Common NameRetinoate
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
Molecular FormulaC20H28O2
Average Mass300.44200
Monoisotopic Mass300.20893
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 NameAlitretinoin
CAS Registry Number302-79-4
SMILESCC1=C(C=CC(C)=CC=CC(C)=CC(=O)[O-])C(C)(C)CCC1
InChI IdentifierInChI=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
CHEBI IDCHEBI:15036
HMDB IDHMDB0001852
Pathways
NameSMPDB/PathBank
Retinol Metabolism
Vitamin A Deficiency
StateSolid
Water Solubility4.77e-03 g/l
logP5.66
logS-4.80
pKa (Strongest Acidic)5.00
pKa (Strongest Basic)Not Available
Hydrogen Acceptor Count2
Hydrogen Donor Count1
Polar Surface Area37.3 Ų
Rotatable Bond Count5
Physiological Charge-1
Formal Charge0
Refractivity97.79 m³·mol⁻¹
Polarizability36.85

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