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Showing metabocard for 2,5-Dihydroxycinnamic acid methyl ester (HMDB0061686)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2014-04-16 18:10:00 UTC
Update Date2023-02-21 17:30:25 UTC
HMDB IDHMDB0061686
Secondary Accession Numbers
  • HMDB61686
Metabolite Identification
Common Name2,5-Dihydroxycinnamic acid methyl ester
Description2,5-Dihydroxycinnamic acid methyl ester, also known as methyl 2,5-dihydroxycinnamate or methyl 3-(2',5'dihydroxyphenyl)acrylate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 2,5-Dihydroxycinnamic acid methyl ester is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1677000625
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0061686 (2,5-Dihydroxycinnamic acid methyl ester)

  Mrv0541 04161411112D          

 14 14  0  0  0  0            999 V2000
   -2.5312    0.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2457   -0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2457   -1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5312   -1.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167   -1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167   -0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9601   -1.4410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1023    0.2089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1023   -1.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3878   -1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266   -1.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266   -2.2660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0411   -1.0285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0411   -0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  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
  3  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
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3D MOL for HMDB0061686 (2,5-Dihydroxycinnamic acid methyl ester)

HMDB0061686
     RDKit          3D
2,5-Dihydroxycinnamic acid methyl ester
 24 24  0  0  0  0  0  0  0  0999 V2000
    4.8497   -0.4817    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4300   -0.4405    0.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7834    0.7735   -0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4961    1.7949   -0.2092 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3338    0.9124   -0.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037   -0.0764    0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9315   -0.0757    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6177   -1.2885    0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9844   -1.3795    0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6115   -2.6313    0.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7608   -0.2598    0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1271    0.9498   -0.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7339    1.0213   -0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2030    2.2632   -0.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500    0.0497   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2858    0.0541    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2193   -1.5190    0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9225    1.8909   -0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0014   -1.0558    0.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0391   -2.2034    0.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8247   -2.9310    1.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8451   -0.3460    0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7336    1.8503   -0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6633    3.1283   -0.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13  7  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  0
  6 19  1  0
  8 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 14 24  1  0
M  END
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3D SDF for HMDB0061686 (2,5-Dihydroxycinnamic acid methyl ester)

  Mrv0541 04161411112D          

 14 14  0  0  0  0            999 V2000
   -2.5312    0.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2457   -0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2457   -1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5312   -1.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167   -1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167   -0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9601   -1.4410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1023    0.2089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1023   -1.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3878   -1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266   -1.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266   -2.2660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0411   -1.0285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0411   -0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  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
  3  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061686

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)\C=C\C1=CC(O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c1-14-10(13)5-2-7-6-8(11)3-4-9(7)12/h2-6,11-12H,1H3/b5-2+

> <INCHI_KEY>
BQCNSTFWSKOWMA-GORDUTHDSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.184

> <EXACT_MASS>
194.057908808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.388058983395297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
1.9081830060000002

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.325139538256966

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.48246932168149

> <JCHEM_PKA_STRONGEST_BASIC>
-5.900227362182577

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
51.7908

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0061686 (2,5-Dihydroxycinnamic acid methyl ester)

HMDB0061686
     RDKit          3D
2,5-Dihydroxycinnamic acid methyl ester
 24 24  0  0  0  0  0  0  0  0999 V2000
    4.8497   -0.4817    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4300   -0.4405    0.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7834    0.7735   -0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4961    1.7949   -0.2092 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3338    0.9124   -0.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037   -0.0764    0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9315   -0.0757    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6177   -1.2885    0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9844   -1.3795    0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6115   -2.6313    0.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7608   -0.2598    0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1271    0.9498   -0.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7339    1.0213   -0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2030    2.2632   -0.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500    0.0497   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2858    0.0541    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2193   -1.5190    0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9225    1.8909   -0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0014   -1.0558    0.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0391   -2.2034    0.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8247   -2.9310    1.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8451   -0.3460    0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7336    1.8503   -0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6633    3.1283   -0.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13  7  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  0
  6 19  1  0
  8 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 14 24  1  0
M  END
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PDB for HMDB0061686 (2,5-Dihydroxycinnamic acid methyl ester)

HEADER    PROTEIN                                 16-APR-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-14         0                                  
HETATM    1  C   UNK     0      -4.725   0.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.059  -0.380   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.059  -1.920   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.725  -2.690   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.391  -1.920   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.391  -0.380   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.392  -2.690   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.058   0.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.058  -2.690   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.724  -1.920   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.610  -2.690   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.610  -4.230   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.943  -1.920   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.943  -0.380   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    1    5    8                                                  
CONECT    7    3                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for HMDB0061686 (2,5-Dihydroxycinnamic acid methyl ester)

COMPND    HMDB0061686
HETATM    1  C1  UNL     1       4.850  -0.482   0.112  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.430  -0.440   0.105  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.783   0.774  -0.066  1.00  0.00           C  
HETATM    4  O2  UNL     1       3.496   1.795  -0.209  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.334   0.912  -0.086  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.504  -0.076   0.053  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.932  -0.076   0.052  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.618  -1.289   0.222  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.984  -1.380   0.234  1.00  0.00           C  
HETATM   10  O3  UNL     1      -3.611  -2.631   0.410  1.00  0.00           O  
HETATM   11  C8  UNL     1      -3.761  -0.260   0.076  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.127   0.950  -0.094  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.734   1.021  -0.103  1.00  0.00           C  
HETATM   14  O4  UNL     1      -1.203   2.263  -0.278  1.00  0.00           O  
HETATM   15  H1  UNL     1       5.250   0.050  -0.801  1.00  0.00           H  
HETATM   16  H2  UNL     1       5.286   0.054   0.970  1.00  0.00           H  
HETATM   17  H3  UNL     1       5.219  -1.519   0.024  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.923   1.891  -0.224  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.001  -1.056   0.191  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.039  -2.203   0.351  1.00  0.00           H  
HETATM   21  H7  UNL     1      -3.825  -2.931   1.357  1.00  0.00           H  
HETATM   22  H8  UNL     1      -4.845  -0.346   0.087  1.00  0.00           H  
HETATM   23  H9  UNL     1      -3.734   1.850  -0.221  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.663   3.128  -0.400  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   18
CONECT    6    7   19
CONECT    7    8    8   13
CONECT    8    9   20
CONECT    9   10   11   11
CONECT   10   21
CONECT   11   12   22
CONECT   12   13   13   23
CONECT   13   14
CONECT   14   24
END
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SMILES for HMDB0061686 (2,5-Dihydroxycinnamic acid methyl ester)

COC(=O)\C=C\C1=CC(O)=CC=C1O
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INCHI for HMDB0061686 (2,5-Dihydroxycinnamic acid methyl ester)

InChI=1S/C10H10O4/c1-14-10(13)5-2-7-6-8(11)3-4-9(7)12/h2-6,11-12H,1H3/b5-2+
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Methyl 2,5-dihydroxycinnamateChEBI
Methyl 3-(2',5'dihydroxyphenyl)acrylateChEBI
Methyl grevillateChEBI
Methyl 2,5-dihydroxycinnamic acidGenerator
Methyl 3-(2',5'dihydroxyphenyl)acrylic acidGenerator
Methyl grevillic acidGenerator
2,5-Dihydroxycinnamate methyl esterGenerator
2,4-DihydroxymethylcinnamateHMDB
Chemical FormulaC10H10O4
Average Molecular Weight194.184
Monoisotopic Molecular Weight194.057908808
IUPAC Namemethyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate
Traditional Namemethyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
COC(=O)\C=C\C1=CC(O)=CC=C1O
InChI Identifier
InChI=1S/C10H10O4/c1-14-10(13)5-2-7-6-8(11)3-4-9(7)12/h2-6,11-12H,1H3/b5-2+
InChI KeyBQCNSTFWSKOWMA-GORDUTHDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Cinnamic acid ester
  • Hydroquinone
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Fatty acyl
  • Monocyclic benzene moiety
  • Benzenoid
  • Methyl ester
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5353609
PDB IDNot Available
ChEBI ID84089
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]