NP-MRD: Showing NP-Card for Physalin L (NP0137019)

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Record Information

Version

2.0

Created at

2022-05-30 16:39:10 UTC

Updated at

2022-05-30 16:39:10 UTC

NP-MRD ID

NP0137019

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Physalin L

Description

Thermophillin, also known as disulfiram or nocceler, belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. Thermophillin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Thermophillin has been detected, but not quantified in, herbs and spices and root vegetables. Physalin L is found in Alkekengi officinarum, Physalis lagascae and Physalis minima. Physalin L was first documented in 1979 (PMID: 385275). This could make thermophillin a potential biomarker for the consumption of these foods (PMID: 21053676) (PMID: 15510281) (PMID: 22409836) (PMID: 15589539).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307442D          

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M  END

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 23 12  1  0  0  0  0
 23 19  1  0  0  0  0
 24  3  1  0  0  0  0
 24 13  1  0  0  0  0
 24 14  1  0  0  0  0
 24 16  1  0  0  0  0
 25  4  1  0  0  0  0
 25 17  1  0  0  0  0
 26  9  1  0  0  0  0
 26 22  1  0  0  0  0
 27 18  1  0  0  0  0
 27 20  1  0  0  0  0
 28 19  1  0  0  0  0
 28 25  1  0  0  0  0
 28 26  1  0  0  0  0
 29 15  1  0  0  0  0
 30 16  2  0  0  0  0
 31 20  2  0  0  0  0
 32 21  2  0  0  0  0
 33 22  2  0  0  0  0
 34 26  1  0  0  0  0
 35 27  1  0  0  0  0
 36 17  1  0  0  0  0
 36 21  1  0  0  0  0
 37 22  1  0  0  0  0
 37 25  1  0  0  0  0
 38 27  1  0  0  0  0
 38 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137019

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(=O)OC2CC1(C)C1C(=O)C3(O)OC11C2(C)OC(=O)C1(O)CCC1C3C(O)C=C2C=CCC(=O)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O10/c1-12-21(32)36-17-11-23(12,2)19-20(31)27(35)18-14(24(3)13(10-15(18)29)6-5-7-16(24)30)8-9-26(34)22(33)37-25(17,4)28(19,26)38-27/h5-6,10,12,14-15,17-19,29,34-35H,7-9,11H2,1-4H3

> <INCHI_KEY>
CUSXWWXXAPEFHY-UHFFFAOYSA-N

> <FORMULA>
C28H32O10

> <MOLECULAR_WEIGHT>
528.5477

> <EXACT_MASS>
528.199547244

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
51.83020594531988

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.3745110146666661

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.72874510062401

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.63509238579701

> <JCHEM_PKA_STRONGEST_BASIC>
-3.081795036922199

> <JCHEM_POLAR_SURFACE_AREA>
156.65999999999997

> <JCHEM_REFRACTIVITY>
128.61499999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

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      -0.332   1.715   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.970   1.019   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.860  -3.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.319  -4.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.324  -0.960   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.280   0.172   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.865  -2.430   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.744  -3.504   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.613  -4.530   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.734   0.967   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.834  -1.612   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.149   0.186   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.777  -0.165   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.816  -1.973   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.231   0.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.362  -2.768   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.234  -2.925   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.772  -0.840   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.887  -1.072   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.422  -2.124   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.475  -0.731   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.367  -5.688   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.381  -0.404   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.318  -1.635   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.596  -3.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.053  -4.345   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.104  -0.747   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.981  -3.059   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.187   1.762   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.903  -4.238   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.289  -3.397   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.892  -0.127   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       4.016  -7.085   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.778  -5.703   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.916   0.850   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -1.222  -2.300   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       1.864  -5.337   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.596  -1.883   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5    6    7                                                       
CONECT    6    5   13                                                       
CONECT    7    5   16                                                       
CONECT    8    9   14                                                       
CONECT    9    8   26                                                       
CONECT   10   13   15                                                       
CONECT   11   17   23                                                       
CONECT   12    1   21   23                                                  
CONECT   13    6   10   24                                                  
CONECT   14    8   18   24                                                  
CONECT   15   10   18   29                                                  
CONECT   16    7   24   30                                                  
CONECT   17   11   25   36                                                  
CONECT   18   14   15   27                                                  
CONECT   19   20   23   28                                                  
CONECT   20   19   27   31                                                  
CONECT   21   12   32   36                                                  
CONECT   22   26   33   37                                                  
CONECT   23    2   11   12   19                                             
CONECT   24    3   13   14   16                                             
CONECT   25    4   17   28   37                                             
CONECT   26    9   22   28   34                                             
CONECT   27   18   20   35   38                                             
CONECT   28   19   25   26   38                                             
CONECT   29   15                                                            
CONECT   30   16                                                            
CONECT   31   20                                                            
CONECT   32   21                                                            
CONECT   33   22                                                            
CONECT   34   26                                                            
CONECT   35   27                                                            
CONECT   36   17   21                                                       
CONECT   37   22   25                                                       
CONECT   38   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Value	Source
1,1',1'',1'''-[dithiobis(carbonothioylnitrilo)]tetraethane	HMDB
1,1'-Dithiobis(N,N-diethylthio)-formamide	HMDB
1,1'-Dithiobis(N,N-diethylthio-formamide	HMDB
1,1'-Dithiobis(N,N-diethylthioformamide)	HMDB
1,1'-Dithiobis[N,N-diethylthioformamide]	HMDB
2,5-Dimethoxy-1,4-benzoquinone	HMDB
Abstenisil	HMDB
Abstensil	HMDB
Abstinil	HMDB
Abstinyl	HMDB
Accel tet	HMDB
Accel tet-R	HMDB
Alcophobin	HMDB
Alk-aubs	HMDB
Allphar brand OF disulfiram	HMDB
Altana pharma brand OF disulfiram	HMDB
Antab use	HMDB
Antabus	HMDB
Antabuse	HMDB
Antadix	HMDB
Antaenyl	HMDB
Antaethan	HMDB
Antaethyl	HMDB
Antaetil	HMDB
Antalcol	HMDB
Antetan	HMDB
Antethyl	HMDB
Antetil	HMDB
Anteyl	HMDB
Anthethyl	HMDB
Anti-ethyl	HMDB
Antiaethan	HMDB
Anticol	HMDB
Antietanol	HMDB
Antiethanol	HMDB
Antietil	HMDB
Antikol	HMDB
Antivitium	HMDB
Antivitium (spain)	HMDB
Artu brand OF disulfiram	HMDB
Aversan	HMDB
Averzan	HMDB
Bis((diethylamino)thioxomethyl) disulfide	HMDB
Bis((diethylamino)thioxomethyl)disulfide	HMDB
Bis((diethylamino)thioxomethyl)disulphide	HMDB
Bis(diethylthiocarbamoyl) disulfide	HMDB
Bis(diethylthiocarbamoyl)disulphide	HMDB
Bis(diethylthiocarbamyl) disulfide	HMDB
Bis(N,N-diethylthiocarbamoyl) disulfide	HMDB
Bis(N,N-diethylthiocarbamoyl)disulphide	HMDB
Bis-(diethylthiocarbamoyl)disulfide	HMDB
Bis[(diethylamino)thioxomethyl] disulfide	HMDB
Bohm brand OF disulfiram	HMDB
Bonibal	HMDB
Contralin	HMDB
Contrapot	HMDB
Cronetal	HMDB
Dicupral	HMDB
Diethylcarbamothioylsulfanyl diethylaminomethanedithioate	HMDB
Disetil	HMDB
Disulfamide	HMDB
Disulfan	HMDB
Disulfide, bis(diethylthiocarbamoyl)	HMDB
Disulfide, tetraethylthiuram	HMDB
Disulfiram	HMDB
Disulfiram (JP15/usp/inn)	HMDB
Disulfiram (tetraethylthiuram disulfide)	HMDB
Disulfirame	HMDB
Disulfiramo	HMDB
Disulfiramum	HMDB
Disulfirm	HMDB
Disulfuram	HMDB
Disulphuram	HMDB
Dumex brand OF disulfiram	HMDB
Dupont fungicide 4472	HMDB
Ekagom dtet	HMDB
Ekagom teds	HMDB
Ekagom tetds	HMDB
Ephorran	HMDB
Espenal	HMDB
Esperal	HMDB
eta Bus	HMDB
Etabus	HMDB
Ethyl thiram	HMDB
Ethyl thiudad	HMDB
Ethyl thiurad	HMDB
Ethyl tuads	HMDB
Ethyl tuex	HMDB
Ethyldithiourame	HMDB
Ethyldithiurame	HMDB
Exhoran	HMDB
Exhorran	HMDB
HOCA	HMDB
Krotenal	HMDB
N,N,N',n'-tetraethylthiuram disulfide	HMDB
N,N,N',n'-tetraethylthiuram disulphide	HMDB
Nocbin	HMDB
Nocceler	HMDB
Nocceler tet	HMDB
Nocceler tet-g	HMDB
Noxal	HMDB
Odyssey brand OF disulfiram	HMDB
Orphan brand OF disulfiram	HMDB
Refusal	HMDB
Ro-sulfiram	HMDB
Ro-sulfram-500 (usa)	HMDB
Robac tet	HMDB
Sanceler tet	HMDB
Sanceler tet-g	HMDB
Sanofi synthelabo brand OF disulfiram	HMDB
Soxinol tet	HMDB
Stopaethyl	HMDB
Stopethyl	HMDB
Stopety	HMDB
Stopetyl	HMDB
TATD	HMDB
Tenurid	HMDB
Tenutex	HMDB
Tet raethylthiuram	HMDB
TETD	HMDB
Tetidis	HMDB
Tetradin	HMDB
Tetradine	HMDB
Tetraethyl-thioperoxydicarbonic diamide	HMDB
Tetraethyl-thioperoxydicarbonic diamide (((H2N)C(S))2S2)	HMDB
Tetraethyl-thioperoxydicarbonic diamide ((H2N)C(S))2S2	HMDB
Tetraethyl-thioperoxydicarbonic diamide ([(H2N)C(S)]2S2)	HMDB
Tetraethyl-thiuram disulfide	HMDB
Tetraethylthioperoxydicarbonic diamide	HMDB
Tetraethylthioperoxydicarbonic diamide, ((H2N)C(S))2S2	HMDB
Tetraethylthioperoxydicarbonothioic diamide	HMDB
Tetraethylthiram disulfide	HMDB
Tetraethylthiram disulphide	HMDB
Tetraethylthiuram	HMDB
Tetraethylthiuram disulfide	HMDB
Tetraethylthiuram disulphide	HMDB
Tetraethylthiuram sulfide	HMDB
Tetraethylthiuran disulfide	HMDB
Tetraethylthiurium disulfide	HMDB
Tetraetil	HMDB
Teturam	HMDB
Teturamin	HMDB
Thermophyllin	HMDB
Thiocid	HMDB
Thiosan	HMDB
Thioscabin	HMDB
Thireranide	HMDB
Thiuram e	HMDB
Thiuranide	HMDB
Tillram	HMDB
Tiuram	HMDB
TTD	HMDB
TTS	HMDB
Tuads, ethyl	HMDB
2,5-Dimethoxy-4-benzoquinone	HMDB
Physalin L	MeSH

