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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:01:05 UTC

Update Date

2023-02-21 17:23:15 UTC

HMDB ID

HMDB0033303

Secondary Accession Numbers

HMDB33303

Metabolite Identification

Common Name

Anofinic acid

Description

Anofinic acid, also known as anofinate, belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Anofinic acid has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make anofinic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Anofinic acid.

Structure

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


  Mrv1652309272007332D          

 15 16  0  0  0  0            999 V2000
10002.552110000.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.022010001.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1723 9999.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4578 9999.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1723 9998.5585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.600910001.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.886410000.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8863 9999.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6008 9999.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.026910001.0358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.312410000.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3124 9999.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0269 9999.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7414 9999.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.741410000.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8  3  1  0  0  0  0
 11 12  1  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
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
  1 15  1  0  0  0  0
 15  2  1  0  0  0  0
 11  6  2  0  0  0  0
  9 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033303

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OC2=CC=C(C=C2C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H12O3/c1-12(2)6-5-8-7-9(11(13)14)3-4-10(8)15-12/h3-7H,1-2H3,(H,13,14)

> <INCHI_KEY>
AXICIBPYBONRSP-UHFFFAOYSA-N

> <FORMULA>
C12H12O3

> <MOLECULAR_WEIGHT>
204.2219

> <EXACT_MASS>
204.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.452689370428466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2-dimethyl-2H-chromene-6-carboxylic acid

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.531452126

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.298908531318648

> <JCHEM_PKA_STRONGEST_BASIC>
-4.924753032597022

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
57.707600000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2-dimethylchromene-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8671.4318667.569   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8670.4418669.283   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8663.2558665.516   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8661.9218666.284   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8663.2558663.976   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8665.9228668.600   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.5888667.830   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.5888666.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.9218665.520   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8668.5848668.600   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8667.2508667.830   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.2508666.290   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.5848665.520   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8669.9178666.290   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.9178667.830   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3    4    5    8                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    7   11                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9    3                                                  
CONECT    9    8   12                                                       
CONECT   10   11   15                                                       
CONECT   11   12   10    6                                                  
CONECT   12   11   13    9                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10    1    2                                             
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0033303
HETATM    1  C1  UNL     1      -3.130   0.696   0.717  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.244  -0.141  -0.216  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.034  -1.337  -0.726  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.846   0.650  -1.386  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.585   0.917  -1.651  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.482   0.442  -0.799  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.815   0.705  -1.050  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.800   0.231  -0.209  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.217   0.517  -0.487  1.00  0.00           C  
HETATM   10  O1  UNL     1       4.516   1.201  -1.503  1.00  0.00           O  
HETATM   11  O2  UNL     1       5.166   0.025   0.378  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.471  -0.518   0.903  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.148  -0.792   1.172  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.167  -0.306   0.313  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.156  -0.572   0.570  1.00  0.00           O  
HETATM   16  H1  UNL     1      -2.442   1.416   1.210  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.512   0.006   1.487  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.931   1.193   0.141  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.582  -1.849   0.074  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.341  -2.063  -1.179  1.00  0.00           H  
HETATM   21  H6  UNL     1      -3.701  -0.980  -1.519  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.603   1.032  -2.060  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.276   1.500  -2.511  1.00  0.00           H  
HETATM   24  H9  UNL     1       2.065   1.284  -1.912  1.00  0.00           H  
HETATM   25  H10 UNL     1       5.424  -0.973   0.400  1.00  0.00           H  
HETATM   26  H11 UNL     1       3.247  -0.902   1.583  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.866  -1.384   2.049  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4   15
CONECT    3   19   20   21
CONECT    4    5    5   22
CONECT    5    6   23
CONECT    6    7    7   14
CONECT    7    8   24
CONECT    8    9   12   12
CONECT    9   10   10   11
CONECT   11   25
CONECT   12   13   26
CONECT   13   14   14   27
CONECT   14   15
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Anofinate	Generator
1-Hydroxy-3',3'-dimethylchromene	HMDB
2,2-Dimethyl-6-chromenecarboxylic acid	HMDB
2,2-Dimethyl-2H-chromene-6-carboxylate	Generator
2,2-Dimethyl-2H-1-benzopyran-6-carboxylic acid	PhytoBank
2,2-Dimethyl-(2H)-1-chromene-6-carboxylic acid	PhytoBank
2,2-Dimethylchromene-6-carboxylic acid	PhytoBank
1-Hydroxy-3’,3’-dimethylchromene	PhytoBank

Chemical Formula

C₁₂H₁₂O₃

Average Molecular Weight

204.2219

Monoisotopic Molecular Weight

204.07864425

IUPAC Name

2,2-dimethyl-2H-chromene-6-carboxylic acid

Traditional Name

2,2-dimethylchromene-6-carboxylic acid

CAS Registry Number

34818-56-9

SMILES

CC1(C)OC2=CC=C(C=C2C=C1)C(O)=O

InChI Identifier

InChI=1S/C12H12O3/c1-12(2)6-5-8-7-9(11(13)14)3-4-10(8)15-12/h3-7H,1-2H3,(H,13,14)

