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Showing metabocard for 1H-Pyrrole-2-carboxaldehyde (HMDB0036057)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:07:34 UTC
Update Date2023-02-21 17:25:01 UTC
HMDB IDHMDB0036057
Secondary Accession Numbers
  • HMDB36057
Metabolite Identification
Common Name1H-Pyrrole-2-carboxaldehyde
Description1H-Pyrrole-2-carboxaldehyde, also known as alpha-pyrrolaldehyde or 2-carboxaldehyde-1H-pyrrole, belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring. 1H-Pyrrole-2-carboxaldehyde is an ethereal tasting compound. 1H-Pyrrole-2-carboxaldehyde is found, on average, in the highest concentration within beer. 1H-Pyrrole-2-carboxaldehyde has also been detected, but not quantified in, several different foods, such as teas (Camellia sinensis), blackberries (Rubus), asparagus (Asparagus officinalis), pulses, and evergreen blackberries (Rubus laciniatus). This could make 1H-pyrrole-2-carboxaldehyde a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 1H-Pyrrole-2-carboxaldehyde.
Structure
Data?1677000301
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0036057 (1H-Pyrrole-2-carboxaldehyde)


  Mrv0541 05061308522D          

  7  7  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  5  2  2  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
M  END
Download

3D MOL for HMDB0036057 (1H-Pyrrole-2-carboxaldehyde)

HMDB0036057
     RDKit          3D
1H-Pyrrole-2-carboxaldehyde
 12 12  0  0  0  0  0  0  0  0999 V2000
    2.8282   -0.5097   -0.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0248    0.4349    0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5857    0.1267    0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0167   -1.0943   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3871   -0.9554   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5893    0.3861    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4040    1.0160    0.2072 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3549    1.4433    0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5504   -2.0131   -0.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1365   -1.7274   -0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5694    0.8459    0.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2410    2.0469    0.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  3  1  0
  2  8  1  0
  4  9  1  0
  5 10  1  0
  6 11  1  0
  7 12  1  0
M  END
Download

3D SDF for HMDB0036057 (1H-Pyrrole-2-carboxaldehyde)


  Mrv0541 05061308522D          

  7  7  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  5  2  2  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036057

> <DATABASE_NAME>
hmdb

> <SMILES>
O=CC1=CC=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C5H5NO/c7-4-5-2-1-3-6-5/h1-4,6H

> <INCHI_KEY>
ZSKGQVFRTSEPJT-UHFFFAOYSA-N

> <FORMULA>
C5H5NO

> <MOLECULAR_WEIGHT>
95.0993

> <EXACT_MASS>
95.037113787

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
9.304001912919093

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-pyrrole-2-carbaldehyde

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
0.6856333969999998

> <ALOGPS_LOGS>
0.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.20772906883365

> <JCHEM_PKA_STRONGEST_BASIC>
-7.4927144250304885

> <JCHEM_POLAR_SURFACE_AREA>
32.86

> <JCHEM_REFRACTIVITY>
27.2783

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.04e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyrrole-2-carboxaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0036057 (1H-Pyrrole-2-carboxaldehyde)

HMDB0036057
     RDKit          3D
1H-Pyrrole-2-carboxaldehyde
 12 12  0  0  0  0  0  0  0  0999 V2000
    2.8282   -0.5097   -0.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0248    0.4349    0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5857    0.1267    0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0167   -1.0943   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3871   -0.9554   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5893    0.3861    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4040    1.0160    0.2072 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3549    1.4433    0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5504   -2.0131   -0.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1365   -1.7274   -0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5694    0.8459    0.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2410    2.0469    0.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  3  1  0
  2  8  1  0
  4  9  1  0
  5 10  1  0
  6 11  1  0
  7 12  1  0
M  END
Download

PDB for HMDB0036057 (1H-Pyrrole-2-carboxaldehyde)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    5    7                                                       
CONECT    5    2    4    6                                                  
CONECT    6    3    5                                                       
CONECT    7    4                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
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3D PDB for HMDB0036057 (1H-Pyrrole-2-carboxaldehyde)

COMPND    HMDB0036057
HETATM    1  O1  UNL     1       2.828  -0.510  -0.179  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.025   0.435   0.025  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.586   0.127   0.008  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.017  -1.094  -0.210  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.387  -0.955  -0.144  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.589   0.386   0.120  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.404   1.016   0.207  1.00  0.00           N  
HETATM    8  H1  UNL     1       2.355   1.443   0.210  1.00  0.00           H  
HETATM    9  H2  UNL     1       0.550  -2.013  -0.403  1.00  0.00           H  
HETATM   10  H3  UNL     1      -2.137  -1.727  -0.271  1.00  0.00           H  
HETATM   11  H4  UNL     1      -2.569   0.846   0.237  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.241   2.047   0.401  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    8
CONECT    3    4    4    7
CONECT    4    5    9
CONECT    5    6    6   10
CONECT    6    7   11
CONECT    7   12
END
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SMILES for HMDB0036057 (1H-Pyrrole-2-carboxaldehyde)

O=CC1=CC=CN1
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INCHI for HMDB0036057 (1H-Pyrrole-2-carboxaldehyde)

InChI=1S/C5H5NO/c7-4-5-2-1-3-6-5/h1-4,6H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1(H)-Pyrrole carboxaldehydeChEBI
1-Pyrrole-2-carboxaldehydeChEBI
1H-Pyrrole-2-carboxyaldehydeChEBI
2-Carboxaldehyde-1H-pyrroleChEBI
2-FormylpyrroleChEBI
2-PyrrolaldehydeChEBI
2-PyrrolcarbaldehydeChEBI
2-Pyrrole aldehydeChEBI
2-PyrrolecarbaldehydeChEBI
2-PyrrolecarboxaldehydeChEBI
2-PyrrolylcarboxaldehydeChEBI
alpha-PyrrolaldehydeChEBI
Pyrrol-2-carboxaldehydeChEBI
Pyrrole-2-aldehydeChEBI
Pyrrole-2-carbaldehydeChEBI
a-PyrrolaldehydeGenerator
Α-pyrrolaldehydeGenerator
1( H)-Pyrrole carboxaldehydeHMDB
1H-Pyrrole-2-carbaldehydeHMDB
Pyrrole-2-carboxaldehydeHMDB, MeSH
Pyrrole-2-carboxaldehyde (8ci)HMDB
1H-Pyrrole-2-carboxaldehydeChEBI
Chemical FormulaC5H5NO
Average Molecular Weight95.0993
Monoisotopic Molecular Weight95.037113787
IUPAC Name1H-pyrrole-2-carbaldehyde
Traditional Namepyrrole-2-carboxaldehyde
CAS Registry Number1003-29-8
SMILES
O=CC1=CC=CN1
InChI Identifier
InChI=1S/C5H5NO/c7-4-5-2-1-3-6-5/h1-4,6H
InChI KeyZSKGQVFRTSEPJT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl-aldehydes
Alternative Parents
Substituents
  • Aryl-aldehyde
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point50 - 51 °CNot Available
Boiling Point216.00 to 218.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility34300 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.64Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility304 g/LALOGPS
logP0.52ALOGPS
logP0.69ChemAxon
logS0.5ALOGPS
pKa (Strongest Acidic)14.21ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.86 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.28 m³·mol⁻¹ChemAxon
Polarizability9.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+115.02531661259
DarkChem[M-H]-110.46831661259
DeepCCS[M+H]+119.19330932474
DeepCCS[M-H]-117.16430932474
DeepCCS[M-2H]-153.06230932474
DeepCCS[M+Na]+127.60430932474
AllCCS[M+H]+119.432859911
AllCCS[M+H-H2O]+114.332859911
AllCCS[M+NH4]+124.232859911
AllCCS[M+Na]+125.632859911
AllCCS[M-H]-116.432859911
AllCCS[M+Na-2H]-119.432859911
AllCCS[M+HCOO]-122.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1H-Pyrrole-2-carboxaldehydeO=CC1=CC=CN11924.1Standard polar33892256
1H-Pyrrole-2-carboxaldehydeO=CC1=CC=CN1953.5Standard non polar33892256
1H-Pyrrole-2-carboxaldehydeO=CC1=CC=CN11016.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1H-Pyrrole-2-carboxaldehyde,1TMS,isomer #1C[Si](C)(C)N1C=CC=C1C=O1165.3Semi standard non polar33892256
1H-Pyrrole-2-carboxaldehyde,1TMS,isomer #1C[Si](C)(C)N1C=CC=C1C=O1302.6Standard non polar33892256
1H-Pyrrole-2-carboxaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=CC=C1C=O1432.8Semi standard non polar33892256
1H-Pyrrole-2-carboxaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=CC=C1C=O1498.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1H-Pyrrole-2-carboxaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9000000000-5f2e8ffab711dbfed89a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1H-Pyrrole-2-carboxaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1H-Pyrrole-2-carboxaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Pyrrole-2-carboxaldehyde 10V, Positive-QTOFsplash10-0002-9000000000-8b5ca5b4e63626d5b0c92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Pyrrole-2-carboxaldehyde 20V, Positive-QTOFsplash10-00kb-9000000000-b56e5fbfb2163d229a212016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Pyrrole-2-carboxaldehyde 40V, Positive-QTOFsplash10-014i-9000000000-b40daf136319bc0639bf2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Pyrrole-2-carboxaldehyde 10V, Negative-QTOFsplash10-0006-9000000000-146097e8a420f5d9d1282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Pyrrole-2-carboxaldehyde 20V, Negative-QTOFsplash10-0006-9000000000-fa12013eb915691d9b662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Pyrrole-2-carboxaldehyde 40V, Negative-QTOFsplash10-0006-9000000000-3d161254a77dfc3829c22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Pyrrole-2-carboxaldehyde 10V, Negative-QTOFsplash10-014l-9000000000-5ffd41c3abfd6adaa9992021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Pyrrole-2-carboxaldehyde 20V, Negative-QTOFsplash10-014i-9000000000-3f070060c5785123e18c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Pyrrole-2-carboxaldehyde 40V, Negative-QTOFsplash10-014i-9000000000-80bc8672cf39bfa9cc282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Pyrrole-2-carboxaldehyde 10V, Positive-QTOFsplash10-00kb-9000000000-2f76e9a1377d985ef7e72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Pyrrole-2-carboxaldehyde 20V, Positive-QTOFsplash10-014i-9000000000-2419053da3a96c61562e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1H-Pyrrole-2-carboxaldehyde 40V, Positive-QTOFsplash10-0f79-9000000000-6d571bd229680b1b1ab62021-09-23Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB014879
KNApSAcK IDC00052636
Chemspider ID13254
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13854
PDB IDNot Available
ChEBI ID59978
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1279691
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .