NP-MRD: Showing NP-Card for (-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+ (NP0035654)

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Record Information

Version

2.0

Created at

2021-06-20 19:02:25 UTC

Updated at

2021-06-30 00:06:47 UTC

NP-MRD ID

NP0035654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+

Provided By

JEOL Database JEOL Logo

Description

(-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid 18,20-lactone belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+ is found in Fraxinus sieboldiana. (-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+ was first documented in 2010 (Lin, S., et al.). Based on a literature review very few articles have been published on (-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid 18,20-lactone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121023D          

 50 53  0  0  0  0            999 V2000
    0.0937   -5.0534   -2.9414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075   -4.9096   -1.5400 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.0562   -1.2558   -0.0781 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121023D          

 50 53  0  0  0  0            999 V2000
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   -2.5993    3.5322   -1.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2407    3.0826   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7062    0.7756   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9751    1.3345   -1.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5593    3.1657    1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5764    4.3841    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0351   -0.9532   -1.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0  0  0  0
 21 22  2  0  0  0  0
  6  5  1  0  0  0  0
  5  4  2  0  0  0  0
  4 23  1  0  0  0  0
 23 22  1  0  0  0  0
 13 11  1  0  0  0  0
 23 24  2  0  0  0  0
 16 21  1  0  0  0  0
  4  2  1  0  0  0  0
 10  9  1  0  0  0  0
  2  1  1  0  0  0  0
  9  8  1  0  0  0  0
  2  3  1  0  0  0  0
  8  6  1  0  0  0  0
  6  7  1  6  0  0  0
 21  6  1  0  0  0  0
 11 20  1  0  0  0  0
 11 10  1  0  0  0  0
 16 17  1  6  0  0  0
 16 15  1  0  0  0  0
 10 38  1  1  0  0  0
 16 10  1  0  0  0  0
 11 12  1  1  0  0  0
 20 19  1  0  0  0  0
 17 19  1  0  0  0  0
 14 13  1  0  0  0  0
 17 18  2  0  0  0  0
 14 44  1  0  0  0  0
 14 45  1  0  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 15 46  1  0  0  0  0
 15 47  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  5 32  1  0  0  0  0
 22 50  1  0  0  0  0
  2 28  1  6  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  7 33  1  0  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12C([H])=C(C(=O)C([H])=C1[C@@]13C(=O)OC([H])([H])[C@@](C([H])([H])[H])(C([H])([H])C([H])([H])C1([H])[H])[C@]3([H])C([H])([H])C2([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O4/c1-12(2)13-10-19(23)8-5-15-18(3)6-4-7-20(15,17(22)24-11-18)16(19)9-14(13)21/h9-10,12,15,23H,4-8,11H2,1-3H3/t15-,18+,19+,20+/m0/s1

> <INCHI_KEY>
JSFRLZQSBVCOOF-YGWPLHOASA-N

> <FORMULA>
C20H26O4

> <MOLECULAR_WEIGHT>
330.424

> <EXACT_MASS>
330.183109317

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.142016466551766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,7R,10S,11S)-7-hydroxy-11-methyl-5-(propan-2-yl)-13-oxatetracyclo[9.3.3.0^{1,10}.0^{2,7}]heptadeca-2,5-diene-4,14-dione

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
3.0253345083333327

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.689220215696157

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3721350776545

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
91.54069999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,7R,10S,11S)-7-hydroxy-5-isopropyl-11-methyl-13-oxatetracyclo[9.3.3.0^{1,10}.0^{2,7}]heptadeca-2,5-diene-4,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
    0.0937   -5.0534   -2.9414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075   -4.9096   -1.5400 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3375   -5.6997   -0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6960   -3.4428   -1.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1270   -2.7036   -0.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0562   -1.2558   -0.0781 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1068   -0.6023   -0.5665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0888   -1.0900    1.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2046    0.3814    1.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4409    1.0610    1.2161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5404    2.5726    1.5345 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4567    2.8610    3.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142    3.1031    1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1924    2.8480   -0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9034    1.4017   -0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    0.8724   -0.3205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4702    1.7123   -1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0019    1.3648   -2.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1491    2.9174   -0.5406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3894    3.3038    0.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2977   -0.6220   -0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1352   -1.3500   -1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179   -2.7852   -1.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7410   -3.3912   -2.4192 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1823   -6.1096   -3.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0932   -4.6071   -2.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5315   -4.5666   -3.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947   -5.3907   -1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0523   -5.5853    0.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860   -5.3825   -0.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3185   -6.7682   -0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0325   -3.1527   -0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574   -0.3806   -1.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8315   -1.4869    1.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9267   -1.6521    1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2672    0.4257    2.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7168    0.9026    1.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3152    0.5633    1.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2053    2.2834    3.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339    3.9228    3.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4717    2.6177    3.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109    2.6266    1.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9971    4.1804    1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5993    3.5322   -1.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2407    3.0826   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7062    0.7756   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9751    1.3345   -1.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5593    3.1657    1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5764    4.3841    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0351   -0.9532   -1.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 21 22  2  0
  6  5  1  0
  5  4  2  0
  4 23  1  0
 23 22  1  0
 13 11  1  0
 23 24  2  0
 16 21  1  0
  4  2  1  0
 10  9  1  0
  2  1  1  0
  9  8  1  0
  2  3  1  0
  8  6  1  0
  6  7  1  6
 21  6  1  0
 11 20  1  0
 11 10  1  0
 16 17  1  6
 16 15  1  0
 10 38  1  1
 16 10  1  0
 11 12  1  1
 20 19  1  0
 17 19  1  0
 14 13  1  0
 17 18  2  0
 14 44  1  0
 14 45  1  0
 13 42  1  0
 13 43  1  0
 15 46  1  0
 15 47  1  0
  9 36  1  0
  9 37  1  0
  8 34  1  0
  8 35  1  0
  5 32  1  0
 22 50  1  0
  2 28  1  6
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  7 33  1  0
 20 48  1  0
 20 49  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.094  -5.053  -2.941  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.507  -4.910  -1.540  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.338  -5.700  -0.532  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.696  -3.443  -1.193  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.127  -2.704  -0.428  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.056  -1.256  -0.078  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.107  -0.602  -0.567  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.089  -1.090   1.445  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.205   0.381   1.845  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.441   1.061   1.216  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.540   2.573   1.535  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.457   2.861   3.047  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.914   3.103   1.047  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.192   2.848  -0.426  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.903   1.402  -0.818  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.525   0.872  -0.321  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.470   1.712  -1.064  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.002   1.365  -2.148  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.149   2.917  -0.541  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.389   3.304   0.826  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.298  -0.622  -0.676  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.135  -1.350  -1.441  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.918  -2.785  -1.742  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.741  -3.391  -2.419  0.00  0.00           O+0
HETATM   25  H   UNK     0       0.182  -6.110  -3.218  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.093  -4.607  -2.994  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.532  -4.567  -3.698  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.495  -5.391  -1.542  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.052  -5.585   0.485  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.386  -5.383  -0.539  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.319  -6.768  -0.775  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.032  -3.153  -0.027  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.957  -0.381  -1.508  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.832  -1.487   1.894  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.927  -1.652   1.879  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.267   0.426   2.938  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.717   0.903   1.563  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.315   0.563   1.665  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.205   2.283   3.600  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.634   3.923   3.254  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.472   2.618   3.458  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.711   2.627   1.635  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.997   4.180   1.241  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.599   3.532  -1.043  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.241   3.083  -0.646  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.706   0.776  -0.405  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.975   1.335  -1.912  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.559   3.166   1.357  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.576   4.384   0.819  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.035  -0.953  -1.896  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    4    1    3   28                                             
CONECT    3    2   29   30   31                                             
CONECT    4    5   23    2                                                  
CONECT    5    6    4   32                                                  
CONECT    6    5    8    7   21                                             
CONECT    7    6   33                                                       
CONECT    8    9    6   34   35                                             
CONECT    9   10    8   36   37                                             
CONECT   10    9   11   38   16                                             
CONECT   11   13   20   10   12                                             
CONECT   12   11   39   40   41                                             
CONECT   13   11   14   42   43                                             
CONECT   14   15   13   44   45                                             
CONECT   15   14   16   46   47                                             
CONECT   16   21   17   15   10                                             
CONECT   17   16   19   18                                                  
CONECT   18   17                                                            
CONECT   19   20   17                                                       
CONECT   20   11   19   48   49                                             
CONECT   21   22   16    6                                                  
CONECT   22   21   23   50                                                  
CONECT   23    4   22   24                                                  
CONECT   24   23                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    2                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    5                                                            
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   22                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  106    0
END

