NP-MRD: Showing NP-Card for Xylomolone B (NP0084474)

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Record Information

Version

2.0

Created at

2022-04-29 05:11:58 UTC

Updated at

2022-04-29 05:11:58 UTC

NP-MRD ID

NP0084474

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xylomolone B

Description

Methyl (2R)-2-(acetyloxy)-2-[(1R,4bR,7S,8R,10aR,12aR)-1-(furan-3-yl)-7,9,9,12a-tetramethyl-3,6-dioxo-1,3,4b,5,6,7,8,9,10a,11,12,12a-dodecahydro-2,10-dioxatetraphen-8-yl]acetate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Xylomolone B is found in Xylocarpus moluccensis . Based on a literature review very few articles have been published on methyl (2R)-2-(acetyloxy)-2-[(1R,4bR,7S,8R,10aR,12aR)-1-(furan-3-yl)-7,9,9,12a-tetramethyl-3,6-dioxo-1,3,4b,5,6,7,8,9,10a,11,12,12a-dodecahydro-2,10-dioxatetraphen-8-yl]acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207112D          

 42 46  0  0  1  0            999 V2000
   -2.6835   -0.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4135   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9535   -1.9066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6835   -2.6861    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2236   -3.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0365   -4.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7429   -4.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3665   -3.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0456   -3.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4936   -2.5302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734   -2.8421    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4135   -3.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -3.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3333   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -1.4389    0.0000 C   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  1  0  0  0  0
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  7  8  1  0  0  0  0
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  5  9  1  0  0  0  0
  4 10  1  1  0  0  0
  4 11  1  0  0  0  0
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 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 11 41  1  0  0  0  0
 41 42  2  0  0  0  0
  2 42  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292207112D          

 42 46  0  0  1  0            999 V2000
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    2.9874   -3.7775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174   -2.9980    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9073   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5117   -3.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7797   -3.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0971   -0.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0169   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5231   -2.3743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7932   -1.5948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -1.4389    0.0000 C   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  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  9  1  0  0  0  0
  4 10  1  1  0  0  0
  4 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  2  0  0  0  0
 23 33  1  6  0  0  0
 23 34  1  0  0  0  0
 18 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 20 37  2  0  0  0  0
 19 38  1  0  0  0  0
 38 39  1  0  0  0  0
 15 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 11 41  1  0  0  0  0
 41 42  2  0  0  0  0
  2 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084474

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@]3(C)C(=CC(=O)O[C@@]3([H])C3=COC=C3)[C@@]1([H])CC1=C(O2)C(C)(C)[C@]([H])([C@@H](OC(C)=O)C(=O)OC)[C@H](C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O9/c1-14-22(24(27(33)34-6)36-15(2)30)28(3,4)26-18(23(14)32)11-17-19-12-21(31)38-25(16-8-10-35-13-16)29(19,5)9-7-20(17)37-26/h8,10,12-14,17,20,22,24-25H,7,9,11H2,1-6H3/t14-,17+,20+,22-,24+,25-,29+/m0/s1

> <INCHI_KEY>
SJCPKGIZJXDTCN-OYNJIYSRSA-N

> <FORMULA>
C29H34O9

> <MOLECULAR_WEIGHT>
526.582

> <EXACT_MASS>
526.220282675

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
56.043593127367316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2R)-2-(acetyloxy)-2-[(1R,4bR,7S,8R,10aR,12aR)-1-(furan-3-yl)-7,9,9,12a-tetramethyl-3,6-dioxo-1,3,4b,5,6,7,8,9,10a,11,12,12a-dodecahydro-2,10-dioxatetraphen-8-yl]acetate

> <ALOGPS_LOGP>
4.30

> <JCHEM_LOGP>
3.408900177666664

> <ALOGPS_LOGS>
-4.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.570516372675645

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.742135695202336

> <JCHEM_PKA_STRONGEST_BASIC>
-2.883691710188332

> <JCHEM_POLAR_SURFACE_AREA>
118.34

> <JCHEM_REFRACTIVITY>
134.91700000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(R)-(methyl (acetyloxy)[(1R,4bR,7S,8R,10aR,12aR)-1-(furan-3-yl)-7,9,9,12a-tetramethyl-3,6-dioxo-1,4b,5,7,8,10a,11,12-octahydro-2,10-dioxatetraphen-8-yl]acetate)

