Np mrd loader

Showing NP-Card for Indole-3-carboxylic acid (NP0001160)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2006-05-22 15:12:50 UTC
Updated at2021-10-07 20:40:59 UTC
NP-MRD IDNP0001160
Secondary Accession NumbersNone
Natural Product Identification
Common NameIndole-3-carboxylic acid
DescriptionIndole-3-carboxylic acid, also known as 3-carboxyindole or 3-indolecarboxylate, belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. Naphthylmethylindoles: Any compound containing a 1H-indol-3-yl-(1-naphthyl)methane structure with substitution at the nitrogen atom of the indole ring by an alkyl, haloalkyl, alkenyl, cycloalkylmethyl, cycloalkylethyl, 1-(N-methyl-2-piperidinyl)methyl, or 2-(4-morpholinyl)ethyl group whether or not further substituted in the indole ring to any extent and whether or not substituted in the naphthyl ring to any extent. One example given is JWH-250. Outside of the human body, indole-3-carboxylic acid has been detected, but not quantified in several different foods, such as brassicas, broccoli, pulses, common beets, and barley. This could make indole-3-carboxylic acid a potential biomarker for the consumption of these foods. Notice the pentyl group substituted onto the nitrogen atom of the indole ring. Note that this definition encompasses only those compounds that have OH groups attached to both the phenyl and the cyclohexyl rings, and so does not include compounds such as O-1871 which lacks the cyclohexyl OH group, or compounds such as JWH-337 or JWH-344 which lack the phenolic OH group.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001160 (Indole-3-carboxylic acid)


  Mrv1652305271900162D          

 12 13  0  0  0  0            999 V2000
   26.4963  -17.4113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1381  -16.9674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4328  -19.6935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6890  -17.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6522  -19.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4328  -18.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6522  -18.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9143  -19.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9376  -19.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9376  -18.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2231  -19.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2231  -18.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  4  2  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  7 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
Download

3D MOL for NP0001160 (Indole-3-carboxylic acid)

HMDB0003320
     RDKit          3D
Indole-3-carboxylic acid
 19 20  0  0  0  0  0  0  0  0999 V2000
    2.0963   -2.0904    0.9508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3562   -0.9342    0.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6852   -0.5492    0.4948 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3239    0.0066    0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4836    1.3028   -0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746    1.8284   -0.5977 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6982    0.9397   -0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0739    0.9796   -0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7807   -0.1451   -0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1545   -1.2896    0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -1.3084    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0398   -0.2023    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862   -0.4887   -0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674    1.7659   -0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0836    2.7847   -0.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136    1.8929   -0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8497   -0.1350   -0.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7236   -2.1710    0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2384   -2.1868    0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  4  1  0
 12  7  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0001160 (Indole-3-carboxylic acid)


  Mrv1652305271900162D          

 12 13  0  0  0  0            999 V2000
   26.4963  -17.4113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1381  -16.9674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4328  -19.6935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6890  -17.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6522  -19.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4328  -18.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6522  -18.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9143  -19.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9376  -19.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9376  -18.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2231  -19.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2231  -18.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  4  2  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  7 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001160

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO2/c11-9(12)7-5-10-8-4-2-1-3-6(7)8/h1-5,10H,(H,11,12)

> <INCHI_KEY>
KMAKOBLIOCQGJP-UHFFFAOYSA-N

> <FORMULA>
C9H7NO2

> <MOLECULAR_WEIGHT>
161.1574

> <EXACT_MASS>
161.047678473

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.956151131125452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-indole-3-carboxylic acid

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.729590717

> <ALOGPS_LOGS>
-1.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.853175363146892

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5201821132292035

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
44.4007

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indole - 3 carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001160 (Indole-3-carboxylic acid)

HMDB0003320
     RDKit          3D
Indole-3-carboxylic acid
 19 20  0  0  0  0  0  0  0  0999 V2000
    2.0963   -2.0904    0.9508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3562   -0.9342    0.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6852   -0.5492    0.4948 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3239    0.0066    0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4836    1.3028   -0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746    1.8284   -0.5977 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6982    0.9397   -0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0739    0.9796   -0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7807   -0.1451   -0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1545   -1.2896    0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -1.3084    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0398   -0.2023    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862   -0.4887   -0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674    1.7659   -0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0836    2.7847   -0.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136    1.8929   -0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8497   -0.1350   -0.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7236   -2.1710    0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2384   -2.1868    0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  4  1  0
 12  7  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

PDB for NP0001160 (Indole-3-carboxylic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      49.460 -32.501   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      46.924 -31.672   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      47.475 -36.761   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      47.953 -32.819   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      46.017 -36.292   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      47.475 -34.282   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      46.017 -34.752   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      48.373 -35.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      44.684 -37.062   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      44.684 -33.982   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      43.350 -36.292   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      43.350 -34.752   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    4                                                            
CONECT    3    5    8                                                       
CONECT    4    1    2    6                                                  
CONECT    5    3    7    9                                                  
CONECT    6    4    7    8                                                  
CONECT    7    5    6   10                                                  
CONECT    8    3    6                                                       
CONECT    9    5   11                                                       
CONECT   10    7   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
Download

3D PDB for NP0001160 (Indole-3-carboxylic acid)

COMPND    HMDB0003320
HETATM    1  O1  UNL     1       2.096  -2.090   0.951  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.356  -0.934   0.547  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.685  -0.549   0.495  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.324   0.007   0.136  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.484   1.303  -0.326  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.275   1.828  -0.598  1.00  0.00           N  
HETATM    7  C4  UNL     1      -0.698   0.940  -0.339  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.074   0.980  -0.444  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.781  -0.145  -0.082  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.155  -1.290   0.377  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.785  -1.308   0.475  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.040  -0.202   0.121  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.086  -0.489  -0.454  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.467   1.766  -0.429  1.00  0.00           H  
HETATM   15  H3  UNL     1       0.084   2.785  -0.959  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.514   1.893  -0.806  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.850  -0.135  -0.156  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.724  -2.171   0.660  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.238  -2.187   0.831  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    5   12
CONECT    5    6   14
CONECT    6    7   15
CONECT    7    8    8   12
CONECT    8    9   16
CONECT    9   10   10   17
CONECT   10   11   18
CONECT   11   12   12   19
END
Download

SMILES for NP0001160 (Indole-3-carboxylic acid)

OC(=O)C1=CNC2=CC=CC=C12
Download

INCHI for NP0001160 (Indole-3-carboxylic acid)

InChI=1S/C9H7NO2/c11-9(12)7-5-10-8-4-2-1-3-6(7)8/h1-5,10H,(H,11,12)
Download
View in JSmol
Synonyms
ValueSource
Indole-3-carboxylateGenerator
3-CarboxyindoleHMDB
1H-Indole-3-carboxylateHMDB
1H-Indole-3-carboxylic acidHMDB
3-Indole carboxylic acidHMDB
3-IndolecarboxylateHMDB
3-Indolecarboxylic acidHMDB
3-IndoleformateHMDB
3-Indoleformic acidHMDB
3-IndolylcarboxylateHMDB
3-Indolylcarboxylic acidHMDB
Indole - 3 carboxylateHMDB
Indole - 3 carboxylic acidHMDB
Indole-3-carboxylicacidHMDB
Indole-b-carboxylateHMDB
Indole-b-carboxylic acidHMDB
Indole-beta-carboxylateHMDB
Indole-β-carboxylateHMDB
Indole-β-carboxylic acidHMDB
Indole-3-carboxylic acidKEGG
Chemical FormulaC9H7NO2
Average Mass161.1574 Da
Monoisotopic Mass161.04768 Da
IUPAC Name1H-indole-3-carboxylic acid
Traditional Nameindole - 3 carboxylic acid
CAS Registry Number771-50-6
SMILES
OC(=O)C1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C9H7NO2/c11-9(12)7-5-10-8-4-2-1-3-6(7)8/h1-5,10H,(H,11,12)
InChI KeyKMAKOBLIOCQGJP-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)Varshavi.d262021-08-17View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Albizia julibrissinLOTUS Database
Arabidopsis thalianaKNApSAcK Database
Aristolochia heterophyllaLOTUS Database
Aster indicusLOTUS Database
Bacillus marinusLOTUS Database
Begonia nantoensisKNApSAcK Database
Beta vulgarisKNApSAcK Database
Botryocladia leptopodaLOTUS Database
Brassica rapaLOTUS Database
Cephalanceropsis gracilis-
Cucumis sativusLOTUS Database
Cucumis sativus L.KNApSAcK Database
Diplodia quercivoraLOTUS Database
Hebeloma hiemaleLOTUS Database
Houttuynia cordataKNApSAcK Database
Isatis tinctoriaLOTUS Database
Jurinea deltoideaLOTUS Database
Nicotiana tabacumKNApSAcK Database
Paraphaeosphaeria minitansLOTUS Database
Penicillium herqueiLOTUS Database
Phyllanthus virgatusLOTUS Database
Pinus sylvestrisKNApSAcK Database
Pisum sativumKNApSAcK Database
Prionitis lanceolataLOTUS Database
Pyrus malusKNApSAcK Database
Streptomyces abikoensisLOTUS Database
Streptomyces tendaeLOTUS Database
Taraxacum formosanumKNApSAcK Database
Taraxacum mongolicumLOTUS Database
Trewia nudifloraLOTUS Database
Wallemia sebiLOTUS Database
Xanthium strumariumLOTUS Database
Species Where Detected
Species NameSourceReference
Haliclona oculataKNApSAcK Database
Undaria pinnatifidaKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolecarboxylic acids and derivatives
Direct ParentIndolecarboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolecarboxylic acid derivative
  • Indole
  • Pyrrole-3-carboxylic acid
  • Pyrrole-3-carboxylic acid or derivatives
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Vinylogous amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point206.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1351 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.99Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility2.42 g/LALOGPS
logP1.79ALOGPS
logP1.73ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.52ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.4 m³·mol⁻¹ChemAxon
Polarizability15.96 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003320
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000935
KNApSAcK IDC00000113
Chemspider ID63063
KEGG Compound IDC19837
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkStructural scheduling of synthetic cannabinoids
METLIN ID3795
PubChem Compound69867
PDB IDNot Available
ChEBI ID24809
Good Scents IDrw1251531
References
General References
  1. Davis PJ, Gustafson ME, Rosazza JP: Formation of indole-3-carboxylic acid by Chromobacterium violaceum. J Bacteriol. 1976 Apr;126(1):544-6. doi: 10.1128/jb.126.1.544-546.1976. [PubMed:1262308 ]
  2. Lacan G, Magnus V, Simaga S, Iskric S, Hall PJ: Metabolism of tryptophol in higher and lower plants. Plant Physiol. 1985 Jul;78(3):447-54. doi: 10.1104/pp.78.3.447. [PubMed:16664264 ]