NP-MRD: Showing NP-Card for paratunamide C (NP0032468)

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Record Information

Version

2.0

Created at

2021-06-19 23:15:50 UTC

Updated at

2021-06-30 00:01:40 UTC

NP-MRD ID

NP0032468

Secondary Accession Numbers

None

Natural Product Identification

Common Name

paratunamide C

Provided By

JEOL Database JEOL Logo

Description

CHEMBL448248 belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. paratunamide C is found in Cinnamodendron axillare. paratunamide C was first documented in 2006 (Kagata, T., et al.). Based on a literature review very few articles have been published on CHEMBL448248.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101153D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202101153D          

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M  END
> <DATABASE_ID>
NP0032468

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])OC([H])=C3C(=O)N(C(=O)C([H])([H])[C@@]3([H])[C@@]2([H])C([H])=C([H])[H])C([H])([H])C([H])([H])[C@]2(O[H])C(=O)N([H])C3=C([H])C([H])=C([H])C([H])=C23)[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H30N2O11/c1-2-12-13-9-18(30)28(8-7-26(36)15-5-3-4-6-16(15)27-25(26)35)22(34)14(13)11-37-23(12)39-24-21(33)20(32)19(31)17(10-29)38-24/h2-6,11-13,17,19-21,23-24,29,31-33,36H,1,7-10H2,(H,27,35)/t12-,13+,17-,19-,20+,21-,23+,24+,26-/m1/s1

> <INCHI_KEY>
MWJJDCGSBJVCSS-WFCCQOBFSA-N

> <FORMULA>
C26H30N2O11

> <MOLECULAR_WEIGHT>
546.529

> <EXACT_MASS>
546.184959794

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.28969949127628

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4R,4aS)-4-ethenyl-7-{2-[(3R)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl]ethyl}-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H,4H,4aH,5H,6H,7H,8H-pyrano[3,4-c]pyridine-6,8-dione

> <ALOGPS_LOGP>
0.02

> <JCHEM_LOGP>
-1.9605904113333332

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.289210391901788

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.540681560116774

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615592584

> <JCHEM_POLAR_SURFACE_AREA>
195.32

> <JCHEM_REFRACTIVITY>
132.10219999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R,4aS)-4-ethenyl-7-{2-[(3R)-3-hydroxy-2-oxo-1H-indol-3-yl]ethyl}-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H,4H,4aH,5H-pyrano[3,4-c]pyridine-6,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 69 73  0  0  0  0  0  0  0  0999 V2000
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 15 16  1  0
 19 18  2  0
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M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.339  -5.475   0.485  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.160  -4.357  -0.058  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.418  -3.077   0.719  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.913  -2.669   0.642  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.116  -1.621   1.592  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.479  -1.307   1.857  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.577  -0.766   3.181  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.386   0.657   3.301  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.926   1.072   3.038  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.643   1.211   1.648  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.404   1.443   2.452  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.410   2.029   3.302  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.117   0.538   1.446  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.786   1.353   0.467  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.121  -0.400   0.778  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.829  -1.172  -0.215  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.302  -2.273  -0.689  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.399  -1.484  -1.359  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.142  -1.239  -0.965  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.702  -0.302  -1.752  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.268   0.238  -2.767  0.00  0.00           O+0
HETATM   22  N   UNK     0      -1.986  -0.084  -1.253  0.00  0.00           N+0
HETATM   23  C   UNK     0      -2.737   1.040  -1.817  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.159   2.419  -1.459  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.513   2.974  -0.075  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.857   4.230   0.092  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.134   2.011   1.096  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.022   1.560   1.337  0.00  0.00           O+0
HETATM   29  N   UNK     0      -3.285   1.780   1.835  0.00  0.00           N+0
HETATM   30  C   UNK     0      -4.372   2.453   1.296  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.672   2.439   1.757  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.610   3.200   1.056  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.230   3.949  -0.073  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.907   3.945  -0.524  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.983   3.181   0.170  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.643  -0.942  -0.372  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.788  -0.757   0.039  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.895  -2.196   0.011  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.435  -1.866   0.260  0.00  0.00           C+0
HETATM   40  H   UNK     0      -0.601  -5.539   1.538  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.498  -6.364  -0.120  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.407  -4.359  -1.119  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.169  -3.256   1.775  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.533  -3.530   0.923  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.039  -2.249   1.906  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.572   0.863   4.363  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.728   2.043   3.503  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.237   0.331   3.456  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.669   1.326   1.577  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.931   2.296   1.952  0.00  0.00           H+0
HETATM   51  H   UNK     0       6.074   2.402   2.689  0.00  0.00           H+0
HETATM   52  H   UNK     0       5.914  -0.037   1.935  0.00  0.00           H+0
HETATM   53  H   UNK     0       6.010   0.733  -0.257  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.374   0.176   0.223  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.140  -1.648  -0.720  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.843  -1.074  -2.260  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.690   0.931  -2.909  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.797   0.981  -1.554  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.067   2.413  -1.568  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.512   3.135  -2.214  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.903   4.042   0.160  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.324   1.179   2.644  0.00  0.00           H+0
HETATM   63  H   UNK     0      -5.963   1.862   2.627  0.00  0.00           H+0
HETATM   64  H   UNK     0      -7.646   3.218   1.387  0.00  0.00           H+0
HETATM   65  H   UNK     0      -6.976   4.542  -0.598  0.00  0.00           H+0
HETATM   66  H   UNK     0      -4.612   4.535  -1.386  0.00  0.00           H+0
HETATM   67  H   UNK     0      -2.034  -2.919  -0.802  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.349  -2.610   0.919  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.393  -1.109   1.057  0.00  0.00           H+0
CONECT    1    2   40   41                                                  
CONECT    2    3    1   42                                                  
CONECT    3   39    4    2   43                                             
CONECT    4    3   17    5   44                                             
CONECT    5    4    6                                                       
CONECT    6   15    7    5   45                                             
CONECT    7    8    6                                                       
CONECT    8   11    7    9   46                                             
CONECT    9   10    8   47   48                                             
CONECT   10    9   49                                                       
CONECT   11   13    8   12   50                                             
CONECT   12   11   51                                                       
CONECT   13   15   11   14   52                                             
CONECT   14   13   53                                                       
CONECT   15   16    6   13   54                                             
CONECT   16   15   55                                                       
CONECT   17    4   18                                                       
CONECT   18   19   17   56                                                  
CONECT   19   18   20   39                                                  
CONECT   20   21   19   22                                                  
CONECT   21   20                                                            
CONECT   22   23   36   20                                                  
CONECT   23   22   24   57   58                                             
CONECT   24   25   23   59   60                                             
CONECT   25   27   35   24   26                                             
CONECT   26   25   61                                                       
CONECT   27   29   25   28                                                  
CONECT   28   27                                                            
CONECT   29   30   27   62                                                  
CONECT   30   31   35   29                                                  
CONECT   31   30   32   63                                                  
CONECT   32   31   33   64                                                  
CONECT   33   34   32   65                                                  
CONECT   34   33   35   66                                                  
CONECT   35   34   30   25                                                  
CONECT   36   37   38   22                                                  
CONECT   37   36                                                            
CONECT   38   36   39   67   68                                             
CONECT   39    3   38   19   69                                             
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    2                                                            
CONECT   43    3                                                            
CONECT   44    4                                                            
CONECT   45    6                                                            
CONECT   46    8                                                            
CONECT   47    9                                                            
CONECT   48    9                                                            
CONECT   49   10                                                            
CONECT   50   11                                                            
CONECT   51   12                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   15                                                            
CONECT   55   16                                                            
CONECT   56   18                                                            
CONECT   57   23                                                            
CONECT   58   23                                                            
CONECT   59   24                                                            
CONECT   60   24                                                            
CONECT   61   26                                                            
CONECT   62   29                                                            
CONECT   63   31                                                            
CONECT   64   32                                                            
CONECT   65   33                                                            
CONECT   66   34                                                            
CONECT   67   38                                                            
CONECT   68   38                                                            
CONECT   69   39                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  146    0
END

RDKit          3D

69 73  0  0  0  0  0  0  0  0999 V2000
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  1 41  1  0
 23 57  1  0
 23 58  1  0
 31 63  1  0
 34 66  1  0
 33 65  1  0
 32 64  1  0
 29 62  1  0
 24 59  1  0
 24 60  1  0
 26 61  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀N₂O₁₁

Average Mass

546.5290 Da

Monoisotopic Mass

546.18496 Da

IUPAC Name

(3S,4R,4aS)-4-ethenyl-7-{2-[(3R)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl]ethyl}-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H,4H,4aH,5H,6H,7H,8H-pyrano[3,4-c]pyridine-6,8-dione

Traditional Name

(3S,4R,4aS)-4-ethenyl-7-{2-[(3R)-3-hydroxy-2-oxo-1H-indol-3-yl]ethyl}-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H,4H,4aH,5H-pyrano[3,4-c]pyridine-6,8-dione

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])OC([H])=C3C(=O)N(C(=O)C([H])([H])[C@@]3([H])[C@@]2([H])C([H])=C([H])[H])C([H])([H])C([H])([H])[C@]2(O[H])C(=O)N([H])C3=C([H])C([H])=C([H])C([H])=C23)[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C26H30N2O11/c1-2-12-13-9-18(30)28(8-7-26(36)15-5-3-4-6-16(15)27-25(26)35)22(34)14(13)11-37-23(12)39-24-21(33)20(32)19(31)17(10-29)38-24/h2-6,11-13,17,19-21,23-24,29,31-33,36H,1,7-10H2,(H,27,35)/t12-,13+,17-,19-,20+,21-,23+,24+,26-/m1/s1

InChI Key

MWJJDCGSBJVCSS-WFCCQOBFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cinnamodendron axillare	JEOL database	Kagata, T., et al, J. Nat. Prod. 69, 1517 (2006)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Indole or derivatives
Dihydroindole
Piperidinedione
Delta-lactam
Piperidinone
Monosaccharide
Carboxylic acid imide, n-substituted
Oxane
Benzenoid
Piperidine
Carboxylic acid imide
Dicarboximide
Vinylogous ester
Tertiary alcohol
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Lactam
Polyol
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Azacycle
Alcohol
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.02	ALOGPS
logP	-2	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	11.54	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	195.32 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.1 m³·mol⁻¹	ChemAxon
Polarizability	53.29 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17250254

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16091683

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kagata, T., et al. (2006). Kagata, T., et al, J. Nat. Prod. 69, 1517 (2006) . J. Nat. Prod..

Showing NP-Card for paratunamide C (NP0032468)

MOL for NP0032468 (paratunamide C)

3D MOL for NP0032468 (paratunamide C)

3D SDF for NP0032468 (paratunamide C)

3D-SDF for NP0032468 (paratunamide C)

PDB for NP0032468 (paratunamide C)

3D PDB for NP0032468 (paratunamide C)

SMILES for NP0032468 (paratunamide C)

INCHI for NP0032468 (paratunamide C)

Structure for NP0032468 (paratunamide C)

3D Structure for NP0032468 (paratunamide C)