InChI Key

AXICIBPYBONRSP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
Alkyl aryl ether
Benzenoid
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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: HMDB0033303)
Cell membrane (HMDB: HMDB0033303)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033303)

Source

Exogenous

Exogenous (HMDB: HMDB0033303)

Food

Food (HMDB: HMDB0033303)

Plant (HMDB: HMDB0033303)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033303)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	160 °C	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	0.27 g/L	ALOGPS
logP	3.05	ALOGPS
logP	2.53	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	57.71 m³·mol⁻¹	ChemAxon
Polarizability	21.45 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
DarkChem	[M+H]+	148.703	31661259
DarkChem	[M-H]-	144.015	31661259
DeepCCS	[M+H]+	147.665	30932474
DeepCCS	[M-H]-	145.307	30932474
DeepCCS	[M-2H]-	179.029	30932474
DeepCCS	[M+Na]+	153.893	30932474
AllCCS	[M+H]+	143.4	32859911
AllCCS	[M+H-H2O]+	139.1	32859911
AllCCS	[M+NH4]+	147.4	32859911
AllCCS	[M+Na]+	148.5	32859911
AllCCS	[M-H]-	146.7	32859911
AllCCS	[M+Na-2H]-	146.8	32859911
AllCCS	[M+HCOO]-	147.0	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.	5.86 minutes	32390414
Predicted by Siyang on May 30, 2022	11.094 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.2 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Anofinic acid	CC1(C)OC2=C(C=C1)C=C(C=C2)C(O)=O	2781.0	Standard polar	33892256
Anofinic acid	CC1(C)OC2=C(C=C1)C=C(C=C2)C(O)=O	1661.4	Standard non polar	33892256
Anofinic acid	CC1(C)OC2=C(C=C1)C=C(C=C2)C(O)=O	1762.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Anofinic acid,1TMS,isomer #1	CC1(C)C=CC2=CC(C(=O)O[Si](C)(C)C)=CC=C2O1	1823.7	Semi standard non polar	33892256
Anofinic acid,1TBDMS,isomer #1	CC1(C)C=CC2=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C2O1	2089.2	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 - Anofinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0910000000-2fd6ca0a975066078f62	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anofinic acid GC-MS (1 TMS) - 70eV, Positive	splash10-024r-9750000000-412f70df1fe99ef6347f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anofinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anofinic acid 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 - Anofinic acid 10V, Positive-QTOF	splash10-0a4i-0090000000-7dc72695b37646477da4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anofinic acid 20V, Positive-QTOF	splash10-0a4i-1690000000-8a11769c4240ccab2700	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anofinic acid 40V, Positive-QTOF	splash10-0fr2-2900000000-43388bdb4cfd5374cb71	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anofinic acid 10V, Negative-QTOF	splash10-0udi-0390000000-642c6f6bb3f2847986b1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anofinic acid 20V, Negative-QTOF	splash10-0pb9-0950000000-740953ce6b8aae5ea5b5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anofinic acid 40V, Negative-QTOF	splash10-001c-0900000000-dc715d345a9f729ff7ff	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anofinic acid 10V, Negative-QTOF	splash10-0udi-0290000000-fd22e01ca2a79a6885c7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anofinic acid 20V, Negative-QTOF	splash10-0pb9-0970000000-7bf06eb5c7dcd01a03d9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anofinic acid 40V, Negative-QTOF	splash10-014l-0900000000-b92d52ec107c8c3304b9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anofinic acid 10V, Positive-QTOF	splash10-052r-0980000000-8543268c25c80bbf2f5f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anofinic acid 20V, Positive-QTOF	splash10-052r-1930000000-0835d36b6e65ee0b26b0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anofinic acid 40V, Positive-QTOF	splash10-0007-6900000000-697581cadfc7406b0a9e	2021-09-24	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+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

FDB011327

KNApSAcK ID

C00029692

Chemspider ID

4477586

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319235

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

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

Showing metabocard for Anofinic acid (HMDB0033303)

MOL for HMDB0033303 (Anofinic acid)

3D MOL for HMDB0033303 (Anofinic acid)

3D SDF for HMDB0033303 (Anofinic acid)

3D-SDF for HMDB0033303 (Anofinic acid)

PDB for HMDB0033303 (Anofinic acid)

3D PDB for HMDB0033303 (Anofinic acid)

SMILES for HMDB0033303 (Anofinic acid)

INCHI for HMDB0033303 (Anofinic acid)

Structure for HMDB0033303 (Anofinic acid)

3D Structure for HMDB0033303 (Anofinic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra