NP-MRD: Showing NP-Card for Monacolin L (NP0021268)

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Record Information

Version

2.0

Created at

2021-01-06 06:32:10 UTC

Updated at

2021-07-15 17:35:54 UTC

NP-MRD ID

NP0021268

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Monacolin L

Provided By

NPAtlas

Description

Monacolin L is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Monacolin L is found in Monascus ruber. Monacolin L was first documented in 1989 (PMID: 2708134). Based on a literature review a small amount of articles have been published on Monacolin L (PMID: 21495633) (PMID: 22995742) (PMID: 24534845).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120413D          

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M  END

     RDKit          3D

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  Mrv1652306242120413D          

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  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 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
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22  2  1  0  0  0  0
 20  4  1  0  0  0  0
 19 12  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  2 26  1  1  0  0  0
  3 27  1  0  0  0  0
  5 28  1  0  0  0  0
  6 29  1  0  0  0  0
  7 30  1  1  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  9 34  1  1  0  0  0
 10 35  1  0  0  0  0
 10 36  1  0  0  0  0
 11 37  1  0  0  0  0
 11 38  1  0  0  0  0
 12 39  1  1  0  0  0
 13 40  1  0  0  0  0
 13 41  1  0  0  0  0
 14 42  1  6  0  0  0
 15 43  1  0  0  0  0
 16 44  1  0  0  0  0
 16 45  1  0  0  0  0
 20 46  1  6  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 22 49  1  0  0  0  0
 22 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021268

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])C(=O)O[C@]([H])(C([H])([H])C([H])([H])[C@@]2([H])[C@]([H])(C([H])=C([H])C3=C([H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]23[H])C([H])([H])[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O3/c1-12-3-7-18-14(9-12)5-4-13(2)17(18)8-6-16-10-15(20)11-19(21)22-16/h4-5,9,12-13,15-18,20H,3,6-8,10-11H2,1-2H3/t12-,13+,15-,16-,17+,18+/m1/s1

> <INCHI_KEY>
BKZPCUPKVCPRQW-MHMDBQTNSA-N

> <FORMULA>
C19H28O3

> <MOLECULAR_WEIGHT>
304.43

> <EXACT_MASS>
304.203844762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
35.24834368737716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,6R)-6-{2-[(1S,2S,6R,8aR)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}-4-hydroxyoxan-2-one

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
3.0817355106666664

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.914537666957496

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8361812244727904

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
88.636

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
monacolin L

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.3753   -0.1992    1.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4110   -0.2932    0.4439 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0791    1.0031   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9280    1.2998   -0.7491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6628    2.5915   -1.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4175    2.9248   -1.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2631    2.0012   -1.5653 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0948    1.2593   -2.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5581    1.0992   -0.4199 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5400    0.1900    0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    0.9483    0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    0.1310    0.9069 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4434   -0.8148   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7836   -1.3261    0.3610 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7645   -0.5158   -0.2124 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9047   -1.3631    1.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5377   -1.5812    2.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2085   -2.6076    3.0683 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6267   -0.5392    2.1339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8345    0.3144   -0.7659 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0423   -0.8368    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4724   -1.3410   -0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6349    0.5473    2.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1658   -1.1765    2.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3781    0.1252    2.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4702   -0.5372    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9104    1.7398   -0.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981    3.2711   -1.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    3.8852   -2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6678    2.5633   -1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896    0.2195   -2.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339    1.2308   -3.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6558    1.7946   -3.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8601    1.7679    0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1407   -0.3587    0.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7180   -0.6027   -0.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4815    1.6558    1.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1281    1.5960   -0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7122    0.8508    1.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5825   -0.3111   -1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8057   -1.6916   -0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9076   -2.3931    0.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3956    0.4117   -0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2738   -0.3724    2.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5768   -2.1846    2.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7359   -0.0957   -1.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3893   -1.6875   -0.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0172   -0.4848    1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6701   -1.4768   -1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6251   -2.3058    0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  9 20  1  0
 20 21  1  0
 21 22  1  0
 22  2  1  0
 20  4  1  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  1
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  1
 13 40  1  0
 13 41  1  0
 14 42  1  6
 15 43  1  0
 16 44  1  0
 16 45  1  0
 20 46  1  6
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
M  END

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  C   UNK     0      -4.375  -0.199   1.953  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.411  -0.293   0.444  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.079   1.003  -0.198  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.928   1.300  -0.749  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.663   2.591  -1.364  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.418   2.925  -1.748  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.263   2.001  -1.565  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.095   1.259  -2.875  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.558   1.099  -0.420  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.540   0.190   0.015  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.729   0.948   0.439  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.896   0.131   0.907  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.443  -0.815  -0.118  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.784  -1.326   0.361  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.765  -0.516  -0.212  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.905  -1.363   1.868  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.538  -1.581   2.412  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.208  -2.608   3.068  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.627  -0.539   2.134  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.835   0.314  -0.766  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.042  -0.837   0.155  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.472  -1.341  -0.079  0.00  0.00           C+0
HETATM   23  H   UNK     0      -3.635   0.547   2.305  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.166  -1.177   2.429  0.00  0.00           H+0
HETATM   25  H   UNK     0      -5.378   0.125   2.299  0.00  0.00           H+0
HETATM   26  H   UNK     0      -5.470  -0.537   0.147  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.910   1.740  -0.176  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.498   3.271  -1.500  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.241   3.885  -2.200  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.668   2.563  -1.368  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.290   0.220  -2.700  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.034   1.231  -3.464  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.656   1.795  -3.492  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.860   1.768   0.442  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.141  -0.359   0.921  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.718  -0.603  -0.730  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.482   1.656   1.257  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.128   1.596  -0.394  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.712   0.851   1.131  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.583  -0.311  -1.095  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.806  -1.692  -0.309  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.908  -2.393   0.010  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.396   0.412  -0.196  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.274  -0.372   2.231  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.577  -2.185   2.147  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.736  -0.096  -1.809  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.389  -1.688  -0.050  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.017  -0.485   1.204  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.670  -1.477  -1.157  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.625  -2.306   0.459  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    1    3   22   26                                             
CONECT    3    2    4   27                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6   28                                                  
CONECT    6    5    7   29                                                  
CONECT    7    6    8    9   30                                             
CONECT    8    7   31   32   33                                             
CONECT    9    7   10   20   34                                             
CONECT   10    9   11   35   36                                             
CONECT   11   10   12   37   38                                             
CONECT   12   11   13   19   39                                             
CONECT   13   12   14   40   41                                             
CONECT   14   13   15   16   42                                             
CONECT   15   14   43                                                       
CONECT   16   14   17   44   45                                             
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12                                                       
CONECT   20    9   21    4   46                                             
CONECT   21   20   22   47   48                                             
CONECT   22   21    2   49   50                                             
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    2                                                            
CONECT   27    3                                                            
CONECT   28    5                                                            
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    8                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   13                                                            
CONECT   41   13                                                            
CONECT   42   14                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   22                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

RDKit          3D

50 52  0  0  0  0  0  0  0  0999 V2000
   -4.3753   -0.1992    1.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4110   -0.2932    0.4439 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0791    1.0031   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9280    1.2998   -0.7491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6628    2.5915   -1.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4175    2.9248   -1.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2631    2.0012   -1.5653 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0948    1.2593   -2.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5581    1.0992   -0.4199 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5400    0.1900    0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    0.9483    0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    0.1310    0.9069 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4434   -0.8148   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7836   -1.3261    0.3610 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7645   -0.5158   -0.2124 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9047   -1.3631    1.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5377   -1.5812    2.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2085   -2.6076    3.0683 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6267   -0.5392    2.1339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8345    0.3144   -0.7659 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0423   -0.8368    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4724   -1.3410   -0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6349    0.5473    2.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1658   -1.1765    2.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3781    0.1252    2.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4702   -0.5372    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9104    1.7398   -0.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981    3.2711   -1.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    3.8852   -2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6678    2.5633   -1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896    0.2195   -2.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339    1.2308   -3.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6558    1.7946   -3.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8601    1.7679    0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1407   -0.3587    0.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7180   -0.6027   -0.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4815    1.6558    1.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1281    1.5960   -0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7122    0.8508    1.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5825   -0.3111   -1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8057   -1.6916   -0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9076   -2.3931    0.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3956    0.4117   -0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2738   -0.3724    2.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5768   -2.1846    2.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7359   -0.0957   -1.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3893   -1.6875   -0.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0172   -0.4848    1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6701   -1.4768   -1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6251   -2.3058    0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  9 20  1  0
 20 21  1  0
 21 22  1  0
 22  2  1  0
 20  4  1  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  1
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  1
 13 40  1  0
 13 41  1  0
 14 42  1  6
 15 43  1  0
 16 44  1  0
 16 45  1  0
 20 46  1  6
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(4R,6R)-6-{2-[(1S,2S,6R,8ar)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}-4-hydroxytetrahydro-2H-pyran-2-one	ChEBI
Monacolin L lactone	ChEBI

Chemical Formula

C₁₉H₂₈O₃

Average Mass

304.4300 Da

Monoisotopic Mass

304.20384 Da

IUPAC Name

(4R,6R)-6-{2-[(1S,2S,6R,8aR)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}-4-hydroxyoxan-2-one

Traditional Name

monacolin L

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@H]2[C@@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@@H](C)C=CC2=C1

InChI Identifier

InChI=1S/C19H28O3/c1-12-3-7-18-14(9-12)5-4-13(2)17(18)8-6-16-10-15(20)11-19(21)22-16/h4-5,9,12-13,15-18,20H,3,6-8,10-11H2,1-2H3/t12-,13+,15-,16-,17+,18+/m1/s1

InChI Key

BKZPCUPKVCPRQW-MHMDBQTNSA-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
Monascus ruber	NPAtlas	3839227

Species Where Detected

Species Name	Source	Reference
Monascus ruber No. 1005	KNApSAcK Database	22123792

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	3.75	ALOGPS
logP	3.08	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	14.91	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.64 m³·mol⁻¹	ChemAxon
Polarizability	35.25 Å³	ChemAxon
Number of Rings	3	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

NPAtlas ID

NPA016140

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018633

Chemspider ID

21865707

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15294098

PDB ID

Not Available

ChEBI ID

50130

Good Scents ID

Not Available

References

General References

Barriuso J, Nguyen DT, Li JW, Roberts JN, MacNevin G, Chaytor JL, Marcus SL, Vederas JC, Ro DK: Double oxidation of the cyclic nonaketide dihydromonacolin L to monacolin J by a single cytochrome P450 monooxygenase, LovA. J Am Chem Soc. 2011 Jun 1;133(21):8078-81. doi: 10.1021/ja201138v. Epub 2011 Apr 15. [PubMed:21495633 ]
Bizukojc M, Pawlak M, Boruta T, Gonciarz J: Effect of pH on biosynthesis of lovastatin and other secondary metabolites by Aspergillus terreus ATCC 20542. J Biotechnol. 2012 Dec 31;162(2-3):253-61. doi: 10.1016/j.jbiotec.2012.09.007. Epub 2012 Sep 17. [PubMed:22995742 ]
Boruta T, Bizukojc M: Culture-based and sequence-based insights into biosynthesis of secondary metabolites by Aspergillus terreus ATCC 20542. J Biotechnol. 2014 Apr 10;175:53-62. doi: 10.1016/j.jbiotec.2014.01.038. Epub 2014 Feb 15. [PubMed:24534845 ]
Komagata D, Shimada H, Murakawa S, Endo A: Biosynthesis of monacolins: conversion of monacolin L to monacolin J by a monooxygenase of Monascus ruber. J Antibiot (Tokyo). 1989 Mar;42(3):407-12. doi: 10.7164/antibiotics.42.407. [PubMed:2708134 ]

Showing NP-Card for Monacolin L (NP0021268)

MOL for NP0021268 (Monacolin L)

3D MOL for NP0021268 (Monacolin L)

3D SDF for NP0021268 (Monacolin L)

3D-SDF for NP0021268 (Monacolin L)

PDB for NP0021268 (Monacolin L)

3D PDB for NP0021268 (Monacolin L)

SMILES for NP0021268 (Monacolin L)

INCHI for NP0021268 (Monacolin L)

Structure for NP0021268 (Monacolin L)

3D Structure for NP0021268 (Monacolin L)