Coproporphyrinogen III

Identification

Generic Name
Coproporphyrinogen III
DrugBank Accession Number
DB04461
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 660.7566
Monoisotopic: 660.315914404
Chemical Formula
C36H44N4O8
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

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UUroporphyrinogen decarboxylaseNot AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Porphyrin MetabolismMetabolic
Acute Intermittent PorphyriaDisease
Porphyria Variegata (PV)Disease
Hereditary Coproporphyria (HCP)Disease
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aromatic heteropolycyclic compound / Azacycle / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
coproporphyrinogen (CHEBI:15439)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
2624-63-7
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-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]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

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
Human Metabolome Database
HMDB0001261
KEGG Compound
C03263
PubChem Compound
321
PubChem Substance
46508802
ChemSpider
315
ChEBI
15439
ChEMBL
CHEMBL1231891
ZINC
ZINC000004096059
PDBe Ligand
CP3
Wikipedia
Coproporphyrinogen_III
PDB Entries
1r3t / 1r3w / 1r3y / 2q71

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
Polarizability72.85 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-MSsplash10-0uxu-1000029000-41e3094ebb1945eeb049
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0000009000-be04df6a3d071def22ca
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-0000009000-43f0898eb32a3065d4da
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0000019000-985689094dbd26cbd53e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052g-4000049000-80341c650cc57553e8ac
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dj-0000092000-707cc6b02e1dc6f3ea09
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01dj-0000092000-ea929eabb6eeca5ea26f
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-261.9176756
predicted
DarkChem Lite v0.1.0
[M-H]-260.6209756
predicted
DarkChem Lite v0.1.0
[M-H]-263.7480756
predicted
DarkChem Lite v0.1.0
[M-H]-244.86432
predicted
DeepCCS 1.0 (2019)
[M+H]+247.18938
predicted
DeepCCS 1.0 (2019)
[M+Na]+252.9298
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52