Coproporphyrinogen III

Identification

Name
Coproporphyrinogen III
Accession Number
DB04461  (EXPT00993)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 3,8,13,17-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropionic acid
  • 5,10,15,20,22,24-hexahydro-3,8,13,17-tetramethyl-21H,23H-porphine-2,7,12,18-tetrapropanoic acid
Categories
UNII
Not Available
CAS number
2624-63-7
Weight
Average: 660.7566
Monoisotopic: 660.315914404
Chemical Formula
C36H44N4O8
InChI Key
NIUVHXTXUXOFEB-UHFFFAOYSA-N
InChI
InChI=1S/C36H44N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)
IUPAC Name
3-[10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid
SMILES
CC1=C2CC3=C(C)C(CCC(O)=O)=C(CC4=C(CCC(O)=O)C(C)=C(CC5=C(CCC(O)=O)C(C)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UUroporphyrinogen decarboxylaseNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Hereditary Coproporphyria (HCP)Disease
Porphyrin MetabolismMetabolic
Acute Intermittent PorphyriaDisease
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseDisease
Porphyria Variegata (PV)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Ichiro Kojima, Kenji Maruhashi, Yasuo Fujiwara, "Process for producing coproporphyrin III." U.S. Patent US4334021, issued September, 1978.

US4334021
General References
Not Available
External Links
Human Metabolome Database
HMDB01261
KEGG Compound
C03263
PubChem Compound
321
PubChem Substance
46508802
ChemSpider
315
ChEBI
15439
ChEMBL
CHEMBL1231891
HET
CP3
PDB Entries
1r3t / 1r3w / 1r3y / 2q71

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0112 mg/mLALOGPS
logP1.96ALOGPS
logP4.89ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.8ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area212.36 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity181.86 m3·mol-1ChemAxon
Polarizability72.88 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6451
Blood Brain Barrier+0.5266
Caco-2 permeable-0.7329
P-glycoprotein substrateSubstrate0.5913
P-glycoprotein inhibitor INon-inhibitor0.9249
P-glycoprotein inhibitor IINon-inhibitor0.9142
Renal organic cation transporterNon-inhibitor0.8865
CYP450 2C9 substrateNon-substrate0.7881
CYP450 2D6 substrateNon-substrate0.8374
CYP450 3A4 substrateNon-substrate0.5507
CYP450 1A2 substrateNon-inhibitor0.6181
CYP450 2C9 inhibitorNon-inhibitor0.8409
CYP450 2D6 inhibitorNon-inhibitor0.9245
CYP450 2C19 inhibitorNon-inhibitor0.8905
CYP450 3A4 inhibitorNon-inhibitor0.9546
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9661
Ames testNon AMES toxic0.8623
CarcinogenicityNon-carcinogens0.9338
BiodegradationNot ready biodegradable0.759
Rat acute toxicity2.5108 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9795
hERG inhibition (predictor II)Non-inhibitor0.9091
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-0000049000-0387f74262a47cf81121
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05mn-0000095000-92704e3251119447de7c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0000190000-117c439eaa250aa4b3b3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-0000049000-0387f74262a47cf81121
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05mn-0000095000-92704e3251119447de7c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0000190000-117c439eaa250aa4b3b3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-0000029000-96c0bca58c9caf08416f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052g-1000079000-1da57e7f8a138a6c5516
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052g-7000097000-2c52075e18d7d944ae80
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-0000029000-96c0bca58c9caf08416f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052g-1000079000-1da57e7f8a138a6c5516
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052g-7000097000-2c52075e18d7d944ae80

Taxonomy

Description
This compound belongs to the class of organic compounds known as porphyrins. These 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
Tetracarboxylic acids and derivatives / Substituted pyrroles / Heteroaromatic compounds / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Porphyrin / Tetracarboxylic acid or derivatives / Substituted pyrrole / Pyrrole / Heteroaromatic compound / Carboxylic acid derivative / Carboxylic acid / Azacycle / Carbonyl group / Hydrocarbon derivative
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
coproporphyrinogen (CHEBI:15439)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Uroporphyrinogen decarboxylase activity
Specific Function
Catalyzes the decarboxylation of four acetate groups of uroporphyrinogen-III to yield coproporphyrinogen-III.
Gene Name
UROD
Uniprot ID
P06132
Uniprot Name
Uroporphyrinogen decarboxylase
Molecular Weight
40786.58 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:42