ChemFOnt: Showing chemical card for Deuteroporphyrin IX (CFc000000452)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:50 UTC

Chemfont ID

CFc000000452

Molecule Identification

Common Name

Deuteroporphyrin IX

Definition

Deuteroporphyrin IX is a non-natural dicarboxylic porphyrin. Deuteroporphyrins are porphyrins with four methyl and two propionic acid side chains attached to the pyrrole rings. Deuteroporphyrin IX is described as a fecal porphyrin in patients with endemic chronic arsenic poisoning. (Environmental Sciences (Tokyo, Japan) (2001), 8(6), 561-570.). Excess accumulation of the biosynthetic intermediate protoporphyrin can lead to extensive tissue damage upon exposure to light since protoporpyhyrin is a potent photosensitizing agent, giving rise to membrane-destroying oxygen radicals or singlet oxygen. For instance, in the human porphyria disease porphyria variegata, a genetic deficiency in a heme biosynthetic enzyme, protoporphyrinogen oxidase, leads to protoporphyrin accumulation and lightdependent skin photosensitivity. Horseradish peroxidase (HRP) in the presence of glutathione (GSH) could oxidize the non-natural porphyrin deuteroporphyrin IX, which is closely related to protoporphyrin IX. The product is a unique green chlorin. One of the pyrrole rings had been modified by addition of an hydroxy and an oxo group, thus giving the characteristic reduced pyrrole ring of the chlorine. Of most importance for human medicine, peroxidative enzymes present in mammalian cells can also carry out these GSH-dependent oxidative conversions of protoporphyrin and deuteroporphyrin. (PMID: 10334939 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Deuteroporphyrin	HMDB
Deuteroporphyrin-IX	HMDB
3-[20-(2-Carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoate	HMDB

Chemical Formula

C₃₀H₃₀N₄O₄

Average Molecular Weight

510.5836

Monoisotopic Molecular Weight

510.226705468

IUPAC Name

3-[20-(2-carboxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid

Traditional Name

3-[20-(2-carboxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid

CAS Registry Number

448-65-7

SMILES

CC1=C/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(C=C4C)\C=C\1/N\2)/C(CCC(O)=O)=C3C

InChI Identifier

InChI=1S/C30H30N4O4/c1-15-9-20-12-25-17(3)21(5-7-29(35)36)27(33-25)14-28-22(6-8-30(37)38)18(4)26(34-28)13-24-16(2)10-19(32-24)11-23(15)31-20/h9-14,31,34H,5-8H2,1-4H3,(H,35,36)(H,37,38)/b19-11-,20-12-,23-11-,24-13-,25-12-,26-13-,27-14-,28-14-

InChI Key

KWKUIRGQJJFUCG-LMKUSPAJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Porphyrins

Direct Parent

Porphyrins

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Not Available

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cell

Hematocyte

Platelet (HMDB: HMDB0000579)

Source

Endogenous

Endogenous (HMDB: HMDB0000579)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.026 g/L	ALOGPS
logP	3.55	ALOGPS
logP	5.04	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	5.13	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	131.96 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	144.44 m³·mol⁻¹	ChemAxon
Polarizability	58.99 Å³	ChemAxon
Number of Rings	5	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

HMDB0000579

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022126

KNApSAcK ID

Not Available

Chemspider ID

16736707

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5561

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Borovkov, V. V.; Filippovich, E. I.; Evstigneeva, R. P. Synthesis and spectral investigation of deuteroporphyrin IX-based porphyrinquinone derivatives. Khimiya Geterotsiklicheskikh Soedinenii (1988), (5), 608-16.

Showing chemical card for Deuteroporphyrin IX (CFc000000452)

MOL for CFc000000452 (Deuteroporphyrin IX)

3D MOL for CFc000000452 (Deuteroporphyrin IX)

3D SDF for CFc000000452 (Deuteroporphyrin IX)

3D-SDF for CFc000000452 (Deuteroporphyrin IX)

PDB for CFc000000452 (Deuteroporphyrin IX)

3D PDB for CFc000000452 (Deuteroporphyrin IX)

SMILES for CFc000000452 (Deuteroporphyrin IX)

INCHI for CFc000000452 (Deuteroporphyrin IX)

Structure for CFc000000452 (Deuteroporphyrin IX)

3D Structure for CFc000000452 (Deuteroporphyrin IX)