NP-MRD: Showing NP-Card for (-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+ (NP0035661)

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Record Information

Version

2.0

Created at

2021-06-20 19:02:43 UTC

Updated at

2021-06-30 00:06:48 UTC

NP-MRD ID

NP0035661

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+

Provided By

JEOL Database JEOL Logo

Description

(1R,5S,8S,10S,17S)-5-methyl-13-(propan-2-yl)-7,9-dioxapentacyclo[8.6.2.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]Octadeca-11,13,15-trien-14-ol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+ is found in Fraxinus sieboldiana. (-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+ was first documented in 2010 (Lin, S., et al.). Based on a literature review very few articles have been published on (1R,5S,8S,10S,17S)-5-methyl-13-(propan-2-yl)-7,9-dioxapentacyclo[8.6.2.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]Octadeca-11,13,15-trien-14-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121023D          

 49 53  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121023D          

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    0.3249   -1.2409    1.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763   -0.7331    2.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5007    1.3299    3.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0  0  0  0
 13 12  1  0  0  0  0
  7  8  1  0  0  0  0
  6  5  1  0  0  0  0
  5  4  2  0  0  0  0
  4  9  1  0  0  0  0
  9  8  2  0  0  0  0
 14 15  1  0  0  0  0
  9 10  1  0  0  0  0
 11  7  1  0  0  0  0
  4  2  1  0  0  0  0
 23 22  1  0  0  0  0
  2  1  1  0  0  0  0
 22 21  1  0  0  0  0
  2  3  1  0  0  0  0
 21  6  1  0  0  0  0
 15 17  1  0  0  0  0
  7  6  2  0  0  0  0
 11 19  1  0  0  0  0
 15 23  1  0  0  0  0
 23 49  1  1  0  0  0
 11 12  1  1  0  0  0
 15 16  1  1  0  0  0
 11 23  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 19 18  1  0  0  0  0
 17 18  1  0  0  0  0
 13 36  1  0  0  0  0
 13 37  1  0  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
 21 46  1  6  0  0  0
  5 31  1  0  0  0  0
  8 32  1  0  0  0  0
 10 33  1  0  0  0  0
  2 27  1  6  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
 17 43  1  0  0  0  0
 17 44  1  0  0  0  0
 19 45  1  6  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035661

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C([H])=C1C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]1([H])O[C@]3([H])OC([H])([H])[C@@]4(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]23[C@@]4([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O3/c1-11(2)12-7-13-14(8-15(12)21)20-6-4-5-19(3)10-22-18(20)23-16(13)9-17(19)20/h7-8,11,16-18,21H,4-6,9-10H2,1-3H3/t16-,17-,18-,19+,20-/m0/s1

> <INCHI_KEY>
PNHPVNJXLPYREE-FSGKZVOOSA-N

> <FORMULA>
C20H26O3

> <MOLECULAR_WEIGHT>
314.425

> <EXACT_MASS>
314.188194697

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
35.56360740877826

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5S,8S,10S,17S)-5-methyl-13-(propan-2-yl)-7,9-dioxapentacyclo[8.6.2.0^{1,8}.0^{5,17}.0^{11,16}]octadeca-11(16),12,14-trien-14-ol

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
4.4203366299999995

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.872951964188056

> <JCHEM_PKA_STRONGEST_BASIC>
-4.050587193133131

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
88.78229999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S,8S,10S,17S)-13-isopropyl-5-methyl-7,9-dioxapentacyclo[8.6.2.0^{1,8}.0^{5,17}.0^{11,16}]octadeca-11(16),12,14-trien-14-ol

