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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:26:16 UTC

Update Date

2021-09-26 23:06:59 UTC

HMDB ID

HMDB0253637

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isoflavone

Description

This compound has been identified in human blood as reported by (PMID: 31557052 ). Isoflavone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isoflavone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1533004251512352D          

 17 19  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
  6 11  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253637

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1C(=COC2=CC=CC=C12)C1=CC=CC=C1

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

> <INCHI_KEY>
GOMNOOKGLZYEJT-UHFFFAOYSA-N

> <FORMULA>
C15H10O2

> <MOLECULAR_WEIGHT>
222.243

> <EXACT_MASS>
222.068079562

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
23.639497788367777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.51

> <JCHEM_LOGP>
3.3375683546666663

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.324883683559229

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
65.74020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.43e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoflavone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2    6                                                  
CONECT   12    3   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0253637
HETATM    1  O1  UNL     1      -0.119  -1.891   0.299  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.397  -0.761   0.206  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.353   0.399   0.153  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.797   0.350   0.204  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.517  -0.559  -0.544  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.894  -0.568  -0.464  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.563   0.317   0.355  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.847   1.237   1.113  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.466   1.236   1.022  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.347   1.586   0.050  1.00  0.00           C  
HETATM   11  O2  UNL     1       1.655   1.613   0.005  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.399   0.551   0.052  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.768   0.706  -0.003  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.576  -0.400   0.044  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.974  -1.649   0.148  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.597  -1.788   0.203  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.776  -0.675   0.155  1.00  0.00           C  
HETATM   18  H1  UNL     1      -2.014  -1.280  -1.208  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.442  -1.287  -1.057  1.00  0.00           H  
HETATM   20  H3  UNL     1      -5.660   0.324   0.433  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.346   1.934   1.756  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.919   1.955   1.616  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.180   2.520   0.005  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.184   1.703  -0.084  1.00  0.00           H  
HETATM   25  H8  UNL     1       5.646  -0.294   0.002  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.643  -2.495   0.183  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.157  -2.783   0.284  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   17
CONECT    3    4   10   10
CONECT    4    5    5    9
CONECT    5    6   18
CONECT    6    7    7   19
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   22
CONECT   10   11   23
CONECT   11   12
CONECT   12   13   13   17
CONECT   13   14   24
CONECT   14   15   15   25
CONECT   15   16   26
CONECT   16   17   17   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Phenyl-4H-1-benzopyran-4-one	ChEBI
3-Phenylchromone	ChEBI
Isoflavon	ChEBI

Chemical Formula

C₁₅H₁₀O₂

Average Molecular Weight

222.243

Monoisotopic Molecular Weight

222.068079562

IUPAC Name

3-phenyl-4H-chromen-4-one

Traditional Name

isoflavone

CAS Registry Number

Not Available

SMILES

O=C1C(=COC2=CC=CC=C12)C1=CC=CC=C1

InChI Identifier

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

InChI Key

GOMNOOKGLZYEJT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Isoflavone
Chromone
Benzopyran
1-benzopyran
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoflavones (CHEBI:18220 )
Isoflavonoids (LMPK12050000 )
a small molecule (ISOFLAVONE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.51	ALOGPS
logP	3.34	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	65.74 m³·mol⁻¹	ChemAxon
Polarizability	23.64 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
DeepCCS	[M-2H]-	183.251	30932474
DeepCCS	[M+Na]+	158.452	30932474
AllCCS	[M+H]+	148.8	32859911
AllCCS	[M+H-H2O]+	144.5	32859911
AllCCS	[M+NH4]+	152.9	32859911
AllCCS	[M+Na]+	154.0	32859911
AllCCS	[M-H]-	151.2	32859911
AllCCS	[M+Na-2H]-	150.4	32859911
AllCCS	[M+HCOO]-	149.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoflavone	O=C1C(=COC2=CC=CC=C12)C1=CC=CC=C1	2893.3	Standard polar	33892256
Isoflavone	O=C1C(=COC2=CC=CC=C12)C1=CC=CC=C1	2043.2	Standard non polar	33892256
Isoflavone	O=C1C(=COC2=CC=CC=C12)C1=CC=CC=C1	2108.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isoflavone EI-B (Non-derivatized)	splash10-00di-4390000000-b4cbfa0f201f2f6fa3db	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoflavone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fkc-1930000000-ad1b3c073891e277eeea	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoflavone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflavone 10V, Positive-QTOF	splash10-00di-0090000000-d2813a23a3a7cae9117e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflavone 20V, Positive-QTOF	splash10-00di-0090000000-221e22d062e39de9d66e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflavone 40V, Positive-QTOF	splash10-0fk9-4920000000-2276b8f75ec8c4ebc34f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflavone 10V, Negative-QTOF	splash10-00di-0090000000-473d362410b84031ad4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflavone 20V, Negative-QTOF	splash10-00di-0090000000-2ab2dbdf74b299bf80c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflavone 40V, Negative-QTOF	splash10-0v4i-1920000000-d80cb2276224094ce372	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflavone 10V, Positive-QTOF	splash10-00di-0090000000-4526ea1529fb7968e1f9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflavone 20V, Positive-QTOF	splash10-00di-0090000000-4526ea1529fb7968e1f9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflavone 40V, Positive-QTOF	splash10-0fi1-5920000000-568aaba65774a70c8906	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflavone 10V, Negative-QTOF	splash10-00di-0090000000-67222288c14ba81150ce	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflavone 20V, Negative-QTOF	splash10-00di-0090000000-67222288c14ba81150ce	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoflavone 40V, Negative-QTOF	splash10-01b9-0940000000-0eae70b1b1deee2e0e01	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB12007

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005582

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00799

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isoflavone

METLIN ID

Not Available

PubChem Compound

72304

PDB ID

Not Available

ChEBI ID

18220

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Isoflavone (HMDB0253637)

MOL for HMDB0253637 (Isoflavone)

3D MOL for HMDB0253637 (Isoflavone)

3D SDF for HMDB0253637 (Isoflavone)

3D-SDF for HMDB0253637 (Isoflavone)

PDB for HMDB0253637 (Isoflavone)

3D PDB for HMDB0253637 (Isoflavone)

SMILES for HMDB0253637 (Isoflavone)

INCHI for HMDB0253637 (Isoflavone)

Structure for HMDB0253637 (Isoflavone)

3D Structure for HMDB0253637 (Isoflavone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra