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Showing metabocard for Pyrrolidine (HMDB0031641)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:35 UTC
Update Date2023-02-21 17:21:05 UTC
HMDB IDHMDB0031641
Secondary Accession Numbers
  • HMDB31641
Metabolite Identification
Common NamePyrrolidine
DescriptionPyrrolidine is found in alcoholic beverages. Pyrrolidine is widely distributed in foodstuffs in trace amts., presumably as bacterial decarboxylation produced of proline. Pyrrolidine is present in bread, milk, cheese, carrots, celery stalks, beer, spirits, coffee, caviar and fatty fish. Pyrrolidine is a flavouring agent.Pyrrolidine is a clear liquid with an unpleasant odor that is ammoniacal, fishy, shellfish-like and seaweed-like. Pyrrolidine is found naturally in the leaves of tobacco and carrot. The pyrrolidine ring structure is present in numerous natural alkaloids such as nicotine and hygrine. It is found in many pharmaceutical drugs such as procyclidine and bepridil. It also forms the basis for the racetam compounds (e.g. piracetam, aniracetam). Pyrrolidine is a pyrrolidine ring is the central structure of the amino acids proline and hydroxyproline. (Wikipedia ) Pyrrolidine has been found to be a metabolite in Xenorhabdus (PMID: 19598185 ).
Structure
Data?1677000065
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031641 (Pyrrolidine)


  Mrv1652303202019012D          

  5  5  0  0  0  0            999 V2000
    1.5202    0.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6952    0.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4403    1.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1077    1.5066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7752    1.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
M  END
Download

3D MOL for HMDB0031641 (Pyrrolidine)

HMDB0031641
     RDKit          3D
Pyrrolidine
 14 14  0  0  0  0  0  0  0  0999 V2000
    0.3414   -1.1076   -0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0232   -0.5399    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8404    0.9184   -0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5113    1.2373    0.0574 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.0216    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4953   -1.3137   -1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4730   -2.0267    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419   -1.0272   -0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1194   -0.5782    1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5895    1.5562    0.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9673    1.0878   -1.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5969    1.8980    0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1743    0.0766   -0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5420   -0.2026    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  2  9  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
M  END
Download

3D SDF for HMDB0031641 (Pyrrolidine)


  Mrv1652303202019012D          

  5  5  0  0  0  0            999 V2000
    1.5202    0.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6952    0.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4403    1.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1077    1.5066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7752    1.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031641

> <DATABASE_NAME>
hmdb

> <SMILES>
C1CCNC1

> <INCHI_IDENTIFIER>
InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2

> <INCHI_KEY>
RWRDLPDLKQPQOW-UHFFFAOYSA-N

> <FORMULA>
C4H9N

> <MOLECULAR_WEIGHT>
71.121

> <EXACT_MASS>
71.073499293

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
8.57813565899375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyrrolidine

> <ALOGPS_LOGP>
0.16

> <JCHEM_LOGP>
0.212918995

> <ALOGPS_LOGS>
0.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
11.402039831164966

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
22.2344

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.91e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyrrolidine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0031641 (Pyrrolidine)

HMDB0031641
     RDKit          3D
Pyrrolidine
 14 14  0  0  0  0  0  0  0  0999 V2000
    0.3414   -1.1076   -0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0232   -0.5399    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8404    0.9184   -0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5113    1.2373    0.0574 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.0216    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4953   -1.3137   -1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4730   -2.0267    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419   -1.0272   -0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1194   -0.5782    1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5895    1.5562    0.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9673    1.0878   -1.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5969    1.8980    0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1743    0.0766   -0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5420   -0.2026    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  2  9  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
M  END
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PDB for HMDB0031641 (Pyrrolidine)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       2.838   0.443   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.298   0.443   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.822   1.907   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.068   2.812   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.314   1.907   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1                                                       
MASTER        0    0    0    0    0    0    0    0    5    0   10    0
END
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3D PDB for HMDB0031641 (Pyrrolidine)

