NP-MRD: Showing NP-Card for Oxandrastin A (NP0331323)

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Record Information

Version

2.0

Created at

2022-12-22 20:01:19 UTC

Updated at

2026-02-11 21:11:04 UTC

NP-MRD ID

NP0331323

Natural Product DOI

https://doi.org/10.57994/0243

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oxandrastin A

Description

Oxandrastin A was first documented in 2021 (PMID: 34885725).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652312222221012D          

 40 43  0  0  1  0            999 V2000
    6.6328    1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6353    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7026   -0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4223   -1.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542   -2.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6102   -1.7701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3875    1.8191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1721    1.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2027   -0.0231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6421   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2737    1.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713    2.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3748    2.0599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7902    1.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607    0.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    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
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  2  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 28 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END


  Mrv1652312222221012D          

 40 43  0  0  1  0            999 V2000
    6.6328    1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6353    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7026   -0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4223   -1.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542   -2.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6102   -1.7701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3875    1.8191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1721    1.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2027   -0.0231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6421   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2737    1.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713    2.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3748    2.0599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7902    1.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607    0.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    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
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  2  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 28 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331323

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC[C@@]3(C)[C@@]([H])(C=C(C)[C@@]4(C)C(=O)C(C)=C(O)[C@@]34C(=O)OC)[C@]1(C)C[C@H](OC(C)=O)[C@H](OC(C)=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O8/c1-15-13-21-27(7)14-19(37-17(3)31)24(38-18(4)32)26(5,6)20(27)11-12-28(21,8)30(25(35)36-10)23(34)16(2)22(33)29(15,30)9/h13,19-21,24,34H,11-12,14H2,1-10H3/t19-,20+,21-,24-,27+,28-,29-,30+/m0/s1

> <INCHI_KEY>
ADSMLNLFVFIIIP-AQYOGRKJSA-N

> <FORMULA>
C30H42O8

> <MOLECULAR_WEIGHT>
530.658

> <EXACT_MASS>
530.287968312

$$$$

HEADER    PROTEIN                                 22-DEC-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-DEC-22         0                                  
HETATM    1  C   UNK     0      12.381   2.992   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.519   3.664   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.067   0.406   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.028  -1.314   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.512  -1.585   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.988  -3.033   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.981  -4.210   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.472  -3.304   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0      10.057   3.396   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.921   2.832   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       5.978  -0.043   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.932  -2.940   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.355   2.629   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.244   3.696   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.613   5.192   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.300   3.845   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.342   3.559   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.047   1.738   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.978  -1.480   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   17                                             
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16   17   23                                             
CONECT   16   15                                                            
CONECT   17   15    2   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   30                                             
CONECT   22   21                                                            
CONECT   23   21   15   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   39                                             
CONECT   29   28                                                            
CONECT   30   28   21   31   35                                             
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31                                                            
CONECT   35   30   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   28   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂O₈

Average Mass

530.6580 Da

Monoisotopic Mass

530.28797 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

[H][C@]12CC[C@@]3(C)[C@@]([H])(C=C(C)[C@@]4(C)C(=O)C(C)=C(O)[C@@]34C(=O)OC)[C@]1(C)C[C@H](OC(C)=O)[C@H](OC(C)=O)C2(C)C

InChI Identifier

InChI=1S/C30H42O8/c1-15-13-21-27(7)14-19(37-17(3)31)24(38-18(4)32)26(5,6)20(27)11-12-28(21,8)30(25(35)36-10)23(34)16(2)22(33)29(15,30)9/h13,19-21,24,34H,11-12,14H2,1-10H3/t19-,20+,21-,24-,27+,28-,29-,30+/m0/s1

InChI Key

ADSMLNLFVFIIIP-AQYOGRKJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2022-12-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2022-12-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2022-12-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2022-12-22	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.0, Methanol-d4, simulated)	[email protected]	Not Available	Not Available	2026-02-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.0, Methanol-d4, simulated)	[email protected]	Not Available	Not Available	2026-02-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Penicillium sp. CMB-MD14		Not Available

Chemical Taxonomy

Classification

Not classified

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

External Links

Not Available

References

General References

Showing NP-Card for Oxandrastin A (NP0331323)

MOL for NP0331323 (Oxandrastin A)

3D MOL for NP0331323 (Oxandrastin A)

3D SDF for NP0331323 (Oxandrastin A)

3D-SDF for NP0331323 (Oxandrastin A)

PDB for NP0331323 (Oxandrastin A)

3D PDB for NP0331323 (Oxandrastin A)

SMILES for NP0331323 (Oxandrastin A)

INCHI for NP0331323 (Oxandrastin A)

Structure for NP0331323 (Oxandrastin A)

3D Structure for NP0331323 (Oxandrastin A)