Hematoporphyrin IX (CHEM034935)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:20:54 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM034935
Identification
Common NameHematoporphyrin IX
ClassSmall Molecule
DescriptionIron-free derivatives of heme with 4 methyl groups, 2 hydroxyethyl groups and 2 propionic acid groups attached to the pyrrole rings. Some of these phosphosensitizing agents are used in the phototherapy of malignant neoplasms. -- Pubchem [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3,5,8-Tetramethyl-2,4-bis( -hydroxyethyl)porphine-6,7-dipropionateHMDB
1,3,5,8-Tetramethyl-2,4-bis( -hydroxyethyl)porphine-6,7-dipropionic acidHMDB
1,3,5,8-Tetramethyl-2,4-bis(a-hydroxyethyl)porphine-6,7-dipropionateHMDB
1,3,5,8-Tetramethyl-2,4-bis(a-hydroxyethyl)porphine-6,7-dipropionic acidHMDB
1,3,5,8-Tetramethyl-2,4-bis(alpha-hydroxyethyl)prophine-6,7-dipropionateHMDB
1,3,5,8-Tetramethyl-2,4-bis(alpha-hydroxyethyl)prophine-6,7-dipropionic acidHMDB
7,12-Bis(1-hydroxyethyl)-3,8,13,17-tetramethyl-2,18-porphinedipropionateHMDB
7,12-Bis(1-hydroxyethyl)-3,8,13,17-tetramethyl-2,18-porphinedipropionic acidHMDB
HaematoporphyrinHMDB
HematoporphyrinHMDB
HPHMDB
HpIXHMDB
PhotodynHMDB
3-[20-(2-Carboxyethyl)-10,15-bis(1-hydroxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoateHMDB
Chemical FormulaC34H38N4O6
Average Molecular Mass598.689 g/mol
Monoisotopic Mass598.279 g/mol
CAS Registry Number14459-29-1
IUPAC Name3-[20-(2-carboxyethyl)-10,15-bis(1-hydroxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid
Traditional Name3-[20-(2-carboxyethyl)-10,15-bis(1-hydroxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid
SMILESCC(O)C1=C2NC(\C=C3/N\C(=C/C4=N/C(=C\C5=N\C(=C/2)\C(C)=C5C(C)O)/C(C)=C4CCC(O)=O)C(CCC(O)=O)=C3C)=C1C
InChI IdentifierInChI=1S/C34H38N4O6/c1-15-21(7-9-31(41)42)27-14-28-22(8-10-32(43)44)16(2)24(36-28)12-29-34(20(6)40)18(4)26(38-29)13-30-33(19(5)39)17(3)25(37-30)11-23(15)35-27/h11-14,19-20,35,37,39-40H,7-10H2,1-6H3,(H,41,42)(H,43,44)/b23-11-,24-12-,25-11-,26-13-,27-14-,28-14-,29-12-,30-13-
InChI KeyQXNKGOQXMZXHIB-AMPAVEGJSA-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassPorphyrins
Direct ParentPorphyrins
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.037 g/LALOGPS
logP2.74ALOGPS
logP4.85ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)4.88ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area172.42 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity166.91 m³·mol⁻¹ChemAxon
Polarizability69.32 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001u-1000090000-70e24f05dddc49e6dee5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-5000009000-2352934c5f80e33586d9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0000090000-4eb971e218f7bc04e22aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-0000090000-694741f189b1a163fc7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00tu-1000490000-0474129e72c380285fc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-0000090000-56f782011bf88e1430daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0000090000-4d668424ee425cdd532aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-5000090000-c3029d22ed5bafd7281eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0000090000-ac12325f1e8be5544ae4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000090000-760f126f332f1a968145Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-0000090000-95fe0a36d2dc419d6134Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-0000090000-b33f75717dcead300fbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000090000-68625cb3c0bceaf2da3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-0000190000-e325465cd23fcf3d8201Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000668
FooDB IDFDB022173
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5638
PDB IDNot Available
Wikipedia LinkHematoporphyrin
Chemspider ID35013024
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Muschter R: Photodynamic therapy: a new approach to prostate cancer. Curr Urol Rep. 2003 Jun;4(3):221-8.
2. Ricchelli F, Gobbo S, Jori G, Salet C, Moreno G: Temperature-induced changes in fluorescence properties as a probe of porphyrin microenvironment in lipid membranes. 2. The partition of hematoporphyrin and protoporphyrin in mitochondria. Eur J Biochem. 1995 Oct 1;233(1):165-70.
3. Kongshaug M, Moan J: Separation of lipoproteins, albumin and gamma-globulin by single-step ultracentrifugation of human serum. Application. I: Binding of hematoporphyrin to human serum and to albumin. Int J Biochem Cell Biol. 1995 Apr;27(4):371-84.
4. Benson RC Jr, Farrow GM, Kinsey JH, Cortese DA, Zincke H, Utz DC: Detection and localization of In situ carcinoma of the bladder with hematoporphyrin derivative. Mayo Clin Proc. 1982 Sep;57(9):548-55.
5. Benson RC Jr: The use of hematoporphyrin derivative (HpD) in the localization and treatment of transitional cell carcinoma (TCC) of the bladder. Prog Clin Biol Res. 1984;170:795-804.
6. Polo L, Valduga G, Jori G, Reddi E: Low-density lipoprotein receptors in the uptake of tumour photosensitizers by human and rat transformed fibroblasts. Int J Biochem Cell Biol. 2002 Jan;34(1):10-23.
7. Severina IS, Pyatakova NV, Shchegolev AY, Ponomarev GV: YC-1-like potentiation of NO-dependent activation of soluble guanylate cyclase by derivatives of protoporphyrin IX. Biochemistry (Mosc). 2006 Mar;71(3):340-4.
8. Jan CY, Kimura M, Takahama U: [Effects of quercetin on photosensitized oxidation of alpha-tocopherol in human blood cells in the presence of hematoporphyrin]. Shoni Shikagaku Zasshi. 1990;28(3):600-7.
9. Michaux MA, Dautant A, Gallois B, Granier T, d'Estaintot BL, Precigoux G: Structural investigation of the complexation properties between horse spleen apoferritin and metalloporphyrins. Proteins. 1996 Mar;24(3):314-21.
10. Kongshaug M, Rimington C, Evensen JF, Peng Q, Moan J: Hematoporphyrin diethers--V. Plasma protein binding and photosensitizing efficiency. Int J Biochem. 1990;22(10):1127-31.
11. Li C, Chen Y, Wang Q: [Whole bladder wall laser irradiation to prevent bladder cancer recurrence with intravesical HpD and ascorbic acid]. Zhonghua Zhong Liu Za Zhi. 1997 Nov;19(6):463-5.