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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:17:09 UTC

Update Date

2021-09-26 22:51:35 UTC

HMDB ID

HMDB0244095

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Deoxybenzoin

Description

Deoxybenzoin belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Based on a literature review very few articles have been published on Deoxybenzoin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Deoxybenzoin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Deoxybenzoin 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

  Mrv1572004221604222D          

 15 16  0  0  0  0            999 V2000
    0.0000    4.9500    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
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    0.0000    3.3000    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244095

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(CC1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O/c15-14(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12/h1-10H,11H2

> <INCHI_KEY>
OTKCEEWUXHVZQI-UHFFFAOYSA-N

> <FORMULA>
C14H12O

> <MOLECULAR_WEIGHT>
196.249

> <EXACT_MASS>
196.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.548904711851463

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2-diphenylethan-1-one

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
3.3652331543333327

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.946522555977275

> <JCHEM_PKA_STRONGEST_BASIC>
-7.524677397228144

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
61.18270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-phenylacetophenone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   12                                                       
CONECT    8    4   12                                                       
CONECT    9    5   13                                                       
CONECT   10    6   13                                                       
CONECT   11   12   14                                                       
CONECT   12    7    8   11                                                  
CONECT   13    9   10   14                                                  
CONECT   14   11   13   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0244095
HETATM    1  O1  UNL     1      -0.268   0.697   1.334  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.368   0.207   0.373  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.391  -0.458  -0.710  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.832  -0.384  -0.384  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.549   0.699  -0.824  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.889   0.789  -0.533  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.489  -0.229   0.205  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.761  -1.311   0.642  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.410  -1.398   0.347  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.832   0.296   0.333  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.496   0.922   1.362  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.860   0.993   1.303  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.589   0.456   0.245  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.882  -0.174  -0.783  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.512  -0.249  -0.730  1.00  0.00           C  
HETATM   16  H1  UNL     1      -0.249   0.043  -1.690  1.00  0.00           H  
HETATM   17  H2  UNL     1      -0.052  -1.526  -0.808  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.047   1.461  -1.390  1.00  0.00           H  
HETATM   19  H4  UNL     1      -4.420   1.645  -0.890  1.00  0.00           H  
HETATM   20  H5  UNL     1      -5.539  -0.140   0.422  1.00  0.00           H  
HETATM   21  H6  UNL     1      -4.254  -2.095   1.218  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.831  -2.241   0.683  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.969   1.351   2.197  1.00  0.00           H  
HETATM   24  H9  UNL     1       4.439   1.473   2.080  1.00  0.00           H  
HETATM   25  H10 UNL     1       5.648   0.526   0.226  1.00  0.00           H  
HETATM   26  H11 UNL     1       4.385  -0.612  -1.632  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.999  -0.742  -1.541  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4   16   17
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   11   15
CONECT   11   12   23
CONECT   12   13   13   24
CONECT   13   14   25
CONECT   14   15   15   26
CONECT   15   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Deoxybenzoin	MeSH

Chemical Formula

C₁₄H₁₂O

Average Molecular Weight

196.249

Monoisotopic Molecular Weight

196.088815006

IUPAC Name

1,2-diphenylethan-1-one

Traditional Name

2-phenylacetophenone

CAS Registry Number

Not Available

SMILES

O=C(CC1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H12O/c15-14(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12/h1-10H,11H2

InChI Key

OTKCEEWUXHVZQI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Alkyl-phenylketone
Phenylketone
Aryl alkyl ketone
Aryl ketone
Benzoyl
Benzenoid
Monocyclic benzene moiety
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	3.15	ALOGPS
logP	3.37	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	15.95	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	61.18 m³·mol⁻¹	ChemAxon
Polarizability	21.55 Å³	ChemAxon
Number of Rings	2	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+H]+	143.673	30932474
DeepCCS	[M-H]-	141.277	30932474
DeepCCS	[M-2H]-	175.171	30932474
DeepCCS	[M+Na]+	149.776	30932474
AllCCS	[M+H]+	145.4	32859911
AllCCS	[M+H-H2O]+	141.3	32859911
AllCCS	[M+NH4]+	149.3	32859911
AllCCS	[M+Na]+	150.4	32859911
AllCCS	[M-H]-	146.6	32859911
AllCCS	[M+Na-2H]-	146.5	32859911
AllCCS	[M+HCOO]-	146.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Deoxybenzoin	O=C(CC1=CC=CC=C1)C1=CC=CC=C1	2540.8	Standard polar	33892256
Deoxybenzoin	O=C(CC1=CC=CC=C1)C1=CC=CC=C1	1744.7	Standard non polar	33892256
Deoxybenzoin	O=C(CC1=CC=CC=C1)C1=CC=CC=C1	1742.7	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 - Deoxybenzoin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9400000000-363493299dee429ba2ad	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxybenzoin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxybenzoin 60V, Positive-QTOF	splash10-0a4i-2900000000-dc4717eb9684d6895b87	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxybenzoin 45V, Positive-QTOF	splash10-0a4i-0900000000-410ca01bc6d3423eeed6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxybenzoin 15V, Positive-QTOF	splash10-0a4j-0900000000-29f41952dfb90054028a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxybenzoin 30V, Positive-QTOF	splash10-0a4i-0900000000-65a4d0b19500287456f4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxybenzoin 90V, Positive-QTOF	splash10-052e-9300000000-7ffc1ef9e47419dc2a9d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxybenzoin 75V, Positive-QTOF	splash10-0a4j-8900000000-b79b827ddda79ff51305	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxybenzoin 10V, Positive-QTOF	splash10-0002-0900000000-ba0605c258658ab45af1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxybenzoin 20V, Positive-QTOF	splash10-0a4i-1900000000-d2dc8b98eccd12b356f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxybenzoin 40V, Positive-QTOF	splash10-0a4i-6900000000-b0bbae653b1a65fbfb04	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxybenzoin 10V, Negative-QTOF	splash10-0002-0900000000-ec5306a9e5678cd1ad21	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxybenzoin 20V, Negative-QTOF	splash10-0002-1900000000-88702d556ca1a759659f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxybenzoin 40V, Negative-QTOF	splash10-004l-9800000000-cbe7b8d156ce45e8dc9d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxybenzoin 10V, Positive-QTOF	splash10-0002-0900000000-891bc25c33a232823c15	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxybenzoin 20V, Positive-QTOF	splash10-0002-2900000000-390b3ded551951d387bc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxybenzoin 40V, Positive-QTOF	splash10-0006-9000000000-c944abc7c6a8e0f9c4bf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxybenzoin 10V, Negative-QTOF	splash10-0002-0900000000-77507de8ce9f2a5de18f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxybenzoin 20V, Negative-QTOF	splash10-0002-2900000000-1adda602b463d21bbe03	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxybenzoin 40V, Negative-QTOF	splash10-016v-4900000000-c5fba96b02e279eb8874	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00019159

Chemspider ID

9554

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9948

PDB ID

Not Available

ChEBI ID

Not Available

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 Deoxybenzoin (HMDB0244095)

MOL for HMDB0244095 (Deoxybenzoin)

3D MOL for HMDB0244095 (Deoxybenzoin)

3D SDF for HMDB0244095 (Deoxybenzoin)

3D-SDF for HMDB0244095 (Deoxybenzoin)

PDB for HMDB0244095 (Deoxybenzoin)

3D PDB for HMDB0244095 (Deoxybenzoin)

SMILES for HMDB0244095 (Deoxybenzoin)

INCHI for HMDB0244095 (Deoxybenzoin)

Structure for HMDB0244095 (Deoxybenzoin)

3D Structure for HMDB0244095 (Deoxybenzoin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra