2.0 2012-08-15 08:51:34 -0600 2015-09-13 15:15:34 -0600 ECMDB21659 M2MDB002049 Retinal A 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 -Retinene 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-Nonatetraenal a-Retinene All-E-Retinal All-epsilon-Retinal All-trans-Retinal All-trans-Retinaldehyde All-trans-retinene All-trans-vitamin a aldehyde Alpha-Retinene Axerophthal E-Retinal Epsilon-Retinal Retinal Retinal (ACD/Name 4.0) Retinaldehyde Retinene Retinene 1 Trans-Retinal Trans-Vitamin A aldehyde Vitamin a aldehyde Vitamin A1 aldehyde α-Retinene C20H28O 284.4357 284.214015518 (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal 13-cis retinal 116-31-4 C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O InChI=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-N Solid Membrane melting_point 63 oC logp 4.86 ChemAxon pka_strongest_basic -4.1 ChemAxon iupac (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal ChemAxon average_mass 284.4357 ChemAxon mono_mass 284.214015518 ChemAxon smiles C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O ChemAxon formula C20H28O ChemAxon inchi InChI=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+ ChemAxon inchikey NCYCYZXNIZJOKI-OVSJKPMPSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 96.87 ChemAxon polarizability 35.47 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21054 Specdb::CMs 134974 Specdb::CMs 142708 Specdb::NmrOneD 5189 Specdb::MsMs 78228 Specdb::MsMs 78229 Specdb::MsMs 78230 Specdb::MsMs 138528 Specdb::MsMs 138529 Specdb::MsMs 138530 Specdb::MsMs 2426503 Specdb::MsMs 2426504 Specdb::MsMs 2426505 Specdb::MsMs 2509774 Specdb::MsMs 2509775 Specdb::MsMs 2509776 Specdb::NmrTwoD 2026 HMDB01358 1070 553582 C00376 17898 RET Retinal Chang M, Herbert WN: Retinal arteriolar occlusions following amniotic fluid embolism. Ophthalmology. 1984 Dec;91(12):1634-7. 6521996 Nguyen QD, Van Do D, Feke GT, Demirjian ZN, Lashkari K: Heparin-induced antiheparin-platelet antibody associated with retinal venous thrombosis. Ophthalmology. 2003 Mar;110(3):600-3. 12623829 Aarli JA, Mork SJ, Myrseth E, Larsen JL: Glioblastoma associated with multiple sclerosis: coincidence or induction? Eur Neurol. 1989;29(6):312-6. 2691257 Wu WC, Lai CC, Liu JH, Singh T, Li LM, Peumans WJ, Van Damme EJ, Wu AM: Differential Binding to Glycotopes Among the Layers of Three Mammalian Retinal Neurons by Man-Containing N-linked Glycan, T(alpha) (Galbeta1-3GalNAcalpha1-), Tn (GalNAcalpha1-Ser/Thr) and I (beta)/II (beta) (Galbeta1-3/4GlcNAcbeta-) Reactive Lectins. Neurochem Res. 2006 May 23;. 16718528 Jankowska R, Witkowska D, Porebska I, Kuropatwa M, Kurowska E, Gorczyca WA: Serum antibodies to retinal antigens in lung cancer and sarcoidosis. Pathobiology. 2004;71(6):323-8. 15627843 Weiland JD, Liu W, Humayun MS: Retinal prosthesis. Annu Rev Biomed Eng. 2005;7:361-401. 16004575 Fukushima A, Ueno H, Fujimoto S: Antigenic cross-reactivity between human T lymphotropic virus type I (HTLV-I) and retinal antigens recognized by T cells. Clin Exp Immunol. 1994 Mar;95(3):459-64. 8137541 Bradbury MW, Lightman SL: The blood-brain interface. Eye. 1990;4 ( Pt 2):249-54. 2199234 Bringmann A, Reichenbach A, Wiedemann P: Pathomechanisms of cystoid macular edema. Ophthalmic Res. 2004 Sep-Oct;36(5):241-9. 15583429 Wu WC, Lai CC, Liu JH, Singh T, Li LM, Peumans WJ, Van Damme EJ, Wu AM: Differential binding to glycotopes among the layers of three mammalian retinal neurons by man-containing N-linked glycan, T(alpha) (Galbeta1-3GalNAcalpha1-), Tn (GalNAcalpha1-Ser/Thr) and I (beta)/II (beta) (Galbeta1-3/4GlcNAcbeta-) reactive lectins. Neurochem Res. 2006 May;31(5):619-28. Epub 2006 May 23. 16770733 Yamashiro 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. 12819029 Ramirez 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. 11747361 Duhamel, 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?1358463246 S-(hydroxymethyl)glutathione dehydrogenase P25437 FRMA_ECOLI frmA http://ecmdb.ca/proteins/P25437.xml Alcohol dehydrogenase, propanol-preferring P39451 ADHP_ECOLI adhP http://ecmdb.ca/proteins/P39451.xml Retinol + NAD <> Retinal + NADH + Hydrogen ion R02124