NP-MRD: Showing NP-Card for 14-O-benzoylperegrine (NP0069432)

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Record Information

Version

2.0

Created at

2022-04-28 14:46:38 UTC

Updated at

2022-04-28 14:46:38 UTC

NP-MRD ID

NP0069432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-O-benzoylperegrine

Description

(1R,2S,3S,4R,5S,6S,8S,9S,10S,13S,16S,17S,18R)-18-(acetyloxy)-11-ethyl-6,8,16-trimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-4-yl benzoate belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom. 14-O-benzoylperegrine is found in Delphinium munzianum Kit Tan. Based on a literature review very few articles have been published on (1R,2S,3S,4R,5S,6S,8S,9S,10S,13S,16S,17S,18R)-18-(acetyloxy)-11-ethyl-6,8,16-trimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-4-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216462D          

 41 47  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652304282216462D          

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   -1.3222    0.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7761   -0.3995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6918    1.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2971   -0.2217    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3905   -1.0257    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9370   -1.5782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7321   -2.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447   -1.4331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7789   -0.5704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1226   -0.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6686   -0.4476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3856   -0.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0960   -1.7277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8242   -2.2859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9414   -3.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -3.4782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2878   -3.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3969   -4.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7433   -4.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9806   -4.6741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8714   -3.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5250   -3.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059    0.7038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    1.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5556   -2.9220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4273   -3.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1429   -1.9319    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
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10  1  1  1  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
  5 13  1  0  0  0  0
  9 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
  9 20  1  0  0  0  0
 20 21  1  6  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 24  1  0  0  0  0
 23 25  1  6  0  0  0
 25 26  1  0  0  0  0
 22 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 18 37  1  1  0  0  0
 37 38  1  0  0  0  0
  8 39  1  1  0  0  0
 39 40  1  0  0  0  0
  5 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0069432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@@]2(C)CC[C@H](OC)[C@]34[C@H]5C[C@@H]6[C@@H](OC(=O)C7=CC=CC=C7)[C@H]5[C@](C[C@@H]6OC)(OC)[C@H]([C@H](OC(C)=O)[C@@H]23)[C@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C33H45NO7/c1-7-34-17-31(3)14-13-23(38-5)33-21-15-20-22(37-4)16-32(39-6,25(29(33)34)27(28(31)33)40-18(2)35)24(21)26(20)41-30(36)19-11-9-8-10-12-19/h8-12,20-29H,7,13-17H2,1-6H3/t20-,21-,22-,23-,24-,25+,26+,27-,28-,29-,31+,32-,33+/m0/s1

> <INCHI_KEY>
LSOJZRZHOZOMMR-KVBWOLKZSA-N

> <FORMULA>
C33H45NO7

> <MOLECULAR_WEIGHT>
567.723

> <EXACT_MASS>
567.319602793

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
62.11285027346879

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,4R,5S,6S,8S,9S,10S,13S,16S,17S,18R)-18-(acetyloxy)-11-ethyl-6,8,16-trimethoxy-13-methyl-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
2.8994118619999987

> <ALOGPS_LOGS>
-5.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.425148712161933

> <JCHEM_POLAR_SURFACE_AREA>
83.53

> <JCHEM_REFRACTIVITY>
151.4679

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,4R,5S,6S,8S,9S,10S,13S,16S,17S,18R)-18-(acetyloxy)-11-ethyl-6,8,16-trimethoxy-13-methyl-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