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
   -5.7595    0.1579   -2.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7440    0.7158   -0.7646 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4167   -0.2574    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3313    1.0635   -0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    0.0641   -0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0594    0.3943    0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7110    1.7181    0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6730    2.7187    0.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9700    2.3841    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9158    3.3694   -0.0884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2350    1.8605    0.8928 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1834    3.3196    1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6060    3.4993    1.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9526    2.4961    2.7721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5826    1.0259    2.4350 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9646    0.1677    3.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3742    0.5431    1.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9855    1.2053   -0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5777    1.1749   -0.2586 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1539   -0.1886   -0.4917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9265   -0.5847    0.3688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4513   -0.4903    1.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0557    0.9565    2.1321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7887   -0.0089   -2.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2282   -0.7971   -2.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2881    0.8580   -2.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3600    1.6227   -0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4588   -0.4312   -0.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4149    0.1450    1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9132   -1.2298    0.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5862   -0.9688   -0.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260    3.7489    0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5102    4.2197    0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4876    3.7476    1.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0547    3.9278    0.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7231    4.5170    2.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3213    3.4247    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0248    2.5755    2.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294    2.7946    3.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612    0.4376    4.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0182    0.3136    3.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296   -0.9025    3.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2746   -0.5378    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4450    0.7321    1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182    1.7146   -1.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2259   -1.6058    0.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -1.2409    1.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763   -0.7331    2.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5007    1.3299    3.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 13 12  1  0
  7  8  1  0
  6  5  1  0
  5  4  2  0
  4  9  1  0
  9  8  2  0
 14 15  1  0
  9 10  1  0
 11  7  1  0
  4  2  1  0
 23 22  1  0
  2  1  1  0
 22 21  1  0
  2  3  1  0
 21  6  1  0
 15 17  1  0
  7  6  2  0
 11 19  1  0
 15 23  1  0
 23 49  1  1
 11 12  1  1
 15 16  1  1
 11 23  1  0
 20 19  1  0
 21 20  1  0
 19 18  1  0
 17 18  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 12 34  1  0
 12 35  1  0
 22 47  1  0
 22 48  1  0
 21 46  1  6
  5 31  1  0
  8 32  1  0
 10 33  1  0
  2 27  1  6
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  6
 16 40  1  0
 16 41  1  0
 16 42  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      -5.760   0.158  -2.191  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.744   0.716  -0.765  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.417  -0.257   0.208  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.331   1.063  -0.318  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.349   0.064  -0.219  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.059   0.394   0.192  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.711   1.718   0.507  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.673   2.719   0.412  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.970   2.384   0.004  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.916   3.369  -0.088  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.235   1.861   0.893  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.183   3.320   1.164  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.606   3.499   1.679  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.953   2.496   2.772  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.583   1.026   2.435  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.965   0.168   3.656  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.374   0.543   1.195  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.986   1.205  -0.008  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.578   1.175  -0.259  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.154  -0.189  -0.492  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.927  -0.585   0.369  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.451  -0.490   1.828  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.056   0.957   2.132  0.00  0.00           C+0
HETATM   24  H   UNK     0      -6.789  -0.009  -2.527  0.00  0.00           H+0
HETATM   25  H   UNK     0      -5.228  -0.797  -2.265  0.00  0.00           H+0
HETATM   26  H   UNK     0      -5.288   0.858  -2.890  0.00  0.00           H+0
HETATM   27  H   UNK     0      -6.360   1.623  -0.776  0.00  0.00           H+0
HETATM   28  H   UNK     0      -7.459  -0.431  -0.082  0.00  0.00           H+0
HETATM   29  H   UNK     0      -6.415   0.145   1.227  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.913  -1.230   0.232  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.586  -0.969  -0.459  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.426   3.749   0.642  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.510   4.220   0.144  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.488   3.748   1.921  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.055   3.928   0.260  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.723   4.517   2.071  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.321   3.425   0.853  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.025   2.575   2.993  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.429   2.795   3.691  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.361   0.438   4.530  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.018   0.314   3.922  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.830  -0.903   3.476  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.275  -0.538   1.044  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.445   0.732   1.335  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.418   1.715  -1.200  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.226  -1.606   0.113  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.325  -1.241   1.996  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.276  -0.733   2.510  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.501   1.330   3.004  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    4    1    3   27                                             
CONECT    3    2   28   29   30                                             
CONECT    4    5    9    2                                                  
CONECT    5    6    4   31                                                  
CONECT    6    5   21    7                                                  
CONECT    7    8   11    6                                                  
CONECT    8    7    9   32                                                  
CONECT    9    4    8   10                                                  
CONECT   10    9   33                                                       
CONECT   11    7   19   12   23                                             
CONECT   12   13   11   34   35                                             
CONECT   13   14   12   36   37                                             
CONECT   14   13   15   38   39                                             
CONECT   15   14   17   23   16                                             
CONECT   16   15   40   41   42                                             
CONECT   17   15   18   43   44                                             
CONECT   18   19   17                                                       
CONECT   19   11   20   18   45                                             
CONECT   20   19   21                                                       
CONECT   21   22    6   20   46                                             
CONECT   22   23   21   47   48                                             
CONECT   23   22   15   49   11                                             
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    2                                                            
CONECT   28    3                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    5                                                            
CONECT   32    8                                                            
CONECT   33   10                                                            
CONECT   34   12                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   13                                                            
CONECT   38   14                                                            
CONECT   39   14                                                            
CONECT   40   16                                                            
CONECT   41   16                                                            
CONECT   42   16                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   19                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   23                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  106    0
END

