NP-MRD: Showing NP-Card for Acyl-surugamide A2 (NP0333110)

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Record Information

Version

2.0

Created at

2024-05-09 01:27:06 UTC

Updated at

2025-12-20 11:41:06 UTC

NP-MRD ID

NP0333110

Natural Product DOI

https://doi.org/10.57994/2410

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acyl-surugamide A2

Description

Acyl-surugamide A2 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. Acyl-surugamide A2 was first documented in 2024 (PMID: 38611762). Based on a literature review very few articles have been published on Acyl-surugamide A2.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01212304032D          

 68 69  0  0  1  0            999 V2000
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M  END


  Mrv2104 01212304032D          

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M  END
> <DATABASE_ID>
NP0333110

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C50H83N9O9/c1-13-29(7)39-47(65)52-33(11)43(61)56-42(32(10)16-4)50(68)59-41(31(9)15-3)48(66)53-36(24-20-21-25-51-34(12)60)44(62)57-40(30(8)14-2)49(67)55-38(27-35-22-18-17-19-23-35)45(63)54-37(26-28(5)6)46(64)58-39/h17-19,22-23,28-33,36-42H,13-16,20-21,24-27H2,1-12H3,(H,51,60)(H,52,65)(H,53,66)(H,54,63)(H,55,67)(H,56,61)(H,57,62)(H,58,64)(H,59,68)/t29-,30-,31-,32-,33?,36-,37+,38+,39-,40-,41+,42-/m0/s1

> <INCHI_KEY>
AHEYSFSPGAVHHU-QQKAANEGSA-N

> <FORMULA>
C50H83N9O9

> <MOLECULAR_WEIGHT>
954.268

> <EXACT_MASS>
953.631375289

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
151

> <JCHEM_AVERAGE_POLARIZABILITY>
105.37629293868584

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{4-[(2S,5S,8R,11R,14S,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}acetamide

> <JCHEM_LOGP>
3.6334860053333355

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.947779572532447

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.572304643300757

> <JCHEM_POLAR_SURFACE_AREA>
261.9

> <JCHEM_REFRACTIVITY>
257.8142000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-{4-[(2S,5S,8R,11R,14S,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}acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-23         0                                  
HETATM    1  C   UNK     0       7.463  -2.714   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.374  -1.625   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.773  -0.138   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.260   0.261   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.886  -2.024   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.798  -0.935   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.310  -1.334   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.540  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.770  -1.334   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -2.258  -0.935   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.656   0.552   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.144   0.951   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.233  -0.138   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.542   2.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.346  -2.024   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -2.948  -3.512   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -4.282  -4.282   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.282  -5.822   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -2.948  -6.592   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -3.346  -8.079   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.834  -8.478   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.258  -9.168   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      -0.770  -8.769   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       0.000 -10.103   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.770 -11.437   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.310 -11.437   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000 -12.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.770 -14.104   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.540 -10.103   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       2.310  -8.769   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       3.798  -9.168   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.886  -8.079   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       4.488  -6.592   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       5.822  -5.822   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.155  -6.592   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.489  -5.822   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.823  -6.592   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.156  -5.822   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      12.490  -6.592   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      13.824  -5.822   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      15.157  -6.592   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      13.824  -4.282   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       6.374  -8.478   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       4.196 -10.656   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       3.107 -11.745   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.684 -11.054   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.082 -12.542   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       2.310 -11.437   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -2.656 -10.656   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -5.615  -6.592   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -5.615  -3.512   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -6.949  -4.282   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -5.615  -1.972   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -6.949  -1.202   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -4.834  -1.625   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      -0.770   1.334   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      -0.000   2.667   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -0.770   4.001   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -0.000   5.335   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       1.540   5.335   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0       4.196   0.552   0.000  0.00  0.00           O+0
HETATM   66  N   UNK     0       4.488  -3.512   0.000  0.00  0.00           N+0
HETATM   67  C   UNK     0       5.822  -4.282   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0       7.155  -3.512   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6   66                                                  
CONECT    6    5    7   65                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   58                                                  
CONECT    9    8   10   57                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17   56                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   52                                                  
CONECT   19   18   20   51                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   50                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   25   31   49                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   45                                                  
CONECT   33   32   34   44                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   67                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   33                                                            
CONECT   45   32   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47                                                            
CONECT   49   30                                                            
CONECT   50   23                                                            
CONECT   51   19                                                            
CONECT   52   18   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55                                                       
CONECT   55   54                                                            
CONECT   56   16                                                            
CONECT   57    9                                                            
CONECT   58    8   59                                                       
CONECT   59   58   60   64                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   59                                                       
CONECT   65    6                                                            
CONECT   66    5   67                                                       
CONECT   67   66   35   68                                                  
CONECT   68   67                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  138    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₀H₈₃N₉O₉

Average Mass

954.2680 Da

Monoisotopic Mass

953.63138 Da

IUPAC Name

N-{4-[(2S,5S,8R,11R,14S,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}acetamide

Traditional Name

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C50H83N9O9/c1-13-29(7)39-47(65)52-33(11)43(61)56-42(32(10)16-4)50(68)59-41(31(9)15-3)48(66)53-36(24-20-21-25-51-34(12)60)44(62)57-40(30(8)14-2)49(67)55-38(27-35-22-18-17-19-23-35)45(63)54-37(26-28(5)6)46(64)58-39/h17-19,22-23,28-33,36-42H,13-16,20-21,24-27H2,1-12H3,(H,51,60)(H,52,65)(H,53,66)(H,54,63)(H,55,67)(H,56,61)(H,57,62)(H,58,64)(H,59,68)/t29-,30-,31-,32-,33?,36-,37+,38+,39-,40-,41+,42-/m0/s1

InChI Key

AHEYSFSPGAVHHU-QQKAANEGSA-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
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
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	zachmaw@gmail.com	University of prince edward island	Zacharie Maw	2024-05-09	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	zachmaw@gmail.com	University of prince edward island	Zacharie Maw	2024-05-09	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	zachmaw@gmail.com	University of prince edward island	Zacharie Maw	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	zachmaw@gmail.com	University of prince edward island	Zacharie Maw	2024-05-09	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 599.8737042, C2D6OS, simulated)	zachmaw@gmail.com	University of Prince Edward Island	Zacharie Maw	2024-05-09	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Streptomyces albidoflavus		Not Available
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
Acetamide
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	3.63	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	257.81 m³·mol⁻¹	ChemAxon
Polarizability	105.38 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

Maw ZA, Haltli B, Guo JJ, Baldisseri DM, Cartmell C, Kerr RG: Discovery of Acyl-Surugamide A2 from Marine Streptomyces albidoflavus RKJM-0023-A New Cyclic Nonribosomal Peptide Containing an N-epsilon-acetyl-L-lysine Residue. Molecules. 2024 Mar 27;29(7):1482. doi: 10.3390/molecules29071482. [PubMed:38611762 ]
DOI: 10.3390/md22070312

Showing NP-Card for Acyl-surugamide A2 (NP0333110)

MOL for NP0333110 (Acyl-surugamide A2)

3D MOL for NP0333110 (Acyl-surugamide A2)

3D SDF for NP0333110 (Acyl-surugamide A2)

3D-SDF for NP0333110 (Acyl-surugamide A2)

PDB for NP0333110 (Acyl-surugamide A2)

3D PDB for NP0333110 (Acyl-surugamide A2)

SMILES for NP0333110 (Acyl-surugamide A2)

INCHI for NP0333110 (Acyl-surugamide A2)

Structure for NP0333110 (Acyl-surugamide A2)

3D Structure for NP0333110 (Acyl-surugamide A2)