ChemFOnt: Showing chemical card for Mesoporphyrin IX (CFc000001605)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:16 UTC

Chemfont ID

CFc000001605

Molecule Identification

Common Name

Mesoporphyrin IX

Definition

Mesoporphyrins are porphyrins with four methyl, two ethyl, and two propionic acid side chains attached to the pyrrole rings. There are fifteen isomers of mesoporphyrin. Mesoporphyrin has anti-inflammatory action. Mesoporphyrin inhibits interferon-gamma and interleukin-6 production, which is closely related to the suppression of prostaglandin E2 generation by interfering cyclooxygenase 1 and 2 enzyme activities suggesting that the inhibition of cytokine production is one of the anti-inflammatory mechanisms of mesoporphyrin. (PMID: 10446754 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
7,12-Diethyl-3,8,13,17-tetramethyl-2,18-porphinedipropionic acid	HMDB
7,12-Diethyl-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoate	HMDB
7,12-Diethyl-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoic acid	HMDB
Mesoporphyrin	HMDB
MPIX	HMDB
3-[20-(2-Carboxyethyl)-10,15-diethyl-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6(24),7,9,11,13,15,17,19-undecaen-4-yl]propanoate	Generator, HMDB

Chemical Formula

C₃₄H₃₈N₄O₄

Average Molecular Weight

566.6899

Monoisotopic Molecular Weight

566.289305724

IUPAC Name

3-[20-(2-carboxyethyl)-10,15-diethyl-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),4,6,8,10,12,14,16,18(21),19-undecaen-4-yl]propanoic acid

Traditional Name

MPIX

CAS Registry Number

493-90-3

SMILES

CCC1=C(C)/C2=C/C3=C(CC)C(C)=C(N3)\C=C3/N=C(/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)C(CCC(O)=O)=C3C

InChI Identifier

InChI=1S/C34H38N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h13-16,35-36H,7-12H2,1-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-

InChI Key

NCAJWYASAWUEBY-UJJXFSCMSA-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: HMDB0002379)
Cell membrane (HMDB: HMDB0002379)

Organ

Spleen (HMDB: HMDB0002379)

Source

Endogenous

Endogenous (HMDB: HMDB0002379)

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	0.024 g/L	ALOGPS
logP	4.82	ALOGPS
logP	7.29	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	4.95	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	8	ChemAxon
Refractivity	163.72 m³·mol⁻¹	ChemAxon
Polarizability	67.28 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

HMDB0002379

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022986

KNApSAcK ID

Not Available

Chemspider ID

65350

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6655

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Fabry, T. L.; Simo, C.; Javaherian, K. Preparation of mesoporphyrin IX and copper and manganese mesoporphyrin complexes of apohemoglobin. Biochimica et Biophysica Acta, Protein Structure (1968), 160(1), 118-22.

Showing chemical card for Mesoporphyrin IX (CFc000001605)

MOL for CFc000001605 (Mesoporphyrin IX)

3D MOL for CFc000001605 (Mesoporphyrin IX)

3D SDF for CFc000001605 (Mesoporphyrin IX)

3D-SDF for CFc000001605 (Mesoporphyrin IX)

PDB for CFc000001605 (Mesoporphyrin IX)

3D PDB for CFc000001605 (Mesoporphyrin IX)

SMILES for CFc000001605 (Mesoporphyrin IX)

INCHI for CFc000001605 (Mesoporphyrin IX)

Structure for CFc000001605 (Mesoporphyrin IX)

3D Structure for CFc000001605 (Mesoporphyrin IX)