ChemFOnt: Showing chemical card for Protochlorophyllide (CFc000012345)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:00:23 UTC

Chemfont ID

CFc000012345

Molecule Identification

Common Name

Protochlorophyllide

Definition

Protochlorophyllide is found in fruits. Protochlorophyllide is isolated from the seed husks of Cucurbita pepo Chlorophyll itself is bound to proteins and can transfer the absorbed energy in the required direction. Protochlorophyllide, differently, mostly occurs in the free form and under light conditions acts 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 D-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. Despite of numerous past attempts to find the mutant that overacumulates protochlorophyllide under usual conditions, only one such gene (flu) is currently (2009) known. Flu (first described in ) is a nuclear - encoded, chloroplast - located protein that appears containing only protein - protein interaction sites. It is currently not know which other proteins interact through this linker. The regulatory protein is a transmembrane protein that is located in the thylakoid membrane. Later it was discovered that Tigrina mutants in barley, known long time ago, are also mutated in the same gene It is not obvious why no mutants of any other gene were observed; maybe mutations in other proteins, involved into the regulatory chain, are fatal. Flu is a single gene, not a member of the gene family. Protochlorophyllide , more accurate monovinyl protochlorophyllide, is an immediate precursor of chlorophyll a that lacks the phytol side chain of chlorophyll. Unlike chlorophyll, protochlorophyllide is highly fluorescent; mutants that accumulate it glow in red if irradiated by the blue lightIn Angiosperms, the last step, conversion of protochlorophyllide to chlorophyll, is light - dependent and such plants are pale (etiolated) if grown in the darkness. Gymnosperms, algae, and photosynthetic bacteria additionally have another, light - independent enzyme and grow green in the darkness as well. The enzyme that converts protochlorophyllide to chlorophyll is protochlorophyllide reductase , EC 1.3.1.33. There are two structurally unrelated proteins with this activity: the light - dependent and the dark - operative. The light dependent reductase needs light to operate. The dark - operative version is a completely different protein, consisting of three subunits that exhibit significant sequence similarity to the three subunits of nitrogenase, which catalyzes the formation of ammonia from dinitrogen. This enzyme might be evolutionary older but (being similar to nitrogenase) is highly sensitive to free oxygen and does not work if its concentration exceeds about 3 %. Hence the alternative, light dependent version needed to evolve

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₃₅H₃₀MgN₄O₅

Average Molecular Weight

610.953

Monoisotopic Molecular Weight

610.20666178

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

14751-08-7

SMILES

COC(=O)C1C(=O)C2=C3N4C(C=C5C(C=C)=C(C)C6=[N]5[Mg]44N5C(=CC7=[N]4C(C(CCC(O)=O)=C7C)=C13)C(C)=C(C=C)C5=C6)=C2C

InChI Identifier

InChI=1S/C35H30N4O5.Mg/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;/h8-9,12-14,31H,1-2,10-11H2,3-7H3,(H,40,41);/q-2;+2/b22-12-,25-14-,26-13-;

InChI Key

DOAUWHZUFICIHX-XPFHVPSNSA-N

Chemical Taxonomy

Classification

Not classified

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031148)
Cytoplasm (HMDB: HMDB0031148)

Source

Exogenous

Exogenous (HMDB: HMDB0031148)

Food

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Endogenous (HMDB: HMDB0031148)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	1.35	ALOGPS
logS	-4.2	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	127.26 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	179.65 m³·mol⁻¹	ChemAxon
Polarizability	69.68 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Protochlorophyllide (CFc000012345)

MOL for CFc000012345 (Protochlorophyllide)

3D MOL for CFc000012345 (Protochlorophyllide)

3D SDF for CFc000012345 (Protochlorophyllide)

3D-SDF for CFc000012345 (Protochlorophyllide)

PDB for CFc000012345 (Protochlorophyllide)

3D PDB for CFc000012345 (Protochlorophyllide)

SMILES for CFc000012345 (Protochlorophyllide)

INCHI for CFc000012345 (Protochlorophyllide)

Structure for CFc000012345 (Protochlorophyllide)

3D Structure for CFc000012345 (Protochlorophyllide)