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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:41:58 UTC

Update Date

2022-03-07 02:53:54 UTC

HMDB ID

HMDB0033925

Secondary Accession Numbers

HMDB33925

Metabolite Identification

Common Name

Oroselone

Description

Oroselone belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Oroselone has been detected, but not quantified in, a few different foods, such as fats and oils, green vegetables, and herbs and spices. This could make oroselone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Oroselone.

Structure

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


  Mrv0541 05061307272D          

 17 19  0  0  0  0            999 V2000
    5.0883   -0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3355   -1.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613   -0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15 13  2  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033925

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1=CC2=C(O1)C=CC1=C2OC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O3/c1-8(2)12-7-10-11(16-12)5-3-9-4-6-13(15)17-14(9)10/h3-7H,1H2,2H3

> <INCHI_KEY>
FQCPXIJRWHRHIP-UHFFFAOYSA-N

> <FORMULA>
C14H10O3

> <MOLECULAR_WEIGHT>
226.2274

> <EXACT_MASS>
226.062994186

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.772836981193947

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-(prop-1-en-2-yl)-2H-furo[2,3-h]chromen-2-one

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
2.8985808126666663

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.174168268297907

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
64.2355

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.498  -0.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.093  -2.271   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.406  -0.502   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.141  -0.731   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.289  -1.848   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.719   1.616   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.062  -0.587   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    5    9                                                       
CONECT    4    6    9                                                       
CONECT    5    3   11                                                       
CONECT    6    4   13                                                       
CONECT    7   10   12                                                       
CONECT    8    1    2   12                                                  
CONECT    9    3    4   14                                                  
CONECT   10    7   11   14                                                  
CONECT   11    5   10   16                                                  
CONECT   12    7    8   16                                                  
CONECT   13    6   15   17                                                  
CONECT   14    9   10   17                                                  
CONECT   15   13                                                            
CONECT   16   11   12                                                       
CONECT   17   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0033925
HETATM    1  C1  UNL     1       4.214  -0.959   0.188  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.351   0.037   0.150  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.836   1.434   0.185  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.923  -0.281   0.074  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.904   0.649   0.028  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.281  -0.072  -0.038  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.074  -1.402  -0.029  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.958  -2.337  -0.088  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.284  -1.962  -0.154  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.617  -0.636  -0.163  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.938  -0.198  -0.229  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.148   1.165  -0.231  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.079   2.014  -0.170  1.00  0.00           C  
HETATM   14  O1  UNL     1      -3.274   3.263  -0.172  1.00  0.00           O  
HETATM   15  O2  UNL     1      -1.854   1.600  -0.109  1.00  0.00           O  
HETATM   16  C14 UNL     1      -1.617   0.301  -0.105  1.00  0.00           C  
HETATM   17  O3  UNL     1       1.379  -1.478   0.038  1.00  0.00           O  
HETATM   18  H1  UNL     1       5.291  -0.802   0.245  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.914  -2.004   0.166  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.793   1.814  -0.863  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.207   2.073   0.850  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.900   1.452   0.472  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.959   1.723   0.037  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.696  -3.366  -0.081  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.097  -2.676  -0.201  1.00  0.00           H  
HETATM   26  H9  UNL     1      -4.730  -0.914  -0.274  1.00  0.00           H  
HETATM   27  H10 UNL     1      -5.171   1.566  -0.281  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3    4
CONECT    3   20   21   22
CONECT    4    5    5   17
CONECT    5    6   23
CONECT    6    7    7   16
CONECT    7    8   17
CONECT    8    9    9   24
CONECT    9   10   25
CONECT   10   11   16   16
CONECT   11   12   12   26
CONECT   12   13   27
CONECT   13   14   14   15
CONECT   15   16
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-(1-Methylethenyl)-2H-furo(2,3-H)-1-benzopyran-2-one	HMDB
8-(1-Methylethenyl)-2H-furo[2,3-H]-1-benzopyran-2-one	HMDB
8-(1-Methylethenyl)-2H-furo[2,3-H]-1-benzopyran-2-one, 9ci	HMDB
8-Isopropenyl-2H-furo[2,3-H]-1-benzopyran-2-one	HMDB
Kvannin	HMDB

Chemical Formula

C₁₄H₁₀O₃

Average Molecular Weight

226.2274

Monoisotopic Molecular Weight

226.062994186

IUPAC Name

8-(prop-1-en-2-yl)-2H-furo[2,3-h]chromen-2-one

Traditional Name

8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one

CAS Registry Number

1760-27-6

SMILES

CC(=C)C1=CC2=C(O1)C=CC1=C2OC(=O)C=C1

InChI Identifier

InChI=1S/C14H10O3/c1-8(2)12-7-10-11(16-12)5-3-9-4-6-13(15)17-14(9)10/h3-7H,1H2,2H3

InChI Key

FQCPXIJRWHRHIP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Angular furanocoumarins

Alternative Parents

Substituents

Angular furanocoumarin
Benzopyran
1-benzopyran
Benzofuran
Pyranone
Pyran
Benzenoid
Furan
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033925)

Cellular substructure

Membrane (HMDB: HMDB0033925)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033925)

Source

Exogenous

Food

Food (HMDB: HMDB0033925)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0033925)

Not Available

Nutrient (HMDB: HMDB0033925)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	188 - 189 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	32.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.046 g/L	ALOGPS
logP	3.03	ALOGPS
logP	2.9	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.24 m³·mol⁻¹	ChemAxon
Polarizability	23.77 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]+	153.16	31661259
DarkChem	[M-H]-	153.014	31661259
DeepCCS	[M+H]+	155.747	30932474
DeepCCS	[M-H]-	153.351	30932474
DeepCCS	[M-2H]-	186.352	30932474
DeepCCS	[M+Na]+	161.793	30932474
AllCCS	[M+H]+	147.6	32859911
AllCCS	[M+H-H2O]+	143.3	32859911
AllCCS	[M+NH4]+	151.6	32859911
AllCCS	[M+Na]+	152.8	32859911
AllCCS	[M-H]-	150.4	32859911
AllCCS	[M+Na-2H]-	149.7	32859911
AllCCS	[M+HCOO]-	149.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oroselone	CC(=C)C1=CC2=C(O1)C=CC1=C2OC(=O)C=C1	2988.0	Standard polar	33892256
Oroselone	CC(=C)C1=CC2=C(O1)C=CC1=C2OC(=O)C=C1	2136.2	Standard non polar	33892256
Oroselone	CC(=C)C1=CC2=C(O1)C=CC1=C2OC(=O)C=C1	2136.8	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 - Oroselone GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-1930000000-d6eba9b1402a5b0d1c8c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oroselone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oroselone 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 - Oroselone LC-ESI-qTof , Positive-QTOF	splash10-044j-0920000000-79bae7dd10afc3ff53e1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oroselone , positive-QTOF	splash10-004i-0900000000-aa75a40270ceb8223de8	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oroselone 10V, Positive-QTOF	splash10-004i-0090000000-48d0c1ca72aa57e56bb5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oroselone 20V, Positive-QTOF	splash10-004i-0190000000-317976988d69d14e98ce	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oroselone 40V, Positive-QTOF	splash10-01qc-2950000000-dd9f4b93a026b36eb187	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oroselone 10V, Negative-QTOF	splash10-004i-0190000000-d926c74b3c1b81648a3f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oroselone 20V, Negative-QTOF	splash10-004i-0390000000-c0822bfa6ca696e6ae8f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oroselone 40V, Negative-QTOF	splash10-05o0-0930000000-a9900d4b944f85033e63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oroselone 10V, Negative-QTOF	splash10-004i-0090000000-6929adb4eb50cc47a297	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oroselone 20V, Negative-QTOF	splash10-004r-0590000000-7a7c4a2f6e90d6f650fe	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oroselone 40V, Negative-QTOF	splash10-0a4r-0920000000-98895bc4c2acdeb7e08c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oroselone 10V, Positive-QTOF	splash10-004i-0090000000-1158eb6b952d47f22859	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oroselone 20V, Positive-QTOF	splash10-004j-0890000000-fca1e9d03b20ba965adb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oroselone 40V, Positive-QTOF	splash10-001i-1910000000-5f7ce41c262268ce292e	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB012125

KNApSAcK ID

C00057149

Chemspider ID

67063

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74477

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1839291

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Oroselone (HMDB0033925)

MOL for HMDB0033925 (Oroselone)

3D MOL for HMDB0033925 (Oroselone)

3D SDF for HMDB0033925 (Oroselone)

3D-SDF for HMDB0033925 (Oroselone)

PDB for HMDB0033925 (Oroselone)

3D PDB for HMDB0033925 (Oroselone)

SMILES for HMDB0033925 (Oroselone)

INCHI for HMDB0033925 (Oroselone)

Structure for HMDB0033925 (Oroselone)

3D Structure for HMDB0033925 (Oroselone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra