NP-MRD: Showing NP-Card for (2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid (NP0145349)

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Record Information

Version

2.0

Created at

2022-09-02 00:31:51 UTC

Updated at

2022-09-02 00:31:51 UTC

NP-MRD ID

NP0145349

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid

Description

Manumycin A, also known as NSC 622141 or UCF 1C, belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Thus, manumycin a is considered to be a fatty amide. Manumycin A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid is found in Streptomyces griseoaurantiacus and Streptomyces parvulus. (2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid was first documented in 2020 (PMID: 33166494). Based on a literature review a small amount of articles have been published on manumycin A (PMID: 34200371) (PMID: 33719954) (PMID: 32344935) (PMID: 32298799).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022202312D          

 40 42  0  0  1  0            999 V2000
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 16 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309022202312D          

 40 42  0  0  1  0            999 V2000
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    5.1855   -2.6680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2461   -2.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9639   -1.8928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4942   -1.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2120   -0.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7423    0.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4602    0.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9905    1.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8029    1.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7083    2.3289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2386    2.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0390    3.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2741    4.0705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7387    4.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3706    3.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0616    2.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4988    2.2037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  4  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  2  0  0  0  0
 18 36  1  0  0  0  0
 36 37  1  6  0  0  0
 38 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 16 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0145349

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC[C@@H](C)\C=C(/C)\C=C(/C)C(O)=NC1=C[C@@](O)(\C=C\C=C\C=C\C(O)=NC2=C(O)CCC2=O)[C@@H]2O[C@@H]2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H38N2O7/c1-5-6-11-19(2)16-20(3)17-21(4)30(38)32-22-18-31(39,29-28(40-29)27(22)37)15-10-8-7-9-12-25(36)33-26-23(34)13-14-24(26)35/h7-10,12,15-19,28-29,34,39H,5-6,11,13-14H2,1-4H3,(H,32,38)(H,33,36)/b8-7+,12-9+,15-10+,20-16+,21-17+/t19-,28-,29-,31+/m1/s1

> <INCHI_KEY>
TWWQHCKLTXDWBD-MVTGTTCWSA-N

> <FORMULA>
C31H38N2O7

> <MOLECULAR_WEIGHT>
550.652

> <EXACT_MASS>
550.267901572

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
61.41779629421144

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E,6R)-N-[(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-C-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
4.695957824000001

> <ALOGPS_LOGS>
-5.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
6.16404196223336

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.5420822278399395

> <JCHEM_PKA_STRONGEST_BASIC>
2.012815160686508

> <JCHEM_POLAR_SURFACE_AREA>
152.31

> <JCHEM_REFRACTIVITY>
160.4515

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.43e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
manumycin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667 -10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334 -13.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001 -13.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668 -13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002 -10.780   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       8.002  -9.240   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.680  -4.980   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.659  -4.980   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.133  -3.533   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.123  -2.353   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.596  -0.906   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.586   0.273   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.059   1.721   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.049   2.900   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.565   2.633   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0      12.522   4.347   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      13.512   5.527   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.139   7.021   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.712   7.598   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.445   7.837   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.625   6.847   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.048   5.420   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      15.864   4.114   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.003  -8.470   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      10.669 -10.780   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   39                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20   36                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29   35                                                  
CONECT   35   34                                                            
CONECT   36   18   37   38                                                  
CONECT   37   36   38                                                       
CONECT   38   37   36   39                                                  
CONECT   39   38   16   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

View in JSmol

Synonyms

Value	Source
(-)-Manumycin a	ChEBI
(2E,4E,6R)-N-[(1S,5S,6R)-5-Hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-7-oxo-1,3,5-heptatrien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyl-2,4-decadienamide	ChEBI
Manumycin	ChEBI
NSC 622141	ChEBI
UCF 1C	ChEBI
UCF1-C	ChEBI

Chemical Formula

C₃₁H₃₈N₂O₇

Average Mass

550.6520 Da

Monoisotopic Mass

550.26790 Da

IUPAC Name

(2E,4E,6R)-N-[(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-C-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid

