1.0 2010-04-08 22:12:20 UTC 2025-11-19 01:45:54 UTC FDB016268 Chlorophyll d Widely distributed photosynthetic pigment Chlorophyll is a chlorin pigment, which is structurally similar to and produced through the same metabolic pathway as other porphyrin pigments such as heme. At the center of the chlorin ring is a magnesium ion. For the structures depicted in this article, some of the ligands attached to the Mg2+ center are omitted for clarity. The chlorin ring can have several different side chains, usually including a long phytol chain. There are a few different forms that occur naturally, but the most widely distributed form in terrestrial plants is chlorophyll a. The general structure of chlorophyll a was elucidated by Hans Fischer in 1940, and by 1960, when most of the stereochemistry of chlorophyll a was known, Robert Burns Woodward published a total synthesis of the molecule as then known. In 1967, the last remaining stereochemical elucidation was completed by Ian Fleming, and in 1990 Woodward and co-authors published an updated synthesis.; Chlorophyll is a green pigment found in most plants, algae, and cyanobacteria. Its name is derived from the Greek ?????? (chloros "green") and ?????? (phyllon "leaf"). Chlorophyll absorbs light most strongly in the blue and red but poorly in the green portions of the electromagnetic spectrum, hence the green colour of chlorophyll-containing tissues such as plant leaves.; Chlorophyll itself is bound to proteins and can transfer the absorbed energy in the required direction. Protochlorophyllide, differently, mostly occur in the free form and under light conditions act as photosensitizer, forming highly toxic free radicals. Hence plants need an efficient mechanism of regulating the amount of chlorophyll precursor. In angiosperms, this is done at the step of aminolevulinic acid (ALA), one of the intermediate compounds in the biosynthesis pathway. Plants that are fed by ALA accumulate high and toxic levels of protochlorophyllide, so do the mutants with the damaged regulatory system.; Chlorosis is a condition in which leaves produce insufficient chlorophyll, turning them yellow. Chlorosis can be caused by a nutrient deficiency including iron - called iron chlorosis, or in a shortage of magnesium or nitrogen. Soil pH sometimes play a role in nutrient-caused chlorosis, many plants are adapted to grow in soils with specific pHs and their ability to absorb nutrients from the soil can be dependent on the soil pH. Chlorosis can also be caused by pathogens including viruses, bacteria and fungal infections or sap sucking insects. [3,7,11,15-Tetramethyl-2-hexadecenyl-14-ethyl-9-formyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoato(2-)-N23,N24,N25,N26]magnesium, 9CI C54H70MgN4O6 895.462 894.51457789 methyl (5R,8S,9S,16Z,21Z)-19-ethyl-14-formyl-9,13,18,25-tetramethyl-4-oxo-8-(3-oxo-3-{[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-1,24,26,27-tetraaza-23-magnesaheptacyclo[10.10.2.1^{3,22}.1^{7,10}.1^{17,20}.0^{2,6}.0^{15,24}]heptacosa-2(6),3(25),7(27),10,12,14,16,18,20(26),21-decaene-5-carboxylate methyl (5R,8S,9S,16Z,21Z)-19-ethyl-14-formyl-9,13,18,25-tetramethyl-4-oxo-8-(3-oxo-3-{[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-1,24,26,27-tetraaza-23-magnesaheptacyclo[10.10.2.1^{3,22}.1^{7,10}.1^{17,20}.0^{2,6}.0^{15,24}]heptacosa-2(6),3(25),7(27),10,12,14,16,18,20(26),21-decaene-5-carboxylate 519-63-1 CCC1=C(C)C2=[N]3C1=CC1=C(C)C4=C5N1[Mg]31N3C(=CC6=[N]1C([C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@@H]6C)=C5[C@@H](C(=O)OC)C4=O)C(C)=C(C=O)C3=C2 InChI=1S/C54H71N4O6.Mg/c1-12-38-34(7)42-27-46-40(29-59)36(9)41(56-46)26-43-35(8)39(51(57-43)49-50(54(62)63-11)53(61)48-37(10)44(58-52(48)49)28-45(38)55-42)22-23-47(60)64-25-24-33(6)21-15-20-32(5)19-14-18-31(4)17-13-16-30(2)3;/h24,26-32,35,39,50H,12-23,25H2,1-11H3,(H-,55,56,57,58,59,61);/q-1;+2/p-1/b33-24+;/t31-,32-,35+,39+,50-;/m1./s1 QXWRYZIMSXOOPY-SKHCYZARSA-M belongs to the class of organic compounds known as chlorins. These are large heterocyclic aromatic ring systems consisting, at the core, of three pyrroles and one pyrroline coupled through four methine linkages. Chlorins Organic compounds Organoheterocyclic compounds Tetrapyrroles and derivatives Chlorins Aromatic heteropolycyclic compounds 1,3-dicarbonyl compounds Aryl alkyl ketones Aryl-aldehydes Azacyclic compounds Dicarboxylic acids and derivatives Diterpenoids Fatty acid esters Heteroaromatic compounds Hydrocarbon derivatives Metallotetrapyrroles Methyl esters Organic oxides Organic salts Organic zwitterions Organonitrogen compounds Phorbines Substituted pyrroles 1,3-dicarbonyl compound Aldehyde Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Aryl-aldehyde Azacycle Carbonyl group Carboxylic acid derivative Carboxylic acid ester Chlorin Dicarboxylic acid or derivatives Diterpenoid Fatty acid ester Fatty acyl Heteroaromatic compound Hydrocarbon derivative Ketone Metallotetrapyrrole skeleton Methyl ester Organic nitrogen compound Organic oxide Organic oxygen compound Organic salt Organic zwitterion Organonitrogen compound Organooxygen compound Phorbine skeleton Pyrrole Substituted pyrrole chlorophyll methyl ester logp 7.94 ALOGPS logs -6.19 ALOGPS solubility 5.78e-04 g/l ALOGPS logp 11.58 ChemAxon pka_strongest_acidic 3.94 ChemAxon pka_strongest_basic 7.05 ChemAxon iupac methyl (5R,8S,9S,16Z,21Z)-19-ethyl-14-formyl-9,13,18,25-tetramethyl-4-oxo-8-(3-oxo-3-{[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-1,24,26,27-tetraaza-23-magnesaheptacyclo[10.10.2.1^{3,22}.1^{7,10}.1^{17,20}.0^{2,6}.0^{15,24}]heptacosa-2(6),3(25),7(27),10,12,14,16,18,20(26),21-decaene-5-carboxylate ChemAxon average_mass 895.462 ChemAxon mono_mass 894.51457789 ChemAxon smiles CCC1=C(C)C2=[N]3C1=CC1=C(C)C4=C5N1[Mg]31N3C(=CC6=[N]1C([C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@@H]6C)=C5[C@@H](C(=O)OC)C4=O)C(C)=C(C=O)C3=C2 ChemAxon formula C54H70MgN4O6 ChemAxon inchi InChI=1S/C54H71N4O6.Mg/c1-12-38-34(7)42-27-46-40(29-59)36(9)41(56-46)26-43-35(8)39(51(57-43)49-50(54(62)63-11)53(61)48-37(10)44(58-52(48)49)28-45(38)55-42)22-23-47(60)64-25-24-33(6)21-15-20-32(5)19-14-18-31(4)17-13-16-30(2)3;/h24,26-32,35,39,50H,12-23,25H2,1-11H3,(H-,55,56,57,58,59,61);/q-1;+2/p-1/b33-24+;/t31-,32-,35+,39+,50-;/m1./s1 ChemAxon inchikey QXWRYZIMSXOOPY-SKHCYZARSA-M ChemAxon polar_surface_area 122.38 ChemAxon refractivity 258.33 ChemAxon polarizability 107.46 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 6 ChemAxon donor_count 0 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 1259689 Specdb::MsMs 1259690 Specdb::MsMs 1259691 Specdb::MsMs 1374811 Specdb::MsMs 1374812 Specdb::MsMs 1374813 Specdb::MsMs 2831026 Specdb::MsMs 2831027 Specdb::MsMs 2831028 Specdb::MsMs 2847239 Specdb::MsMs 2847240 Specdb::MsMs 2847241 HMDB37256 38199 #<Reference:0x000055ce32c62770>