ChemFOnt: Showing chemical card for Uroporphyrin II (CFc000000692)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:09 UTC

Chemfont ID

CFc000000692

Molecule Identification

Common Name

Uroporphyrin II

Definition

Uroporphyrin is the porphyrin produced by oxidation of the methylene bridges in uroporphyrinogen. They have four acetic acid and four propionic acid side chains attached to the pyrrole rings. Uroporphyrinogen I and III are formed from polypyrryl methane in the presence of uroporphyrinogen III cosynthetase and uroporphyrin I synthetase, respectively. They can yield uroporphyrins by autooxidation or coproporphyrinogens by decarboxylation. Excessive amounts of uroporphyrin I are excreted in congenital erythropoietic porphyria, and both types I and III are excreted in porphyria cutanea tarda. Uroporphyrin I and III are the most common isomemrs. Uroporphyrin II is a rare isomer.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Isouroporphyrin (II) octamethyl ester	HMDB
Uroporphyrin I octamethyl ester	HMDB
Methyl 9,19-bis(2-methoxy-2-oxoethyl)-5,10,14,15,20-pentakis(3-methoxy-3-oxopropyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaene-4-carboxylic acid	HMDB

Chemical Formula

C₄₈H₅₄N₄O₁₆

Average Molecular Weight

942.9596

Monoisotopic Molecular Weight

942.3534817

IUPAC Name

methyl 9,19-bis(2-methoxy-2-oxoethyl)-5,10,14,15,20-pentakis(3-methoxy-3-oxopropyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaene-4-carboxylate

Traditional Name

uroporphyrin II

CAS Registry Number

531-42-0

SMILES

COC(=O)CCC1=C(CCC(=O)OC)/C2=C/C3=N/C(=C\C4=C(C(=O)OC)C(CCC(=O)OC)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(=O)OC)=C4CC(=O)OC)/C(CCC(=O)OC)=C3CC(=O)OC

InChI Identifier

InChI=1S/C48H54N4O16/c1-61-40(53)14-9-25-26(10-15-41(54)62-2)33-22-37-31(20-46(59)67-7)28(12-17-43(56)64-4)35(51-37)24-39-47(48(60)68-8)29(13-18-44(57)65-5)36(52-39)23-38-30(19-45(58)66-6)27(11-16-42(55)63-3)34(50-38)21-32(25)49-33/h21-24,49,52H,9-20H2,1-8H3/b32-21-,33-22-,34-21-,35-24-,36-23-,37-22-,38-23-,39-24-

InChI Key

JXFYRPWVBHUVFB-BGKHBZPASA-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

Membrane (HMDB: HMDB0000869)
Cell membrane (HMDB: HMDB0000869)

Source

Endogenous

Endogenous (HMDB: HMDB0000869)

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	0.013 g/L	ALOGPS
logP	2.91	ALOGPS
logP	5.34	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	10.87	ChemAxon
pKa (Strongest Basic)	4.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	267.76 Å²	ChemAxon
Rotatable Bond Count	28	ChemAxon
Refractivity	240.02 m³·mol⁻¹	ChemAxon
Polarizability	102.6 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

HMDB0000869

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022291

KNApSAcK ID

Not Available

Chemspider ID

4575518

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5830

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Arsenault, G. P.; Bullock, E.; MacDonald, S. F. Pyrromethanes and porphyrins therefrom. Journal of the American Chemical Society (1960), 82 4384-9.

Showing chemical card for Uroporphyrin II (CFc000000692)

MOL for CFc000000692 (Uroporphyrin II)

3D MOL for CFc000000692 (Uroporphyrin II)

3D SDF for CFc000000692 (Uroporphyrin II)

3D-SDF for CFc000000692 (Uroporphyrin II)

PDB for CFc000000692 (Uroporphyrin II)

3D PDB for CFc000000692 (Uroporphyrin II)

SMILES for CFc000000692 (Uroporphyrin II)

INCHI for CFc000000692 (Uroporphyrin II)

Structure for CFc000000692 (Uroporphyrin II)

3D Structure for CFc000000692 (Uroporphyrin II)