Traditional Name

manumycin

CAS Registry Number

Not Available

SMILES

CCCC[C@@H](C)\C=C(/C)\C=C(/C)C(O)=NC1=C[C@@](O)(\C=C\C=C\C=C\C(O)=NC2=C(O)CCC2=O)[C@@H]2O[C@@H]2C1=O

InChI Identifier

InChI=1S/C31H38N2O7/c1-5-6-11-19(2)16-20(3)17-21(4)30(38)32-22-18-31(39,29-28(40-29)27(22)37)15-10-8-7-9-12-25(36)33-26-23(34)13-14-24(26)35/h7-10,12,15-19,28-29,34,39H,5-6,11,13-14H2,1-4H3,(H,32,38)(H,33,36)/b8-7+,12-9+,15-10+,20-16+,21-17+/t19-,28-,29-,31+/m1/s1

InChI Key

TWWQHCKLTXDWBD-MVTGTTCWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces griseoaurantiacus	LOTUS Database	35616633
Streptomyces parvulus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
N-acyl-amine
Tertiary alcohol
Vinylogous acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Organopnictogen compound
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

fatty amide (CHEBI:29623 )

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	4.26	ALOGPS
logP	4.7	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	5.54	ChemAxon
pKa (Strongest Basic)	2.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	152.31 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	160.45 m³·mol⁻¹	ChemAxon
Polarizability	61.42 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

4942813

KEGG Compound ID

C12111

BioCyc ID

CPD-18768

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6438330

PDB ID

Not Available

ChEBI ID

29623

Good Scents ID

Not Available

References

General References

Sojka DR, Hasterok S, Vydra N, Toma-Jonik A, Wieczorek A, Gogler-Piglowska A, Scieglinska D: Inhibition of the Heat Shock Protein A (HSPA) Family Potentiates the Anticancer Effects of Manumycin A. Cells. 2021 Jun 7;10(6). pii: cells10061418. doi: 10.3390/cells10061418. [PubMed:34200371 ]
Silva LR, da Silva-Junior EF: Inhibiting the "Undruggable" RAS/Farnesyltransferase (FTase) Cancer Target by Manumycin-related Natural Products. Curr Med Chem. 2021 Mar 15. pii: CMC-EPUB-114887. doi: 10.2174/0929867328666210315123848. [PubMed:33719954 ]
Mofers A, Selvaraju K, Gubat J, D'Arcy P, Linder S: Identification of proteasome inhibitors using analysis of gene expression profiles. Eur J Pharmacol. 2020 Dec 15;889:173709. doi: 10.1016/j.ejphar.2020.173709. Epub 2020 Nov 6. [PubMed:33166494 ]
Hrdy J, Sukenikova L, Petraskova P, Novotna O, Kahoun D, Petricek M, Chronakova A, Petrickova K: Inhibition of Pro-Inflammatory Cytokines by Metabolites of Streptomycetes-A Potential Alternative to Current Anti-Inflammatory Drugs? Microorganisms. 2020 Apr 25;8(5). pii: microorganisms8050621. doi: 10.3390/microorganisms8050621. [PubMed:32344935 ]
Macejova M, Sackova V, Hradicka P, Jendzelovsky R, Demeckova V, Fedorocko P: Combination of photoactive hypericin and Manumycin A exerts multiple anticancer effects on oxaliplatin-resistant colorectal cells. Toxicol In Vitro. 2020 Aug;66:104860. doi: 10.1016/j.tiv.2020.104860. Epub 2020 Apr 13. [PubMed:32298799 ]
LOTUS database [Link]

Showing NP-Card for (2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid (NP0145349)

MOL for NP0145349 ((2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid)

3D MOL for NP0145349 ((2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid)

3D SDF for NP0145349 ((2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid)

3D-SDF for NP0145349 ((2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid)

PDB for NP0145349 ((2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid)

3D PDB for NP0145349 ((2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid)

SMILES for NP0145349 ((2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid)

INCHI for NP0145349 ((2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid)

Structure for NP0145349 ((2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid)

3D Structure for NP0145349 ((2e,4e,6r)-n-[(1s,5s,6r)-5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienimidic acid)