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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:05:38 UTC

Update Date

2021-09-26 22:57:53 UTC

HMDB ID

HMDB0247940

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Acifran

Description

5-methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2-carboxylic acid, also known as reductol, belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. Based on a literature review very few articles have been published on 5-methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Acifran is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Acifran 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

  Mrv1533004261507042D          

 16 17  0  0  0  0            999 V2000
    0.6320   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1841   -1.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8515   -1.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6361   -1.2872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -2.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7716   -2.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5166   -1.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2866   -2.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6222   -3.7479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5338   -2.9080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7361   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4812    0.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0332    0.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8402    0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0951   -0.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5431   -0.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247940

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O4/c1-12(8-5-3-2-4-6-8)10(13)7-9(16-12)11(14)15/h2-7H,1H3,(H,14,15)

> <INCHI_KEY>
DFDGRKNOFOJBAJ-UHFFFAOYSA-N

> <FORMULA>
C12H10O4

> <MOLECULAR_WEIGHT>
218.208

> <EXACT_MASS>
218.057908802

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.33379679462061

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2-carboxylic acid

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
1.9534052129999993

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9012576644031145

> <JCHEM_PKA_STRONGEST_BASIC>
-5.132941056757414

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
57.38880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acifran

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       1.180  -0.829   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.210  -1.974   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.456  -2.879   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.921  -2.403   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.980  -4.343   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.440  -4.343   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.964  -2.879   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.535  -5.589   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.161  -6.996   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.997  -5.428   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.241  -0.829   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.765   0.636   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.795   1.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.302   1.460   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.778  -0.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.747  -1.149   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   11                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0247940
HETATM    1  C1  UNL     1       0.744   0.150   1.747  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.318  -0.227   0.338  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.105  -0.018   0.108  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.011  -0.956   0.552  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.367  -0.723   0.312  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.816   0.402  -0.346  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.904   1.325  -0.780  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.542   1.104  -0.547  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.151   0.515  -0.534  1.00  0.00           O  
HETATM   10  C9  UNL     1       2.399  -0.141  -0.595  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.677   0.450  -0.954  1.00  0.00           C  
HETATM   12  O2  UNL     1       4.699  -0.272  -0.960  1.00  0.00           O  
HETATM   13  O3  UNL     1       3.831   1.783  -1.295  1.00  0.00           O  
HETATM   14  C11 UNL     1       2.220  -1.418  -0.263  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.797  -1.607   0.027  1.00  0.00           C  
HETATM   16  O4  UNL     1       0.171  -2.692   0.007  1.00  0.00           O  
HETATM   17  H1  UNL     1       0.941   1.256   1.763  1.00  0.00           H  
HETATM   18  H2  UNL     1      -0.052  -0.105   2.446  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.687  -0.402   1.961  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.722  -1.857   1.074  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.058  -1.476   0.671  1.00  0.00           H  
HETATM   22  H6  UNL     1      -4.893   0.545  -0.513  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.268   2.201  -1.294  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.871   1.872  -0.916  1.00  0.00           H  
HETATM   25  H9  UNL     1       4.001   2.508  -0.605  1.00  0.00           H  
HETATM   26  H10 UNL     1       2.973  -2.216  -0.205  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    9   15
CONECT    3    4    4    8
CONECT    4    5   20
CONECT    5    6    6   21
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8   24
CONECT    9   10
CONECT   10   11   14   14
CONECT   11   12   12   13
CONECT   13   25
CONECT   14   15   26
CONECT   15   16   16
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Reductol	Kegg
5-Methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2-carboxylate	Generator
2-Methyl-2-phenyl-3(2H)furanone-5-carboxylic acid	MeSH

Chemical Formula

C₁₂H₁₀O₄

Average Molecular Weight

218.208

Monoisotopic Molecular Weight

218.057908802

IUPAC Name

5-methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2-carboxylic acid

Traditional Name

acifran

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H10O4/c1-12(8-5-3-2-4-6-8)10(13)7-9(16-12)11(14)15/h2-7H,1H3,(H,14,15)

InChI Key

DFDGRKNOFOJBAJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Furanones

Alternative Parents

Substituents

Monocyclic benzene moiety
3-furanone
Benzenoid
Vinylogous ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.02	ALOGPS
logP	1.95	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	2.9	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.39 m³·mol⁻¹	ChemAxon
Polarizability	21.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	154.497	30932474
DeepCCS	[M-H]-	152.102	30932474
DeepCCS	[M-2H]-	185.349	30932474
DeepCCS	[M+Na]+	160.496	30932474
AllCCS	[M+H]+	147.4	32859911
AllCCS	[M+H-H2O]+	143.2	32859911
AllCCS	[M+NH4]+	151.4	32859911
AllCCS	[M+Na]+	152.5	32859911
AllCCS	[M-H]-	148.5	32859911
AllCCS	[M+Na-2H]-	148.5	32859911
AllCCS	[M+HCOO]-	148.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acifran	CC1(OC(=CC1=O)C(O)=O)C1=CC=CC=C1	3095.9	Standard polar	33892256
Acifran	CC1(OC(=CC1=O)C(O)=O)C1=CC=CC=C1	1755.5	Standard non polar	33892256
Acifran	CC1(OC(=CC1=O)C(O)=O)C1=CC=CC=C1	1833.0	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 - Acifran GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udm-3900000000-3fd7c6fab0a082a38234	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acifran GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acifran GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acifran GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - Acifran 10V, Positive-QTOF	splash10-014i-0190000000-c95d0b923be3a12a199e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acifran 20V, Positive-QTOF	splash10-014i-2490000000-9fe492522f67d63687a7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acifran 40V, Positive-QTOF	splash10-0zfr-5900000000-927839d261a8d15d6d1c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acifran 10V, Negative-QTOF	splash10-014i-0190000000-18e16028c47e16faab6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acifran 20V, Negative-QTOF	splash10-01b9-1980000000-2b7dbd31ffb6dbbf243f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acifran 40V, Negative-QTOF	splash10-0a6s-8900000000-1653856e95dde1947753	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acifran 10V, Positive-QTOF	splash10-0ldi-0970000000-a2402138c9044ca36173	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acifran 20V, Positive-QTOF	splash10-0pb9-3900000000-846e0d1bc2525ce19f51	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acifran 40V, Positive-QTOF	splash10-0udi-8900000000-84c223239279433f1d5c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acifran 10V, Negative-QTOF	splash10-014i-0290000000-eb010b2d705c6707f7d9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acifran 20V, Negative-QTOF	splash10-0f6t-9800000000-5aca951713cd28fea79a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acifran 40V, Negative-QTOF	splash10-0fb9-9400000000-d9061c5c33d2cf0bda5a	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

Not Available

Chemspider ID

46712

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 ]

Enzymes

Enzyme Details

1. G-protein coupled receptor 109A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Acts as a high affinity receptor for both nicotinic acid (also known as niacin) and (D)-beta-hydroxybutyrate and mediates increased adiponectin secretion and decreased lipolysis through G(i)-protein-mediated inhibition of adenylyl cyclase. This pharmacological effect requires nicotinic acid doses that are much higher than those provided by a normal diet. Mediates nicotinic acid-induced apoptosis in mature neutrophils. Receptor activation by nicotinic acid results in reduced cAMP levels which may affect activity of cAMP-dependent protein kinase A and phosphorylation of target proteins, leading to neutrophil apoptosis. The rank order of potency for the displacement of nicotinic acid binding is 5- methyl pyrazole-3-carboxylic acid = pyridine-3-acetic acid > acifran > 5-methyl nicotinic acid = acipimox >> nicotinuric acid = nicotinamide
Gene Name:: GPR109A
Uniprot ID:: Q8TDS4
Molecular weight:: 41849.1

Showing metabocard for Acifran (HMDB0247940)

MOL for HMDB0247940 (Acifran)

3D MOL for HMDB0247940 (Acifran)

3D SDF for HMDB0247940 (Acifran)

3D-SDF for HMDB0247940 (Acifran)

PDB for HMDB0247940 (Acifran)

3D PDB for HMDB0247940 (Acifran)

SMILES for HMDB0247940 (Acifran)

INCHI for HMDB0247940 (Acifran)

Structure for HMDB0247940 (Acifran)

3D Structure for HMDB0247940 (Acifran)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes