NP-MRD: Showing NP-Card for Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro) (NP0012296)

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Record Information

Version

2.0

Created at

2021-01-05 21:43:19 UTC

Updated at

2021-07-15 17:11:23 UTC

NP-MRD ID

NP0012296

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro)

Provided By

NPAtlas

Description

Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro) is found in Streptomyces. Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro) was first documented in 2014 (PMID: 24304298). Based on a literature review very few articles have been published on Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117073D          

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     RDKit          3D

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 38 70  1  6
M  END


  Mrv1652306242117073D          

 70 74  0  0  0  0            999 V2000
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 38 70  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0012296

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])[C@]1([H])N([H])C(=O)[C@@]2([H])N(C(=O)[C@@]([H])(N([H])C(=O)[C@@]3([H])N(C1=O)C([H])([H])[C@]([H])(O[H])C3([H])[H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])C([H])([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H32N4O6/c33-19-10-8-18(9-11-19)14-22-28(38)32-16-20(34)15-24(32)26(36)30-21(13-17-5-2-1-3-6-17)27(37)31-12-4-7-23(31)25(35)29-22/h1-3,5-6,8-11,20-24,33-34H,4,7,12-16H2,(H,29,35)(H,30,36)/t20-,21+,22+,23+,24+/m1/s1

> <INCHI_KEY>
ZGIGRYSYJMUJMP-DFWAIWNTSA-N

> <FORMULA>
C28H32N4O6

> <MOLECULAR_WEIGHT>
520.586

> <EXACT_MASS>
520.232184766

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.4909879545752

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6S,8R,12S,15S)-3-benzyl-8-hydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13-tetraazatricyclo[13.3.0.0^{6,10}]octadecane-2,5,11,14-tetrone

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
0.26064496666666703

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.913845084546018

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.47947799410581

> <JCHEM_PKA_STRONGEST_BASIC>
-2.887698621751359

> <JCHEM_POLAR_SURFACE_AREA>
139.28

> <JCHEM_REFRACTIVITY>
137.10459999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S,8R,12S,15S)-3-benzyl-8-hydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13-tetraazatricyclo[13.3.0.0^{6,10}]octadecane-2,5,11,14-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 74  0  0  0  0  0  0  0  0999 V2000
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    0.5501   -4.2367   -1.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8012   -2.6339   -2.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559   -1.8789   -3.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1579   -0.3094   -2.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
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  7  8  1  0
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  4 13  1  0
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 37 69  1  0
 38 70  1  6
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -0.269  -2.802  -0.122  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.387  -1.600  -0.545  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.262  -0.717   0.138  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.084   0.280  -0.522  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.333  -0.267  -1.099  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.284  -0.906  -0.214  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.332  -0.209   0.328  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.248  -0.820   1.194  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.108  -2.144   1.520  0.00  0.00           C+0
HETATM   10  O   UNK     0      -7.024  -2.763   2.389  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.068  -2.852   0.988  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.177  -2.234   0.137  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.233   1.509   0.279  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.149   1.581   1.132  0.00  0.00           O+0
HETATM   15  N   UNK     0      -1.394   2.650   0.155  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.623   4.085   0.366  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.534   4.742  -0.451  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.871   4.798  -1.790  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.631   3.813  -0.189  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.006   2.444  -0.261  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.641   1.603   0.747  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.273   1.758   1.958  0.00  0.00           O+0
HETATM   23  N   UNK     0       1.635   0.644   0.449  0.00  0.00           N+0
HETATM   24  C   UNK     0       2.646   0.828  -0.542  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.967   1.277   0.092  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.468   0.285   1.078  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.343  -0.715   0.768  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.754  -1.599   1.732  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.272  -1.462   3.008  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.392  -0.456   3.321  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.985   0.419   2.369  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.781  -0.353  -1.401  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.855  -0.394  -2.111  0.00  0.00           O+0
HETATM   34  N   UNK     0       1.852  -1.412  -1.504  0.00  0.00           N+0
HETATM   35  C   UNK     0       2.119  -2.859  -1.426  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.127  -3.460  -2.402  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.240  -2.317  -2.831  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.425  -1.250  -1.734  0.00  0.00           C+0
HETATM   39  H   UNK     0      -1.304  -0.806   1.179  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.453   0.590  -1.415  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.095  -0.929  -1.969  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.867   0.608  -1.584  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.529   0.829   0.124  0.00  0.00           H+0
HETATM   44  H   UNK     0      -7.078  -0.278   1.627  0.00  0.00           H+0
HETATM   45  H   UNK     0      -6.907  -3.722   2.613  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.974  -3.907   1.259  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.379  -2.822  -0.258  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.600   4.357   1.419  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.596   4.404  -0.054  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.263   5.738  -0.088  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.244   5.695  -1.963  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.976   3.987   0.849  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.462   3.956  -0.876  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.031   2.034  -1.272  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.614  -0.253   1.009  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.396   1.678  -1.242  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.799   2.262   0.525  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.696   1.318  -0.736  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.729  -0.826  -0.225  0.00  0.00           H+0
HETATM   60  H   UNK     0       6.444  -2.388   1.483  0.00  0.00           H+0
HETATM   61  H   UNK     0       5.566  -2.133   3.801  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.024  -0.360   4.323  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.287   1.214   2.627  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.128  -3.075  -1.818  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.999  -3.256  -0.407  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.616  -3.981  -3.233  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.550  -4.237  -1.835  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.801  -2.634  -2.901  0.00  0.00           H+0
HETATM   69  H   UNK     0       0.656  -1.879  -3.760  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.158  -0.309  -2.209  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4   39                                                  
CONECT    4    3    5   13   40                                             
CONECT    5    4    6   41   42                                             
CONECT    6    5    7   12                                                  
CONECT    7    6    8   43                                                  
CONECT    8    7    9   44                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   45                                                       
CONECT   11    9   12   46                                                  
CONECT   12   11    6   47                                                  
CONECT   13    4   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17   48   49                                             
CONECT   17   16   18   19   50                                             
CONECT   18   17   51                                                       
CONECT   19   17   20   52   53                                             
CONECT   20   19   21   15   54                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   55                                                  
CONECT   24   23   25   32   56                                             
CONECT   25   24   26   57   58                                             
CONECT   26   25   27   31                                                  
CONECT   27   26   28   59                                                  
CONECT   28   27   29   60                                                  
CONECT   29   28   30   61                                                  
CONECT   30   29   31   62                                                  
CONECT   31   30   26   63                                                  
CONECT   32   24   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   38                                                  
CONECT   35   34   36   64   65                                             
CONECT   36   35   37   66   67                                             
CONECT   37   36   38   68   69                                             
CONECT   38   37    2   34   70                                             
CONECT   39    3                                                            
CONECT   40    4                                                            
CONECT   41    5                                                            
CONECT   42    5                                                            
CONECT   43    7                                                            
CONECT   44    8                                                            
CONECT   45   10                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   16                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   19                                                            
CONECT   54   20                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   25                                                            
CONECT   58   25                                                            
CONECT   59   27                                                            
CONECT   60   28                                                            
CONECT   61   29                                                            
CONECT   62   30                                                            
CONECT   63   31                                                            
CONECT   64   35                                                            
CONECT   65   35                                                            
CONECT   66   36                                                            
CONECT   67   36                                                            
CONECT   68   37                                                            
CONECT   69   37                                                            
CONECT   70   38                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  148    0
END

