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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:47:25 UTC

Update Date

2021-09-26 22:58:46 UTC

HMDB ID

HMDB0248461

Secondary Accession Numbers

None

Metabolite Identification

Common Name

anthracene-9-carboxylic acid

Description

anthracene-9-carboxylic acid, also known as 9-anthroic acid or A9C, belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. Based on a literature review a small amount of articles have been published on anthracene-9-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Anthracene-9-carboxylic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically anthracene-9-carboxylic acid 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


  Mrv1572004221606462D          

 17 19  0  0  0  0            999 V2000
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  2  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  8  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248461

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=C2C=CC=CC2=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O2/c16-15(17)14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9H,(H,16,17)

> <INCHI_KEY>
XGWFJBFNAQHLEF-UHFFFAOYSA-N

> <FORMULA>
C15H10O2

> <MOLECULAR_WEIGHT>
222.243

> <EXACT_MASS>
222.068079562

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
23.65584340453363

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
anthracene-9-carboxylic acid

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
3.609782237333333

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.188020171789041

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
66.2146

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.54e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ANCA

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    1   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    4   13                                                       
CONECT    9   10   11                                                       
CONECT   10    5    9   12                                                  
CONECT   11    6    9   13                                                  
CONECT   12    7   10   14                                                  
CONECT   13    8   11   14                                                  
CONECT   14   12   13   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0248461
HETATM    1  O1  UNL     1       2.890  -1.542   0.368  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.026  -1.164  -0.458  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.247  -1.440  -1.813  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.811  -0.456  -0.069  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.336  -1.179   0.234  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.309  -2.561   0.163  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.426  -3.317   0.456  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.578  -2.662   0.823  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.604  -1.289   0.894  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.499  -0.515   0.605  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.537   0.870   0.680  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.395   1.582   0.378  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.418   2.959   0.448  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.718   3.694   0.148  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.873   3.031  -0.221  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.871   1.651  -0.283  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.760   0.924   0.009  1.00  0.00           C  
HETATM   18  H1  UNL     1       3.200  -1.603  -2.153  1.00  0.00           H  
HETATM   19  H2  UNL     1       0.606  -3.065  -0.128  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.383  -4.416   0.393  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.484  -3.193   1.064  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.529  -0.769   1.189  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.458   1.363   0.973  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.297   3.521   0.731  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.698   4.783   0.204  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.749   3.605  -0.451  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.804   1.188  -0.578  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   18
CONECT    4    5    5   17
CONECT    5    6   10
CONECT    6    7    7   19
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   10   22
CONECT   10   11   11
CONECT   11   12   23
CONECT   12   13   13   17
CONECT   13   14   24
CONECT   14   15   15   25
CONECT   15   16   26
CONECT   16   17   17   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9-Anthracenecarboxylic acid	ChEBI
9-Carboxyanthracene	ChEBI
A9C	ChEBI
ANCA	ChEBI
Anthracene-10-carboxylic acid	ChEBI
9-Anthracenecarboxylate	Generator
Anthracene-10-carboxylate	Generator
Anthracene-9-carboxylate	Generator
9-Anthroate	HMDB
9-Anthroic acid	HMDB
9-AC CPD	HMDB
9-Anthroic acid, sodium salt	HMDB
9-ACA	HMDB
9-Anthracene carboxylic acid	HMDB
9-Anthroic acid, sodium salt, 11C-labeled	HMDB
Anthracene-9-carboxylic acid	ChEBI

Chemical Formula

C₁₅H₁₀O₂

Average Molecular Weight

222.243

Monoisotopic Molecular Weight

222.068079562

IUPAC Name

anthracene-9-carboxylic acid

Traditional Name

ANCA

CAS Registry Number

Not Available

SMILES

OC(=O)C1=C2C=CC=CC2=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C15H10O2/c16-15(17)14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9H,(H,16,17)

InChI Key

XGWFJBFNAQHLEF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthracenecarboxylic acids and derivatives

Direct Parent

Anthracenecarboxylic acids

Alternative Parents

Substituents

Anthracene carboxylic acid
1-naphthalenecarboxylic acid or derivatives
1-naphthalenecarboxylic acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

anthroic acid (CHEBI:34507 )

