NP-MRD: Showing NP-Card for Pepticinnamin N (NP0332622)

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Record Information

Version

1.0

Created at

2024-03-14 02:45:40 UTC

Updated at

2024-04-22 17:08:12 UTC

NP-MRD ID

NP0332622

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pepticinnamin N

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03142402452D          

 64 68  0  0  1  0            999 V2000
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M  END


  Mrv2104 03142402452D          

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M  END
> <DATABASE_ID>
NP0332622

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC\C=C/C1=CC=CC=C1\C=C\C(=O)N[C@H](CC1=CC=C(O)C=C1)C(=O)N(C)[C@@H](CC1=CC=C(OC)C(O)=C1)C(=O)N(C)[C@@H](CC1=CC=CC=C1)C(=O)OC[C@H]1NC(=O)CNC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C49H55N5O10/c1-5-6-8-15-35-16-11-12-17-36(35)21-25-44(57)51-38(26-33-18-22-37(55)23-19-33)47(60)53(2)40(28-34-20-24-43(63-4)42(56)29-34)48(61)54(3)41(27-32-13-9-7-10-14-32)49(62)64-31-39-46(59)50-30-45(58)52-39/h7-25,29,38-41,55-56H,5-6,26-28,30-31H2,1-4H3,(H,50,59)(H,51,57)(H,52,58)/b15-8-,25-21+/t38-,39-,40+,41+/m1/s1

> <INCHI_KEY>
DWKRCJFWYIJXQP-MZMGGPJWSA-N

> <FORMULA>
C49H55N5O10

> <MOLECULAR_WEIGHT>
874.004

> <EXACT_MASS>
873.394892991

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
119

> <JCHEM_AVERAGE_POLARIZABILITY>
92.49236064518485

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3,6-dioxopiperazin-2-yl]methyl (2S)-2-[(2S)-3-(3-hydroxy-4-methoxyphenyl)-2-[(2R)-3-(4-hydroxyphenyl)-N-methyl-2-[(2E)-3-{2-[(1Z)-pent-1-en-1-yl]phenyl}prop-2-enamido]propanamido]-N-methylpropanamido]-3-phenylpropanoate

> <JCHEM_LOGP>
5.166291907000002

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.949077479227585

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.327890348765246

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6687243707882045

> <JCHEM_POLAR_SURFACE_AREA>
203.90999999999997

> <JCHEM_REFRACTIVITY>
241.74170000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R)-3,6-dioxopiperazin-2-yl]methyl (2S)-2-[(2S)-3-(3-hydroxy-4-methoxyphenyl)-2-[(2R)-3-(4-hydroxyphenyl)-N-methyl-2-[(2E)-3-{2-[(1Z)-pent-1-en-1-yl]phenyl}prop-2-enamido]propanamido]-N-methylpropanamido]-3-phenylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAR-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAR-24         0                                  
HETATM    1  O   UNK     0      -3.573  -3.374   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.334  -5.390   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      13.337  -3.080   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      16.004  -4.620   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      14.670  -0.770   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       0.428  -6.636   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0     -13.337  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   52                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6                                                       
CONECT   13    4   14   51                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   18                                                       
CONECT   27   16   28   50                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   43                                                  
CONECT   31   30   32   42                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   34   40                                                  
CONECT   40   39                                                            
CONECT   41   36                                                            
CONECT   42   31                                                            
CONECT   43   30   44                                                       
CONECT   44   43   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   44                                                       
CONECT   50   27                                                            
CONECT   51   13                                                            
CONECT   52    2   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   59                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   54   60                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  136    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₉H₅₅N₅O₁₀

Average Mass

874.0040 Da

Monoisotopic Mass

873.39489 Da

IUPAC Name

[(2R)-3,6-dioxopiperazin-2-yl]methyl (2S)-2-[(2S)-3-(3-hydroxy-4-methoxyphenyl)-2-[(2R)-3-(4-hydroxyphenyl)-N-methyl-2-[(2E)-3-{2-[(1Z)-pent-1-en-1-yl]phenyl}prop-2-enamido]propanamido]-N-methylpropanamido]-3-phenylpropanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC\C=C/C1=CC=CC=C1\C=C\C(=O)N[C@H](CC1=CC=C(O)C=C1)C(=O)N(C)[C@@H](CC1=CC=C(OC)C(O)=C1)C(=O)N(C)[C@@H](CC1=CC=CC=C1)C(=O)OC[C@H]1NC(=O)CNC1=O

InChI Identifier

InChI=1S/C49H55N5O10/c1-5-6-8-15-35-16-11-12-17-36(35)21-25-44(57)51-38(26-33-18-22-37(55)23-19-33)47(60)53(2)40(28-34-20-24-43(63-4)42(56)29-34)48(61)54(3)41(27-32-13-9-7-10-14-32)49(62)64-31-39-46(59)50-30-45(58)52-39/h7-25,29,38-41,55-56H,5-6,26-28,30-31H2,1-4H3,(H,50,59)(H,51,57)(H,52,58)/b15-8-,25-21+/t38-,39-,40+,41+/m1/s1

InChI Key

DWKRCJFWYIJXQP-MZMGGPJWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 800.086940506 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
mirabilis P8-A2		Not Available

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	5.17	ChemAxon
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-0.67	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	203.91 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	241.74 m³·mol⁻¹	ChemAxon
Polarizability	92.49 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

Not Available

References

General References

Mohamed MMM, Abboud MM, Maleckis M, Souza LDO, Moreira JMA, Gotfredsen CH, Weber T, Ding L: Pepticinnamins N, O, and P, Nonribosomal Peptides from the Soil-Derived Streptomyces mirabilis P8-A2. J Nat Prod. 2024 Apr 9. doi: 10.1021/acs.jnatprod.4c00029. [PubMed:38591246 ]

Showing NP-Card for Pepticinnamin N (NP0332622)

MOL for NP0332622 (Pepticinnamin N)

3D MOL for NP0332622 (Pepticinnamin N)

3D SDF for NP0332622 (Pepticinnamin N)

3D-SDF for NP0332622 (Pepticinnamin N)

PDB for NP0332622 (Pepticinnamin N)

3D PDB for NP0332622 (Pepticinnamin N)

SMILES for NP0332622 (Pepticinnamin N)

INCHI for NP0332622 (Pepticinnamin N)

Structure for NP0332622 (Pepticinnamin N)

3D Structure for NP0332622 (Pepticinnamin N)