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> Main
CHEBI:50648 - 9-
cis
-retinoic acid
Main
ChEBI Ontology
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ChEBI Name
9-
cis
-retinoic acid
ChEBI ID
CHEBI:50648
ChEBI ASCII Name
9-cis-retinoic acid
Definition
A retinoic acid in which the exocyclic double bonds have 7
E
,9
Z
,11
E
,13
E
geometry.
Stars
This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs
CHEBI:63793
Supplier Information
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Read full article at Wikipedia
Formula
C20H28O2
Net Charge
0
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-ZVCIMWCZSA-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 (Br
o
nsted base).
(via
oxoacid
)
Biological Role
(s):
retinoid X receptor agonist
An agonist that selectively binds to and activates a retinoid X receptor.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (
Homo sapiens
).
(via
retinoic acid
)
Application
(s):
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
9-
cis
-retinoic acid (
CHEBI:50648
)
has role
antineoplastic agent (
CHEBI:35610
)
9-
cis
-retinoic acid (
CHEBI:50648
)
has role
keratolytic drug (
CHEBI:50176
)
9-
cis
-retinoic acid (
CHEBI:50648
)
has role
metabolite (
CHEBI:25212
)
9-
cis
-retinoic acid (
CHEBI:50648
)
has role
retinoid X receptor agonist (
CHEBI:63794
)
9-
cis
-retinoic acid (
CHEBI:50648
)
is a
retinoic acid (
CHEBI:26536
)
9-
cis
-retinoic acid (
CHEBI:50648
)
is conjugate acid of
9-
cis
-retinoate (
CHEBI:78630
)
Incoming
9-
cis
-4-hydroxyretinoic acid (
CHEBI:63802
)
has functional parent
9-
cis
-retinoic acid (
CHEBI:50648
)
9-
cis
-4-oxoretinoic acid (
CHEBI:139255
)
has functional parent
9-
cis
-retinoic acid (
CHEBI:50648
)
9-
cis
-retinoyl-β-
D
-glucuronide (
CHEBI:172945
)
has functional parent
9-
cis
-retinoic acid (
CHEBI:50648
)
9-
cis
-retinoate (
CHEBI:78630
)
is conjugate base of
9-
cis
-retinoic acid (
CHEBI:50648
)
IUPAC Name
(9
cis
)-retinoic acid
INNs
Sources
alitretinoína
ChEBI
alitrétinoïne
ChEBI
alitretinoinum
ChEBI
Synonyms
Sources
(2
E
,4
E
,6
Z
,8
E
)-
3,7-
dimethyl-
9-
(2,6,6-
trimethyl-
1-
cyclohexen-
1-
yl)-
2,4,6,8-
nonatetraenoic acid
IUPAC
(7
E
,9
Z
,11
E
,13
E
)-retinoic acid
ChEBI
9(Z)-Retinoic acid
ChemIDplus
9-cis-Tretinoin
ChemIDplus
Alitretinoin
KEGG DRUG
Brand Names
Sources
Panretin
DrugBank
Panretyn
DrugBank
Manual Xrefs
Databases
3862
DrugCentral
Alitretinoin
Wikipedia
C15493
KEGG COMPOUND
D02815
KEGG DRUG
DB00523
DrugBank
HMDB0002369
HMDB
LMPR01090022
LIPID MAPS
View more database links
Registry Numbers
Types
Sources
2057222
Reaxys Registry Number
Reaxys
5300-03-8
CAS Registry Number
ChemIDplus
Citations
Types
Sources
10684759
PubMed citation
Europe PMC
11978340
PubMed citation
Europe PMC
12611604
PubMed citation
Europe PMC
12882648
PubMed citation
Europe PMC
15217968
PubMed citation
Europe PMC
15292987
PubMed citation
Europe PMC
15519497
PubMed citation
Europe PMC
16144296
PubMed citation
Europe PMC
17019405
PubMed citation
Europe PMC
18400206
PubMed citation
Europe PMC
18404486
PubMed citation
Europe PMC
19678713
PubMed citation
Europe PMC
7670094
PubMed citation
Europe PMC
Last Modified
10 January 2022