NP-MRD: Showing NP-Card for acyl-surugamide A4 (NP0333435)

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Record Information

Version

2.0

Created at

2024-06-19 04:36:00 UTC

Updated at

2025-12-20 11:41:06 UTC

NP-MRD ID

NP0333435

Natural Product DOI

https://doi.org/10.57994/2877

Secondary Accession Numbers

None

Natural Product Identification

Common Name

acyl-surugamide A4

Description

Acyl-surugamide A4 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 A4.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03032307112D          

 74 75  0  0  1  0            999 V2000
    1.4627    6.4936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752    5.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2959    3.8979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4185    3.4854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4185    2.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv2104 03032307112D          

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    1.4627    6.4936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 14 48  2  0  0  0  0
 13 49  1  1  0  0  0
 13 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 11 54  2  0  0  0  0
 10 55  1  1  0  0  0
  8 56  2  0  0  0  0
  7 57  1  1  0  0  0
  7 58  1  0  0  0  0
 58 59  1  6  0  0  0
 58 60  1  0  0  0  0
 60 61  1  0  0  0  0
  5 62  2  0  0  0  0
  4 63  1  1  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 64 66  1  0  0  0  0
 67  2  1  0  0  0  0
 67 24  1  0  0  0  0
 67 68  1  1  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
 72 73  1  0  0  0  0
 73 74  2  0  0  0  0
 69 74  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333435

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C51H83N9O10/c1-13-29(7)39-48(67)53-33(11)43(62)57-42(32(10)16-4)51(70)60-41(31(9)15-3)49(68)54-36(24-20-21-25-52-44(63)34(12)61)45(64)58-40(30(8)14-2)50(69)56-38(27-35-22-18-17-19-23-35)46(65)55-37(26-28(5)6)47(66)59-39/h17-19,22-23,28-33,36-42H,13-16,20-21,24-27H2,1-12H3,(H,52,63)(H,53,67)(H,54,68)(H,55,65)(H,56,69)(H,57,62)(H,58,64)(H,59,66)(H,60,70)/t29-,30-,31-,32-,33+,36-,37+,38+,39-,40-,41+,42-/m0/s1

> <INCHI_KEY>
VQNCBRJZOFBNLF-LORDYLPKSA-N

> <FORMULA>
C51H83N9O10

> <MOLECULAR_WEIGHT>
982.278

> <EXACT_MASS>
981.626289909

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
153

> <JCHEM_AVERAGE_POLARIZABILITY>
107.60249003196301

> <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}-2-oxopropanamide

> <JCHEM_LOGP>
3.922705673000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.924796980995762

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.547400345262322

> <JCHEM_POLAR_SURFACE_AREA>
278.96999999999997

> <JCHEM_REFRACTIVITY>
263.16020000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <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}-2-oxopropanamide

> <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       2.730  12.121   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.500  10.788   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.730   9.454   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.243   9.853   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.154   8.764   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.552   7.276   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -0.781   6.506   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.781   4.966   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.552   4.196   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.154   2.709   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.243   1.620   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.730   2.018   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.500   0.685   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.040   0.685   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       5.810   2.018   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       7.298   1.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.387   2.709   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       7.988   4.196   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       9.322   4.966   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.322   6.506   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       7.988   7.276   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       8.387   8.764   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.298   9.853   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       5.810   9.454   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0       7.696  11.340   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0       8.785  10.251   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       9.874   9.162   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.273  10.650   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.963   8.073   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.451   8.472   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.656   7.276   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.656   4.196   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.989   4.966   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.323   4.196   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.657   4.966   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      15.990   4.196   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      17.324   4.966   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      18.658   4.196   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      19.991   4.966   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      18.658   2.656   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      17.324   6.506   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       9.874   2.310   0.000  0.00  0.00           O+0
HETATM   43  H   UNK     0       8.785   1.221   0.000  0.00  0.00           H+0
HETATM   44  C   UNK     0       7.696   0.132   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.607  -0.957   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       9.184  -0.266   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       9.583  -1.754   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       5.810  -0.649   0.000  0.00  0.00           O+0
HETATM   49  H   UNK     0       4.270  -0.649   0.000  0.00  0.00           H+0
HETATM   50  C   UNK     0       2.730  -0.649   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       1.190  -0.649   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       3.500  -1.983   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       2.730  -3.316   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       0.844   0.132   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -2.115   4.196   0.000  0.00  0.00           O+0
HETATM   57  H   UNK     0      -2.115   5.736   0.000  0.00  0.00           H+0
HETATM   58  C   UNK     0      -2.115   7.276   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -2.115   8.816   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      -3.449   6.506   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -4.782   7.276   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      -1.334   9.162   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0       0.844  11.340   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      -0.643  11.739   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      -1.732  10.650   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      -1.042  13.226   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0       5.040  10.788   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0       5.810  12.121   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0       5.040  13.455   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0       3.500  13.455   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0       2.730  14.789   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0       3.500  16.122   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0       5.040  16.122   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0       5.810  14.789   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   67                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   63                                                  
CONECT    5    4    6   62                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   57   58                                             
CONECT    8    7    9   56                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   55                                                  
CONECT   11   10   12   54                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   49   50                                             
CONECT   14   13   15   48                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   43   44                                             
CONECT   17   16   18   42                                                  
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   67                                                       
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   41                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   37                                                            
CONECT   42   17                                                            
CONECT   43   16                                                            
CONECT   44   16   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46                                                            
CONECT   48   14                                                            
CONECT   49   13                                                            
CONECT   50   13   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53                                                       
CONECT   53   52                                                            
CONECT   54   11                                                            
CONECT   55   10                                                            
CONECT   56    8                                                            
CONECT   57    7                                                            
CONECT   58    7   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61                                                       
CONECT   61   60                                                            
CONECT   62    5                                                            
CONECT   63    4   64                                                       
CONECT   64   63   65   66                                                  
CONECT   65   64                                                            
CONECT   66   64                                                            
CONECT   67    2   24   68                                                  
CONECT   68   67   69                                                       
CONECT   69   68   70   74                                                  
CONECT   70   69   71                                                       
CONECT   71   70   72                                                       
CONECT   72   71   73                                                       
CONECT   73   72   74                                                       
CONECT   74   73   69                                                       
MASTER        0    0    0    0    0    0    0    0   74    0  150    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₁H₈₃N₉O₁₀

Average Mass

982.2780 Da

Monoisotopic Mass

981.62629 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}-2-oxopropanamide

Traditional Name

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C51H83N9O10/c1-13-29(7)39-48(67)53-33(11)43(62)57-42(32(10)16-4)51(70)60-41(31(9)15-3)49(68)54-36(24-20-21-25-52-44(63)34(12)61)45(64)58-40(30(8)14-2)50(69)56-38(27-35-22-18-17-19-23-35)46(65)55-37(26-28(5)6)47(66)59-39/h17-19,22-23,28-33,36-42H,13-16,20-21,24-27H2,1-12H3,(H,52,63)(H,53,67)(H,54,68)(H,55,65)(H,56,69)(H,57,62)(H,58,64)(H,59,66)(H,60,70)/t29-,30-,31-,32-,33+,36-,37+,38+,39-,40-,41+,42-/m0/s1

InChI Key

VQNCBRJZOFBNLF-LORDYLPKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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

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
Lactam
Ketone
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	3.92	ChemAxon
pKa (Strongest Acidic)	11.55	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	278.97 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	263.16 m³·mol⁻¹	ChemAxon
Polarizability	107.6 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 A4 (NP0333435)

MOL for NP0333435 (acyl-surugamide A4)

3D MOL for NP0333435 (acyl-surugamide A4)

3D SDF for NP0333435 (acyl-surugamide A4)

3D-SDF for NP0333435 (acyl-surugamide A4)

PDB for NP0333435 (acyl-surugamide A4)

3D PDB for NP0333435 (acyl-surugamide A4)

SMILES for NP0333435 (acyl-surugamide A4)

INCHI for NP0333435 (acyl-surugamide A4)

Structure for NP0333435 (acyl-surugamide A4)

3D Structure for NP0333435 (acyl-surugamide A4)