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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014641

Secondary Accession Numbers

HMDB14641

Metabolite Identification

Common Name

Phenindione

Description

Phenindione is only found in individuals that have used or taken this drug. It is an indandione that has been used as an anticoagulant. Phenindione has actions similar to warfarin, but it is now rarely employed because of its higher incidence of severe adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p234)Phenindione 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

498
  Mrv1652305271900252D          

 17 19  0  0  0  0            999 V2000
    4.1159    1.4482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -1.4482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    0.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  2  0  0  0  0
  8 11  2  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  2  0  0  0  0
 13 14  2  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014641

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1C(C(=O)C2=CC=CC=C12)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O2/c16-14-11-8-4-5-9-12(11)15(17)13(14)10-6-2-1-3-7-10/h1-9,13H

> <INCHI_KEY>
NFBAXHOPROOJAW-UHFFFAOYSA-N

> <FORMULA>
C15H10O2

> <MOLECULAR_WEIGHT>
222.2387

> <EXACT_MASS>
222.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
23.237980906604285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-phenyl-2,3-dihydro-1H-indene-1,3-dione

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
2.880905264666666

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.875342939986653

> <JCHEM_PKA_STRONGEST_BASIC>
-7.504803574210612

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
65.23350000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indon

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 498                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       7.683   2.703   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.683  -2.703   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.104   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.205   1.239   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.205  -1.239   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.644   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.414   1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.414  -1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.954   1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.954  -1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.724   0.000   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    4    5    8                                                  
CONECT    4    1    3    6                                                  
CONECT    5    2    3    7                                                  
CONECT    6    4    7    9                                                  
CONECT    7    5    6   10                                                  
CONECT    8    3   11   12                                                  
CONECT    9    6   13                                                       
CONECT   10    7   14                                                       
CONECT   11    8   15                                                       
CONECT   12    8   16                                                       
CONECT   13    9   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   17                                                       
CONECT   16   12   17                                                       
CONECT   17   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0014641
HETATM    1  O1  UNL     1       0.103  -2.089   0.939  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.532  -1.088   0.313  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.906  -0.585   0.332  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.106  -1.190   0.665  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.291  -0.487   0.601  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.256   0.840   0.196  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.073   1.464  -0.140  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.882   0.755  -0.075  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.493   1.114  -0.357  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.023   2.293  -0.381  1.00  0.00           O  
HETATM   11  C9  UNL     1      -0.209  -0.158  -0.597  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.644  -0.119  -0.332  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.553  -0.490  -1.312  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.908  -0.469  -1.109  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.435  -0.071   0.103  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.535   0.300   1.082  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.167   0.279   0.879  1.00  0.00           C  
HETATM   18  H1  UNL     1       3.087  -2.226   0.975  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.192  -1.000   0.868  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.201   1.373   0.153  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.057   2.500  -0.455  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.022  -0.507  -1.628  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.212  -0.817  -2.294  1.00  0.00           H  
HETATM   24  H7  UNL     1      -4.624  -0.764  -1.887  1.00  0.00           H  
HETATM   25  H8  UNL     1      -5.508  -0.050   0.276  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.921   0.618   2.045  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.462   0.572   1.654  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4    8
CONECT    4    5   18
CONECT    5    6    6   19
CONECT    6    7   20
CONECT    7    8    8   21
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   22
CONECT   12   13   13   17
CONECT   13   14   23
CONECT   14   15   15   24
CONECT   15   16   25
CONECT   16   17   17   26
CONECT   17   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Phenyl-1,3(2H)-indenedione	ChEBI
2-Phenyl-1,3-diketohydrindene	ChEBI
2-Phenyl-1,3-indandione	ChEBI
Fenindiona	ChEBI
Phenindionum	ChEBI
PID	ChEBI
Hedulin	Kegg
Merck lipha santé brand OF phenindione	HMDB
2 Phenyl 1,3 indandione	HMDB
Boots brand OF phenindione	HMDB
Goldshield brand OF phenindione	HMDB
Phenylindanedione	HMDB
Phenyline	HMDB
Pindione	HMDB
Dindevan	HMDB
Fenilin	HMDB

Chemical Formula

C₁₅H₁₀O₂

Average Molecular Weight

222.2387

Monoisotopic Molecular Weight

222.068079564

IUPAC Name

2-phenyl-2,3-dihydro-1H-indene-1,3-dione

Traditional Name

indon

CAS Registry Number

83-12-5

SMILES

O=C1C(C(=O)C2=CC=CC=C12)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H10O2/c16-14-11-8-4-5-9-12(11)15(17)13(14)10-6-2-1-3-7-10/h1-9,13H

