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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:24 UTC
HMDB IDHMDB0014824
Secondary Accession Numbers
  • HMDB14824
Metabolite Identification
Common NamePentosan Polysulfate
DescriptionPentosan Polysulfate is only found in individuals that have used or taken this drug. It is a sulfated pentosyl polysaccharide with heparin-like properties. [PubChem]Pentosan polysulfate is a polymer of xylose hydrogen sulfate and contains two sulfate groups per carbohydrate monomer. It binds Fibroblast growth factors (FGFs) as well as other heparin-binding growth factors. It has been shown to interact also with the heparin-binding site of FGFR-1. It inhibits the growth of SW13 adrenocortical cells transfected with FGF-4 and tumorigenicity of MCF-7 breast carcinoma cells transfected with FGF-1 or FGF-4.
Structure
Data?1582753224
Synonyms
ValueSource
Pentosan polysulfuric acidGenerator
Pentosan polysulphateGenerator
Pentosan polysulphuric acidGenerator
Polyester, pentosan sulfuricHMDB
SP 54, TavanHMDB
946, HOE-bayHMDB
FibrocidHMDB
HOE bay 946HMDB
HemoclarHMDB
Polypentose sulfateHMDB
Polysulfate sodium, pentosanHMDB
Sulfate, xylanHMDB
Sulfuric polyester, pentosaneHMDB
Polyester, pentosane sulfuricHMDB
Polysulfate, pentosanHMDB
Sodium, pentosan polysulfateHMDB
Xylan SP54HMDB
HOE-bay-946HMDB
Pentosan sulfuric polyesterHMDB
Polysulphate sodium, pentosanHMDB
SP54, XylanHMDB
Sulfuric polyester, pentosanHMDB
Xylan, polysulfatedHMDB
ElmironHMDB
PZ-68HMDB
Polysulfated xylanHMDB
Sodium, pentosan polysulphateHMDB
Xylan sulfateHMDB
BAY 946HMDB
BAY-946HMDB
HOE-bay 946HMDB
Pentosan polysulfate sodiumHMDB
SP-54HMDB
Sulfate, polypentoseHMDB
54, Tavan SPHMDB
HOE 946HMDB
HOE-946HMDB
PZ 68HMDB
Pentosan polysulphate sodiumHMDB
Pentosane sulfuric polyesterHMDB
SP 54HMDB
Tavan SP 54HMDB
[(2R,3R,4S,5R)-2-Hydroxy-5-{[(2S,3R,4S,5R)-5-hydroxy-3,4-bis(sulfooxy)oxan-2-yl]oxy}-4-(sulfooxy)oxan-3-yl]oxidanesulfonateGenerator
[(2R,3R,4S,5R)-2-Hydroxy-5-{[(2S,3R,4S,5R)-5-hydroxy-3,4-bis(sulphooxy)oxan-2-yl]oxy}-4-(sulphooxy)oxan-3-yl]oxidanesulphonateGenerator
[(2R,3R,4S,5R)-2-Hydroxy-5-{[(2S,3R,4S,5R)-5-hydroxy-3,4-bis(sulphooxy)oxan-2-yl]oxy}-4-(sulphooxy)oxan-3-yl]oxidanesulphonic acidGenerator
Pentosan polysulfateMeSH
Chemical FormulaC10H18O21S4
Average Molecular Weight602.497
Monoisotopic Molecular Weight601.922340398
IUPAC Name[(2S,3R,4S,5R)-5-hydroxy-2-{[(3R,4S,5R,6R)-6-hydroxy-4,5-bis(sulfooxy)oxan-3-yl]oxy}-4-(sulfooxy)oxan-3-yl]oxidanesulfonic acid
Traditional Namepentosan polysulfate
CAS Registry Number37300-21-3
SMILES
O[C@@H]1CO[C@@H](O[C@@H]2CO[C@@H](O)[C@H](OS(O)(=O)=O)[C@H]2OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O
InChI Identifier
InChI=1S/C10H18O21S4/c11-3-1-26-10(8(31-35(22,23)24)5(3)28-32(13,14)15)27-4-2-25-9(12)7(30-34(19,20)21)6(4)29-33(16,17)18/h3-12H,1-2H2,(H,13,14,15)(H,16,17,18)(H,19,20,21)(H,22,23,24)/t3-,4-,5+,6+,7-,8-,9-,10+/m1/s1
InChI KeyFCCNSUIJIOOXEZ-SJYYZXOBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • Disaccharide
  • O-glycosyl compound
  • Oxane
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Hemiacetal
  • Secondary alcohol
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.49 g/LNot Available
LogP-8Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.49 g/LALOGPS
logP-2.5ALOGPS
logP-11ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)-2.9ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area322.55 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity96.38 m³·mol⁻¹ChemAxon
Polarizability46.17 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ffc-1352290000-21c35dc5952469d74b70Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05vo-7531169000-bff61bd1bd45c07aea0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uec-0161193000-2751c8c17ef9495f99d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-0082390000-473869e5985da4cdd053Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-5976210000-a983df365421163dd754Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udl-0097087000-07678829971646c283dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-3095270000-2e87e56a811da32a40efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056u-2093000000-21f66039d5f58443945bSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00686 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00686 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00686
Phenol Explorer Compound IDNot Available
FooDB IDFDB019140
KNApSAcK IDNot Available
Chemspider ID34595
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPentosan polysulfate
METLIN IDNot Available
PubChem Compound37720
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in growth factor activity
Specific function:
The heparin-binding growth factors are angiogenic agents in vivo and are potent mitogens for a variety of cell types in vitro. There are differences in the tissue distribution and concentration of these 2 growth factors
Gene Name:
FGF2
Uniprot ID:
P09038
Molecular weight:
30769.7
References
  1. Zugmaier G, Favoni R, Jaeger R, Rosen N, Knabbe C: Polysulfated heparinoids selectively inactivate heparin-binding angiogenesis factors. Ann N Y Acad Sci. 1999;886:243-8. [PubMed:10667230 ]
  2. Mucha S, Melen-Mucha G, Stepien T, Godlewski A, Stepien H: Effects of pentosan polysulfate sodium on the estrogen-induced pituitary prolactinoma in Fischer 344 rats. Oncol Rep. 2002 Nov-Dec;9(6):1385-9. [PubMed:12375053 ]
  3. Pluda JM, Shay LE, Foli A, Tannenbaum S, Cohen PJ, Goldspiel BR, Adamo D, Cooper MR, Broder S, Yarchoan R: Administration of pentosan polysulfate to patients with human immunodeficiency virus-associated Kaposi's sarcoma. J Natl Cancer Inst. 1993 Oct 6;85(19):1585-92. [PubMed:7692072 ]
  4. McLeskey SW, Zhang L, Kharbanda S, Kurebayashi J, Lippman ME, Dickson RB, Kern FG: Fibroblast growth factor overexpressing breast carcinoma cells as models of angiogenesis and metastasis. Breast Cancer Res Treat. 1996;39(1):103-17. [PubMed:8738610 ]
  5. Jerebtsova M, Wong E, Przygodzki R, Tang P, Ray PE: A novel role of fibroblast growth factor-2 and pentosan polysulfate in the pathogenesis of intestinal bleeding in mice. Am J Physiol Heart Circ Physiol. 2007 Feb;292(2):H743-50. Epub 2006 Oct 27. [PubMed:17071728 ]
General function:
Involved in fibroblast growth factor receptor binding
Specific function:
The heparin-binding growth factors are angiogenic agents in vivo and are potent mitogens for a variety of cell types in vitro. There are differences in the tissue distribution and concentration of these 2 growth factors
Gene Name:
FGF1
Uniprot ID:
P05230
Molecular weight:
17459.6
References
  1. Pascu C, Ljungh A, Wadstrom T: Staphylococci bind heparin-binding host growth factors. Curr Microbiol. 1996 Apr;32(4):201-7. [PubMed:8867461 ]
  2. Zenjari C, Boilly-Marer Y, Desbiens X, Oudghir M, Hondermarck H, Boilly B: Experimental evidence for FGF-1 control of blastema cell proliferation during limb regeneration of the amphibian Pleurodeles waltl. Int J Dev Biol. 1996 Oct;40(5):965-71. [PubMed:8946244 ]
  3. Jerebtsova M, Wong E, Przygodzki R, Tang P, Ray PE: A novel role of fibroblast growth factor-2 and pentosan polysulfate in the pathogenesis of intestinal bleeding in mice. Am J Physiol Heart Circ Physiol. 2007 Feb;292(2):H743-50. Epub 2006 Oct 27. [PubMed:17071728 ]
General function:
Involved in growth factor activity
Specific function:
Can transform NIH 3T3 cells from a human stomach tumor (hst) and from karposi's sarcoma (KS3). It has a mitogenic activity
Gene Name:
FGF4
Uniprot ID:
P08620
Molecular weight:
22047.4
References
  1. Zugmaier G, Lippman ME, Wellstein A: Inhibition by pentosan polysulfate (PPS) of heparin-binding growth factors released from tumor cells and blockage by PPS of tumor growth in animals. J Natl Cancer Inst. 1992 Nov 18;84(22):1716-24. [PubMed:1279186 ]
  2. McLeskey SW, Zhang L, Kharbanda S, Kurebayashi J, Lippman ME, Dickson RB, Kern FG: Fibroblast growth factor overexpressing breast carcinoma cells as models of angiogenesis and metastasis. Breast Cancer Res Treat. 1996;39(1):103-17. [PubMed:8738610 ]
  3. Wellstein A, Zugmaier G, Califano JA 3rd, Kern F, Paik S, Lippman ME: Tumor growth dependent on Kaposi's sarcoma-derived fibroblast growth factor inhibited by pentosan polysulfate. J Natl Cancer Inst. 1991 May 15;83(10):716-20. [PubMed:1708834 ]