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -5.009  -0.940   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.505  -2.395   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.513  -3.559   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -5.009  -5.014   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.017  -6.178   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.668  -7.678   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.987  -8.474   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.151  -7.466   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.552  -6.047   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      -6.521  -4.723   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0      -3.497  -5.305   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.505  -6.469   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.993  -6.760   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.481  -7.051   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.472  -5.887   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       0.536  -4.723   0.000  0.00  0.00           H+0
HETATM   17  O   UNK     0       1.040  -6.178   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.048  -5.014   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.544  -3.559   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.552  -2.395   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.064  -2.686   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.072  -1.522   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.568  -4.141   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.081  -4.432   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.089  -3.268   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.601  -3.559   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.609  -2.395   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.105  -5.014   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.585  -5.887   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.097  -6.178   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.601  -7.633   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.577  -7.051   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0       5.072  -5.596   0.000  0.00  0.00           H+0
HETATM   34  C   UNK     0       3.560  -5.305   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.688  -6.353   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.322  -6.827   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.048  -0.940   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.032  -3.268   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.977  -4.432   0.000  0.00  0.00           C+0
HETATM   40  H   UNK     0      -1.481  -2.977   0.000  0.00  0.00           H+0
HETATM   41  C   UNK     0      -2.489  -4.141   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -2.993  -2.686   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   42                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10   11                                             
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    4                                                            
CONECT   11    4   12   13   41                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   39                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   34                                                  
CONECT   19   18   20   38                                                  
CONECT   20   19   21   37                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   33   34                                             
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29                                                            
CONECT   33   23                                                            
CONECT   34   23   18   35   36                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   20                                                            
CONECT   38   19   39                                                       
CONECT   39   38   15   40   41                                             
CONECT   40   39                                                            
CONECT   41   39   11   42                                                  
CONECT   42   41    2                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2R)-2-(acetyloxy)-2-[(1R,4BR,7S,8R,10ar,12ar)-1-(furan-3-yl)-7,9,9,12a-tetramethyl-3,6-dioxo-1,3,4b,5,6,7,8,9,10a,11,12,12a-dodecahydro-2,10-dioxatetraphen-8-yl]acetic acid	Generator

Chemical Formula

C₂₉H₃₄O₉

Average Mass

526.5820 Da

Monoisotopic Mass

526.22028 Da

IUPAC Name

methyl (2R)-2-(acetyloxy)-2-[(1R,4bR,7S,8R,10aR,12aR)-1-(furan-3-yl)-7,9,9,12a-tetramethyl-3,6-dioxo-1,3,4b,5,6,7,8,9,10a,11,12,12a-dodecahydro-2,10-dioxatetraphen-8-yl]acetate

Traditional Name

(R)-(methyl (acetyloxy)[(1R,4bR,7S,8R,10aR,12aR)-1-(furan-3-yl)-7,9,9,12a-tetramethyl-3,6-dioxo-1,4b,5,7,8,10a,11,12-octahydro-2,10-dioxatetraphen-8-yl]acetate)

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@]3(C)C(=CC(=O)O[C@@]3([H])C3=COC=C3)[C@@]1([H])CC1=C(O2)C(C)(C)[C@]([H])([C@@H](OC(C)=O)C(=O)OC)[C@H](C)C1=O

InChI Identifier

InChI=1S/C29H34O9/c1-14-22(24(27(33)34-6)36-15(2)30)28(3,4)26-18(23(14)32)11-17-19-12-21(31)38-25(16-8-10-35-13-16)29(19,5)9-7-20(17)37-26/h8,10,12-14,17,20,22,24-25H,7,9,11H2,1-6H3/t14-,17+,20+,22-,24+,25-,29+/m0/s1

InChI Key

SJCPKGIZJXDTCN-OYNJIYSRSA-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
Xylocarpus moluccensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Cyclohexenone
Dihydropyranone
Pyran
Heteroaromatic compound
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Furan
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.3	ALOGPS
logP	3.41	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	15.74	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	118.34 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	134.92 m³·mol⁻¹	ChemAxon
Polarizability	56.04 Å³	ChemAxon
Number of Rings	5	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

C00053906

Chemspider ID

71266951

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163184194

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Xylomolone B (NP0084474)

MOL for NP0084474 (Xylomolone B)

3D MOL for NP0084474 (Xylomolone B)

3D SDF for NP0084474 (Xylomolone B)

3D-SDF for NP0084474 (Xylomolone B)

PDB for NP0084474 (Xylomolone B)

3D PDB for NP0084474 (Xylomolone B)

SMILES for NP0084474 (Xylomolone B)

INCHI for NP0084474 (Xylomolone B)

Structure for NP0084474 (Xylomolone B)

3D Structure for NP0084474 (Xylomolone B)