NP-MRD: Showing NP-Card for (2e,4e,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid (NP0202665)

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Record Information

Version

2.0

Created at

2022-09-04 21:55:30 UTC

Updated at

2022-09-04 21:55:30 UTC

NP-MRD ID

NP0202665

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4e,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid

Description

Asukamycin, also known as AM 1042, 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, asukamycin is considered to be a fatty amide. Asukamycin 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,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid is found in Apis cerana, Streptomyces nodosus and Streptomyces nodosus. (2e,4e,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid was first documented in 1986 (PMID: 3553432). Based on a literature review a significant number of articles have been published on asukamycin (PMID: 24838618) (PMID: 32344935) (PMID: 35218125) (PMID: 30696899) (PMID: 20522559) (PMID: 23995809).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042223552D          

 40 43  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042223552D          

 40 43  0  0  1  0            999 V2000
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    4.7631   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4776   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1921   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9066   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6210   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3355   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0500   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7644   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4789   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4789   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7644   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0500   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  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  0  0  0  0
  5  7  2  0  0  0  0
  2  7  1  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 20  1  4  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 20 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  1  0  0  0
 40 39  1  1  0  0  0
 38 40  1  0  0  0  0
 17 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0202665

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(\C=C\C=C\C=C\[C@]1(O)C=C(N=C(O)\C=C\C=C\C=C\C2CCCCC2)C(=O)[C@H]2O[C@@H]12)=NC1=C(O)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H34N2O7/c34-23-17-18-24(35)27(23)33-26(37)16-10-3-4-11-19-31(39)20-22(28(38)29-30(31)40-29)32-25(36)15-9-2-1-6-12-21-13-7-5-8-14-21/h1-4,6,9-12,15-16,19-21,29-30,34,39H,5,7-8,13-14,17-18H2,(H,32,36)(H,33,37)/b2-1+,4-3+,12-6+,15-9+,16-10+,19-11+/t29-,30-,31+/m1/s1

> <INCHI_KEY>
SSHVAUUEPNULMP-JHWDTTIQSA-N

> <FORMULA>
C31H34N2O7

> <MOLECULAR_WEIGHT>
546.62

> <EXACT_MASS>
546.236601443

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
60.75563598664883

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E,6E)-7-[(1R,2S,6S)-4-{[(2E,4E,6E)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-N-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid

> <JCHEM_LOGP>
4.120535833666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
6.162943549289844

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.541365786998944

> <JCHEM_PKA_STRONGEST_BASIC>
2.007854328730956

> <JCHEM_POLAR_SURFACE_AREA>
152.31

> <JCHEM_REFRACTIVITY>
160.3288

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
asukamycin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0      14.106   9.210   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      15.533   8.633   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.839   9.449   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.019   8.459   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.442   7.031   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      18.258   5.725   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      15.906   7.139   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      14.916   5.959   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      13.400   6.227   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.873   7.674   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.410   5.047   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.893   5.314   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.903   4.135   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.387   4.402   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.397   3.222   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.880   3.490   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.890   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.900   3.490   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.224   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.224   0.000   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       7.558  -0.770   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       7.558  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.224  -3.080   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.891  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.225  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.559  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.892  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.226  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.560  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.893  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      18.227  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      19.561  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      19.561  -4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      18.227  -5.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.893  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.890  -0.770   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.890  -2.310   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.556   0.000   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.223   0.770   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       3.556   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   40                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   36                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   20   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38   40                                                       
CONECT   40   39   38   17                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
AM 1042	ChEBI
Asukamycin a1	ChEBI

Chemical Formula

C₃₁H₃₄N₂O₇

Average Mass

546.6200 Da

Monoisotopic Mass

546.23660 Da

IUPAC Name

(2E,4E,6E)-7-[(1R,2S,6S)-4-{[(2E,4E,6E)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-N-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid

Traditional Name

asukamycin

CAS Registry Number

Not Available

SMILES

OC(\C=C\C=C\C=C\[C@]1(O)C=C(N=C(O)\C=C\C=C\C=C\C2CCCCC2)C(=O)[C@H]2O[C@@H]12)=NC1=C(O)CCC1=O

InChI Identifier

InChI=1S/C31H34N2O7/c34-23-17-18-24(35)27(23)33-26(37)16-10-3-4-11-19-31(39)20-22(28(38)29-30(31)40-29)32-25(36)15-9-2-1-6-12-21-13-7-5-8-14-21/h1-4,6,9-12,15-16,19-21,29-30,34,39H,5,7-8,13-14,17-18H2,(H,32,36)(H,33,37)/b2-1+,4-3+,12-6+,15-9+,16-10+,19-11+/t29-,30-,31+/m1/s1

InChI Key

SSHVAUUEPNULMP-JHWDTTIQSA-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
Apis cerana	LOTUS Database	35616633
Streptomyces nodosus	LOTUS Database	35616633
Streptomyces nodosus subsp. asukaensis	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

epoxide (CHEBI:73481 )
enamide (CHEBI:73481 )
polyketide (CHEBI:73481 )
organic heterobicyclic compound (CHEBI:73481 )

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	4.12	ChemAxon
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	10	ChemAxon
Refractivity	160.33 m³·mol⁻¹	ChemAxon
Polarizability	60.76 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

C00018105

Chemspider ID

4945243

KEGG Compound ID

C12099

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6441014

PDB ID

Not Available

ChEBI ID

73481

Good Scents ID

Not Available

References

General References

Petrickova K, Pospisil S, Kuzma M, Tylova T, Jagr M, Tomek P, Chronakova A, Brabcova E, Andera L, Kristufek V, Petricek M: Biosynthesis of colabomycin E, a new manumycin-family metabolite, involves an unusual chain-length factor. Chembiochem. 2014 Jun 16;15(9):1334-45. doi: 10.1002/cbic.201400068. Epub 2014 May 18. [PubMed:24838618 ]
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 ]
Yan X, Zhang J, Tan H, Liu Z, Jiang K, Tian W, Zheng M, Lin Z, Deng Z, Qu X: A Pair of Atypical KAS III Homologues with Initiation and Elongation Functions Program the Polyketide Biosynthesis in Asukamycin. Angew Chem Int Ed Engl. 2022 May 2;61(19):e202200879. doi: 10.1002/anie.202200879. Epub 2022 Mar 10. [PubMed:35218125 ]
Hu D, Gao C, Sun C, Jin T, Fan G, Mok KM, Lee SM: Genome-guided and mass spectrometry investigation of natural products produced by a potential new actinobacterial strain isolated from a mangrove ecosystem in Futian, Shenzhen, China. Sci Rep. 2019 Jan 29;9(1):823. doi: 10.1038/s41598-018-37475-w. [PubMed:30696899 ]
Rui Z, Petrickova K, Skanta F, Pospisil S, Yang Y, Chen CY, Tsai SF, Floss HG, Petricek M, Yu TW: Biochemical and genetic insights into asukamycin biosynthesis. J Biol Chem. 2010 Aug 6;285(32):24915-24. doi: 10.1074/jbc.M110.128850. Epub 2010 Jun 3. [PubMed:20522559 ]
Ito T: [Biosynthetic study of actinomycetes-metabolites for creating novel analogs]. Yakugaku Zasshi. 2013;133(9):1007-15. doi: 10.1248/yakushi.13-00175. [PubMed:23995809 ]
Rui Z, Sandy M, Jung B, Zhang W: Tandem enzymatic oxygenations in biosynthesis of epoxyquinone pharmacophore of manumycin-type metabolites. Chem Biol. 2013 Jul 25;20(7):879-87. doi: 10.1016/j.chembiol.2013.05.006. [PubMed:23890006 ]
Bai L: Tandem modifications of an epoxyquinone C7N pharmacophore. Chem Biol. 2013 Jul 25;20(7):859-60. doi: 10.1016/j.chembiol.2013.07.003. [PubMed:23890003 ]
Xie P, Sheng Y, Ito T, Mahmud T: Transcriptional regulation and increased production of asukamycin in engineered Streptomyces nodosus subsp. asukaensis strains. Appl Microbiol Biotechnol. 2012 Oct;96(2):451-60. doi: 10.1007/s00253-012-4084-2. Epub 2012 May 5. [PubMed:22555913 ]
Pospisil S, Petrickova K, Sedmera P, Halada P, Olsovska J, Petricek M: Effect of starter unit availability on the spectrum of manumycin-type metabolites produced by Streptomyces nodosus ssp. asukaensis. J Appl Microbiol. 2011 Nov;111(5):1116-28. doi: 10.1111/j.1365-2672.2011.05132.x. Epub 2011 Sep 8. [PubMed:21854515 ]
Shipley PR, Donnelly CC, Le CH, Bernauer AD, Klegeris A: Antitumor activity of asukamycin, a secondary metabolite from the actinomycete bacterium Streptomyces nodosus subspecies asukaensis. Int J Mol Med. 2009 Nov;24(5):711-5. doi: 10.3892/ijmm_00000283. [PubMed:19787206 ]
Petricek M, Petrickova K, Havlicek L, Felsberg J: Occurrence of two 5-aminolevulinate biosynthetic pathways in Streptomyces nodosus subsp. asukaensis is linked with the production of asukamycin. J Bacteriol. 2006 Jul;188(14):5113-23. doi: 10.1128/JB.01919-05. [PubMed:16816183 ]
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LOTUS database [Link]

Showing NP-Card for (2e,4e,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid (NP0202665)

MOL for NP0202665 ((2e,4e,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid)

3D MOL for NP0202665 ((2e,4e,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid)

3D SDF for NP0202665 ((2e,4e,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid)

3D-SDF for NP0202665 ((2e,4e,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid)

PDB for NP0202665 ((2e,4e,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid)

3D PDB for NP0202665 ((2e,4e,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid)

SMILES for NP0202665 ((2e,4e,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid)

INCHI for NP0202665 ((2e,4e,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid)

Structure for NP0202665 ((2e,4e,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid)

3D Structure for NP0202665 ((2e,4e,6e)-7-[(1r,2s,6s)-4-{[(2e,4e,6e)-7-cyclohexyl-1-hydroxyhepta-2,4,6-trien-1-ylidene]amino}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienimidic acid)