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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:22 UTC
HMDB IDHMDB0000668
Secondary Accession Numbers
  • HMDB00668
Metabolite Identification
Common NameHematoporphyrin IX
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.
Structure
Data?1563860662
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 Weight598.6887
Monoisotopic Molecular Weight598.279134968
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
CAS Registry Number14459-29-1
SMILES
CC(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 Identifier
InChI=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
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point172.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001u-1000090000-70e24f05dddc49e6dee5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-5000009000-2352934c5f80e33586d9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0000090000-4eb971e218f7bc04e22aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-0000090000-694741f189b1a163fc7bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00tu-1000490000-0474129e72c380285fc7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-0000090000-56f782011bf88e1430daJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0000090000-4d668424ee425cdd532aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-5000090000-c3029d22ed5bafd7281eJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Bladder
  • Fibroblasts
  • Platelet
  • Spleen
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022173
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHematoporphyrin
METLIN ID5638
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Muschter R: Photodynamic therapy: a new approach to prostate cancer. Curr Urol Rep. 2003 Jun;4(3):221-8. [PubMed:12756086 ]
  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. [PubMed:7588741 ]
  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. [PubMed:7540498 ]
  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. [PubMed:7109683 ]
  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. [PubMed:6241716 ]
  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. [PubMed:11733181 ]
  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. [PubMed:16545073 ]
  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. [PubMed:2133961 ]
  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. [PubMed:8778778 ]
  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. [PubMed:2149708 ]
  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. [PubMed:10920885 ]