> <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  N   UNK     0      -0.123  -0.151   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.810   1.625   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.392   3.202   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.233  -1.434   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.594  -2.926   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.199  -4.461   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.290  -4.934   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.373  -3.785   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.022  -2.189   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.459  -0.318   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530  -0.038   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.604  -0.672   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.790  -2.300   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.851   0.445   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.468   0.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.315  -0.746   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.158   1.917   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.288  -0.414   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.462  -1.915   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.616  -2.946   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.100  -3.978   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.617  -2.675   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.054  -1.065   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.829  -0.025   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.715  -0.836   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.053  -1.699   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.779  -3.225   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.138  -4.267   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.357  -5.906   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.781  -6.493   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.137  -6.846   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.341  -8.372   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.121  -9.312   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.697  -8.725   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.493  -7.199   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.713  -6.259   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.304   1.314   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.156   2.677   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.904  -5.454   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.664  -7.110   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.133  -3.606   0.000  0.00  0.00           C+0
CONECT    1    2    4   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6   13   41                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   39                                                  
CONECT    9    8   10   13   20                                             
CONECT   10    9    1   11                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    5    9                                                  
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   11   19   24   37                                             
CONECT   19   18   20   27                                                  
CONECT   20   19    9   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   18                                                       
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   22   19   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   18   38                                                       
CONECT   38   37                                                            
CONECT   39    8   40                                                       
CONECT   40   39                                                            
CONECT   41    5                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,3S,4R,5S,6S,8S,9S,10S,13S,16S,17S,18R)-18-(Acetyloxy)-11-ethyl-6,8,16-trimethoxy-13-methyl-11-azahexacyclo[7.7.2.1,.0,.0,.0,]nonadecan-4-yl benzoic acid	Generator

Chemical Formula

C₃₃H₄₅NO₇

Average Mass

567.7230 Da

Monoisotopic Mass

567.31960 Da

IUPAC Name

(1R,2S,3S,4R,5S,6S,8S,9S,10S,13S,16S,17S,18R)-18-(acetyloxy)-11-ethyl-6,8,16-trimethoxy-13-methyl-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

Traditional Name

(1R,2S,3S,4R,5S,6S,8S,9S,10S,13S,16S,17S,18R)-18-(acetyloxy)-11-ethyl-6,8,16-trimethoxy-13-methyl-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

CAS Registry Number

Not Available

SMILES

CCN1C[C@@]2(C)CC[C@H](OC)[C@]34[C@H]5C[C@@H]6[C@@H](OC(=O)C7=CC=CC=C7)[C@H]5[C@](C[C@@H]6OC)(OC)[C@H]([C@H](OC(C)=O)[C@@H]23)[C@H]14

InChI Identifier

InChI=1S/C33H45NO7/c1-7-34-17-31(3)14-13-23(38-5)33-21-15-20-22(37-4)16-32(39-6,25(29(33)34)27(28(31)33)40-18(2)35)24(21)26(20)41-30(36)19-11-9-8-10-12-19/h8-12,20-29H,7,13-17H2,1-6H3/t20-,21-,22-,23-,24-,25+,26+,27-,28-,29-,31+,32-,33+/m0/s1

InChI Key

LSOJZRZHOZOMMR-KVBWOLKZSA-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
Delphinium munzianum Kit Tan	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Aconitane-type diterpenoid alkaloids

Alternative Parents

Substituents

Aconitane-type diterpenoid alkaloid
Quinolidine
Benzoate ester
Alkaloid or derivatives
Benzoic acid or derivatives
Benzoyl
Azepane
Benzenoid
Piperidine
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	3.4	ALOGPS
logP	2.9	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	10.43	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	83.53 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	151.47 m³·mol⁻¹	ChemAxon
Polarizability	62.11 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	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

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

163104945

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 14-O-benzoylperegrine (NP0069432)

MOL for NP0069432 (14-O-benzoylperegrine)

3D MOL for NP0069432 (14-O-benzoylperegrine)

3D SDF for NP0069432 (14-O-benzoylperegrine)

3D-SDF for NP0069432 (14-O-benzoylperegrine)

PDB for NP0069432 (14-O-benzoylperegrine)

3D PDB for NP0069432 (14-O-benzoylperegrine)

SMILES for NP0069432 (14-O-benzoylperegrine)

INCHI for NP0069432 (14-O-benzoylperegrine)

Structure for NP0069432 (14-O-benzoylperegrine)

3D Structure for NP0069432 (14-O-benzoylperegrine)