RDKit          3D

49 53  0  0  0  0  0  0  0  0999 V2000
   -5.7595    0.1579   -2.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7440    0.7158   -0.7646 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4167   -0.2574    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3313    1.0635   -0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    0.0641   -0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0594    0.3943    0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7110    1.7181    0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6730    2.7187    0.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9700    2.3841    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9158    3.3694   -0.0884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2350    1.8605    0.8928 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1834    3.3196    1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6060    3.4993    1.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9526    2.4961    2.7721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5826    1.0259    2.4350 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9646    0.1677    3.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3742    0.5431    1.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9855    1.2053   -0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5777    1.1749   -0.2586 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1539   -0.1886   -0.4917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9265   -0.5847    0.3688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4513   -0.4903    1.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0557    0.9565    2.1321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7887   -0.0089   -2.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2282   -0.7971   -2.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2881    0.8580   -2.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3600    1.6227   -0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4588   -0.4312   -0.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4149    0.1450    1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9132   -1.2298    0.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5862   -0.9688   -0.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260    3.7489    0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5102    4.2197    0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4876    3.7476    1.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0547    3.9278    0.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7231    4.5170    2.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3213    3.4247    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0248    2.5755    2.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294    2.7946    3.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612    0.4376    4.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0182    0.3136    3.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296   -0.9025    3.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2746   -0.5378    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4450    0.7321    1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182    1.7146   -1.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2259   -1.6058    0.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -1.2409    1.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763   -0.7331    2.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5007    1.3299    3.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 13 12  1  0
  7  8  1  0
  6  5  1  0
  5  4  2  0
  4  9  1  0
  9  8  2  0
 14 15  1  0
  9 10  1  0
 11  7  1  0
  4  2  1  0
 23 22  1  0
  2  1  1  0
 22 21  1  0
  2  3  1  0
 21  6  1  0
 15 17  1  0
  7  6  2  0
 11 19  1  0
 15 23  1  0
 23 49  1  1
 11 12  1  1
 15 16  1  1
 11 23  1  0
 20 19  1  0
 21 20  1  0
 19 18  1  0
 17 18  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 12 34  1  0
 12 35  1  0
 22 47  1  0
 22 48  1  0
 21 46  1  6
  5 31  1  0
  8 32  1  0
 10 33  1  0
  2 27  1  6
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  6
 16 40  1  0
 16 41  1  0
 16 42  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₃

Average Mass

314.4250 Da

Monoisotopic Mass

314.18819 Da

IUPAC Name

(1R,5S,8S,10S,17S)-5-methyl-13-(propan-2-yl)-7,9-dioxapentacyclo[8.6.2.0^{1,8}.0^{5,17}.0^{11,16}]octadeca-11(16),12,14-trien-14-ol

Traditional Name

(1R,5S,8S,10S,17S)-13-isopropyl-5-methyl-7,9-dioxapentacyclo[8.6.2.0^{1,8}.0^{5,17}.0^{11,16}]octadeca-11(16),12,14-trien-14-ol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C([H])=C1C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]1([H])O[C@]3([H])OC([H])([H])[C@@]4(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]23[C@@]4([H])C1([H])[H]

InChI Identifier

InChI=1S/C20H26O3/c1-11(2)12-7-13-14(8-15(12)21)20-6-4-5-19(3)10-22-18(20)23-16(13)9-17(19)20/h7-8,11,16-18,21H,4-6,9-10H2,1-3H3/t16-,17-,18-,19+,20-/m0/s1

InChI Key

PNHPVNJXLPYREE-FSGKZVOOSA-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 diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Naphthopyran
Phenanthrene
Benzopyran
Isochromane
Naphthalene
2-benzopyran
Tetralin
Cumene
1-hydroxy-2-unsubstituted benzenoid
Oxane
Benzenoid
Pyran
Acetal
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.14	ALOGPS
logP	4.42	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.78 m³·mol⁻¹	ChemAxon
Polarizability	35.56 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

50900508

PDB ID

Not Available

ChEBI ID

Not Available

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,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+ (NP0035661)

MOL for NP0035661 ((-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+)

3D MOL for NP0035661 ((-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+)

3D SDF for NP0035661 ((-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+)

3D-SDF for NP0035661 ((-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+)

PDB for NP0035661 ((-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+)

3D PDB for NP0035661 ((-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+)

SMILES for NP0035661 ((-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+)

INCHI for NP0035661 ((-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+)

Structure for NP0035661 ((-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+)

3D Structure for NP0035661 ((-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde+)