RDKit          3D

50 53  0  0  0  0  0  0  0  0999 V2000
    0.0937   -5.0534   -2.9414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075   -4.9096   -1.5400 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3375   -5.6997   -0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6960   -3.4428   -1.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1270   -2.7036   -0.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0562   -1.2558   -0.0781 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1068   -0.6023   -0.5665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0888   -1.0900    1.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2046    0.3814    1.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4409    1.0610    1.2161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5404    2.5726    1.5345 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4567    2.8610    3.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142    3.1031    1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1924    2.8480   -0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9034    1.4017   -0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    0.8724   -0.3205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4702    1.7123   -1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0019    1.3648   -2.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1491    2.9174   -0.5406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3894    3.3038    0.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2977   -0.6220   -0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1352   -1.3500   -1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179   -2.7852   -1.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7410   -3.3912   -2.4192 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1823   -6.1096   -3.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0932   -4.6071   -2.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5315   -4.5666   -3.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947   -5.3907   -1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0523   -5.5853    0.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860   -5.3825   -0.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3185   -6.7682   -0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0325   -3.1527   -0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574   -0.3806   -1.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8315   -1.4869    1.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9267   -1.6521    1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2672    0.4257    2.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7168    0.9026    1.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3152    0.5633    1.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2053    2.2834    3.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339    3.9228    3.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4717    2.6177    3.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109    2.6266    1.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9971    4.1804    1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5993    3.5322   -1.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2407    3.0826   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7062    0.7756   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9751    1.3345   -1.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5593    3.1657    1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5764    4.3841    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0351   -0.9532   -1.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 21 22  2  0
  6  5  1  0
  5  4  2  0
  4 23  1  0
 23 22  1  0
 13 11  1  0
 23 24  2  0
 16 21  1  0
  4  2  1  0
 10  9  1  0
  2  1  1  0
  9  8  1  0
  2  3  1  0
  8  6  1  0
  6  7  1  6
 21  6  1  0
 11 20  1  0
 11 10  1  0
 16 17  1  6
 16 15  1  0
 10 38  1  1
 16 10  1  0
 11 12  1  1
 20 19  1  0
 17 19  1  0
 14 13  1  0
 17 18  2  0
 14 44  1  0
 14 45  1  0
 13 42  1  0
 13 43  1  0
 15 46  1  0
 15 47  1  0
  9 36  1  0
  9 37  1  0
  8 34  1  0
  8 35  1  0
  5 32  1  0
 22 50  1  0
  2 28  1  6
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  7 33  1  0
 20 48  1  0
 20 49  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
M  END

View in JSmol

Synonyms

Value	Source
(-)-(4S,5S,8R,10R)-8,18-Dihydroxy-12-oxo-abieta-9(11),13-dien-20-Oate 18,20-lactone	Generator

Chemical Formula

C₂₀H₂₆O₄

Average Mass

330.4240 Da

Monoisotopic Mass

330.18311 Da

IUPAC Name

(1R,7R,10S,11S)-7-hydroxy-11-methyl-5-(propan-2-yl)-13-oxatetracyclo[9.3.3.0^{1,10}.0^{2,7}]heptadeca-2,5-diene-4,14-dione

Traditional Name

(1R,7R,10S,11S)-7-hydroxy-5-isopropyl-11-methyl-13-oxatetracyclo[9.3.3.0^{1,10}.0^{2,7}]heptadeca-2,5-diene-4,14-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@]12C([H])=C(C(=O)C([H])=C1[C@@]13C(=O)OC([H])([H])[C@@](C([H])([H])[H])(C([H])([H])C([H])([H])C1([H])[H])[C@]3([H])C([H])([H])C2([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H26O4/c1-12(2)13-10-19(23)8-5-15-18(3)6-4-7-20(15,17(22)24-11-18)16(19)9-14(13)21/h9-10,12,15,23H,4-8,11H2,1-3H3/t15-,18+,19+,20+/m0/s1

InChI Key

JSFRLZQSBVCOOF-YGWPLHOASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fraxinus sieboldiana	JEOL database	Lin, S., et al, J. Nat. Prod. 73, 1914 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Abietane diterpenoid
Diterpenoid
Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Pyran
Oxane
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

abietane diterpenoid (CHEBI:70552 )
tetracyclic diterpenoid (CHEBI:70552 )
diterpene lactone (CHEBI:70552 )
cyclic terpene ketone (CHEBI:70552 )

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	2.57	ALOGPS
logP	3.03	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.69	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.54 m³·mol⁻¹	ChemAxon
Polarizability	36.14 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26391408

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

70552

Good Scents ID

Not Available

References

General References

Lin, S., et al. (2010). Lin, S., et al, J. Nat. Prod. 73, 1914 (2010). J. Nat. Prod..

Showing NP-Card for (-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+ (NP0035654)

MOL for NP0035654 ((-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+)

3D MOL for NP0035654 ((-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+)

3D SDF for NP0035654 ((-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+)

3D-SDF for NP0035654 ((-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+)

PDB for NP0035654 ((-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+)

3D PDB for NP0035654 ((-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+)

SMILES for NP0035654 ((-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+)

INCHI for NP0035654 ((-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+)

Structure for NP0035654 ((-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+)

3D Structure for NP0035654 ((-)-(4S,5S,8R,10R)-8,18-dihydroxy-12-oxo-abieta-9(11),13-dien-20-oic acid+)