NP-MRD: Showing NP-Card for Iturin A2 (NP0332390)

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Record Information

Version

2.0

Created at

2024-01-19 08:17:11 UTC

Updated at

2024-05-02 10:38:04 UTC

NP-MRD ID

NP0332390

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Iturin A2

Description

Iturin A2 belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. Iturin A2 was first documented in 2007 (PMID: 17534613). Based on a literature review a significant number of articles have been published on Iturin A2 (PMID: 25084426) (PMID: 34451760) (PMID: 31836057) (PMID: 37512926) (PMID: 28858210).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01192408172D          

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M  END


  Mrv2104 01192408172D          

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  8 41  2  0  0  0  0
  7 42  1  6  0  0  0
 42 43  1  0  0  0  0
 44 43  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 48 47  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 51 50  1  0  0  0  0
 51 52  1  0  0  0  0
 28 52  1  0  0  0  0
 51 53  1  1  0  0  0
 53 54  1  0  0  0  0
 50 55  2  0  0  0  0
 48 56  1  6  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 46 67  2  0  0  0  0
 44 68  1  1  0  0  0
 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 69 71  2  0  0  0  0
 43 72  2  0  0  0  0
  5 73  1  0  0  0  0
 73 74  2  0  0  0  0
  2 74  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332390

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCC[C@@H]1CC(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](CC2=CC=C(O)C=C2)C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N2CCC[C@H]2C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C48H74N12O14/c1-2-3-4-5-6-7-8-9-10-12-28-22-41(67)54-32(23-38(50)64)43(69)56-31(21-27-14-16-29(62)17-15-27)42(68)57-33(24-39(51)65)44(70)55-30(18-19-37(49)63)48(74)60-20-11-13-36(60)47(73)58-34(25-40(52)66)45(71)59-35(26-61)46(72)53-28/h14-17,28,30-36,61-62H,2-13,18-26H2,1H3,(H2,49,63)(H2,50,64)(H2,51,65)(H2,52,66)(H,53,72)(H,54,67)(H,55,70)(H,56,69)(H,57,68)(H,58,73)(H,59,71)/t28-,30+,31?,32+,33-,34?,35+,36+/m1/s1

> <INCHI_KEY>
HNAPWDKFUSLFFE-PLPRWMNOSA-N

> <FORMULA>
C48H74N12O14

> <MOLECULAR_WEIGHT>
1043.19

> <EXACT_MASS>
1042.544745111

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
148

> <JCHEM_AVERAGE_POLARIZABILITY>
108.47482780170634

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3R,6S,9R,13S,16R,19R,22S,27aS)-3,13,19-tris(carbamoylmethyl)-6-(hydroxymethyl)-16-[(4-hydroxyphenyl)methyl]-1,4,7,11,14,17,20,23-octaoxo-9-undecyl-hexacosahydro-1H-pyrrolo[2,1-i]1,4,7,10,13,16,19,22-octaazacyclopentacosan-22-yl]propanamide

> <JCHEM_LOGP>
-4.611528312666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.343497966436558

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.496528825789037

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8443920553902426

> <JCHEM_POLAR_SURFACE_AREA>
436.8299999999998

> <JCHEM_REFRACTIVITY>
260.95460000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3R,6S,9R,13S,16R,19R,22S,27aS)-3,13,19-tris(carbamoylmethyl)-6-(hydroxymethyl)-16-[(4-hydroxyphenyl)methyl]-1,4,7,11,14,17,20,23-octaoxo-9-undecyl-octadecahydro-2H-pyrrolo[2,1-i]1,4,7,10,13,16,19,22-octaazacyclopentacosan-22-yl]propanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JAN-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JAN-24         0                                  
HETATM    1  O   UNK     0      11.466  -6.480   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.435  -5.336   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.929  -5.656   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.898  -4.511   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.374  -3.047   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.344  -1.902   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.820  -0.438   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.486  -1.208   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.152  -0.438   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.819  -1.208   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.819  -2.748   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.485  -3.518   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.485  -5.058   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       1.151  -2.748   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.485  -0.438   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.151  -1.208   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -0.182  -0.438   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.256   1.246   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -1.286   2.390   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      -0.516   3.724   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.990   3.404   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       2.485   4.182   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       3.819   3.412   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.819   4.952   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.485   5.722   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       1.151   4.952   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0       2.485   7.262   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.152   4.182   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.152   5.722   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.198   1.878   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.547   4.868   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.953   4.242   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.792   2.710   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.280   1.360   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.499  -1.237   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.466  -2.776   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.782  -3.575   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      -2.749  -5.115   0.000  0.00  0.00           N+0
HETATM   39  O   UNK     0      -4.132  -2.834   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       2.485   1.102   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       6.486  -2.748   0.000  0.00  0.00           O+0
HETATM   42  N   UNK     0       9.153  -1.208   0.000  0.00  0.00           N+0
HETATM   43  C   UNK     0      10.487  -0.438   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      11.821  -1.208   0.000  0.00  0.00           C+0
HETATM   45  N   UNK     0      13.154  -0.438   0.000  0.00  0.00           N+0
HETATM   46  C   UNK     0      13.154   1.102   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      11.821   1.872   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      11.821   3.412   0.000  0.00  0.00           C+0
HETATM   49  N   UNK     0      10.487   4.182   0.000  0.00  0.00           N+0
HETATM   50  C   UNK     0       9.153   3.412   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       7.820   4.182   0.000  0.00  0.00           C+0
HETATM   52  N   UNK     0       6.486   3.412   0.000  0.00  0.00           N+0
HETATM   53  C   UNK     0       7.820   5.722   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       9.153   6.492   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       9.153   1.872   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      13.154   4.182   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      14.488   3.412   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      15.822   4.182   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      17.155   3.412   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      18.489   4.182   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      19.823   3.412   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      21.156   4.182   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      22.490   3.412   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      23.824   4.182   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      25.157   3.412   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      26.491   4.182   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      14.488   1.872   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      11.821  -2.748   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      13.154  -3.518   0.000  0.00  0.00           C+0
HETATM   70  N   UNK     0      14.488  -2.748   0.000  0.00  0.00           N+0
HETATM   71  O   UNK     0      13.154  -5.058   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0      10.487   1.102   0.000  0.00  0.00           O+0
HETATM   73  C   UNK     0       9.881  -2.727   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      10.911  -3.871   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   74                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   73                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   42                                                  
CONECT    8    7    9   41                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   40                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   35                                                  
CONECT   18   17   19   34                                                  
CONECT   19   18   20   33                                                  
CONECT   20   19   21   31                                                  
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29   52                                                  
CONECT   29   28                                                            
CONECT   30   21                                                            
CONECT   31   20   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   19                                                       
CONECT   34   18                                                            
CONECT   35   17   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   15                                                            
CONECT   41    8                                                            
CONECT   42    7   43                                                       
CONECT   43   42   44   72                                                  
CONECT   44   43   45   68                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   67                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   56                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   55                                                  
CONECT   51   50   52   53                                                  
CONECT   52   51   28                                                       
CONECT   53   51   54                                                       
CONECT   54   53                                                            
CONECT   55   50                                                            
CONECT   56   48   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65                                                            
CONECT   67   46                                                            
CONECT   68   44   69                                                       
CONECT   69   68   70   71                                                  
CONECT   70   69                                                            
CONECT   71   69                                                            
CONECT   72   43                                                            
CONECT   73    5   74                                                       
CONECT   74   73    2                                                       
MASTER        0    0    0    0    0    0    0    0   74    0  152    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₈H₇₄N₁₂O₁₄

Average Mass

1043.1900 Da

Monoisotopic Mass

1042.54475 Da

IUPAC Name

3-[(3R,6S,9R,13S,16R,19R,22S,27aS)-3,13,19-tris(carbamoylmethyl)-6-(hydroxymethyl)-16-[(4-hydroxyphenyl)methyl]-1,4,7,11,14,17,20,23-octaoxo-9-undecyl-hexacosahydro-1H-pyrrolo[2,1-i]1,4,7,10,13,16,19,22-octaazacyclopentacosan-22-yl]propanamide

Traditional Name

3-[(3R,6S,9R,13S,16R,19R,22S,27aS)-3,13,19-tris(carbamoylmethyl)-6-(hydroxymethyl)-16-[(4-hydroxyphenyl)methyl]-1,4,7,11,14,17,20,23-octaoxo-9-undecyl-octadecahydro-2H-pyrrolo[2,1-i]1,4,7,10,13,16,19,22-octaazacyclopentacosan-22-yl]propanamide

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCC[C@@H]1CC(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](CC2=CC=C(O)C=C2)C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N2CCC[C@H]2C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N1

InChI Identifier

InChI=1S/C48H74N12O14/c1-2-3-4-5-6-7-8-9-10-12-28-22-41(67)54-32(23-38(50)64)43(69)56-31(21-27-14-16-29(62)17-15-27)42(68)57-33(24-39(51)65)44(70)55-30(18-19-37(49)63)48(74)60-20-11-13-36(60)47(73)58-34(25-40(52)66)45(71)59-35(26-61)46(72)53-28/h14-17,28,30-36,61-62H,2-13,18-26H2,1H3,(H2,49,63)(H2,50,64)(H2,51,65)(H2,52,66)(H,53,72)(H,54,67)(H,55,70)(H,56,69)(H,57,68)(H,58,73)(H,59,71)/t28-,30+,31?,32+,33-,34?,35+,36+/m1/s1

InChI Key

HNAPWDKFUSLFFE-PLPRWMNOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Cyclic hybrid peptide
Alpha-oligopeptide
Macrolactam
Beta amino acid or derivatives
Alpha-amino acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Fatty amide
Tertiary carboxylic acid amide
Pyrrolidine
Secondary carboxylic acid amide
Carboxamide group
Lactam
Primary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organonitrogen compound
Organooxygen compound
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	-4.6	ChemAxon
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	436.83 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	260.95 m³·mol⁻¹	ChemAxon
Polarizability	108.47 Å³	ChemAxon
Number of Rings	3	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Iwase N, Rahman MS, Ano T: Production of iturin A homologues under different culture conditions. J Environ Sci (China). 2009;21 Suppl 1:S28-32. doi: 10.1016/S1001-0742(09)60031-0. [PubMed:25084426 ]
Nifakos K, Tsalgatidou PC, Thomloudi EE, Skagia A, Kotopoulis D, Baira E, Delis C, Papadimitriou K, Markellou E, Venieraki A, Katinakis P: Genomic Analysis and Secondary Metabolites Production of the Endophytic Bacillus velezensis Bvel1: A Biocontrol Agent against Botrytis cinerea Causing Bunch Rot in Post-Harvest Table Grapes. Plants (Basel). 2021 Aug 20;10(8):1716. doi: 10.3390/plants10081716. [PubMed:34451760 ]
Rong S, Xu H, Li L, Chen R, Gao X, Xu Z: Antifungal activity of endophytic Bacillus safensis B21 and its potential application as a biopesticide to control rice blast. Pestic Biochem Physiol. 2020 Jan;162:69-77. doi: 10.1016/j.pestbp.2019.09.003. Epub 2019 Sep 11. [PubMed:31836057 ]
Liu CH, Chen X, Liu TT, Lian B, Gu Y, Caer V, Xue YR, Wang BT: Study of the antifungal activity of Acinetobacter baumannii LCH001 in vitro and identification of its antifungal components. Appl Microbiol Biotechnol. 2007 Aug;76(2):459-66. doi: 10.1007/s00253-007-1010-0. Epub 2007 May 30. [PubMed:17534613 ]
Lalanne-Tisne G, Barral B, Taibi A, Coulibaly ZK, Burguet P, Rasoarahona F, Quinton L, Meile JC, Boubakri H, Kodja H: Exploring the Phytobeneficial and Biocontrol Capacities of Endophytic Bacteria Isolated from Hybrid Vanilla Pods. Microorganisms. 2023 Jul 5;11(7):1754. doi: 10.3390/microorganisms11071754. [PubMed:37512926 ]
Andersen AJC, de Medeiros LS, Binzer SB, Rasmussen SA, Hansen PJ, Nielsen KF, Jorgensen K, Larsen TO: HPLC-HRMS Quantification of the Ichthyotoxin Karmitoxin from Karlodinium armiger. Mar Drugs. 2017 Aug 31;15(9):278. doi: 10.3390/md15090278. [PubMed:28858210 ]

Showing NP-Card for Iturin A2 (NP0332390)

MOL for NP0332390 (Iturin A2)

3D MOL for NP0332390 (Iturin A2)

3D SDF for NP0332390 (Iturin A2)

3D-SDF for NP0332390 (Iturin A2)

PDB for NP0332390 (Iturin A2)

3D PDB for NP0332390 (Iturin A2)

SMILES for NP0332390 (Iturin A2)

INCHI for NP0332390 (Iturin A2)

Structure for NP0332390 (Iturin A2)

3D Structure for NP0332390 (Iturin A2)