NP-MRD: Showing NP-Card for Asperdole M (NP0350918)

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Record Information

Version

2.0

Created at

2025-04-06 15:02:28 UTC

Updated at

2025-07-25 01:04:05 UTC

NP-MRD ID

NP0350918

Natural Product DOI

https://doi.org/10.57994/3903

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asperdole M

Description

Based on a literature review very few articles have been published on Asperdole M.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01172317282D          

 34 37  0  0  1  0            999 V2000
    3.0136   -5.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3296   -6.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8447   -7.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1802   -7.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6953   -8.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8748   -8.3995    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3899   -9.0669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393   -7.6458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0338   -7.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1936   -6.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795   -5.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1800   -5.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4074   -6.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7531   -5.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1447   -8.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0242   -6.9784    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2037   -6.8921    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6886   -6.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1736   -5.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9027   -6.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9940   -5.6435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8145   -5.7297    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4790   -4.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.2224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -3.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -4.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -3.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -3.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -2.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -3.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585   -3.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8335   -3.5549    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  6  0  0  0
  8  6  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  8 15  1  6  0  0  0
  8 16  1  0  0  0  0
 16  3  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 20  1  0  0  0  0
 21  2  1  0  0  0  0
 21 19  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 26 31  2  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
 24 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END


  Mrv2104 01172317282D          

 34 37  0  0  1  0            999 V2000
    3.0136   -5.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3296   -6.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8447   -7.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1802   -7.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6953   -8.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8748   -8.3995    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3899   -9.0669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393   -7.6458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0338   -7.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1936   -6.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795   -5.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1800   -5.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4074   -6.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7531   -5.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1447   -8.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0242   -6.9784    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2037   -6.8921    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6886   -6.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1736   -5.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9027   -6.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9940   -5.6435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8145   -5.7297    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4790   -4.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.2224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -3.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -4.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -3.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -3.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -2.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -3.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585   -3.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8335   -3.5549    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  6  0  0  0
  8  6  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  8 15  1  6  0  0  0
  8 16  1  0  0  0  0
 16  3  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 20  1  0  0  0  0
 21  2  1  0  0  0  0
 21 19  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 26 31  2  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
 24 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0350918

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(C[C@]2(O)C(=O)NC3=C2C=CC=C3)CC[C@]2([H])C(=CC[C@H](O)[C@@]2(C)CCC=C(C)C)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H39NO3/c1-18(2)9-8-16-27(5)21-13-12-19(26(3,4)20(21)14-15-24(27)30)17-28(32)22-10-6-7-11-23(22)29-25(28)31/h6-7,9-11,14,19,21,24,30,32H,8,12-13,15-17H2,1-5H3,(H,29,31)/t19-,21+,24-,27-,28+/m0/s1

> <INCHI_KEY>
PTPIUTLSTVYCQI-PAVGVHNBSA-N

> <FORMULA>
C28H39NO3

> <MOLECULAR_WEIGHT>
437.624

> <EXACT_MASS>
437.29299412

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.70522285780752

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-{[(2S,4aR,5S,6S)-6-hydroxy-1,1,5-trimethyl-5-(4-methylpent-3-en-1-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-yl]methyl}-3-hydroxy-2,3-dihydro-1H-indol-2-one

> <JCHEM_LOGP>
5.110653640333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.789522754113966

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.666254153977176

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7117097977657645

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
132.02329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-{[(2S,4aR,5S,6S)-6-hydroxy-1,1,5-trimethyl-5-(4-methylpent-3-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-2-yl]methyl}-3-hydroxy-1H-indol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JAN-23         0                                  
HETATM    1  C   UNK     0       5.625 -11.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.349 -11.941   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.443 -13.187   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.070 -14.594   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.165 -15.840   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.633 -15.679   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.728 -16.925   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.007 -14.272   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.063 -13.164   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.361 -11.684   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.708 -10.576   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.203 -10.949   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.627 -12.429   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.272  -9.841   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.270 -15.133   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.912 -13.026   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       0.380 -12.865   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       1.285 -11.619   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.191 -10.374   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.418 -13.049   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.722 -10.535   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       5.254 -10.695   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       4.627  -9.289   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -7.882   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -8.652   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.466  -7.406   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.799  -8.176   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.133  -7.406   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.133  -5.866   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.799  -5.096   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.466  -5.866   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       3.096  -6.636   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.556  -6.636   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20   21                                             
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   15   16                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    8                                                            
CONECT   16    8    3   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   21                                                       
CONECT   20    2                                                            
CONECT   21    2   19   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26   33                                             
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   26   30   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   24   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₉NO₃

Average Mass

437.6240 Da

Monoisotopic Mass

437.29299 Da

IUPAC Name

(3R)-3-{[(2S,4aR,5S,6S)-6-hydroxy-1,1,5-trimethyl-5-(4-methylpent-3-en-1-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-yl]methyl}-3-hydroxy-2,3-dihydro-1H-indol-2-one

Traditional Name

(3R)-3-{[(2S,4aR,5S,6S)-6-hydroxy-1,1,5-trimethyl-5-(4-methylpent-3-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-2-yl]methyl}-3-hydroxy-1H-indol-2-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C[C@]2(O)C(=O)NC3=C2C=CC=C3)CC[C@]2([H])C(=CC[C@H](O)[C@@]2(C)CCC=C(C)C)C1(C)C

InChI Identifier

InChI=1S/C28H39NO3/c1-18(2)9-8-16-27(5)21-13-12-19(26(3,4)20(21)14-15-24(27)30)17-28(32)22-10-6-7-11-23(22)29-25(28)31/h6-7,9-11,14,19,21,24,30,32H,8,12-13,15-17H2,1-5H3,(H,29,31)/t19-,21+,24-,27-,28+/m0/s1

InChI Key

PTPIUTLSTVYCQI-PAVGVHNBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	2466892493@qq.com	School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology	Jun Yao	2025-04-06	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	2466892493@qq.com	School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology	Jun Yao	2025-04-06	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	2466892493@qq.com	School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology	Jun Yao	2025-04-06	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	2466892493@qq.com	School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology	Jun Yao	2025-04-06	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	2466892493@qq.com	School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology	Jun Yao	2025-04-06	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	2466892493@qq.com	School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology	Jun Yao	2025-04-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	2466892493@qq.com	School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology	Jun Yao	2025-04-06	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	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, 400, CDCl₃, simulated)	2466892493@qq.com	School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology	Jun Yao	2025-04-06	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Aspergillus sp. TJ403-YJ22.		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
logP	5.11	ChemAxon
pKa (Strongest Acidic)	11.67	ChemAxon
pKa (Strongest Basic)	-0.71	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	132.02 m³·mol⁻¹	ChemAxon
Polarizability	51.71 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Asperdole M (NP0350918)

MOL for NP0350918 (Asperdole M)

3D MOL for NP0350918 (Asperdole M)

3D SDF for NP0350918 (Asperdole M)

3D-SDF for NP0350918 (Asperdole M)

PDB for NP0350918 (Asperdole M)

3D PDB for NP0350918 (Asperdole M)

SMILES for NP0350918 (Asperdole M)

INCHI for NP0350918 (Asperdole M)

Structure for NP0350918 (Asperdole M)

3D Structure for NP0350918 (Asperdole M)