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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-10-30 10:32:48 UTC

Update Date

2023-02-21 17:29:09 UTC

HMDB ID

HMDB0059631

Secondary Accession Numbers

HMDB59631

Metabolite Identification

Common Name

Cis-stilbene oxide

Description

Cis-stilbene oxide 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. Thus, cis-stilbene oxide is considered to be an aromatic polyketide lipid molecule. Cis-stilbene oxide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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


  Mrv0541 10301209512D          

 17 19  0  0  0  0            999 V2000
    5.1118    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5559    1.9520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5518    1.8209    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3528    2.1655    0.0000 H   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
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  6  0  0  0
 14 12  1  6  0  0  0
 14 13  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 13 16  1  1  0  0  0
 14 17  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0059631

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1(O[C@]1([H])C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O/c1-3-7-11(8-4-1)13-14(15-13)12-9-5-2-6-10-12/h1-10,13-14H/t13-,14+

> <INCHI_KEY>
ARCJQKUWGAZPFX-OKILXGFUSA-N

> <FORMULA>
C14H12O

> <MOLECULAR_WEIGHT>
196.2445

> <EXACT_MASS>
196.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
21.09489255408871

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S)-2,3-diphenyloxirane

> <ALOGPS_LOGP>
3.62

> <JCHEM_LOGP>
3.5215048663333324

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.271184639747542

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
59.60910000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cis-stilbene oxide

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 30-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-OCT-12         0                                  
HETATM    1  C   UNK     0       9.542   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.771   8.264   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.542   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.208  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.437   7.494   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.105   7.494   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.208   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.875   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.437   5.954   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.105   5.954   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.875   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.771   5.184   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.541   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.771   3.644   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   16  H   UNK     0       6.630   3.399   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       6.259   4.042   0.000  0.00  0.00           H+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   11                                                       
CONECT    8    4   11                                                       
CONECT    9    5   12                                                       
CONECT   10    6   12                                                       
CONECT   11    7    8   13                                                  
CONECT   12    9   10   14                                                  
CONECT   13   11   14   15   16                                             
CONECT   14   12   13   15   17                                             
CONECT   15   13   14                                                       
CONECT   16   13                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0059631
HETATM    1  C1  UNL     1       3.382   0.461   1.380  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.675  -0.659   0.632  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.795  -1.133  -0.304  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.564  -0.518  -0.554  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.659  -1.056  -1.564  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.057   0.015  -2.417  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.762  -0.931  -1.633  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.628  -0.290  -0.667  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.357   0.820  -0.985  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.188   1.444  -0.084  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.301   0.935   1.206  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.577  -0.180   1.550  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.741  -0.790   0.609  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.280   0.602   0.199  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.173   1.080   1.147  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.080   0.841   2.126  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.628  -1.139   0.823  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.046  -2.015  -0.880  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.150  -1.755  -2.297  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.307  -1.569  -2.367  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.285   1.228  -1.975  1.00  0.00           H  
HETATM   22  H7  UNL     1      -3.773   2.322  -0.317  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.966   1.435   1.925  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.675  -0.561   2.550  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.185  -1.669   0.917  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.353   1.121   0.054  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.907   1.960   1.712  1.00  0.00           H  
CONECT    1    2    2   15   16
CONECT    2    3   17
CONECT    3    4    4   18
CONECT    4    5   14
CONECT    5    6    7   19
CONECT    6    7
CONECT    7    8   20
CONECT    8    9    9   13
CONECT    9   10   21
CONECT   10   11   11   22
CONECT   11   12   23
CONECT   12   13   13   24
CONECT   13   25
CONECT   14   15   15   26
CONECT   15   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
cis-alpha,Alpha'-epoxybibenzyl	ChEBI
cis-a,Alpha'-epoxybibenzyl	Generator
cis-Α,alpha'-epoxybibenzyl	Generator
Stilbene oxide, trans-(+-)-isomer	MeSH
Stilbene oxide, (2R-trans)-isomer	MeSH
Stilbene oxide, (2S-trans)-isomer	MeSH
Stilbene oxide, (cis)-isomer	MeSH
trans-Stilbene oxide	MeSH
Stilbene oxide	MeSH
Stilbene oxide, (trans)-isomer	MeSH

Chemical Formula

C₁₄H₁₂O

Average Molecular Weight

196.2445

Monoisotopic Molecular Weight

196.088815006

IUPAC Name

(2R,3S)-2,3-diphenyloxirane

Traditional Name

cis-stilbene oxide

CAS Registry Number

Not Available

SMILES

[H][C@]1(O[C@]1([H])C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H12O/c1-3-7-11(8-4-1)13-14(15-13)12-9-5-2-6-10-12/h1-10,13-14H/t13-,14+

