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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:51 UTC
HMDB IDHMDB0015081
Secondary Accession Numbers
  • HMDB15081
Metabolite Identification
Common NamePhenprocoumon
DescriptionPhenprocoumon is only found in individuals that have used or taken this drug. It is a coumarin derivative that acts as a long acting oral anticoagulant. [PubChem]Phenprocoumon inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decreased prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.
Structure
Data?1582753256
Synonyms
ValueSource
3-(1'-Phenyl-propyl)-4-oxycoumarinChEBI
3-(1-Phenylpropyl)-4-hydroxycoumarinChEBI
3-(alpha-Ethylbenzyl)-4-hydroxycoumarinChEBI
3-(alpha-Phenylpropyl)-4-hydroxycoumarinChEBI
4-Hydroxy-3-(1-phenylpropyl)-2H-1-benzopyran-2-oneChEBI
4-Hydroxy-3-(1-phenylpropyl)-2H-chromen-2-oneChEBI
FenprocumonChEBI
FenprocumoneChEBI
PhenprocoumarolChEBI
PhenprocoumaroleChEBI
PhenprocoumoneChEBI
PhenprocoumonumChEBI
PhenprocumoneChEBI
LiquamarKegg
3-(a-Ethylbenzyl)-4-hydroxycoumarinGenerator
3-(Α-ethylbenzyl)-4-hydroxycoumarinGenerator
3-(a-Phenylpropyl)-4-hydroxycoumarinGenerator
3-(Α-phenylpropyl)-4-hydroxycoumarinGenerator
FalithromMeSH, HMDB
MarcoumarMeSH, HMDB
PhenprocoumalolMeSH, HMDB
PhenylpropylhydroxycumarinumMeSH, HMDB
MarcumarMeSH, HMDB
PhenprogrammaMeSH, HMDB
Hexal brand OF phenprocoumonMeSH, HMDB
Wörwag brand OF phenprocoumonMeSH, HMDB
Roche brand OF phenprocoumonMeSH, HMDB
Chemical FormulaC18H16O3
Average Molecular Weight280.3178
Monoisotopic Molecular Weight280.109944378
IUPAC Name4-hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one
Traditional Namephenprocoumon
CAS Registry Number435-97-2
SMILES
CCC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2
InChI Identifier
InChI=1S/C18H16O3/c1-2-13(12-8-4-3-5-9-12)16-17(19)14-10-6-7-11-15(14)21-18(16)20/h3-11,13,19H,2H2,1H3
InChI KeyDQDAYGNAKTZFIW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent4-hydroxycoumarins
Alternative Parents
Substituents
  • 4-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • Phenylpropane
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point179.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.049 g/LNot Available
LogP4.4Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM160.030932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.049 g/LALOGPS
logP3.81ALOGPS
logP3.74ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)6.44ChemAxon
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity81.64 m³·mol⁻¹ChemAxon
Polarizability29.92 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.7731661259
DarkChem[M-H]-164.83731661259
DeepCCS[M+H]+167.4330932474
DeepCCS[M-H]-165.07230932474
DeepCCS[M-2H]-197.95930932474
DeepCCS[M+Na]+173.52430932474
AllCCS[M+H]+165.832859911
AllCCS[M+H-H2O]+162.032859911
AllCCS[M+NH4]+169.432859911
AllCCS[M+Na]+170.432859911
AllCCS[M-H]-170.732859911
AllCCS[M+Na-2H]-170.132859911
AllCCS[M+HCOO]-169.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhenprocoumonCCC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C23536.7Standard polar33892256
PhenprocoumonCCC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C22363.0Standard non polar33892256
PhenprocoumonCCC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C22439.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phenprocoumon,1TMS,isomer #1CCC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O2460.1Semi standard non polar33892256
Phenprocoumon,1TBDMS,isomer #1CCC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O2724.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phenprocoumon GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gk9-1390000000-b8adf6e29e27ba0e00322017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenprocoumon GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-6659000000-d206d323114210822b662017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenprocoumon GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenprocoumon GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenprocoumon GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenprocoumon GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenprocoumon 10V, Positive-QTOFsplash10-001i-0190000000-3363e5ab875f54ecfdbe2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenprocoumon 20V, Positive-QTOFsplash10-001i-0390000000-5d8ad9702c75c69b00362016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenprocoumon 40V, Positive-QTOFsplash10-06di-4940000000-8a3c1778a9c418538afb2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenprocoumon 10V, Negative-QTOFsplash10-004i-0090000000-b940e8a82db8a93a61242016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenprocoumon 20V, Negative-QTOFsplash10-01t9-0490000000-9f94c9b5f041d62040962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenprocoumon 40V, Negative-QTOFsplash10-054o-8960000000-ce2be44f7678a353e1462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenprocoumon 10V, Positive-QTOFsplash10-001i-0190000000-e4c63991e04960d284712021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenprocoumon 20V, Positive-QTOFsplash10-001i-2390000000-7d5deb49a774d36523622021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenprocoumon 40V, Positive-QTOFsplash10-00b9-7940000000-2379ac94fd9f7accb4602021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenprocoumon 10V, Negative-QTOFsplash10-004i-0090000000-095b46a5a952085bd4282021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenprocoumon 20V, Negative-QTOFsplash10-03fr-1980000000-5cc9eb499f441aa931682021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenprocoumon 40V, Negative-QTOFsplash10-056r-4970000000-d20cae73879a285527022021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00946 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00946 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10441592
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenprocoumon
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID50438
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Schalekamp T, Brasse BP, Roijers JF, van Meegen E, van der Meer FJ, van Wijk EM, Egberts AC, de Boer A: VKORC1 and CYP2C9 genotypes and phenprocoumon anticoagulation status: interaction between both genotypes affects dose requirement. Clin Pharmacol Ther. 2007 Feb;81(2):185-93. Epub 2006 Dec 27. [PubMed:17192772 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in vitamin-K-epoxide reductase (warfarin-sensi
Specific function:
Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K.
Gene Name:
VKORC1
Uniprot ID:
Q9BQB6
Molecular weight:
18234.3
References
  1. Schalekamp T, Brasse BP, Roijers JF, van Meegen E, van der Meer FJ, van Wijk EM, Egberts AC, de Boer A: VKORC1 and CYP2C9 genotypes and phenprocoumon anticoagulation status: interaction between both genotypes affects dose requirement. Clin Pharmacol Ther. 2007 Feb;81(2):185-93. Epub 2006 Dec 27. [PubMed:17192772 ]
  2. Reitsma PH, van der Heijden JF, Groot AP, Rosendaal FR, Buller HR: A C1173T dimorphism in the VKORC1 gene determines coumarin sensitivity and bleeding risk. PLoS Med. 2005 Oct;2(10):e312. Epub 2005 Oct 11. [PubMed:16201835 ]
  3. Thijssen HH, Baars LG: Microsomal warfarin binding and vitamin K 2,3-epoxide reductase. Biochem Pharmacol. 1989 Apr 1;38(7):1115-20. [PubMed:2706010 ]
  4. Thijssen HH, Baars LG, Vervoort-Peters HT: Vitamin K 2,3-epoxide reductase: the basis for stereoselectivity of 4-hydroxycoumarin anticoagulant activity. Br J Pharmacol. 1988 Nov;95(3):675-82. [PubMed:3207986 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]