NP-MRD: Showing NP-Card for Chaplashin (NP0071022)

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Record Information

Version

2.0

Created at

2022-04-28 16:25:27 UTC

Updated at

2022-04-28 16:25:27 UTC

NP-MRD ID

NP0071022

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chaplashin

Description

(9R)-5,14-dihydroxy-9-(2-hydroxypropan-2-yl)-16-methoxy-15-(3-methylbut-1-en-1-yl)-8,19-dioxatetracyclo[9.8.0.0²,⁷.0¹³,¹⁸]Nonadeca-1(11),2(7),3,5,13(18),14,16-heptaen-12-one belongs to the class of organic compounds known as benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (an unsaturated seven-membered heterocycle with one oxygen atom replacing a carbon atom). Chaplashin is found in Artocarpus altilis (Parkinson) Fosberg , Artocarpus chaplasha, Artocarpus champeden Spreng., Artocarpus chapalasha, Artocarpus kemando Miq. and Artocarpus maingayi King. Based on a literature review very few articles have been published on (9R)-5,14-dihydroxy-9-(2-hydroxypropan-2-yl)-16-methoxy-15-(3-methylbut-1-en-1-yl)-8,19-dioxatetracyclo[9.8.0.0²,⁷.0¹³,¹⁸]Nonadeca-1(11),2(7),3,5,13(18),14,16-heptaen-12-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218252D          

 33 36  0  0  1  0            999 V2000
    6.4334    0.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7765   -0.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982   -1.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4769   -0.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1339   -0.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6121    0.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3126   -0.1131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8343   -0.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1774   -1.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9987   -1.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3418   -2.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8047   -2.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9969   -2.4392    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3623   -1.9121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3787   -1.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0338   -0.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9271    0.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1653    0.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5102    0.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6169   -0.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484    0.3641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7974   -3.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978   -4.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969   -3.0401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5979   -3.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6413   -1.7697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5978   -0.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1052   -2.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9116    1.0754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5685    1.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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 32 33  1  0  0  0  0
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
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    3.2096    0.0038    0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5361   -0.5226    0.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3915   -3.0506    1.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1733   -1.0177    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6873   -1.1459   -0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9145   -0.7713   -0.0787 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8258   -1.9545    0.1015 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0426   -3.1231    0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0101   -1.6728    0.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2843   -2.3232   -1.1754 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6262   -2.7974   -0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9836   -1.1061   -1.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3745   -2.1974   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823   -0.4508    0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6654   -3.7771    1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5857   -3.7466   -0.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
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 20  8  1  0
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 32 61  1  0
M  END


  Mrv1652304282218252D          

 33 36  0  0  1  0            999 V2000
    6.4334    0.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7765   -0.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982   -1.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6121    0.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1052   -2.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0071022

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(\C=C\C(C)C)C(O)=C2C(=O)C3=C(OC2=C1)C1=C(O[C@H](C3)C(C)(C)O)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O7/c1-13(2)6-8-15-18(31-5)12-20-22(23(15)28)24(29)17-11-21(26(3,4)30)32-19-10-14(27)7-9-16(19)25(17)33-20/h6-10,12-13,21,27-28,30H,11H2,1-5H3/b8-6+/t21-/m1/s1

> <INCHI_KEY>
PEZAKJUGIDWOSG-HSTAZWAASA-N

> <FORMULA>
C26H28O7

> <MOLECULAR_WEIGHT>
452.503

> <EXACT_MASS>
452.183503242

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.86677624974241

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9R)-5,14-dihydroxy-9-(2-hydroxypropan-2-yl)-16-methoxy-15-[(1E)-3-methylbut-1-en-1-yl]-8,19-dioxatetracyclo[9.8.0.0^{2,7}.0^{13,18}]nonadeca-1(11),2(7),3,5,13,15,17-heptaen-12-one

