NP-MRD: Showing NP-Card for 6-hydroxy-4-[(6e,8e)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3h-pyridin-2-one (NP0249836)

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Record Information

Version

2.0

Created at

2022-09-07 12:30:41 UTC

Updated at

2022-09-07 12:30:41 UTC

NP-MRD ID

NP0249836

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-hydroxy-4-[(6e,8e)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3h-pyridin-2-one

Description

9-Methylstreptimidone belongs to the class of organic compounds known as piperidinediones. Piperidinediones are compounds containing a piperidine ring which bears two ketones. 6-hydroxy-4-[(6e,8e)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3h-pyridin-2-one was first documented in 2006 (PMID: 16753783). Based on a literature review a significant number of articles have been published on 9-Methylstreptimidone (PMID: 30696946) (PMID: 34520340) (PMID: 25617668) (PMID: 23438151) (PMID: 23035360) (PMID: 22153343).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 47  0  0  0  0  0  0  0  0999 V2000
    5.2482   -3.0710   -3.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1663   -2.0206   -2.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8733   -1.3940   -1.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -0.3764   -1.7291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0650    0.0347   -2.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6581    0.1687   -0.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6723    1.2135   -0.2284 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5013    2.3779    0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7103    0.7275    0.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8573   -0.3855    1.2429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3569    1.6121    1.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3100    1.0507    2.2866 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2425    2.0265    2.6234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9673   -0.2365    1.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7405   -0.1503    0.6056 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9358    0.7881    0.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7620    0.3535    1.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2310    1.2232    2.6892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9671   -1.0314    2.0829 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233   -1.8842    1.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5938   -3.2453    1.6189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3098   -1.5631    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666   -2.9083   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8147   -2.9081   -3.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7679   -4.0629   -2.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6299   -1.7865   -3.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4743   -1.6998   -1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2181   -0.6684   -3.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7697    0.0061   -3.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7132    1.0810   -2.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2781   -0.1696    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1429    1.6442   -1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577    3.3248    0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3866    2.4671   -0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8948    2.1150    1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0974    2.5841    1.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0100    1.9734    0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7754    0.7959    3.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4792    2.0199    3.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039   -1.0569    1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791   -0.5870    2.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1808    0.1813   -0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5432    0.7753   -0.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6060    1.8108    0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1725   -3.7498    0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934   -2.3096    0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7379   -1.5858   -0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 22  1  0
 22 20  1  0
 20 21  1  0
 20 19  2  0
 19 17  1  0
 17 18  2  0
 17 16  1  0
 16 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  5 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  6
  8 33  1  0
  8 34  1  0
  8 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  1
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  6
 22 46  1  0
 22 47  1  0
 21 45  1  0
 16 43  1  0
 16 44  1  0
M  END


  Mrv1652309072214302D          

 22 22  0  0  0  0            999 V2000
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 15 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249836

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C(\C)=C\C(C)C(=O)CC(O)CC1CC(O)=NC(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H25NO4/c1-4-5-11(2)6-12(3)15(20)10-14(19)7-13-8-16(21)18-17(22)9-13/h4-6,12-14,19H,7-10H2,1-3H3,(H,18,21,22)/b5-4+,11-6+

> <INCHI_KEY>
ATUBIBZJAGAIBW-LJIKRCSCSA-N

> <FORMULA>
C17H25NO4

> <MOLECULAR_WEIGHT>
307.39

> <EXACT_MASS>
307.178358289

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
34.01582051729311

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-4-[(6E,8E)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-2,3,4,5-tetrahydropyridin-2-one

> <JCHEM_LOGP>
1.7592104339999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.905460793306109

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4113820678629723

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7666206556279525

> <JCHEM_POLAR_SURFACE_AREA>
86.96

> <JCHEM_REFRACTIVITY>
86.4083

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-4-[(6E,8E)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3H-pyridin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0      13.337  -9.240   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₅NO₄

Average Mass

307.3900 Da

Monoisotopic Mass

307.17836 Da

IUPAC Name

6-hydroxy-4-[(6E,8E)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-2,3,4,5-tetrahydropyridin-2-one

Traditional Name

6-hydroxy-4-[(6E,8E)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3H-pyridin-2-one

CAS Registry Number

Not Available

SMILES

C\C=C\C(\C)=C\C(C)C(=O)CC(O)CC1CC(O)=NC(=O)C1

InChI Identifier

InChI=1S/C17H25NO4/c1-4-5-11(2)6-12(3)15(20)10-14(19)7-13-8-16(21)18-17(22)9-13/h4-6,12-14,19H,7-10H2,1-3H3,(H,18,21,22)/b5-4+,11-6+

InChI Key

ATUBIBZJAGAIBW-LJIKRCSCSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperidinediones. Piperidinediones are compounds containing a piperidine ring which bears two ketones.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Piperidinones

Direct Parent

Piperidinediones

Alternative Parents

Substituents

Piperidinedione
Delta-lactam
Beta-hydroxy ketone
Carboxylic acid imide
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Secondary alcohol
Lactam
Ketone
Carboxylic acid derivative
Azacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	1.76	ChemAxon
pKa (Strongest Acidic)	3.41	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.96 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	86.41 m³·mol⁻¹	ChemAxon
Polarizability	34.02 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00016473

Chemspider ID

4900267

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6373950

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhao XL, Wang H, Xue ZL, Li JS, Qi H, Zhang H, Zhao T, Wang JD, Xiang WS: Two new glutarimide antibiotics from Streptomyces sp. HS-NF-780. J Antibiot (Tokyo). 2019 Apr;72(4):241-245. doi: 10.1038/s41429-019-0143-6. Epub 2019 Jan 29. [PubMed:30696946 ]
Jiang M, Xu X, Song J, Li D, Han L, Sun X, Guo L, Xiang W, Zhao J, Wang X: Streptomyces botrytidirepellens sp. nov., a novel actinomycete with antifungal activity against Botrytis cinerea. Int J Syst Evol Microbiol. 2021 Sep;71(9). doi: 10.1099/ijsem.0.005004. [PubMed:34520340 ]
Koide N, Kaneda A, Yokochi T, Umezawa K: Inhibition of RANKL- and LPS-induced osteoclast differentiations by novel NF-kappaB inhibitor DTCM-glutarimide. Int Immunopharmacol. 2015 Mar;25(1):162-8. doi: 10.1016/j.intimp.2015.01.004. Epub 2015 Jan 21. [PubMed:25617668 ]
Wang B, Song Y, Luo M, Chen Q, Ma J, Huang H, Ju J: Biosynthesis of 9-methylstreptimidone involves a new decarboxylative step for polyketide terminal diene formation. Org Lett. 2013 Mar 15;15(6):1278-81. doi: 10.1021/ol400224n. Epub 2013 Feb 25. [PubMed:23438151 ]
Takeiri M, Ota E, Nishiyama S, Kiyota H, Umezawa K: Structure-activity relationship of 9-methylstreptimidone, a compound that induces apoptosis selectively in adult T-cell leukemia cells. Oncol Res. 2012;20(1):7-14. doi: 10.3727/096504012x13425470196056. [PubMed:23035360 ]
Ota E, Takeiri M, Tachibana M, Ishikawa Y, Umezawa K, Nishiyama S: Synthesis and biological evaluation of molecular probes based on the 9-methylstreptimidone derivative DTCM-glutarimide. Bioorg Med Chem Lett. 2012 Jan 1;22(1):164-7. doi: 10.1016/j.bmcl.2011.11.045. Epub 2011 Nov 18. [PubMed:22153343 ]
Takeiri M, Tachibana M, Kaneda A, Ito A, Ishikawa Y, Nishiyama S, Goto R, Yamashita K, Shibasaki S, Hirokata G, Ozaki M, Todo S, Umezawa K: Inhibition of macrophage activation and suppression of graft rejection by DTCM-glutarimide, a novel piperidine derived from the antibiotic 9-methylstreptimidone. Inflamm Res. 2011 Sep;60(9):879-88. doi: 10.1007/s00011-011-0348-z. Epub 2011 May 28. [PubMed:21625968 ]
Ishikawa Y, Tachibana M, Matsui C, Obata R, Umezawa K, Nishiyama S: Synthesis and biological evaluation on novel analogs of 9-methylstreptimidone, an inhibitor of NF-kappaB. Bioorg Med Chem Lett. 2009 Mar 15;19(6):1726-8. doi: 10.1016/j.bmcl.2009.01.107. Epub 2009 Feb 5. [PubMed:19231181 ]
Cheng CL, Liu QY, Chen LH, Jin WZ, Si SY, Li DD: Isolation, structure determination and biological activity of a new glutarimide antibiotic, S632A3. J Asian Nat Prod Res. 2006 Jan-Mar;8(1-2):55-60. doi: 10.1080/10286020500382884. [PubMed:16753783 ]
LOTUS database [Link]

Showing NP-Card for 6-hydroxy-4-[(6e,8e)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3h-pyridin-2-one (NP0249836)

MOL for NP0249836 (6-hydroxy-4-[(6e,8e)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3h-pyridin-2-one)

3D MOL for NP0249836 (6-hydroxy-4-[(6e,8e)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3h-pyridin-2-one)

3D SDF for NP0249836 (6-hydroxy-4-[(6e,8e)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3h-pyridin-2-one)

3D-SDF for NP0249836 (6-hydroxy-4-[(6e,8e)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3h-pyridin-2-one)

PDB for NP0249836 (6-hydroxy-4-[(6e,8e)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3h-pyridin-2-one)

3D PDB for NP0249836 (6-hydroxy-4-[(6e,8e)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3h-pyridin-2-one)

SMILES for NP0249836 (6-hydroxy-4-[(6e,8e)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3h-pyridin-2-one)

INCHI for NP0249836 (6-hydroxy-4-[(6e,8e)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3h-pyridin-2-one)

Structure for NP0249836 (6-hydroxy-4-[(6e,8e)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3h-pyridin-2-one)

3D Structure for NP0249836 (6-hydroxy-4-[(6e,8e)-2-hydroxy-5,7-dimethyl-4-oxodeca-6,8-dien-1-yl]-4,5-dihydro-3h-pyridin-2-one)