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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:53:23 UTC

Update Date

2021-09-26 23:00:10 UTC

HMDB ID

HMDB0249377

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Brequinar

Description

Brequinar belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group. Brequinar (DuP-785) is a drug that acts as a potent and selective inhibitor of the enzyme dihydroorotate dehydrogenase. Brequinar is an extremely weak basic (essentially neutral) compound (based on its pKa). It has been investigated as an immunosuppressant for preventing rejection after organ transplant and also as an anti-cancer drug, but was not accepted for medical use in either application largely due to its narrow therapeutic dose range and severe side effects when dosed inappropriately. However it continues to be researched both as part of a potential combination therapy for some cancers, or alternatively as an antiparasitic, or antiviral drug. It blocks synthesis of pyrimidine based nucleotides in the body and so inhibits cell growth. This compound has been identified in human blood as reported by (PMID: 31557052 ). Brequinar is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Brequinar 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


  Mrv0541 02231217002D          

 28 31  0  0  0  0            999 V2000
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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   -1.6500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    1.4289   -1.6500    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
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
   -1.4289    0.8250    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
    0.0000    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
   -2.8579    0.8250    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
   -3.5724    2.0625    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
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  3 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0249377
     RDKit          3D
Brequinar
 43 46  0  0  0  0  0  0  0  0999 V2000
   -1.4007   -1.6234   -1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349   -0.6175   -0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2519    0.1404    0.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1830   -0.0562    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393   -1.2457    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2134   -1.3261    0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9452   -0.1569    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4070   -0.1542    0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0996   -0.9335    1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4778   -0.9451    1.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2020   -0.1829    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5235    0.6053   -0.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1299    0.6075   -0.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4547    1.3775   -1.6713 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268    1.0752    0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602    1.1082    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8312    1.0671    0.9157 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1674    1.2876    0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7242    2.2573    1.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0864    2.4730    1.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8769    1.7080    0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2134    1.9240    0.9486 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3218    0.7487    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9485    0.5154    0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4287   -0.4544   -0.7401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2618   -1.2475   -1.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5610   -0.9276   -2.7790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7839   -2.4539   -1.1277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9974   -1.6653   -2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5501   -2.6670   -1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3836   -1.4049   -1.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2439   -2.1448    0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7069   -2.2770    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5608   -1.5348    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0457   -1.5561    1.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3023   -0.1877    0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0960    1.2059   -1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8913    2.0104   -0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4833    2.0845   -0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0592    2.8366    2.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5106    3.2393    2.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9204    0.1319   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7788   -2.6413   -1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  7 15  1  0
 15 16  2  0
  3 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 25  2  1  0
 16  4  1  0
 24 18  1  0
 13  8  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  5 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 15 38  1  0
 16 39  1  0
 19 40  1  0
 20 41  1  0
 23 42  1  0
 28 43  1  0
M  END


  Mrv0541 02231217002D          

 28 31  0  0  0  0            999 V2000
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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   -1.6500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    1.4289   -1.6500    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
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
   -1.4289    0.8250    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
    0.0000    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
   -2.8579    0.8250    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
   -3.5724    2.0625    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
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  3 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249377

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(N=C2C=CC(F)=CC2=C1C(O)=O)C1=CC=C(C=C1)C1=CC=CC=C1F

> <INCHI_IDENTIFIER>
InChI=1S/C23H15F2NO2/c1-13-21(23(27)28)18-12-16(24)10-11-20(18)26-22(13)15-8-6-14(7-9-15)17-4-2-3-5-19(17)25/h2-12H,1H3,(H,27,28)

> <INCHI_KEY>
PHEZJEYUWHETKO-UHFFFAOYSA-N

> <FORMULA>
C23H15F2NO2

> <MOLECULAR_WEIGHT>
375.3675

> <EXACT_MASS>
375.107085139

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.42921957489858

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methylquinoline-4-carboxylic acid

> <ALOGPS_LOGP>
5.05

> <JCHEM_LOGP>
6.2676096910000005

> <ALOGPS_LOGS>
-5.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3832228760908807

