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Pheophorbide

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Pheophorbide a
Names
IUPAC name (3S,4S)-9-Ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.036.110 Edit this at Wikidata
EC Number
  • 239-738-5
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C35H36N4O5/c1-8-19-15(3)22-12-24-17(5)21(10-11-28(40)41)32(38-24)30-31(35(43)44-7)34(42)29-18(6)25(39-33(29)30)14-27-20(9-2)16(4)23(37-27)13-26(19)36-22/h8,12-14,17,21,31,36,39H,1,9-11H2,2-7H3,(H,40,41)/b22-12-,23-13-,24-12-,25-14-,26-13-,27-14-,32-30-/t17-,21-,31+/m0/s1Key: NSFSLUUZQIAOOX-QEWKCGBTSA-N
  • InChI=1/C35H36N4O5/c1-8-19-15(3)22-12-24-17(5)21(10-11-28(40)41)32(38-24)30-31(35(43)44-7)34(42)29-18(6)25(39-33(29)30)14-27-20(9-2)16(4)23(37-27)13-26(19)36-22/h8,12-14,17,21,31,36,39H,1,9-11H2,2-7H3,(H,40,41)/b22-12-,23-13-,24-12-,25-14-,26-13-,27-14-,32-30-/t17-,21-,31+/m0/s1Key: NSFSLUUZQIAOOX-QEWKCGBTBX
SMILES
  • CCC1=C2C=C3C(=C4C(=O)(C(=C5((C(=N5)C=C6C(=C(C(=CC(=C1C)N2)N6)C=C)C)C)CCC(=O)O)C4=N3)C(=O)OC)C
Properties
Chemical formula C35H36N4O5
Molar mass 592.68 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

Pheophorbide or phaeophorbide is a product of chlorophyll breakdown and a derivative of pheophytin where both the central magnesium has been removed and the phytol tail has been hydrolyzed. It is used as a photosensitizer in photodynamic therapy.

Pheophorbide may be generated by digestion of ingested plant matter. Both worm (Caenorhabditis elegans) and mouse mitochondria are able to use the molecule in a form of ad hoc photoheterotrophy.

References

  1. Chen, K.; et al. (2009). "Novel photosensitizer-protein nanoparticles for Photodynamic therapy: Photophysical characterization and in vitro investigations". Journal of Photochemistry and Photobiology B: Biology. 96 (1): 66–74. doi:10.1016/j.jphotobiol.2009.04.006. PMID 19442534.
  2. Xu, Chen; Zhang, Junhua; Mihai, Doina M.; Washington, Ilyas (2014-01-15). "Light-harvesting chlorophyll pigments enable mammalian mitochondria to capture photonic energy and produce ATP". Journal of Cell Science. 127 (2): 388–399. doi:10.1242/jcs.134262. ISSN 0021-9533. PMC 6518289. PMID 24198392.
Types of tetrapyrroles
Bilanes
(Linear)
Phytobilins
Phycobilins
Macrocycle
Corrinoids
Porphyrins
Protoporphyrins
Phytoporphyrins
Reduced
porphyrins
Porphyrinogens
Chlorins
Bacteriochlorins
Isobacteriochlorins
Corphins
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