InChI Key

ARCJQKUWGAZPFX-OKILXGFUSA-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
Benzenoid
Monocyclic benzene moiety
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

stilbene oxide (CHEBI:50004 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C16014 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090030 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0059631)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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
Water Solubility	0.015 g/L	ALOGPS
logP	3.62	ALOGPS
logP	3.52	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	59.61 m³·mol⁻¹	ChemAxon
Polarizability	21.09 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]+	144.577	31661259
DarkChem	[M-H]-	142.275	31661259
DeepCCS	[M+H]+	141.149	30932474
DeepCCS	[M-H]-	138.753	30932474
DeepCCS	[M-2H]-	172.299	30932474
DeepCCS	[M+Na]+	147.093	30932474
AllCCS	[M+H]+	145.2	32859911
AllCCS	[M+H-H2O]+	140.7	32859911
AllCCS	[M+NH4]+	149.4	32859911
AllCCS	[M+Na]+	150.6	32859911
AllCCS	[M-H]-	148.0	32859911
AllCCS	[M+Na-2H]-	147.6	32859911
AllCCS	[M+HCOO]-	147.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cis-stilbene oxide	[H][C@]1(O[C@]1([H])C1=CC=CC=C1)C1=CC=CC=C1	2601.8	Standard polar	33892256
Cis-stilbene oxide	[H][C@]1(O[C@]1([H])C1=CC=CC=C1)C1=CC=CC=C1	1679.6	Standard non polar	33892256
Cis-stilbene oxide	[H][C@]1(O[C@]1([H])C1=CC=CC=C1)C1=CC=CC=C1	1667.9	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 - Cis-stilbene oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9400000000-4bb20476ced23354ed6e	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cis-stilbene oxide 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 - Cis-stilbene oxide 10V, Positive-QTOF	splash10-0002-0900000000-c38f5cba131fd117556c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-stilbene oxide 20V, Positive-QTOF	splash10-0002-2900000000-aceb347ce6ec7f3ca87d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-stilbene oxide 40V, Positive-QTOF	splash10-0006-9000000000-f1ed447567a446098806	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-stilbene oxide 10V, Negative-QTOF	splash10-0002-0900000000-4b3b0720e7148bc53112	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-stilbene oxide 20V, Negative-QTOF	splash10-0002-1900000000-809e8977ec4fdbf95144	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-stilbene oxide 40V, Negative-QTOF	splash10-00or-9600000000-d46603493ba5d6c6da2e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-stilbene oxide 10V, Negative-QTOF	splash10-0002-0900000000-ca2a4c101599ac9b0050	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-stilbene oxide 20V, Negative-QTOF	splash10-0002-3900000000-2a3d53c4bde6b23c3f91	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-stilbene oxide 40V, Negative-QTOF	splash10-0006-9300000000-72d84142d549a73ad7e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-stilbene oxide 10V, Positive-QTOF	splash10-0002-0900000000-41030259b8ca7e8a2080	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-stilbene oxide 20V, Positive-QTOF	splash10-002b-1900000000-4459b60ff2d7546d3078	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-stilbene oxide 40V, Positive-QTOF	splash10-002f-9400000000-78780d2f98870f209fd9	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16014

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

98511

PDB ID

Not Available

ChEBI ID

50004

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

Not Available

Enzymes

Enzyme Details

1. Epoxide hydrolase 1

General function:: Involved in catalytic activity
Specific function:: Biotransformation enzyme that catalyzes the hydrolysis of arene and aliphatic epoxides to less reactive and more water soluble dihydrodiols by the trans addition of water.
Gene Name:: EPHX1
Uniprot ID:: P07099
Molecular weight:: 52948.48

Reactions

Cis-stilbene oxide + Water → (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol	details

Showing metabocard for Cis-stilbene oxide (HMDB0059631)

MOL for HMDB0059631 (Cis-stilbene oxide)

3D MOL for HMDB0059631 (Cis-stilbene oxide)

3D SDF for HMDB0059631 (Cis-stilbene oxide)

3D-SDF for HMDB0059631 (Cis-stilbene oxide)

PDB for HMDB0059631 (Cis-stilbene oxide)

3D PDB for HMDB0059631 (Cis-stilbene oxide)

SMILES for HMDB0059631 (Cis-stilbene oxide)

INCHI for HMDB0059631 (Cis-stilbene oxide)

Structure for HMDB0059631 (Cis-stilbene oxide)

3D Structure for HMDB0059631 (Cis-stilbene oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions