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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:23:58 UTC

Update Date

2023-02-21 17:26:22 UTC

HMDB ID

HMDB0038115

Secondary Accession Numbers

HMDB38115

Metabolite Identification

Common Name

Setarin

Description

Setarin belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Setarin has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make setarin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Setarin.

Structure

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


  Mrv0541 05061310142D          

 15 16  0  0  0  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    1.4289    0.0000    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 10  9  1  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038115

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)OC1=CC(=O)OC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O3/c1-8(2)14-11-7-12(13)15-10-6-4-3-5-9(10)11/h3-7H,1H2,2H3

> <INCHI_KEY>
UUTFFHNHMRSARV-UHFFFAOYSA-N

> <FORMULA>
C12H10O3

> <MOLECULAR_WEIGHT>
202.206

> <EXACT_MASS>
202.062994186

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
20.227713819891008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(prop-1-en-2-yloxy)-2H-chromen-2-one

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
1.7196538823333332

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.2605453439312235

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
57.703400000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(prop-1-en-2-yloxy)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       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    9                                                       
CONECT    6    4   10                                                       
CONECT    7   11   12                                                       
CONECT    8    1    2   14                                                  
CONECT    9    5   10   11                                                  
CONECT   10    6    9   15                                                  
CONECT   11    7    9   14                                                  
CONECT   12    7   13   15                                                  
CONECT   13   12                                                            
CONECT   14    8   11                                                       
CONECT   15   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₂H₁₀O₃

Average Molecular Weight

202.206

Monoisotopic Molecular Weight

202.062994186

IUPAC Name

4-(prop-1-en-2-yloxy)-2H-chromen-2-one

Traditional Name

4-(prop-1-en-2-yloxy)chromen-2-one

CAS Registry Number

31005-07-9

SMILES

CC(=C)OC1=CC(=O)OC2=CC=CC=C12

InChI Identifier

InChI=1S/C12H10O3/c1-8(2)14-11-7-12(13)15-10-6-4-3-5-9(10)11/h3-7H,1H2,2H3

InChI Key

UUTFFHNHMRSARV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous ester
Lactone
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038115)
Cell membrane (HMDB: HMDB0038115)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038115)

Source

Exogenous

Exogenous (HMDB: HMDB0038115)

Food

Food (HMDB: HMDB0038115)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Plant (HMDB: HMDB0038115)
Poaceae (HMDB: HMDB0038115)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038115)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	104 - 105 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1664 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	0.51 g/L	ALOGPS
logP	2.75	ALOGPS
logP	1.72	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.7 m³·mol⁻¹	ChemAxon
Polarizability	20.23 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
DarkChem	[M+H]+	147.079	31661259
DarkChem	[M-H]-	146.443	31661259
DeepCCS	[M-2H]-	171.14	30932474
DeepCCS	[M+Na]+	146.411	30932474
AllCCS	[M+H]+	141.5	32859911
AllCCS	[M+H-H2O]+	137.1	32859911
AllCCS	[M+NH4]+	145.5	32859911
AllCCS	[M+Na]+	146.7	32859911
AllCCS	[M-H]-	143.0	32859911
AllCCS	[M+Na-2H]-	142.9	32859911
AllCCS	[M+HCOO]-	142.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.82 minutes	32390414
Predicted by Siyang on May 30, 2022	13.8938 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.09 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1910.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	487.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	178.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	279.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	160.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	561.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	502.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	102.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1143.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	410.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1297.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	364.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	367.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	395.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	418.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	14.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Setarin	CC(=C)OC1=CC(=O)OC2=CC=CC=C12	2533.6	Standard polar	33892256
Setarin	CC(=C)OC1=CC(=O)OC2=CC=CC=C12	1772.3	Standard non polar	33892256
Setarin	CC(=C)OC1=CC(=O)OC2=CC=CC=C12	1825.2	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 - Setarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9610000000-30858dd172d540194ebc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Setarin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Setarin 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 - Setarin 10V, Positive-QTOF	splash10-0udi-0290000000-b0053474c438da95a549	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Setarin 20V, Positive-QTOF	splash10-03di-0920000000-ef9ac25f8f61ade1d2e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Setarin 40V, Positive-QTOF	splash10-03k9-3900000000-30df5db711866dcd5e9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Setarin 10V, Negative-QTOF	splash10-0udi-0090000000-1d3910da6b3722099c9e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Setarin 20V, Negative-QTOF	splash10-0udi-0390000000-36c812aff53cf6f4e8a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Setarin 40V, Negative-QTOF	splash10-0296-7900000000-c4063b2e8703879704c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Setarin 10V, Negative-QTOF	splash10-0udi-0490000000-f0b61b46670e6bc8b364	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Setarin 20V, Negative-QTOF	splash10-0ik9-0940000000-e0dca40fe896cef979c1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Setarin 40V, Negative-QTOF	splash10-0006-9800000000-ed0d1268f1778cd9aeed	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Setarin 10V, Positive-QTOF	splash10-0udi-0090000000-cf2deb9bcad1cbe5c298	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Setarin 20V, Positive-QTOF	splash10-0udi-0290000000-c4af471d0df666e2f972	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Setarin 40V, Positive-QTOF	splash10-0udu-8910000000-3d81a75b6e586acdef7f	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

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

FDB017340

KNApSAcK ID

C00020026

Chemspider ID

30777235

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752308

PDB ID

Not Available

ChEBI ID

173557

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1865921

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 Setarin (HMDB0038115)

MOL for HMDB0038115 (Setarin)

3D MOL for HMDB0038115 (Setarin)

3D SDF for HMDB0038115 (Setarin)

3D-SDF for HMDB0038115 (Setarin)

PDB for HMDB0038115 (Setarin)

3D PDB for HMDB0038115 (Setarin)

SMILES for HMDB0038115 (Setarin)

INCHI for HMDB0038115 (Setarin)

Structure for HMDB0038115 (Setarin)

3D Structure for HMDB0038115 (Setarin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra