NP-MRD: Showing NP-Card for acyl-surugamide A1 (NP0333433)

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Record Information

Version

2.0

Created at

2024-06-19 04:02:25 UTC

Updated at

2025-12-20 11:41:06 UTC

NP-MRD ID

NP0333433

Natural Product DOI

https://doi.org/10.57994/2875

Secondary Accession Numbers

None

Natural Product Identification

Common Name

acyl-surugamide A1

Description

Acyl-surugamide A1 belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Based on a literature review very few articles have been published on acyl-surugamide A1.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03032306372D          

 72 73  0  0  1  0            999 V2000
    0.9617    6.8780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3742    6.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1648    5.6626    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.9195    3.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4185    1.8354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv2104 03032306372D          

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    0.9617    6.8780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3742    6.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 62 64  1  0  0  0  0
 65  2  1  0  0  0  0
 65 24  1  0  0  0  0
 65 66  1  1  0  0  0
 66 67  1  0  0  0  0
 67 68  2  0  0  0  0
 68 69  1  0  0  0  0
 69 70  2  0  0  0  0
 70 71  1  0  0  0  0
 71 72  2  0  0  0  0
 67 72  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333433

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(=O)NCCCC[C@@H]1NC(=O)[C@]([H])(NC(=O)[C@@]([H])(NC(=O)[C@@H](C)NC(=O)[C@@]([H])(NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@@]([H])(NC1=O)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C49H81N9O9/c1-12-29(7)38-46(64)51-33(11)42(60)55-41(32(10)15-4)49(67)58-40(31(9)14-3)47(65)52-35(23-19-20-24-50-27-59)43(61)56-39(30(8)13-2)48(66)54-37(26-34-21-17-16-18-22-34)44(62)53-36(25-28(5)6)45(63)57-38/h16-18,21-22,27-33,35-41H,12-15,19-20,23-26H2,1-11H3,(H,50,59)(H,51,64)(H,52,65)(H,53,62)(H,54,66)(H,55,60)(H,56,61)(H,57,63)(H,58,67)/t29-,30-,31-,32-,33+,35-,36+,37+,38-,39-,40+,41-/m0/s1

> <INCHI_KEY>
KMCWUJZSHTUTAM-YNCQOOFJSA-N

> <FORMULA>
C49H81N9O9

> <MOLECULAR_WEIGHT>
940.241

> <EXACT_MASS>
939.615725224

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
148

> <JCHEM_AVERAGE_POLARIZABILITY>
103.46554239975451

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{4-[(2S,5S,8R,11R,14S,17R,20S,23R)-8-benzyl-5,14,20,23-tetrakis[(2S)-butan-2-yl]-17-methyl-11-(2-methylpropyl)-3,6,9,12,15,18,21,24-octaoxo-1,4,7,10,13,16,19,22-octaazacyclotetracosan-2-yl]butyl}formamide

> <JCHEM_LOGP>
3.584787297333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.942446071138395

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.56688757282521

> <JCHEM_POLAR_SURFACE_AREA>
261.9

> <JCHEM_REFRACTIVITY>
253.3237000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-{4-[(2S,5S,8R,11R,14S,17R,20S,23R)-8-benzyl-5,14,20,23-tetrakis[(2S)-butan-2-yl]-17-methyl-11-(2-methylpropyl)-3,6,9,12,15,18,21,24-octaoxo-1,4,7,10,13,16,19,22-octaazacyclotetracosan-2-yl]butyl}formamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAR-23         0                                  
HETATM    1  O   UNK     0       1.795  12.839   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.565  11.505   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.795  10.172   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.308  10.570   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.781   9.481   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.383   7.994   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.716   7.224   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.716   5.684   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.383   4.914   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.781   3.426   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.308   2.337   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.795   2.736   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.565   1.402   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.105   1.402   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.875   2.736   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       6.363   2.337   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.452   3.426   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       7.053   4.914   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       8.387   5.684   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.387   7.224   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       7.053   7.994   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       7.452   9.481   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.363  10.570   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       4.875  10.172   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0       6.761  12.058   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0       7.850  10.969   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       8.939   9.880   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.338  11.367   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.028   8.791   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.516   9.189   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.720   7.994   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.720   4.914   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.054   5.684   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.388   4.914   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.722   5.684   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      15.055   4.914   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      16.389   5.684   0.000  0.00  0.00           C+0
HETATM   38  H   UNK     0      16.389   7.224   0.000  0.00  0.00           H+0
HETATM   39  O   UNK     0      17.723   4.914   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       8.939   3.028   0.000  0.00  0.00           O+0
HETATM   41  H   UNK     0       7.850   1.939   0.000  0.00  0.00           H+0
HETATM   42  C   UNK     0       6.761   0.850   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.672  -0.239   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       8.249   0.451   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       8.647  -1.036   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       4.875   0.068   0.000  0.00  0.00           O+0
HETATM   47  H   UNK     0       3.335   0.068   0.000  0.00  0.00           H+0
HETATM   48  C   UNK     0       1.795   0.068   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.255   0.068   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       2.565  -1.265   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       1.795  -2.599   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -0.091   0.850   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -2.269   3.028   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -3.050   4.914   0.000  0.00  0.00           O+0
HETATM   55  H   UNK     0      -3.050   6.454   0.000  0.00  0.00           H+0
HETATM   56  C   UNK     0      -3.050   7.994   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -3.050   9.534   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -4.384   7.224   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -5.717   7.994   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      -2.269   9.880   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      -0.091  12.058   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -1.578  12.456   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -2.667  11.367   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      -1.977  13.944   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       4.105  11.505   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       4.875  12.839   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0       4.105  14.173   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0       2.565  14.173   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0       1.795  15.506   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0       2.565  16.840   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0       4.105  16.840   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0       4.875  15.506   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   65                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   61                                                  
CONECT    5    4    6   60                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   55   56                                             
CONECT    8    7    9   54                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   53                                                  
CONECT   11   10   12   52                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   47   48                                             
CONECT   14   13   15   46                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   41   42                                             
CONECT   17   16   18   40                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   32                                                  
CONECT   20   19   21   31                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   26   27                                             
CONECT   23   22   24   25                                                  
CONECT   24   23   65                                                       
CONECT   25   23                                                            
CONECT   26   22                                                            
CONECT   27   22   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   20                                                            
CONECT   32   19   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   17                                                            
CONECT   41   16                                                            
CONECT   42   16   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44                                                            
CONECT   46   14                                                            
CONECT   47   13                                                            
CONECT   48   13   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50                                                            
CONECT   52   11                                                            
CONECT   53   10                                                            
CONECT   54    8                                                            
CONECT   55    7                                                            
CONECT   56    7   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59                                                       
CONECT   59   58                                                            
CONECT   60    5                                                            
CONECT   61    4   62                                                       
CONECT   62   61   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62                                                            
CONECT   65    2   24   66                                                  
CONECT   66   65   67                                                       
CONECT   67   66   68   72                                                  
CONECT   68   67   69                                                       
CONECT   69   68   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70   72                                                       
CONECT   72   71   67                                                       
MASTER        0    0    0    0    0    0    0    0   72    0  146    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₉H₈₁N₉O₉

Average Mass

940.2410 Da

Monoisotopic Mass

939.61573 Da

IUPAC Name

N-{4-[(2S,5S,8R,11R,14S,17R,20S,23R)-8-benzyl-5,14,20,23-tetrakis[(2S)-butan-2-yl]-17-methyl-11-(2-methylpropyl)-3,6,9,12,15,18,21,24-octaoxo-1,4,7,10,13,16,19,22-octaazacyclotetracosan-2-yl]butyl}formamide

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]C(=O)NCCCC[C@@H]1NC(=O)[C@]([H])(NC(=O)[C@@]([H])(NC(=O)[C@@H](C)NC(=O)[C@@]([H])(NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@@]([H])(NC1=O)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)CC

InChI Identifier

InChI=1S/C49H81N9O9/c1-12-29(7)38-46(64)51-33(11)42(60)55-41(32(10)15-4)49(67)58-40(31(9)14-3)47(65)52-35(23-19-20-24-50-27-59)43(61)56-39(30(8)13-2)48(66)54-37(26-34-21-17-16-18-22-34)44(62)53-36(25-28(5)6)45(63)57-38/h16-18,21-22,27-33,35-41H,12-15,19-20,23-26H2,1-11H3,(H,50,59)(H,51,64)(H,52,65)(H,53,62)(H,54,66)(H,55,60)(H,56,61)(H,57,63)(H,58,67)/t29-,30-,31-,32-,33+,35-,36+,37+,38-,39-,40+,41-/m0/s1

InChI Key

KMCWUJZSHTUTAM-YNCQOOFJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	The University of Queensland	Angela Salim	2024-06-19	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	The University of Queensland	Angela Salim	2024-06-19	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	The University of Queensland	Angela Salim	2024-06-19	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	The University of Queensland	Angela Salim	2024-06-19	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	The University of Queensland	Angela Salim	2024-06-19	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	The University of Queensland	Angela Salim	2024-06-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	The University of Queensland	Angela Salim	2024-06-19	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	The University of Queensland	Angela Salim	2024-06-19	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces sp. CMB-M0112		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Cyclic alpha peptide
Leucine or derivatives
Isoleucine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alanine or derivatives
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
Fatty acyl
Benzenoid
N-acyl-amine
Fatty amide
Monocyclic benzene moiety
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.58	ChemAxon
pKa (Strongest Acidic)	11.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	261.9 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	253.32 m³·mol⁻¹	ChemAxon
Polarizability	103.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

DOI: 10.3390/md22070312

Showing NP-Card for acyl-surugamide A1 (NP0333433)

MOL for NP0333433 (acyl-surugamide A1)

3D MOL for NP0333433 (acyl-surugamide A1)

3D SDF for NP0333433 (acyl-surugamide A1)

3D-SDF for NP0333433 (acyl-surugamide A1)

PDB for NP0333433 (acyl-surugamide A1)

3D PDB for NP0333433 (acyl-surugamide A1)

SMILES for NP0333433 (acyl-surugamide A1)

INCHI for NP0333433 (acyl-surugamide A1)

Structure for NP0333433 (acyl-surugamide A1)

3D Structure for NP0333433 (acyl-surugamide A1)