Protoporphyrin

Identification

Name
Protoporphyrin
Accession Number
DB02285  (EXPT02636)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • Protoporphyrin IX
Categories
UNII
C2K325S808
CAS number
553-12-8
Weight
Average: 562.6582
Monoisotopic: 562.258005596
Chemical Formula
C34H34N4O4
InChI Key
KSFOVUSSGSKXFI-UJJXFSCMSA-N
InChI
InChI=1S/C34H34N4O4/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/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-
IUPAC Name
3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid
SMILES
CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UFerritin light chainNot 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
Acute Intermittent PorphyriaDisease
Porphyrin MetabolismMetabolic
Porphyrin MetabolismMetabolic
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseDisease
Porphyrin Metabolism Metabolic
Porphyrin MetabolismMetabolic
Hereditary Coproporphyria (HCP)Disease
Porphyria Variegata (PV)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
Porfimer sodiumProtoporphyrin may increase the photosensitizing activities of Porfimer sodium.
VerteporfinProtoporphyrin may increase the photosensitizing activities of Verteporfin.
Food Interactions
Not Available

References

Synthesis Reference

Elaine A. Best, Charles Lee Hershberger, Christopher Carl Frye, "Methods of reducing the levels of protoporphyrin IX in recombinant hemoglobin preparations." U.S. Patent US6136565, issued April, 1998.

US6136565
General References
Not Available
External Links
Human Metabolome Database
HMDB0000241
KEGG Compound
C02191
PubChem Compound
4971
PubChem Substance
46506247
ChemSpider
10469486
BindingDB
50004784
ChEBI
15430
ChEMBL
CHEMBL1325592
Therapeutic Targets Database
DNC001154
HET
PP9
Wikipedia
Protoporphyrin_IX

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
PropertyValueSource
water solubility169 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility0.0217 mg/mLALOGPS
logP4.4ALOGPS
logP6.78ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)4.96ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area131.96 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity163.81 m3·mol-1ChemAxon
Polarizability65.97 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.622
Blood Brain Barrier+0.6268
Caco-2 permeable-0.7138
P-glycoprotein substrateSubstrate0.6404
P-glycoprotein inhibitor INon-inhibitor0.705
P-glycoprotein inhibitor IINon-inhibitor0.8478
Renal organic cation transporterNon-inhibitor0.8067
CYP450 2C9 substrateNon-substrate0.8106
CYP450 2D6 substrateNon-substrate0.8237
CYP450 3A4 substrateSubstrate0.5341
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.7052
CYP450 2C19 inhibitorNon-inhibitor0.8749
CYP450 3A4 inhibitorNon-inhibitor0.8733
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8535
Ames testNon AMES toxic0.7111
CarcinogenicityNon-carcinogens0.9123
BiodegradationNot ready biodegradable0.9479
Rat acute toxicity2.5655 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9808
hERG inhibition (predictor II)Non-inhibitor0.9459
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Iron ion binding
Specific Function
Stores iron in a soluble, non-toxic, readily available form. Important for iron homeostasis. Iron is taken up in the ferrous form and deposited as ferric hydroxides after oxidation. Also plays a ro...
Gene Name
FTL
Uniprot ID
P02792
Uniprot Name
Ferritin light chain
Molecular Weight
20019.49 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:15