> <JCHEM_PKA_STRONGEST_BASIC>
0.7462509173862394

> <JCHEM_POLAR_SURFACE_AREA>
50.190000000000005

> <JCHEM_REFRACTIVITY>
102.60990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.39e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methylquinoline-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249377
     RDKit          3D
Brequinar
 43 46  0  0  0  0  0  0  0  0999 V2000
   -1.4007   -1.6234   -1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349   -0.6175   -0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2519    0.1404    0.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1830   -0.0562    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393   -1.2457    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2134   -1.3261    0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9452   -0.1569    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4070   -0.1542    0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0996   -0.9335    1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4778   -0.9451    1.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2020   -0.1829    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5235    0.6053   -0.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1299    0.6075   -0.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4547    1.3775   -1.6713 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268    1.0752    0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602    1.1082    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8312    1.0671    0.9157 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1674    1.2876    0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7242    2.2573    1.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0864    2.4730    1.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8769    1.7080    0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2134    1.9240    0.9486 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3218    0.7487    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9485    0.5154    0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4287   -0.4544   -0.7401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2618   -1.2475   -1.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5610   -0.9276   -2.7790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7839   -2.4539   -1.1277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9974   -1.6653   -2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5501   -2.6670   -1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3836   -1.4049   -1.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2439   -2.1448    0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7069   -2.2770    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5608   -1.5348    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0457   -1.5561    1.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3023   -0.1877    0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0960    1.2059   -1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8913    2.0104   -0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4833    2.0845   -0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0592    2.8366    2.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5106    3.2393    2.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9204    0.1319   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7788   -2.6413   -1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  7 15  1  0
 15 16  2  0
  3 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 25  2  1  0
 16  4  1  0
 24 18  1  0
 13  8  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  5 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 15 38  1  0
 16 39  1  0
 19 40  1  0
 20 41  1  0
 23 42  1  0
 28 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  F   UNK     0       8.002  -3.080   0.000  0.00  0.00           F+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   28  F   UNK     0      -2.667   4.620   0.000  0.00  0.00           F+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11    2   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    3   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0249377
HETATM    1  C1  UNL     1      -1.401  -1.623  -1.565  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.035  -0.618  -0.694  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.252   0.140   0.130  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.183  -0.056   0.140  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.839  -1.246   0.225  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.213  -1.326   0.219  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.945  -0.157   0.124  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.407  -0.154   0.112  1.00  0.00           C  
HETATM    9  C9  UNL     1       5.100  -0.933   1.014  1.00  0.00           C  
HETATM   10  C10 UNL     1       6.478  -0.945   1.019  1.00  0.00           C  
HETATM   11  C11 UNL     1       7.202  -0.183   0.127  1.00  0.00           C  
HETATM   12  C12 UNL     1       6.524   0.605  -0.786  1.00  0.00           C  
HETATM   13  C13 UNL     1       5.130   0.607  -0.779  1.00  0.00           C  
HETATM   14  F1  UNL     1       4.455   1.377  -1.671  1.00  0.00           F  
HETATM   15  C14 UNL     1       2.327   1.075   0.036  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.960   1.108   0.045  1.00  0.00           C  
HETATM   17  N1  UNL     1      -1.831   1.067   0.916  1.00  0.00           N  
HETATM   18  C16 UNL     1      -3.167   1.288   0.931  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.724   2.257   1.761  1.00  0.00           C  
HETATM   20  C18 UNL     1      -5.086   2.473   1.768  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.877   1.708   0.937  1.00  0.00           C  
HETATM   22  F2  UNL     1      -7.213   1.924   0.949  1.00  0.00           F  
HETATM   23  C20 UNL     1      -5.322   0.749   0.117  1.00  0.00           C  
HETATM   24  C21 UNL     1      -3.949   0.515   0.095  1.00  0.00           C  
HETATM   25  C22 UNL     1      -3.429  -0.454  -0.740  1.00  0.00           C  
HETATM   26  C23 UNL     1      -4.262  -1.247  -1.603  1.00  0.00           C  
HETATM   27  O1  UNL     1      -4.561  -0.928  -2.779  1.00  0.00           O  
HETATM   28  O2  UNL     1      -4.784  -2.454  -1.128  1.00  0.00           O  
HETATM   29  H1  UNL     1      -1.997  -1.665  -2.532  1.00  0.00           H  
HETATM   30  H2  UNL     1      -1.550  -2.667  -1.159  1.00  0.00           H  
HETATM   31  H3  UNL     1      -0.384  -1.405  -1.882  1.00  0.00           H  
HETATM   32  H4  UNL     1       0.244  -2.145   0.303  1.00  0.00           H  
HETATM   33  H5  UNL     1       2.707  -2.277   0.287  1.00  0.00           H  
HETATM   34  H6  UNL     1       4.561  -1.535   1.718  1.00  0.00           H  
HETATM   35  H7  UNL     1       7.046  -1.556   1.727  1.00  0.00           H  
HETATM   36  H8  UNL     1       8.302  -0.188   0.126  1.00  0.00           H  
HETATM   37  H9  UNL     1       7.096   1.206  -1.488  1.00  0.00           H  
HETATM   38  H10 UNL     1       2.891   2.010  -0.039  1.00  0.00           H  
HETATM   39  H11 UNL     1       0.483   2.084  -0.025  1.00  0.00           H  
HETATM   40  H12 UNL     1      -3.059   2.837   2.399  1.00  0.00           H  
HETATM   41  H13 UNL     1      -5.511   3.239   2.426  1.00  0.00           H  
HETATM   42  H14 UNL     1      -5.920   0.132  -0.547  1.00  0.00           H  
HETATM   43  H15 UNL     1      -5.779  -2.641  -1.109  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    3   25
CONECT    3    4   17
CONECT    4    5    5   16
CONECT    5    6   32
CONECT    6    7    7   33
CONECT    7    8   15
CONECT    8    9    9   13
CONECT    9   10   34
CONECT   10   11   11   35
CONECT   11   12   36
CONECT   12   13   13   37
CONECT   13   14
CONECT   15   16   16   38
CONECT   16   39
CONECT   17   18   18
CONECT   18   19   24
CONECT   19   20   20   40
CONECT   20   21   41
CONECT   21   22   23   23
CONECT   23   24   42
CONECT   24   25   25
CONECT   25   26
CONECT   26   27   27   28
CONECT   28   43
END