COMPND    HMDB0031641
HETATM    1  C1  UNL     1       0.341  -1.108  -0.261  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.023  -0.540   0.058  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.840   0.918  -0.299  1.00  0.00           C  
HETATM    4  N1  UNL     1       0.511   1.237   0.057  1.00  0.00           N  
HETATM    5  C4  UNL     1       1.247   0.022   0.203  1.00  0.00           C  
HETATM    6  H1  UNL     1       0.495  -1.314  -1.320  1.00  0.00           H  
HETATM    7  H2  UNL     1       0.473  -2.027   0.324  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.842  -1.027  -0.471  1.00  0.00           H  
HETATM    9  H4  UNL     1      -1.119  -0.578   1.174  1.00  0.00           H  
HETATM   10  H5  UNL     1      -1.589   1.556   0.235  1.00  0.00           H  
HETATM   11  H6  UNL     1      -0.967   1.088  -1.396  1.00  0.00           H  
HETATM   12  H7  UNL     1       0.597   1.898   0.845  1.00  0.00           H  
HETATM   13  H8  UNL     1       2.174   0.077  -0.405  1.00  0.00           H  
HETATM   14  H9  UNL     1       1.542  -0.203   1.256  1.00  0.00           H  
CONECT    1    2    5    6    7
CONECT    2    3    8    9
CONECT    3    4   10   11
CONECT    4    5   12
CONECT    5   13   14
END
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SMILES for HMDB0031641 (Pyrrolidine)

C1CCNC1
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INCHI for HMDB0031641 (Pyrrolidine)

InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1-AzacyclopentaneChEBI
AzacyclopentaneChEBI
AzolidineChEBI
ButylenimineChEBI
PerhydropyrroleChEBI
ProlamineChEBI
TetrahydropyrroleChEBI
TetramethylenimineChEBI
FEMA 3523HMDB
Pyrrolidine hydrochlorideHMDB
Chemical FormulaC4H9N
Average Molecular Weight71.121
Monoisotopic Molecular Weight71.073499293
IUPAC Namepyrrolidine
Traditional Namepyrrolidine
CAS Registry Number123-75-1
SMILES
C1CCNC1
InChI Identifier
InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
InChI KeyRWRDLPDLKQPQOW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassNot Available
Direct ParentPyrrolidines
Alternative Parents
Substituents
  • Pyrrolidine
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-63 °CNot Available
Boiling Point87.00 to 88.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000000 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP0.460The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility291 g/LALOGPS
logP0.16ALOGPS
logP0.21ChemAxon
logS0.61ALOGPS
pKa (Strongest Basic)11.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.23 m³·mol⁻¹ChemAxon
Polarizability8.58 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]+111.64731661259
DarkChem[M-H]-105.6831661259
DeepCCS[M+H]+122.45930932474
DeepCCS[M-H]-120.48430932474
DeepCCS[M-2H]-156.25430932474
DeepCCS[M+Na]+130.66130932474
AllCCS[M+H]+113.232859911
AllCCS[M+H-H2O]+107.932859911
AllCCS[M+NH4]+118.332859911
AllCCS[M+Na]+119.732859911
AllCCS[M-H]-120.832859911
AllCCS[M+Na-2H]-125.432859911
AllCCS[M+HCOO]-130.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PyrrolidineC1CCNC11035.1Standard polar33892256
PyrrolidineC1CCNC1674.4Standard non polar33892256
PyrrolidineC1CCNC1674.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pyrrolidine,1TMS,isomer #1C[Si](C)(C)N1CCCC1878.2Semi standard non polar33892256
Pyrrolidine,1TMS,isomer #1C[Si](C)(C)N1CCCC1951.0Standard non polar33892256
Pyrrolidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCCC11130.7Semi standard non polar33892256
Pyrrolidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCCC11168.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pyrrolidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-9000000000-0159c6ac6a2707c890fb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrrolidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrolidine QTOF 10V, positive-QTOFsplash10-00di-9000000000-b47872c22f260420fe4f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrolidine QTOF 15V, positive-QTOFsplash10-00di-9000000000-6703dc4e588e5b605dd22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrolidine QTOF 17V, positive-QTOFsplash10-00di-9000000000-1200244cbd952b0ff0e42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrolidine QTOF 20V, positive-QTOFsplash10-00di-9000000000-3e962c9c87606d1d4fb42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrolidine QTOF 23V, positive-QTOFsplash10-00di-9000000000-7aa207733141b620c6122020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrolidine QTOF 25V, positive-QTOFsplash10-00di-9000000000-cc43ed19d9780ad479072020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrolidine QTOF 27V, positive-QTOFsplash10-00di-9000000000-6d604c6cb07d4b319fa72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrolidine QTOF 30V, positive-QTOFsplash10-00di-9000000000-201fcadb62ee720ec9e32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrolidine QTOF 33V, positive-QTOFsplash10-00dl-9000000000-2efe28538fd9387c11052020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrolidine QTOF 35V, positive-QTOFsplash10-006x-9000000000-fe10abd985612deaee7b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrolidine QTOF 40V, positive-QTOFsplash10-0006-9000000000-cc3a8f0b0eb43d64f2a42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrolidine QTOF 45V, positive-QTOFsplash10-0006-9000000000-e5549871379e536221f32020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrolidine 10V, Positive-QTOFsplash10-00di-9000000000-50250fbde117c345f1552016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrolidine 20V, Positive-QTOFsplash10-00di-9000000000-9a9bb68d33a6b556f7532016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrolidine 40V, Positive-QTOFsplash10-0ab9-9000000000-4840aa812595ffd33b172016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrolidine 10V, Negative-QTOFsplash10-00di-9000000000-dc4555408f7b7029c1ec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrolidine 20V, Negative-QTOFsplash10-00di-9000000000-d7dcf188af1b7f8ac9b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrolidine 40V, Negative-QTOFsplash10-0udl-9000000000-0e5b8e3fe42b29779d062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrolidine 10V, Positive-QTOFsplash10-00di-9000000000-ae345dd26f637d1e1b0e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrolidine 20V, Positive-QTOFsplash10-00di-9000000000-98df592a95307772b96d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrolidine 40V, Positive-QTOFsplash10-0a4i-9000000000-f474b8622abebc0362222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrolidine 10V, Negative-QTOFsplash10-00di-9000000000-0c177e779175985339232021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrolidine 20V, Negative-QTOFsplash10-00kf-9000000000-12476e11ce42857385902021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrolidine 40V, Negative-QTOFsplash10-00di-9000000000-554f1bc121aa553aac432021-09-23Wishart 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 IDFDB007401
KNApSAcK IDC00002037
Chemspider ID29008
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPyrrolidine
METLIN IDNot Available
PubChem Compound31268
PDB IDNot Available
ChEBI ID33135
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1009391
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Fleming J, Ghose A, Harrison PR: Molecular mechanisms of cancer prevention by selenium compounds. Nutr Cancer. 2001;40(1):42-9. [PubMed:11799922 ]
  2. Hong TM, Teng LJ, Shun CT, Peng MC, Tsai JC: Induced interleukin-8 expression in gliomas by tumor-associated macrophages. J Neurooncol. 2009 Jul;93(3):289-301. doi: 10.1007/s11060-008-9786-z. Epub 2009 Jan 21. [PubMed:19156359 ]
  3. Li X, Li Y, Xu W: Design, synthesis, and evaluation of novel galloyl pyrrolidine derivatives as potential anti-tumor agents. Bioorg Med Chem. 2006 Mar 1;14(5):1287-93. Epub 2005 Oct 4. [PubMed:16213145 ]
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