Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:16:39 UTC
Update Date2024-10-09 20:06:17 UTC
Metabolite IDMMDBc0047935
Metabolite Identification
Common Nameall-trans-Retinoic acid
Descriptionall-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
Synonyms
ValueSource
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acidChEBI
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ecl)ChEBI
AGN 100335ChEBI
all-(e)-Retinoic acidChEBI
all-trans-beta-Retinoic acidChEBI
all-trans-TretinoinChEBI
all-trans-Vitamin a acidChEBI
all-trans-Vitamin a1 acidChEBI
beta-Retinoic acidChEBI
EudynaChEBI
RenovaChEBI
Retin-aChEBI
Retinoic acidChEBI
Retisol-aChEBI
Ro 1-5488ChEBI
SolageChEBI
Stieva-aChEBI
trans-Retinoic acidChEBI
Tretin mChEBI
TretinoinChEBI
VesanoidChEBI
Vitamin a acidChEBI
VitinoinChEBI
all-trans-RetinoateKegg
AvitaKegg
Retin aKegg
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoateGenerator
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoate (ecl)Generator
all-(e)-RetinoateGenerator
all-trans-b-RetinoateGenerator
all-trans-b-Retinoic acidGenerator
all-trans-beta-RetinoateGenerator
all-trans-Β-retinoateGenerator
all-trans-Β-retinoic acidGenerator
b-RetinoateGenerator
b-Retinoic acidGenerator
beta-RetinoateGenerator
Β-retinoateGenerator
Β-retinoic acidGenerator
RetinoateGenerator
trans-RetinoateGenerator
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoateHMDB
Tretinoin zinc saltHMDB
trans Retinoic acidHMDB
Acid, all-trans-retinoicHMDB
Salt, tretinoin sodiumHMDB
beta all trans Retinoic acidHMDB
beta-all-trans-Retinoic acidHMDB
Acid, vitamin aHMDB
Potassium salt, tretinoinHMDB
Sodium salt, tretinoinHMDB
Acid, beta-all-trans-retinoicHMDB
Tretinoin potassium saltHMDB
Zinc salt, tretinoinHMDB
Acid, retinoicHMDB
Acid, trans-retinoicHMDB
Salt, tretinoin potassiumHMDB
Salt, tretinoin zincHMDB
Tretinoin sodium saltHMDB
all trans Retinoic acidHMDB
Retin-a microHMDB
AtralinHMDB
Tretin-XHMDB
all-trans-Retinoic acidMeSH
Molecular FormulaC20H28O2
Average Mass300.442
Monoisotopic Mass300.208930142
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 Nametretinoin
CAS Registry Number302-79-4
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 KeySHGAZHPCJJPHSC-YCNIQYBTSA-N