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Showing NP-Card for 4-Methoxyphenylacetic acid (NP0000214)

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Record Information
Version2.0
Created at2006-05-22 14:17:35 UTC
Updated at2021-10-07 20:40:37 UTC
NP-MRD IDNP0000214
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Methoxyphenylacetic acid
Description4-Methoxyphenylacetic acid is a monocarboxylic acid that is phenylacetic acid carrying a 4-methoxy substituent. It is used as an intermediate for pharmaceuticals and other organic synthesis. It has been found to inhibit the germination of cress and lettuce seeds. It has a role as a plant metabolite, a plant growth retardant and an Aspergillus metabolite. It is a monocarboxylic acid and a monomethoxybenzene. 4-Methoxyphenylacetic acid, also known as 4-methoxybenzeneacetate or 2-(p-anisyl)acetic acid, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. 4-Methoxyphenylacetic acid is a 4-O-Methylated catecholamine metabolite found in normal human urine, cerebrospinal fluid and brain tissue.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000214 (4-Methoxyphenylacetic acid)


  Mrv1652305261923592D          

 12 12  0  0  0  0            999 V2000
   25.9719   -8.2387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -3.7012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4009   -4.9387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9719   -4.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2575   -8.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -4.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9719   -7.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9719   -5.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -7.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2575   -7.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -6.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2575   -6.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  6  1  0  0  0  0
  3  6  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  2  0  0  0  0
  8 12  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
Download

3D MOL for NP0000214 (4-Methoxyphenylacetic acid)

HMDB0002072
     RDKit          3D
4-Methoxyphenylacetic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
   -4.0110    0.1751    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9478    0.7435   -0.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6373    0.3402   -0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7235    1.0646   -0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5995    0.7275   -0.9562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0594   -0.3740   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5154   -0.6608   -0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677   -0.0374    0.8945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1039   -0.6011    2.0110 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8391    1.1717    0.7872 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1783   -1.0888    0.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1827   -0.7381    0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984    1.0012    0.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6017   -0.3077    1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5604   -0.6042    0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0765    1.9212   -1.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    1.2616   -1.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9604   -0.2503   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289   -1.7655   -0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4939    1.2501    0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630   -1.9371    1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8916   -1.2917    1.2175 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  2  0
 12  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

3D SDF for NP0000214 (4-Methoxyphenylacetic acid)


  Mrv1652305261923592D          

 12 12  0  0  0  0            999 V2000
   25.9719   -8.2387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -3.7012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4009   -4.9387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9719   -4.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2575   -8.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -4.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9719   -7.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9719   -5.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -7.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2575   -7.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -6.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2575   -6.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  6  1  0  0  0  0
  3  6  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  2  0  0  0  0
  8 12  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000214

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CC(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O3/c1-12-8-4-2-7(3-5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)

> <INCHI_KEY>
NRPFNQUDKRYCNX-UHFFFAOYSA-N

> <FORMULA>
C9H10O3

> <MOLECULAR_WEIGHT>
166.1739

> <EXACT_MASS>
166.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.855201156554454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-methoxyphenyl)acetic acid

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
1.4533228396666666

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.116021917653093

> <JCHEM_PKA_STRONGEST_BASIC>
-4.824732645952242

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
43.8288

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxyphenylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000214 (4-Methoxyphenylacetic acid)

HMDB0002072
     RDKit          3D
4-Methoxyphenylacetic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
   -4.0110    0.1751    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9478    0.7435   -0.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6373    0.3402   -0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7235    1.0646   -0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5995    0.7275   -0.9562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0594   -0.3740   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5154   -0.6608   -0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677   -0.0374    0.8945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1039   -0.6011    2.0110 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8391    1.1717    0.7872 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1783   -1.0888    0.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1827   -0.7381    0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984    1.0012    0.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6017   -0.3077    1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5604   -0.6042    0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0765    1.9212   -1.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    1.2616   -1.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9604   -0.2503   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289   -1.7655   -0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4939    1.2501    0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630   -1.9371    1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8916   -1.2917    1.2175 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  2  0
 12  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

PDB for NP0000214 (4-Methoxyphenylacetic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      48.481 -15.379   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      49.815  -6.909   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      51.148  -9.219   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      48.481  -9.219   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      47.147 -16.149   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      49.815  -8.449   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      48.481 -13.839   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      48.481 -10.759   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      49.815 -13.069   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      47.147 -13.069   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      49.815 -11.529   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      47.147 -11.529   0.000  0.00  0.00           C+0
CONECT    1    5    7                                                       
CONECT    2    6                                                            
CONECT    3    6                                                            
CONECT    4    6    8                                                       
CONECT    5    1                                                            
CONECT    6    2    3    4                                                  
CONECT    7    1    9   10                                                  
CONECT    8    4   11   12                                                  
CONECT    9    7   11                                                       
CONECT   10    7   12                                                       
CONECT   11    8    9                                                       
CONECT   12    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for NP0000214 (4-Methoxyphenylacetic acid)

COMPND    HMDB0002072
HETATM    1  C1  UNL     1      -4.011   0.175   0.628  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.948   0.743  -0.085  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.637   0.340  -0.101  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.724   1.065  -0.886  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.599   0.728  -0.956  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.059  -0.374  -0.225  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.515  -0.661  -0.287  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.168  -0.037   0.895  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.104  -0.601   2.011  1.00  0.00           O  
HETATM   10  O3  UNL     1       3.839   1.172   0.787  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.178  -1.089   0.544  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.183  -0.738   0.614  1.00  0.00           C  
HETATM   13  H1  UNL     1      -4.698   1.001   0.939  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.602  -0.308   1.561  1.00  0.00           H  
HETATM   15  H3  UNL     1      -4.560  -0.604   0.081  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.076   1.921  -1.462  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.321   1.262  -1.559  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.960  -0.250  -1.212  1.00  0.00           H  
HETATM   19  H7  UNL     1       2.629  -1.766  -0.304  1.00  0.00           H  
HETATM   20  H8  UNL     1       4.494   1.250   0.019  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.463  -1.937   1.130  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.892  -1.292   1.218  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5   16
CONECT    5    6    6   17
CONECT    6    7   11
CONECT    7    8   18   19
CONECT    8    9    9   10
CONECT   10   20
CONECT   11   12   12   21
CONECT   12   22
END
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SMILES for NP0000214 (4-Methoxyphenylacetic acid)

COC1=CC=C(CC(O)=O)C=C1
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INCHI for NP0000214 (4-Methoxyphenylacetic acid)

InChI=1S/C9H10O3/c1-12-8-4-2-7(3-5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)
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View in JSmol
Synonyms
ValueSource
(4-Methoxyphenyl)acetic acidChEBI
(p-Methoxyphenyl)acetic acidChEBI
2-(p-Anisyl)acetic acidChEBI
4-Methoxybenzeneacetic acidChEBI
Homoanisic acidChEBI
p-Methoxy-alpha-toluic acidChEBI
p-Methoxyphenylacetic acidChEBI
(4-Methoxyphenyl)acetateGenerator
(p-Methoxyphenyl)acetateGenerator
2-(p-Anisyl)acetateGenerator
4-MethoxybenzeneacetateGenerator
HomoanisateGenerator
p-Methoxy-a-toluateGenerator
p-Methoxy-a-toluic acidGenerator
p-Methoxy-alpha-toluateGenerator
p-Methoxy-α-toluateGenerator
p-Methoxy-α-toluic acidGenerator
p-MethoxyphenylacetateGenerator
4-MethoxyphenylacetateGenerator
3-Methoxyphenylacetic acid, potassium saltHMDB
3-Methoxyphenylacetic acidHMDB
(4-Methoxy-phenyl)-acetateHMDB
(4-Methoxy-phenyl)-acetic acidHMDB
4-Methoxy phenylacetic acidHMDB
4-Methoxy-benzeneacetateHMDB
4-Methoxy-benzeneacetic acidHMDB
Homo-p-anisic acidHMDB
p-Methoxyphenyl-acetateHMDB
p-Methoxyphenyl-acetic acidHMDB
Chemical FormulaC9H10O3
Average Mass166.1739 Da
Monoisotopic Mass166.06299 Da
IUPAC Name2-(4-methoxyphenyl)acetic acid
Traditional Name4-methoxyphenylacetic acid
CAS Registry Number104-01-8
SMILES
COC1=CC=C(CC(O)=O)C=C1
InChI Identifier
InChI=1S/C9H10O3/c1-12-8-4-2-7(3-5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)
InChI KeyNRPFNQUDKRYCNX-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Berberis koreanaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Gloeophyllum odoratumLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Sargentodoxa cuneataLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point87 °CNot Available
Boiling Point138.00 to 140.00 °C. @ 3.00 mm HgThe Good Scents Company Information System
Water Solubility18 mg/mLNot Available
LogP1.42Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility1.43 g/LALOGPS
logP1.73ALOGPS
logP1.45ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)4.12ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.83 m³·mol⁻¹ChemAxon
Polarizability16.86 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002072
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022832
KNApSAcK IDNot Available
Chemspider ID7406
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6472
PubChem Compound7690
PDB IDNot Available
ChEBI ID55501
Good Scents IDrw1204611
References
General References
  1. Mathieu P, Charvet JC, Chazot G, Trouillas P: [4-O-Methylated catecholamines: 3-hydroxy, 4-methoxyphenylacetic acid (homo-isovanillic acid, iso-HVA) in biological media: urine, cerebrospinal fluid, and brain tissue]. Clin Chim Acta. 1972 Oct;41:5-17. doi: 10.1016/0009-8981(72)90490-1. [PubMed:4645252 ]
  2. Oakley SE, Seakins JW: The metabolism of homoanisic acid in man and guinea pigs. Biochem J. 1971 Jan;121(1):17P-18P. doi: 10.1042/bj1210017pb. [PubMed:5116533 ]