RDKit          3D

70 74  0  0  0  0  0  0  0  0999 V2000
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 36 37  1  0
 37 38  1  0
 38  2  1  0
 12  6  1  0
 20 15  1  0
 31 26  1  0
 38 34  1  0
  3 39  1  0
  4 40  1  6
  5 41  1  0
  5 42  1  0
  7 43  1  0
  8 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  1
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  6
 23 55  1  0
 24 56  1  6
 25 57  1  0
 25 58  1  0
 27 59  1  0
 28 60  1  0
 29 61  1  0
 30 62  1  0
 31 63  1  0
 35 64  1  0
 35 65  1  0
 36 66  1  0
 36 67  1  0
 37 68  1  0
 37 69  1  0
 38 70  1  6
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂N₄O₆

Average Mass

520.5860 Da

Monoisotopic Mass

520.23218 Da

IUPAC Name

(3S,6S,8R,12S,15S)-3-benzyl-8-hydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13-tetraazatricyclo[13.3.0.0^{6,10}]octadecane-2,5,11,14-tetrone

Traditional Name

(3S,6S,8R,12S,15S)-3-benzyl-8-hydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13-tetraazatricyclo[13.3.0.0^{6,10}]octadecane-2,5,11,14-tetrone

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@@H]2N(C1)C(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC1=CC=CC=C1)NC2=O

InChI Identifier

InChI=1S/C28H32N4O6/c33-19-10-8-18(9-11-19)14-22-28(38)32-16-20(34)15-24(32)26(36)30-21(13-17-5-2-1-3-6-17)27(37)31-12-4-7-23(31)25(35)29-22/h1-3,5-6,8-11,20-24,33-34H,4,7,12-16H2,(H,29,35)(H,30,36)/t20-,21+,22+,23+,24+/m1/s1

InChI Key

ZGIGRYSYJMUJMP-DFWAIWNTSA-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
Streptomyces	NPAtlas	24304298

Chemical Taxonomy

Classification

Not classified

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	0.67	ALOGPS
logP	0.26	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.48	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	139.28 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	137.1 m³·mol⁻¹	ChemAxon
Polarizability	53.49 Å³	ChemAxon
Number of Rings	5	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

NPAtlas ID

NPA001747

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

32033801

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583586

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhou H, Yang Y, Yang X, Li W, Xiong Z, Zhao L, Xu L, Ding Z: A new cyclic tetrapeptide from an endophytic Streptomyces sp. YIM67005. Nat Prod Res. 2014;28(5):318-23. doi: 10.1080/14786419.2013.863198. Epub 2013 Dec 4. [PubMed:24304298 ]

Showing NP-Card for Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro) (NP0012296)

MOL for NP0012296 (Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro))

3D MOL for NP0012296 (Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro))

3D SDF for NP0012296 (Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro))

3D-SDF for NP0012296 (Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro))

PDB for NP0012296 (Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro))

3D PDB for NP0012296 (Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro))

SMILES for NP0012296 (Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro))

INCHI for NP0012296 (Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro))

Structure for NP0012296 (Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro))

3D Structure for NP0012296 (Cyclo(L-Tyr-L-Pro-L-Phe-trans-4-hydroxy-L-Pro))