Chemical Formula

C₂₈H₃₂O₁₀

Average Mass

528.5477 Da

Monoisotopic Mass

528.19955 Da

IUPAC Name

5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone

Traditional Name

5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone

CAS Registry Number

Not Available

SMILES

CC1C(=O)OC2CC1(C)C1C(=O)C3(O)OC11C2(C)OC(=O)C1(O)CCC1C3C(O)C=C2C=CCC(=O)C12C

InChI Identifier

InChI=1S/C28H32O10/c1-12-21(32)36-17-11-23(12,2)19-20(31)27(35)18-14(24(3)13(10-15(18)29)6-5-7-16(24)30)8-9-26(34)22(33)37-25(17,4)28(19,26)38-27/h5-6,10,12,14-15,17-19,29,34-35H,7-9,11H2,1-4H3

InChI Key

CUSXWWXXAPEFHY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alkekengi officinarum var. franchetii	LOTUS Database	35616633
Physalis lagascae	LOTUS Database	35616633
Physalis minima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

P-benzoquinones

Alternative Parents

Substituents

P-benzoquinone
Vinylogous ester
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.03	ALOGPS
logP	1.37	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.64	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	156.66 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	128.62 m³·mol⁻¹	ChemAxon
Polarizability	51.83 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034335

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012694

KNApSAcK ID

Not Available

Chemspider ID

91630

KEGG Compound ID

C01692

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101405

PDB ID

Not Available

ChEBI ID

4659

Good Scents ID

Not Available

References

General References

Prancheva MG, Krasteva SA, Tufkova SG, Karaivanova TP, Nizamova VV, Iliev YT: Severe hypotension and ischemic stroke after disulfiram-ethanol reaction. Folia Med (Plovdiv). 2010 Jul-Sep;52(3):70-3. doi: 10.2478/v10153-010-0009-y. [PubMed:21053676 ]
Haley TJ: Disulfiram (tetraethylthioperoxydicarbonic diamide): a reappraisal of its toxicity and therapeutic application. Drug Metab Rev. 1979;9(2):319-35. doi: 10.3109/03602537908993897. [PubMed:385275 ]
Seino H, Yoshikawa T, Hidai M, Mizobe Y: Preparation of mononuclear and dinuclear Rh hydrotris(pyrazolyl)borato complexes containing arenethiolato ligands and conversion of the mononuclear complexes into dinuclear Rh-Rh and Rh-Ir complexes with bridging arenethiolato ligands. Dalton Trans. 2004 Nov 7;(21):3593-600. doi: 10.1039/b409623a. Epub 2004 Sep 29. [PubMed:15510281 ]
Huang CJ, Li Y, Jiang S: Zwitterionic polymer-based platform with two-layer architecture for ultra low fouling and high protein loading. Anal Chem. 2012 Apr 3;84(7):3440-5. doi: 10.1021/ac3003769. Epub 2012 Mar 21. [PubMed:22409836 ]
Kitano H, Kawasaki A, Kawasaki H, Morokoshi S: Resistance of zwitterionic telomers accumulated on metal surfaces against nonspecific adsorption of proteins. J Colloid Interface Sci. 2005 Feb 15;282(2):340-8. doi: 10.1016/j.jcis.2004.08.157. [PubMed:15589539 ]

Showing NP-Card for Physalin L (NP0137019)

MOL for NP0137019 (Physalin L)

3D MOL for NP0137019 (Physalin L)

3D SDF for NP0137019 (Physalin L)

3D-SDF for NP0137019 (Physalin L)

PDB for NP0137019 (Physalin L)

3D PDB for NP0137019 (Physalin L)

SMILES for NP0137019 (Physalin L)

INCHI for NP0137019 (Physalin L)

Structure for NP0137019 (Physalin L)

3D Structure for NP0137019 (Physalin L)