2.02012-08-15 08:51:34 -06002015-09-13 15:15:34 -0600ECMDB21659M2MDB002049RetinalA carotenoid constituent of visual pigments. It is the oxidized form of retinol which functions as the active component of the visual cycle. It is bound to the protein opsin forming the complex rhodopsin. When stimulated by visible light, the retinal component of the rhodopsin complex undergoes isomerization at the 11-position of the double bond to the cis-form; this is reversed in 'dark' reactions to return to the native trans-configuration.; Retinal, also called retinaldehyde or vitamin A aldehyde, is one of the many forms of vitamin A (the number of which varies from species to species). Retinal is a polyene chromophore, and bound to proteins called opsins, is the chemical basis of animal vision. Bound to proteins called type 1 rhodopsins, retinal allows certain microorganisms to convert light into metabolic energy.; The visual cycle is a circular enzymatic pathway, which is the front-end of phototransduction. It regenerates 11-cis-retinal.; Vertebrate animals ingest retinal directly from meat, or produce retinal from one of four carotenoids (beta-carotene, alpha-carotene, gamma-carotene, and beta-cryptoxanthin), which they must obtain from plants or other photosynthetic organisms (no other carotenoids can be converted by animals to retinal, and some carnivores cannot convert any carotenoids at all). The other main forms of vitamin A, retinol, and a partially active form retinoic acid, may both be produced from retinal.; catalyzed by retinal dehydrogenases also known as retinaldehyde dehydrogenases (RALDHs) as well as retinal oxidases. Retinoic acid, sometimes called vitamin A acid, is an important signaling molecule and hormone in vertebrate animals.&alpha(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal-Retinene3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-Nonatetraenala-RetineneAll-E-RetinalAll-epsilon-RetinalAll-trans-RetinalAll-trans-RetinaldehydeAll-trans-retineneAll-trans-vitamin a aldehydeAlpha-RetineneAxerophthalE-RetinalEpsilon-RetinalRetinalRetinal (ACD/Name 4.0)RetinaldehydeRetineneRetinene 1Trans-RetinalTrans-Vitamin A aldehydeVitamin a aldehydeVitamin A1 aldehydeα-RetineneC20H28O284.4357284.214015518(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal13-cis retinal116-31-4C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=OInChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+NCYCYZXNIZJOKI-OVSJKPMPSA-NSolidMembranemelting_point63 oClogp4.86pka_strongest_basic-4.1iupac(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenalaverage_mass284.4357mono_mass284.214015518smilesC\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=OformulaC20H28OinchiInChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+inchikeyNCYCYZXNIZJOKI-OVSJKPMPSA-Npolar_surface_area17.07refractivity96.87polarizability35.47rotatable_bond_count5acceptor_count1donor_count0physiological_charge0formal_charge0Specdb::CMs21054Specdb::CMs134974Specdb::CMs142708Specdb::NmrOneD5189Specdb::MsMs78228Specdb::MsMs78229Specdb::MsMs78230Specdb::MsMs138528Specdb::MsMs138529Specdb::MsMs138530Specdb::MsMs2426503Specdb::MsMs2426504Specdb::MsMs2426505Specdb::MsMs2509774Specdb::MsMs2509775Specdb::MsMs2509776Specdb::NmrTwoD2026HMDB013581070553582C0037617898RETRetinalChang M, Herbert WN: Retinal arteriolar occlusions following amniotic fluid embolism. 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Epub 2006 May 23.16770733Yamashiro K, Tsujikawa A, Ishida S, Usui T, Kaji Y, Honda Y, Ogura Y, Adamis AP: Platelets accumulate in the diabetic retinal vasculature following endothelial death and suppress blood-retinal barrier breakdown. Am J Pathol. 2003 Jul;163(1):253-9.12819029Ramirez JM, Ramirez AI, Salazar JJ, de Hoz R, Trivino A: Changes of astrocytes in retinal ageing and age-related macular degeneration. Exp Eye Res. 2001 Nov;73(5):601-15.11747361Duhamel, Lucette; Duhamel, Pierre; Lecouve, Jean Pierre. A new synthesis of retinals. Journal of Chemical Research, Synopses (1986), (1), 34-5.http://hmdb.ca/system/metabolites/msds/000/001/220/original/HMDB01358.pdf?1358463246S-(hydroxymethyl)glutathione dehydrogenaseP25437FRMA_ECOLIfrmAhttp://ecmdb.ca/proteins/P25437.xmlAlcohol dehydrogenase, propanol-preferringP39451ADHP_ECOLIadhPhttp://ecmdb.ca/proteins/P39451.xmlRetinol + NAD <> Retinal + NADH + Hydrogen ionR02124