NP-MRD: Showing NP-Card for Iturin A6 (NP0332385)

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Record Information

Version

2.0

Created at

2024-01-19 08:11:59 UTC

Updated at

2024-05-02 10:52:58 UTC

NP-MRD ID

NP0332385

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Iturin A6

Description

Iturin A6 was first documented in 2007 (PMID: 17534613). Based on a literature review a small amount of articles have been published on Iturin A6 (PMID: 31836057).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01192408122D          

 76 78  0  0  1  0            999 V2000
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    2.3202    2.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3821    3.2370    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv2104 01192408122D          

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 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 15 40  2  0  0  0  0
  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
 66 67  1  0  0  0  0
 66 68  1  0  0  0  0
 46 69  2  0  0  0  0
 44 70  1  1  0  0  0
 70 71  1  0  0  0  0
 71 72  1  0  0  0  0
 71 73  2  0  0  0  0
 43 74  2  0  0  0  0
  5 75  1  0  0  0  0
 75 76  2  0  0  0  0
  2 76  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332385

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCCCCCCCCC[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/C50H78N12O14/c1-28(2)12-9-7-5-3-4-6-8-10-13-30-23-43(69)56-34(24-40(52)66)45(71)58-33(22-29-15-17-31(64)18-16-29)44(70)59-35(25-41(53)67)46(72)57-32(19-20-39(51)65)50(76)62-21-11-14-38(62)49(75)60-36(26-42(54)68)47(73)61-37(27-63)48(74)55-30/h15-18,28,30,32-38,63-64H,3-14,19-27H2,1-2H3,(H2,51,65)(H2,52,66)(H2,53,67)(H2,54,68)(H,55,74)(H,56,69)(H,57,72)(H,58,71)(H,59,70)(H,60,75)(H,61,73)/t30-,32+,33?,34+,35-,36?,37+,38+/m1/s1

> <INCHI_KEY>
KKIVMGDDVLIFLL-GICUTXCZSA-N

> <FORMULA>
C50H78N12O14

> <MOLECULAR_WEIGHT>
1071.244

> <EXACT_MASS>
1070.57604524

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
154

> <JCHEM_AVERAGE_POLARIZABILITY>
111.18312555501342

> <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]-9-(11-methyldodecyl)-1,4,7,11,14,17,20,23-octaoxo-hexacosahydro-1H-pyrrolo[2,1-i]1,4,7,10,13,16,19,22-octaazacyclopentacosan-22-yl]propanamide

> <JCHEM_LOGP>
-3.8799405513333336

> <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>
270.10420000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <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]-9-(11-methyldodecyl)-1,4,7,11,14,17,20,23-octaoxo-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       2.903  -0.136   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.379   1.328   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.349   2.473   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.825   3.937   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.331   4.258   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.807   5.722   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.313   6.042   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.980   6.812   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.980   8.352   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.646   9.122   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.312   8.352   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.979   9.122   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.355   8.352   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       0.979  10.662   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.646  10.662   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       2.312  11.432   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       2.312  12.972   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.734  13.878   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       4.210  15.342   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.750  15.342   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.225  13.878   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       7.647  12.972   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       7.647  11.432   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.981  12.202   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.981  13.742   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       7.647  14.512   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0      10.314  14.512   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.981  10.662   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.314  11.432   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.008  12.935   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.226  16.807   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.980  17.712   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.734  16.807   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.600  12.605   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.962  13.713   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.354  12.914   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.705  13.655   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      -3.021  12.857   0.000  0.00  0.00           N+0
HETATM   39  O   UNK     0      -1.738  15.195   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       4.980  11.432   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       3.646   6.042   0.000  0.00  0.00           O+0
HETATM   42  N   UNK     0       6.313   4.502   0.000  0.00  0.00           N+0
HETATM   43  C   UNK     0       7.647   3.732   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       7.647   2.192   0.000  0.00  0.00           C+0
HETATM   45  N   UNK     0       8.981   1.422   0.000  0.00  0.00           N+0
HETATM   46  C   UNK     0      10.314   2.192   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      10.314   3.732   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      11.648   4.502   0.000  0.00  0.00           C+0
HETATM   49  N   UNK     0      11.648   6.042   0.000  0.00  0.00           N+0
HETATM   50  C   UNK     0      10.314   6.812   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      10.314   8.352   0.000  0.00  0.00           C+0
HETATM   52  N   UNK     0       8.981   9.122   0.000  0.00  0.00           N+0
HETATM   53  C   UNK     0      11.648   9.122   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      12.982   8.352   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       8.981   6.042   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      12.982   3.732   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      14.315   4.502   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      15.649   3.732   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      16.983   4.502   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      18.316   3.732   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      19.650   4.502   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      20.984   3.732   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      22.317   4.502   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      23.651   3.732   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      24.985   4.502   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      26.319   3.732   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      27.652   4.502   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      26.319   2.192   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      11.648   1.422   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0       6.313   1.422   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0       6.313  -0.118   0.000  0.00  0.00           C+0
HETATM   72  N   UNK     0       7.647  -0.888   0.000  0.00  0.00           N+0
HETATM   73  O   UNK     0       4.980  -0.888   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0       8.981   4.502   0.000  0.00  0.00           O+0
HETATM   75  C   UNK     0       5.362   3.113   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0       4.886   1.649   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   76                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   75                                                  
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   74                                                  
CONECT   44   43   45   70                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   69                                                  
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   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66                                                            
CONECT   69   46                                                            
CONECT   70   44   71                                                       
CONECT   71   70   72   73                                                  
CONECT   72   71                                                            
CONECT   73   71                                                            
CONECT   74   43                                                            
CONECT   75    5   76                                                       
CONECT   76   75    2                                                       
MASTER        0    0    0    0    0    0    0    0   76    0  156    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₀H₇₈N₁₂O₁₄

Average Mass

1071.2440 Da

Monoisotopic Mass

1070.57605 Da

IUPAC Name

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

CAS Registry Number

Not Available

SMILES

CC(C)CCCCCCCCCC[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/C50H78N12O14/c1-28(2)12-9-7-5-3-4-6-8-10-13-30-23-43(69)56-34(24-40(52)66)45(71)58-33(22-29-15-17-31(64)18-16-29)44(70)59-35(25-41(53)67)46(72)57-32(19-20-39(51)65)50(76)62-21-11-14-38(62)49(75)60-36(26-42(54)68)47(73)61-37(27-63)48(74)55-30/h15-18,28,30,32-38,63-64H,3-14,19-27H2,1-2H3,(H2,51,65)(H2,52,66)(H2,53,67)(H2,54,68)(H,55,74)(H,56,69)(H,57,72)(H,58,71)(H,59,70)(H,60,75)(H,61,73)/t30-,32+,33?,34+,35-,36?,37+,38+/m1/s1

InChI Key

KKIVMGDDVLIFLL-GICUTXCZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

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	-3.9	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	23	ChemAxon
Refractivity	270.1 m³·mol⁻¹	ChemAxon
Polarizability	111.18 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

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 ]

Showing NP-Card for Iturin A6 (NP0332385)

MOL for NP0332385 (Iturin A6)

3D MOL for NP0332385 (Iturin A6)

3D SDF for NP0332385 (Iturin A6)

3D-SDF for NP0332385 (Iturin A6)

PDB for NP0332385 (Iturin A6)

3D PDB for NP0332385 (Iturin A6)

SMILES for NP0332385 (Iturin A6)

INCHI for NP0332385 (Iturin A6)

Structure for NP0332385 (Iturin A6)

3D Structure for NP0332385 (Iturin A6)