NP-MRD: Showing NP-Card for Showdomycin (NP0006269)

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Record Information

Version

2.0

Created at

2020-12-09 03:18:25 UTC

Updated at

2021-07-15 16:54:19 UTC

NP-MRD ID

NP0006269

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Showdomycin

Provided By

NPAtlas

Description

Showdomycin belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. Showdomycin is found in Streptomyces lavendulae and Streptomyces showdoensis. Showdomycin was first documented in 1967 (PMID: 16591497). Based on a literature review very few articles have been published on Showdomycin (PMID: 34048627) (PMID: 28418235) (PMID: 26513594) (PMID: 25605563) (PMID: 20433172) (PMID: 19168426).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306242118263D          

 27 28  0  0  0  0            999 V2000
   -4.5303    1.3856   -1.6678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7084    0.7352   -0.9706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2984    1.0451   -0.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7417    0.1399    0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3401    0.0643    0.5041 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4242    1.0637   -0.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329    0.7235    0.2439 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6353    1.4401   -0.7397 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9807    1.1784   -0.5076 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8147   -0.7674    0.1065 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4891   -1.3237    1.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3545   -1.1871    0.0985 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2170   -2.2171    1.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -0.8218    0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6707   -1.8291    1.1177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0166   -0.4488   -0.2424 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7715    1.8930   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2557    0.1746    1.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9266    1.1019    1.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685    2.5349   -0.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3612    1.1312   -1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4923    1.9873   -0.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3180   -1.0408   -0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8771   -1.4558    1.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1152   -1.5344   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1542   -3.0369    0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9408   -0.9359   -0.1819 H   0  0  0  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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16  2  1  0  0  0  0
 12  5  1  0  0  0  0
  3 17  1  0  0  0  0
  5 18  1  1  0  0  0
  7 19  1  1  0  0  0
  8 20  1  0  0  0  0
  8 21  1  0  0  0  0
  9 22  1  0  0  0  0
 10 23  1  6  0  0  0
 11 24  1  0  0  0  0
 12 25  1  6  0  0  0
 13 26  1  0  0  0  0
 16 27  1  0  0  0  0
M  END

  Mrv1652306242118263D          

 27 28  0  0  0  0            999 V2000
   -4.5303    1.3856   -1.6678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7084    0.7352   -0.9706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2984    1.0451   -0.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7417    0.1399    0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3401    0.0643    0.5041 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4242    1.0637   -0.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329    0.7235    0.2439 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6353    1.4401   -0.7397 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9807    1.1784   -0.5076 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8147   -0.7674    0.1065 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4891   -1.3237    1.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3545   -1.1871    0.0985 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2170   -2.2171    1.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -0.8218    0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6707   -1.8291    1.1177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0166   -0.4488   -0.2424 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7715    1.8930   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2557    0.1746    1.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9266    1.1019    1.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685    2.5349   -0.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3612    1.1312   -1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4923    1.9873   -0.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3180   -1.0408   -0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8771   -1.4558    1.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1152   -1.5344   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1542   -3.0369    0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9408   -0.9359   -0.1819 H   0  0  0  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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16  2  1  0  0  0  0
 12  5  1  0  0  0  0
  3 17  1  0  0  0  0
  5 18  1  1  0  0  0
  7 19  1  1  0  0  0
  8 20  1  0  0  0  0
  8 21  1  0  0  0  0
  9 22  1  0  0  0  0
 10 23  1  6  0  0  0
 11 24  1  0  0  0  0
 12 25  1  6  0  0  0
 13 26  1  0  0  0  0
 16 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006269

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(C2=C([H])C(=O)N([H])C2=O)[C@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H11NO6/c11-2-4-6(13)7(14)8(16-4)3-1-5(12)10-9(3)15/h1,4,6-8,11,13-14H,2H2,(H,10,12,15)/t4-,6-,7-,8+/m1/s1

> <INCHI_KEY>
FFLUMYXAPXARJP-JBBNEOJLSA-N

> <FORMULA>
C9H11NO6

> <MOLECULAR_WEIGHT>
229.188

> <EXACT_MASS>
229.058637078

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.86884340083029

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,5-dihydro-1H-pyrrole-2,5-dione

> <ALOGPS_LOGP>
-1.77

> <JCHEM_LOGP>
-2.8807597879999998

> <ALOGPS_LOGS>
0.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.788431811118176

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.891606787598995

> <JCHEM_PKA_STRONGEST_BASIC>
-2.979199673368492

> <JCHEM_POLAR_SURFACE_AREA>
116.09

> <JCHEM_REFRACTIVITY>
49.8231

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.67e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrrole-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -4.530   1.386  -1.668  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.708   0.735  -0.971  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.298   1.045  -0.763  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.742   0.140   0.032  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.340   0.064   0.504  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.424   1.064  -0.091  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.733   0.724   0.244  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.635   1.440  -0.740  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.981   1.178  -0.508  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.815  -0.767   0.107  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.489  -1.324   1.180  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.355  -1.187   0.099  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.217  -2.217   1.023  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.779  -0.822   0.387  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.671  -1.829   1.118  0.00  0.00           O+0
HETATM   16  N   UNK     0      -4.017  -0.449  -0.242  0.00  0.00           N+0
HETATM   17  H   UNK     0      -1.772   1.893  -1.192  0.00  0.00           H+0
HETATM   18  H   UNK     0      -0.256   0.175   1.603  0.00  0.00           H+0
HETATM   19  H   UNK     0       1.927   1.102   1.249  0.00  0.00           H+0
HETATM   20  H   UNK     0       2.469   2.535  -0.686  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.361   1.131  -1.771  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.492   1.987  -0.753  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.318  -1.041  -0.842  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.877  -1.456   1.935  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.115  -1.534  -0.915  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.154  -3.037   0.633  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.941  -0.936  -0.182  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6   12   18                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   10   19                                             
CONECT    8    7    9   20   21                                             
CONECT    9    8   22                                                       
CONECT   10    7   11   12   23                                             
CONECT   11   10   24                                                       
CONECT   12   10   13    5   25                                             
CONECT   13   12   26                                                       
CONECT   14    4   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    2   27                                                  
CONECT   17    3                                                            
CONECT   18    5                                                            
CONECT   19    7                                                            
CONECT   20    8                                                            
CONECT   21    8                                                            
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   12                                                            
CONECT   26   13                                                            
CONECT   27   16                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₉H₁₁NO₆

Average Mass

229.1880 Da

Monoisotopic Mass

229.05864 Da

IUPAC Name

3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,5-dihydro-1H-pyrrole-2,5-dione

Traditional Name

3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrrole-2,5-dione

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)C1=CC(=O)NC1=O

InChI Identifier

InChI=1S/C9H11NO6/c11-2-4-6(13)7(14)8(16-4)3-1-5(12)10-9(3)15/h1,4,6-8,11,13-14H,2H2,(H,10,12,15)/t4-,6-,7-,8+/m1/s1

InChI Key

FFLUMYXAPXARJP-JBBNEOJLSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 lavendulae	LOTUS Database	35616633
Streptomyces showdoensis	NPAtlas	16591497

Species Where Detected

Species Name	Source	Reference
Streptomyces showdoensis n. sp.	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
Pentose monosaccharide
Maleimide
Monosaccharide
Carboxylic acid imide
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Pyrroline
Tetrahydrofuran
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Alcohol
Primary alcohol
Organopnictogen compound
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	-1.8	ALOGPS
logP	-2.9	ChemAxon
logS	0.07	ALOGPS
pKa (Strongest Acidic)	9.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	49.82 m³·mol⁻¹	ChemAxon
Polarizability	20.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA012925

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018717

Chemspider ID

26074

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

28032

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Darnall KR, Townsend LB, Robins RK: The structure of showdomycin, a novel carbon-linked nucleoside antibiotic related to uridine. Proc Natl Acad Sci U S A. 1967 Mar;57(3):548-53. doi: 10.1073/pnas.57.3.548. [PubMed:16591497 ]
Ren D, Kim M, Wang SA, Liu HW: Identification of a Pyrrole Intermediate Which Undergoes C-Glycosidation and Autoxidation to Yield the Final Product in Showdomycin Biosynthesis. Angew Chem Int Ed Engl. 2021 Jul 26;60(31):17148-17154. doi: 10.1002/anie.202105667. Epub 2021 Jun 24. [PubMed:34048627 ]
Palmu K, Rosenqvist P, Thapa K, Ilina Y, Siitonen V, Baral B, Makinen J, Belogurov G, Virta P, Niemi J, Metsa-Ketela M: Discovery of the Showdomycin Gene Cluster from Streptomyces showdoensis ATCC 15227 Yields Insight into the Biosynthetic Logic of C-Nucleoside Antibiotics. ACS Chem Biol. 2017 Jun 16;12(6):1472-1477. doi: 10.1021/acschembio.7b00078. Epub 2017 Apr 27. [PubMed:28418235 ]
De Clercq E: C-Nucleosides To Be Revisited. J Med Chem. 2016 Mar 24;59(6):2301-11. doi: 10.1021/acs.jmedchem.5b01157. Epub 2015 Oct 29. [PubMed:26513594 ]
Rudolf GC, Koch MF, Mandl FA, Sieber SA: Subclass-specific labeling of protein-reactive natural products with customized nucleophilic probes. Chemistry. 2015 Feb 23;21(9):3701-7. doi: 10.1002/chem.201405009. Epub 2015 Jan 21. [PubMed:25605563 ]
Bottcher T, Sieber SA: Showdomycin as a versatile chemical tool for the detection of pathogenesis-associated enzymes in bacteria. J Am Chem Soc. 2010 May 26;132(20):6964-72. doi: 10.1021/ja909150y. [PubMed:20433172 ]
Naz A, Bano K, Bano F, Ghafoor NA, Akhtar N: Conformational analysis (geometry optimization) of nucleosidic antitumor antibiotic showdomycin by Arguslab 4 software. Pak J Pharm Sci. 2009 Jan;22(1):78-82. [PubMed:19168426 ]

Showing NP-Card for Showdomycin (NP0006269)

MOL for NP0006269 (Showdomycin)

3D MOL for NP0006269 (Showdomycin)

3D SDF for NP0006269 (Showdomycin)

3D-SDF for NP0006269 (Showdomycin)

PDB for NP0006269 (Showdomycin)

3D PDB for NP0006269 (Showdomycin)

SMILES for NP0006269 (Showdomycin)

INCHI for NP0006269 (Showdomycin)

Structure for NP0006269 (Showdomycin)

3D Structure for NP0006269 (Showdomycin)