> <ALOGPS_LOGP>
4.38

> <JCHEM_LOGP>
4.538671105333334

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.769937769209594

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.2811821356910205

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1064738436767527

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
126.0138

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R)-5,14-dihydroxy-9-(2-hydroxypropan-2-yl)-16-methoxy-15-[(1E)-3-methylbut-1-en-1-yl]-8,19-dioxatetracyclo[9.8.0.0^{2,7}.0^{13,18}]nonadeca-1(11),2(7),3,5,13,15,17-heptaen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      12.009   0.752   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.649  -0.648   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.757  -1.903   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.224  -1.757   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.583  -0.357   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.476   0.898   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.050  -0.211   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.157  -1.466   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.798  -2.867   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.331  -3.012   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.971  -4.413   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.102  -4.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.594  -4.553   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.410  -3.569   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.440  -2.029   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.663  -1.093   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.464   0.434   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.042   1.025   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.819   0.089   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.018  -1.438   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.397   0.680   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.222  -6.047   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.849  -7.542   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.727  -5.675   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.716  -6.420   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.397  -3.303   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.182  -0.794   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.823  -2.194   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.356  -2.340   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.249  -1.085   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.996  -3.740   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.902   2.007   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.261   3.408   0.000  0.00  0.00           C+0
CONECT    1    2    6   32                                                  
CONECT    2    1    3   27                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15    8   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   15                                                       
CONECT   21   19                                                            
CONECT   22   13   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26    3                                                            
CONECT   27    2   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    1   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₇

Average Mass

452.5030 Da

Monoisotopic Mass

452.18350 Da

IUPAC Name

(9R)-5,14-dihydroxy-9-(2-hydroxypropan-2-yl)-16-methoxy-15-[(1E)-3-methylbut-1-en-1-yl]-8,19-dioxatetracyclo[9.8.0.0^{2,7}.0^{13,18}]nonadeca-1(11),2(7),3,5,13,15,17-heptaen-12-one

Traditional Name

(9R)-5,14-dihydroxy-9-(2-hydroxypropan-2-yl)-16-methoxy-15-[(1E)-3-methylbut-1-en-1-yl]-8,19-dioxatetracyclo[9.8.0.0^{2,7}.0^{13,18}]nonadeca-1(11),2(7),3,5,13,15,17-heptaen-12-one

CAS Registry Number

Not Available

SMILES

COC1=C(\C=C\C(C)C)C(O)=C2C(=O)C3=C(OC2=C1)C1=C(O[C@H](C3)C(C)(C)O)C=C(O)C=C1

InChI Identifier

InChI=1S/C26H28O7/c1-13(2)6-8-15-18(31-5)12-20-22(23(15)28)24(29)17-11-21(26(3,4)30)32-19-10-14(27)7-9-16(19)25(17)33-20/h6-10,12-13,21,27-28,30H,11H2,1-5H3/b8-6+/t21-/m1/s1

InChI Key

PEZAKJUGIDWOSG-HSTAZWAASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Artocarpus altilis	Plant	KNApSAcK
Artocarpus chama	Plant	KNApSAcK
Artocarpus champeden Spreng.	Plant	KNApSAcK
Artocarpus chapalasha	Plant	KNApSAcK
Artocarpus kemando	Plant	KNApSAcK
Artocarpus maingayi King	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (an unsaturated seven-membered heterocycle with one oxygen atom replacing a carbon atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxepines

Sub Class

Not Available

Direct Parent

Benzoxepines

Alternative Parents

Substituents

Benzoxepine
Chromone
Benzopyran
1-benzopyran
Anisole
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Tertiary alcohol
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	4.38	ALOGPS
logP	4.54	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	7.28	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	126.01 m³·mol⁻¹	ChemAxon
Polarizability	49.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162945958

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Chaplashin (NP0071022)

MOL for NP0071022 (Chaplashin)

3D MOL for NP0071022 (Chaplashin)

3D SDF for NP0071022 (Chaplashin)

3D-SDF for NP0071022 (Chaplashin)

PDB for NP0071022 (Chaplashin)

3D PDB for NP0071022 (Chaplashin)

SMILES for NP0071022 (Chaplashin)

INCHI for NP0071022 (Chaplashin)

Structure for NP0071022 (Chaplashin)

3D Structure for NP0071022 (Chaplashin)