatologicals Diterpenes Hydrocarbons, Acyclic Misc. Skin and Mucous Membrane Agents P-glycoprotein substrates Pigments, Biological Polyenes Retinoids Retinoids for cancer treatment Terpenes Vitamin A Vitamins Vitamins (Fat Soluble)
ATC-Code	L01XF02 D11AH04
CAS number	5300-03-8

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Retinoic acid receptor alpha	MASNSSSCPTPGGGHLNGYPVPPYAFFFPPMLGGLSPPGALTTLQHQLPV...	unknown	agonist
Retinoic acid receptor RXR-alpha	MDTKHFLPLDFSTQVNSSLTSPTGRGSMAAPSLHPSLGPGIGSPGQLHSP...	unknown	agonist
Retinoic acid receptor beta	MTTSGHACPVPAVNGHMTHYPATPYPLLFPPVIGGLSLPPLHGLHGHPPP...	unknown	agonist
Retinoic acid receptor RXR-beta	MSWAARPPFLPQRHAAGQCGPVGVRKEMHCGVASRWRRRRPWLDPAAAAA...	unknown	agonist
Retinoic acid receptor gamma	MATNKERLFAAGALGPGSGYPGAGFPFAFPGALRGSPPFEMLSPSFRGLG...	unknown	agonist
Retinoic acid receptor RXR-gamma	MYGNYSHFMKFPAGYGGSPGHTGSTSMSPSAALSTGKPMDSHPSYTDTPV...	unknown	agonist
Insulin-like growth factor-binding protein 3	MQRARPTLWAAALTLLVLLRGPPVARAGASSAGLGPVVRCEPCDARALAQ...	unknown
Pregnancy-specific beta-1-glycoprotein 5	MGPLSAPPCTQHITWKGLLLTASLLNFWNLPITAQVTIEALPPKVSEGKD...	unknown
Cytochrome P450 26C1	MFPWGLSCLSVLGAAGTALLCAGLLLSLAQHLWTLRWMLSRDRASTLPLP...	unknown
Cellular retinoic acid-binding protein 2	MPNFSGNWKIIRSENFEELLKVLGVNVMLRKIAVAAASKPAVEIKQEGDT...	unknown	agonist
Cellular retinoic acid-binding protein 1	MPNFAGTWKMRSSENFDELLKALGVNAMLRKVAVAAASKPHVEIRQDGDQ...	unknown	agonist
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682