HMDB0249377
     RDKit          3D
Brequinar
 43 46  0  0  0  0  0  0  0  0999 V2000
   -1.4007   -1.6234   -1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349   -0.6175   -0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2519    0.1404    0.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1830   -0.0562    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393   -1.2457    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2134   -1.3261    0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9452   -0.1569    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4070   -0.1542    0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0996   -0.9335    1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4778   -0.9451    1.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2020   -0.1829    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5235    0.6053   -0.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1299    0.6075   -0.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4547    1.3775   -1.6713 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268    1.0752    0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602    1.1082    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8312    1.0671    0.9157 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1674    1.2876    0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7242    2.2573    1.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0864    2.4730    1.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8769    1.7080    0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2134    1.9240    0.9486 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3218    0.7487    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9485    0.5154    0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4287   -0.4544   -0.7401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2618   -1.2475   -1.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5610   -0.9276   -2.7790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7839   -2.4539   -1.1277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9974   -1.6653   -2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5501   -2.6670   -1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3836   -1.4049   -1.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2439   -2.1448    0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7069   -2.2770    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5608   -1.5348    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0457   -1.5561    1.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3023   -0.1877    0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0960    1.2059   -1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8913    2.0104   -0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4833    2.0845   -0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0592    2.8366    2.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5106    3.2393    2.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9204    0.1319   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7788   -2.6413   -1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  7 15  1  0
 15 16  2  0
  3 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 25  2  1  0
 16  4  1  0
 24 18  1  0
 13  8  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  5 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 15 38  1  0
 16 39  1  0
 19 40  1  0
 20 41  1  0
 23 42  1  0
 28 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Brequinar potassium	MeSH
DuP-785	MeSH
6-fluoro-2-(2'-fluoro-1,1'-Biphenyl-4-yl)-3-methyl-4-quinolinecarboxylic acid	MeSH
DuP 785	MeSH
Brequinar sodium	MeSH

Chemical Formula

C₂₃H₁₅F₂NO₂

Average Molecular Weight

375.3675

Monoisotopic Molecular Weight

375.107085139

IUPAC Name

6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methylquinoline-4-carboxylic acid

Traditional Name

6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methylquinoline-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=C(N=C2C=CC(F)=CC2=C1C(O)=O)C1=CC=C(C=C1)C1=CC=CC=C1F

InChI Identifier

InChI=1S/C23H15F2NO2/c1-13-21(23(27)28)18-12-16(24)10-11-20(18)26-22(13)15-8-6-14(7-9-15)17-4-2-3-5-19(17)25/h2-12H,1H3,(H,27,28)

InChI Key

PHEZJEYUWHETKO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Phenylquinolines

Direct Parent

Phenylquinolines

Alternative Parents

Substituents

Phenylquinoline
Quinoline-4-carboxylic acid
Biphenyl
2-phenylpyridine
Haloquinoline
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Fluorobenzene
Halobenzene
Methylpyridine
Pyridine
Aryl halide
Benzenoid
Monocyclic benzene moiety
Aryl fluoride
Heteroaromatic compound
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	5.05	ALOGPS
logP	6.27	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	3.38	ChemAxon
pKa (Strongest Basic)	0.75	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.19 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.61 m³·mol⁻¹	ChemAxon
Polarizability	38.43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	186.034	30932474
DeepCCS	[M-H]-	183.676	30932474
DeepCCS	[M-2H]-	217.376	30932474
DeepCCS	[M+Na]+	192.511	30932474
AllCCS	[M+H]+	192.6	32859911
AllCCS	[M+H-H2O]+	189.4	32859911
AllCCS	[M+NH4]+	195.6	32859911
AllCCS	[M+Na]+	196.4	32859911
AllCCS	[M-H]-	178.5	32859911
AllCCS	[M+Na-2H]-	177.4	32859911
AllCCS	[M+HCOO]-	176.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Brequinar	CC1=C(N=C2C=CC(F)=CC2=C1C(O)=O)C1=CC=C(C=C1)C1=CC=CC=C1F	4152.1	Standard polar	33892256
Brequinar	CC1=C(N=C2C=CC(F)=CC2=C1C(O)=O)C1=CC=C(C=C1)C1=CC=CC=C1F	3108.2	Standard non polar	33892256
Brequinar	CC1=C(N=C2C=CC(F)=CC2=C1C(O)=O)C1=CC=C(C=C1)C1=CC=CC=C1F	3256.5	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 - Brequinar GC-MS (Non-derivatized) - 70eV, Positive	splash10-06ur-0109000000-0c61c39a69edcb37dca4	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brequinar GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brequinar GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brequinar 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 - Brequinar 10V, Positive-QTOF	splash10-004i-0009000000-cfc146d01062d4aa72cd	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brequinar 20V, Positive-QTOF	splash10-0a6r-0009000000-c76b6e723f17a6f3ae71	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brequinar 40V, Positive-QTOF	splash10-08gi-0229000000-3b5064e233b3f24cf3ac	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brequinar 10V, Negative-QTOF	splash10-00di-0009000000-0e0cf3d9d8272e4a75df	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brequinar 20V, Negative-QTOF	splash10-0089-0009000000-5a13e64a1842d9c89762	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brequinar 40V, Negative-QTOF	splash10-01q9-0009000000-d529ecb13b65523e396b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brequinar 10V, Positive-QTOF	splash10-004i-0009000000-60ddba19b56407be8c25	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brequinar 20V, Positive-QTOF	splash10-0a6r-0009000000-c944db276c17264f1e74	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brequinar 40V, Positive-QTOF	splash10-03e9-0029000000-80730351467047f1c37d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brequinar 10V, Negative-QTOF	splash10-00di-0009000000-a0a5598e6cb170022e62	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brequinar 20V, Negative-QTOF	splash10-00e9-0009000000-4a1e120dcca841a1707c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brequinar 40V, Negative-QTOF	splash10-0wa0-0079000000-87edcd7c0a600dac61c2	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

DB03523

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Brequinar

METLIN ID

Not Available

PubChem Compound

57030

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 ]

Showing metabocard for Brequinar (HMDB0249377)

MOL for HMDB0249377 (Brequinar)

3D MOL for HMDB0249377 (Brequinar)

3D SDF for HMDB0249377 (Brequinar)

3D-SDF for HMDB0249377 (Brequinar)

PDB for HMDB0249377 (Brequinar)

3D PDB for HMDB0249377 (Brequinar)

SMILES for HMDB0249377 (Brequinar)

INCHI for HMDB0249377 (Brequinar)

Structure for HMDB0249377 (Brequinar)

3D Structure for HMDB0249377 (Brequinar)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra