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Showing NP-Card for Indole-3-carbinol (NP0000064)

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Record Information
Version1.0
Created at2007-01-22 13:00:01 UTC
Updated at2024-04-19 10:00:03 UTC
NP-MRD IDNP0000064
Secondary Accession NumbersNone
Natural Product Identification
Common NameIndole-3-carbinol
DescriptionIndole-3-carbinol, also known as 3-indolylcarbinol or 1H-indole-3-methanol, belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Indole-3-carbinol is a dietary indole present in cruciferous vegetables that has been shown to influence estradiol metabolism in humans and may provide a new chemopreventive approach to estrogen-dependent diseases (PMID:2342128 ). Indole-3-carbinol is produced by members of the family Cruciferae, particularly members of the genus Brassica (e.G. Cabbage, radishes, cauliflower, broccoli, Brussels sprouts, and daikon). Indole-3-carbinol is metabolized into a number of products, including the dimeric 3,3'-diindolylmethane. Both 3,3'-diindolylmethane and indole-3-carbinol are thought to have biological effects. Indole-3-carbinol is a natural chemopreventive compound. It has multiple anticarcinogenic and antitumorigenic properties; it can suppress the proliferation of certain cancer cells, including breast cancer, prostate cancer, endometrial cancer, colon cancer, and leukemic cells (PMID:16634522 , 16082211 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000064 (Indole-3-carbinol)


  Mrv1652301272022212D          

 11 12  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0000064 (Indole-3-carbinol)

HMDB0005785
     RDKit          3D
Indole-3-carbinol
 20 21  0  0  0  0  0  0  0  0999 V2000
    3.4899    0.0235    0.4371 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548   -0.6788    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776    0.1991    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1712    1.5017    0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1136    1.8969    0.6084 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991    0.9049    0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2705    0.7817   -0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8351   -0.3809   -0.5525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317   -1.4733   -0.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724   -1.3703   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1258   -0.1997   -0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7666   -0.3401    1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2173   -1.6294    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785   -0.8513   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0318    2.1015    0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4391    2.8488    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8603    1.6593    0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9056   -0.4144   -0.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5099   -2.3682   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245   -2.2110   -0.8150 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  3  1  0
 11  6  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
M  END
Download

3D SDF for NP0000064 (Indole-3-carbinol)


  Mrv1652301272022212D          

 11 12  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000064

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2

> <INCHI_KEY>
IVYPNXXAYMYVSP-UHFFFAOYSA-N

> <FORMULA>
C9H9NO

> <MOLECULAR_WEIGHT>
147.1739

> <EXACT_MASS>
147.068413915

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.870666832234898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1H-indol-3-yl)methanol

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
1.3046580416666664

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.34307132623539

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.0959887942937

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7165363605434028

> <JCHEM_POLAR_SURFACE_AREA>
36.019999999999996

> <JCHEM_REFRACTIVITY>
43.9604

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.75e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indole-3-carbinol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000064 (Indole-3-carbinol)

HMDB0005785
     RDKit          3D
Indole-3-carbinol
 20 21  0  0  0  0  0  0  0  0999 V2000
    3.4899    0.0235    0.4371 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548   -0.6788    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776    0.1991    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1712    1.5017    0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1136    1.8969    0.6084 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991    0.9049    0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2705    0.7817   -0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8351   -0.3809   -0.5525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317   -1.4733   -0.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724   -1.3703   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1258   -0.1997   -0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7666   -0.3401    1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2173   -1.6294    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785   -0.8513   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0318    2.1015    0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4391    2.8488    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8603    1.6593    0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9056   -0.4144   -0.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5099   -2.3682   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245   -2.2110   -0.8150 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  3  1  0
 11  6  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
M  END
Download

PDB for NP0000064 (Indole-3-carbinol)

HEADER    PROTEIN                                 27-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-JAN-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8667.8208665.395   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for NP0000064 (Indole-3-carbinol)

COMPND    HMDB0005785
HETATM    1  O1  UNL     1       3.490   0.024   0.437  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.355  -0.679   0.039  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.178   0.199   0.188  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.171   1.502   0.643  1.00  0.00           C  
HETATM    5  N1  UNL     1      -0.114   1.897   0.608  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.899   0.905   0.156  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.271   0.782  -0.071  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.835  -0.381  -0.552  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.032  -1.473  -0.826  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.672  -1.370  -0.608  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.126  -0.200  -0.126  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.767  -0.340   1.313  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.217  -1.629   0.571  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.479  -0.851  -1.069  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.032   2.101   0.968  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.439   2.849   0.897  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.860   1.659   0.157  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.906  -0.414  -0.708  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.510  -2.368  -1.203  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.025  -2.211  -0.815  1.00  0.00           H  
CONECT    1    2   12
CONECT    2    3   13   14
CONECT    3    4    4   11
CONECT    4    5   15
CONECT    5    6   16
CONECT    6    7    7   11
CONECT    7    8   17
CONECT    8    9    9   18
CONECT    9   10   19
CONECT   10   11   11   20
END
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SMILES for NP0000064 (Indole-3-carbinol)

OCC1=CNC2=C1C=CC=C2
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INCHI for NP0000064 (Indole-3-carbinol)

InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
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View in JSmol
Synonyms
ValueSource
3-HydroxymethylindoleChEBI
3-IndolylcarbinolChEBI
1H-indol-3-YlmethanolHMDB
1H-Indole-3-methanolHMDB
3-(Hydroxymethyl)indoleHMDB
3-IndolecarbinolHMDB
3-IndolylmethanolHMDB
IndinolHMDB
Indole-3-methanolHMDB
I3c CPDHMDB
(1H-indol-3-yl)MethanolHMDB
Indole-3-carbinolChEBI
Chemical FormulaC9H9NO
Average Mass147.1739 Da
Monoisotopic Mass147.06841 Da
IUPAC Name(1H-indol-3-yl)methanol
Traditional Nameindole-3-carbinol
CAS Registry Number700-06-1
SMILES
OCC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
InChI KeyIVYPNXXAYMYVSP-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-11-07View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-11-07View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-11-07View Spectrum
1D NMR[13C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-11-07View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-11-07View Spectrum
1D NMR1H NMR Spectrum (1D, 600.133705802 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201.216488466 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View 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
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)Varshavi.d262021-07-25View Spectrum
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaLOTUS Database
Brassica oleraceaLOTUS Database
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. italicaFooDB
Brassica sp.KNApSAcK Database
Leptosphaeria maculansLOTUS Database
Pinus sylvestrisLOTUS Database
Raphanus sativusKNApSAcK Database
Species Where Detected
Species NameSourceReference
Haliclona oculataKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Azacycle
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point90 °CNot Available
Boiling Point360.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility8339 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.366 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility3.75 g/LALOGPS
logP1.66ALOGPS
logP1.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)15.1ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area36.02 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.96 m³·mol⁻¹ChemAxon
Polarizability15.87 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0005785
DrugBank IDDB12881
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000939
KNApSAcK IDC00041598
Chemspider ID3581
KEGG Compound IDNot Available
BioCyc IDCPDQT-428
BiGG IDNot Available
Wikipedia LinkIndole-3-carbinol
METLIN IDNot Available
PubChem Compound3712
PDB IDNot Available
ChEBI ID24814
Good Scents IDrw1448011
References
General References
  1. Michnovicz JJ, Bradlow HL: Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J Natl Cancer Inst. 1990 Jun 6;82(11):947-9. [PubMed:2342128 ]
  2. Aggarwal BB, Ichikawa H: Molecular targets and anticancer potential of indole-3-carbinol and its derivatives. Cell Cycle. 2005 Sep;4(9):1201-15. Epub 2005 Sep 6. [PubMed:16082211 ]
  3. Rogan EG: The natural chemopreventive compound indole-3-carbinol: state of the science. In Vivo. 2006 Mar-Apr;20(2):221-8. [PubMed:16634522 ]
  4. Mazzei M, Miele M, Nieddu E, Barbieri F, Bruzzo C, Alama A: Unsymmetrical methylene derivatives of indoles as antiproliferative agents. Eur J Med Chem. 2001 Nov-Dec;36(11-12):915-23. [PubMed:11755234 ]
  5. Nguyen HH, Aronchik I, Brar GA, Nguyen DH, Bjeldanes LF, Firestone GL: The dietary phytochemical indole-3-carbinol is a natural elastase enzymatic inhibitor that disrupts cyclin E protein processing. Proc Natl Acad Sci U S A. 2008 Dec 16;105(50):19750-5. doi: 10.1073/pnas.0806581105. Epub 2008 Dec 8. [PubMed:19064917 ]