InChI Key

NFBAXHOPROOJAW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indanediones. Indanediones are compounds containing an indane ring bearing two ketone groups.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Indanedione
Aryl alkyl ketone
Aryl ketone
1,3-diketone
1,3-dicarbonyl compound
Monocyclic benzene moiety
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

aromatic ketone (CHEBI:8066 )
beta-diketone (CHEBI:8066 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	148 - 151 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.023 g/L	Not Available
LogP	2.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	145.917	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000760

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	3.1	ALOGPS
logP	2.88	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.88	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	65.23 m³·mol⁻¹	ChemAxon
Polarizability	23.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	149.702	31661259
DarkChem	[M-H]-	150.065	31661259
DeepCCS	[M-2H]-	185.832	30932474
DeepCCS	[M+Na]+	161.363	30932474
AllCCS	[M+H]+	149.3	32859911
AllCCS	[M+H-H2O]+	145.1	32859911
AllCCS	[M+NH4]+	153.2	32859911
AllCCS	[M+Na]+	154.4	32859911
AllCCS	[M-H]-	152.6	32859911
AllCCS	[M+Na-2H]-	151.9	32859911
AllCCS	[M+HCOO]-	151.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenindione	O=C1C(C(=O)C2=CC=CC=C12)C1=CC=CC=C1	3201.9	Standard polar	33892256
Phenindione	O=C1C(C(=O)C2=CC=CC=C12)C1=CC=CC=C1	2019.5	Standard non polar	33892256
Phenindione	O=C1C(C(=O)C2=CC=CC=C12)C1=CC=CC=C1	2069.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenindione GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-8950000000-db616a8e7e559a5a5f6f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenindione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenindione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-4690000000-3b0da30c88d7d0ecf339	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindione 10V, Positive-QTOF	splash10-00di-0090000000-9b298f1072fd790bda04	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindione 20V, Positive-QTOF	splash10-00di-3390000000-11fefa0e023507256e68	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindione 40V, Positive-QTOF	splash10-0a4l-9460000000-25e9eb850e8f08d73284	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindione 10V, Negative-QTOF	splash10-00di-0090000000-3ff702d3fba3b4ba61c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindione 20V, Negative-QTOF	splash10-00di-0090000000-782f754ab0024fcab923	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindione 40V, Negative-QTOF	splash10-0gi9-5940000000-5905bd66b8f78a2f70a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindione 10V, Positive-QTOF	splash10-00di-0090000000-4526ea1529fb7968e1f9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindione 20V, Positive-QTOF	splash10-00di-2390000000-dafe0249a10821f9782f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindione 40V, Positive-QTOF	splash10-0006-9100000000-ee672ba3244610e83f29	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindione 10V, Negative-QTOF	splash10-00di-0090000000-67222288c14ba81150ce	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindione 20V, Negative-QTOF	splash10-00di-0090000000-67222288c14ba81150ce	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindione 40V, Negative-QTOF	splash10-01c0-0920000000-f427c2360b8ee97f9d00	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Phenindione Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00498	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00498	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00498

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4596

KEGG Compound ID

C07584

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenindione

METLIN ID

Not Available

PubChem Compound

4760

PDB ID

Not Available

ChEBI ID

8066

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Patient.co.uk [Link]

Enzymes

Enzyme Details

1. Vitamin K epoxide reductase complex subunit 1

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

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 ]
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 ]
Mentre F, Pousset F, Comets E, Plaud B, Diquet B, Montalescot G, Ankri A, Mallet A, Lechat P: Population pharmacokinetic-pharmacodynamic analysis of fluindione in patients. Clin Pharmacol Ther. 1998 Jan;63(1):64-78. [PubMed:9465843 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Phenindione (HMDB0014641)

MOL for HMDB0014641 (Phenindione)

3D MOL for HMDB0014641 (Phenindione)

3D SDF for HMDB0014641 (Phenindione)

3D-SDF for HMDB0014641 (Phenindione)

PDB for HMDB0014641 (Phenindione)

3D PDB for HMDB0014641 (Phenindione)

SMILES for HMDB0014641 (Phenindione)

INCHI for HMDB0014641 (Phenindione)

Structure for HMDB0014641 (Phenindione)

3D Structure for HMDB0014641 (Phenindione)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References