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	3.84	ALOGPS
logP	3.61	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.19	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.21 m³·mol⁻¹	ChemAxon
Polarizability	23.66 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
DeepCCS	[M-2H]-	177.883	30932474
DeepCCS	[M+Na]+	152.769	30932474
AllCCS	[M+H]+	148.4	32859911
AllCCS	[M+H-H2O]+	144.3	32859911
AllCCS	[M+NH4]+	152.3	32859911
AllCCS	[M+Na]+	153.4	32859911
AllCCS	[M-H]-	150.8	32859911
AllCCS	[M+Na-2H]-	150.0	32859911
AllCCS	[M+HCOO]-	149.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
anthracene-9-carboxylic acid	OC(=O)C1=C2C=CC=CC2=CC2=CC=CC=C12	3478.7	Standard polar	33892256
anthracene-9-carboxylic acid	OC(=O)C1=C2C=CC=CC2=CC2=CC=CC=C12	1857.4	Standard non polar	33892256
anthracene-9-carboxylic acid	OC(=O)C1=C2C=CC=CC2=CC2=CC=CC=C12	2268.5	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 - anthracene-9-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kmi-0290000000-cfeecdc4fa169677ba88	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - anthracene-9-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - anthracene-9-carboxylic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - anthracene-9-carboxylic acid 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - anthracene-9-carboxylic acid 35V, Negative-QTOF	splash10-004i-0920000000-1af97793795cb14e001c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anthracene-9-carboxylic acid 10V, Positive-QTOF	splash10-00di-0090000000-835e51a2f7c66432e76a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anthracene-9-carboxylic acid 20V, Positive-QTOF	splash10-00di-0290000000-ba8132e83055e73c65fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anthracene-9-carboxylic acid 40V, Positive-QTOF	splash10-004i-0910000000-694b93d332d85948c819	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anthracene-9-carboxylic acid 10V, Negative-QTOF	splash10-00di-0390000000-96e76dceee8056ec011d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anthracene-9-carboxylic acid 20V, Negative-QTOF	splash10-00b9-0950000000-592aaff3e4b5a50b2067	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anthracene-9-carboxylic acid 40V, Negative-QTOF	splash10-004i-0910000000-9661eabbebd70f263e5d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anthracene-9-carboxylic acid 10V, Positive-QTOF	splash10-05fr-0090000000-b543437712d1f8949117	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anthracene-9-carboxylic acid 20V, Positive-QTOF	splash10-0a4i-0090000000-c5d6915c8145b8f7c770	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anthracene-9-carboxylic acid 40V, Positive-QTOF	splash10-056r-0970000000-dbc7a960db8fd068d255	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anthracene-9-carboxylic acid 10V, Negative-QTOF	splash10-00fr-0690000000-34c9ae981f0c284e5f8b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anthracene-9-carboxylic acid 20V, Negative-QTOF	splash10-00fr-0590000000-41aa5fdf80768fd441b7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anthracene-9-carboxylic acid 40V, Negative-QTOF	splash10-004i-0900000000-a5c7c61e51665431ac9b	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

2116

KEGG Compound ID

C13699

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2201

PDB ID

Not Available

ChEBI ID

34507

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 ]

Showing metabocard for anthracene-9-carboxylic acid (HMDB0248461)

MOL for HMDB0248461 (anthracene-9-carboxylic acid)

3D MOL for HMDB0248461 (anthracene-9-carboxylic acid)

3D SDF for HMDB0248461 (anthracene-9-carboxylic acid)

3D-SDF for HMDB0248461 (anthracene-9-carboxylic acid)

PDB for HMDB0248461 (anthracene-9-carboxylic acid)

3D PDB for HMDB0248461 (anthracene-9-carboxylic acid)

SMILES for HMDB0248461 (anthracene-9-carboxylic acid)

INCHI for HMDB0248461 (anthracene-9-carboxylic acid)

Structure for HMDB0248461 (anthracene-9-carboxylic acid)

3D Structure for HMDB0248461 (anthracene-9-carboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra