| Record Information |
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| Version | 2.0 |
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| Created at | 2024-09-09 23:16:19 UTC |
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| Updated at | 2024-09-09 23:16:19 UTC |
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| NP-MRD ID | NP0334347 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | chlorophyllide b |
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| Description | Chlorophyllide b is a member of the class of compounds known as metallotetrapyrroles. Metallotetrapyrroles are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom. Chlorophyllide b is practically insoluble (in water) and an extremely strong acidic compound (based on its pKa). Chlorophyllide b can be found in a number of food items such as cardoon, peach (variety), lime, and loquat, which makes chlorophyllide b a potential biomarker for the consumption of these food products. |
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| Structure | [Mg++].CCC1=C2\C=C3/N=C4/C(/C(C(=O)OC)C(=O)C4=C3C)=C3\N=C(\C=C4/[N-]/C(=C\C(=N2)\C\1=C/[O-])C(C=C)=C4C)C(C)C3CCC(O)=O InChI=1/C35H34N4O6.Mg/c1-7-18-15(3)22-11-23-16(4)20(9-10-28(41)42)32(38-23)30-31(35(44)45-6)34(43)29-17(5)24(39-33(29)30)12-26-19(8-2)21(14-40)27(37-26)13-25(18)36-22;/h7,11-14,16,20,31H,1,8-10H2,2-6H3,(H3,36,37,38,39,40,41,42,43);/q;+2/p-2 |
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| Synonyms | Not Available |
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| Chemical Formula | C35H32MgN4O6 |
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| Average Mass | 628.9680 Da |
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| Monoisotopic Mass | 628.21723 Da |
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| IUPAC Name | magnesium(2+) (1Z,8Z,12Z,14Z,18Z)-22-(2-carboxyethyl)-16-ethenyl-11-ethyl-3-(methoxycarbonyl)-17,21,26-trimethyl-12-(oxidomethylidene)-4-oxo-7,23,24,25-tetraazahexacyclo[18.2.1.1^{5,8}.1^{10,13}.1^{15,18}.0^{2,6}]hexacosa-1,5(26),6,8,10,13(25),14,16,18,20(23)-decaen-24-ide |
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| Traditional Name | magnesium(2+) (1Z,8Z,12Z,14Z,18Z)-22-(2-carboxyethyl)-16-ethenyl-11-ethyl-3-(methoxycarbonyl)-17,21,26-trimethyl-12-(oxidomethylidene)-4-oxo-7,23,24,25-tetraazahexacyclo[18.2.1.1^{5,8}.1^{10,13}.1^{15,18}.0^{2,6}]hexacosa-1,5(26),6,8,10,13(25),14,16,18,20(23)-decaen-24-ide |
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| CAS Registry Number | Not Available |
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| SMILES | [Mg++].CCC1=C2\C=C3/N=C4/C(/C(C(=O)OC)C(=O)C4=C3C)=C3\N=C(\C=C4/[N-]/C(=C\C(=N2)\C\1=C/[O-])C(C=C)=C4C)C(C)C3CCC(O)=O |
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| InChI Identifier | InChI=1/C35H34N4O6.Mg/c1-7-18-15(3)22-11-23-16(4)20(9-10-28(41)42)32(38-23)30-31(35(44)45-6)34(43)29-17(5)24(39-33(29)30)12-26-19(8-2)21(14-40)27(37-26)13-25(18)36-22;/h7,11-14,16,20,31H,1,8-10H2,2-6H3,(H3,36,37,38,39,40,41,42,43);/q;+2/p-2 |
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| InChI Key | QPDWBRHRBKXUNS-UHFFFAOYNA-L |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | Not Available |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Tetrapyrroles and derivatives |
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| Sub Class | Metallotetrapyrroles |
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| Direct Parent | Metallotetrapyrroles |
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| Alternative Parents | |
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| Substituents | - Metallotetrapyrrole skeleton
- Dicarboxylic acid or derivatives
- Substituted pyrrole
- Pyrrole
- Pyrroline
- Methyl ester
- Heteroaromatic compound
- Carboxylic acid ester
- Carboxylic acid salt
- Ketimine
- Carboxylic acid derivative
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Azacycle
- Carboxylic acid
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Aldehyde
- Imine
- Organic nitrogen compound
- Organopnictogen compound
- Carbonyl group
- Organic zwitterion
- Organic salt
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| General References | - Xiong J, Wen G, Song J, Liu X, Chen Q, Zhang G, Xiao Y, Liu X, Deng H, Tang W, Wang F, Lu X: Knockout of the Chlorophyll a Oxygenase Gene OsCAO1 Reduces Chilling Tolerance in Rice Seedlings. Genes (Basel). 2024 Jun 2;15(6):721. doi: 10.3390/genes15060721. [PubMed:38927664 ]
- Chen K, Li Y, Zhou C, Wang Y, Zalan Z, Cai T: Inhibitory effects of chlorophyll pigments on the bioaccessibility of beta-carotene: Influence of chlorophyll structure and oil matrix. Food Chem. 2024 Sep 1;451:139457. doi: 10.1016/j.foodchem.2024.139457. Epub 2024 Apr 24. [PubMed:38703726 ]
- Zhang L, Zhang J, Mao Y, Yin Y, Shen X: Physiological analysis and transcriptome sequencing of a delayed-green leaf mutant 'Duojiao' of ornamental crabapple (Malus sp.). Physiol Mol Biol Plants. 2022 Oct;28(10):1833-1848. doi: 10.1007/s12298-022-01248-7. Epub 2022 Nov 27. [PubMed:36484024 ]
- Zhao Y, Zhang F, Mickan B, Wang D, Wang W: Physiological, proteomic, and metabolomic analysis provide insights into Bacillus sp.-mediated salt tolerance in wheat. Plant Cell Rep. 2022 Jan;41(1):95-118. doi: 10.1007/s00299-021-02788-0. Epub 2021 Sep 21. [PubMed:34546426 ]
- Wang YT, Yang CH, Huang KS, Shaw JF: Chlorophyllides: Preparation, Purification, and Application. Biomolecules. 2021 Jul 28;11(8):1115. doi: 10.3390/biom11081115. [PubMed:34439782 ]
- Loh CH, Inbaraj BS, Liu MH, Chen BH: Determination of chlorophylls in Taraxacum formosanum by high-performance liquid chromatography-diode array detection-mass spectrometry and preparation by column chromatography. J Agric Food Chem. 2012 Jun 20;60(24):6108-15. doi: 10.1021/jf301422m. Epub 2012 Jun 12. [PubMed:22656126 ]
- Mueller AH, Dockter C, Gough SP, Lundqvist U, von Wettstein D, Hansson M: Characterization of mutations in barley fch2 encoding chlorophyllide a oxygenase. Plant Cell Physiol. 2012 Jul;53(7):1232-46. doi: 10.1093/pcp/pcs062. Epub 2012 Apr 25. [PubMed:22537757 ]
- Reinbothe C, Bartsch S, Eggink LL, Hoober JK, Brusslan J, Andrade-Paz R, Monnet J, Reinbothe S: A role for chlorophyllide a oxygenase in the regulated import and stabilization of light-harvesting chlorophyll a/b proteins. Proc Natl Acad Sci U S A. 2006 Mar 21;103(12):4777-82. doi: 10.1073/pnas.0511066103. Epub 2006 Mar 10. [PubMed:16537436 ]
- Pattanayak GK, Biswal AK, Reddy VS, Tripathy BC: Light-dependent regulation of chlorophyll b biosynthesis in chlorophyllide a oxygenase overexpressing tobacco plants. Biochem Biophys Res Commun. 2005 Jan 14;326(2):466-71. doi: 10.1016/j.bbrc.2004.11.049. [PubMed:15582600 ]
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