NP-MRD: Showing NP-Card for kravanhin C (NP0043220)

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Record Information

Version

1.0

Created at

2021-06-21 00:41:08 UTC

Updated at

2021-06-30 00:18:47 UTC

NP-MRD ID

NP0043220

Secondary Accession Numbers

None

Natural Product Identification

Common Name

kravanhin C

Provided By

JEOL Database JEOL Logo

Description

Kravanhin C belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. kravanhin C is found in Amomum kravanh. It was first documented in 2002 (PMID: 29437326). Based on a literature review a significant number of articles have been published on Kravanhin C (PMID: 27466641) (PMID: 27253005) (PMID: 27124237) (PMID: 23394284).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102413D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212102413D          

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    3.1115    0.8229   -0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636   -0.7243    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0  0  0  0
 21 16  1  0  0  0  0
  6  4  1  0  0  0  0
  6  7  1  0  0  0  0
  4  2  1  0  0  0  0
  8 24  1  0  0  0  0
 10 11  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 18 19  2  0  0  0  0
 24 14  1  0  0  0  0
  2  1  1  6  0  0  0
  2 10  1  0  0  0  0
  8  9  1  6  0  0  0
  8  7  1  0  0  0  0
 16 44  1  6  0  0  0
  8 10  1  0  0  0  0
  2  3  1  0  0  0  0
 10 38  1  1  0  0  0
 24 23  1  0  0  0  0
 24 50  1  1  0  0  0
 14 16  1  0  0  0  0
 14 15  1  1  0  0  0
 21 22  1  0  0  0  0
  4  5  2  0  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
  7 33  1  0  0  0  0
  7 34  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 22 46  1  0  0  0  0
 22 47  1  0  0  0  0
 23 48  1  0  0  0  0
 23 49  1  0  0  0  0
 20 45  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  9 35  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  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
 15 41  1  0  0  0  0
 15 42  1  0  0  0  0
 15 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043220

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C2C([H])([H])C([H])([H])[C@@]3([H])[C@@](C(=O)C([H])([H])[C@@]4([H])C(C(=O)C([H])([H])C([H])([H])[C@]34C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])[C@@]2([H])OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O4/c1-18(2)13-10-15(22)20(4)12(19(13,3)8-7-14(18)21)6-5-11-9-16(23)24-17(11)20/h9,12-13,17H,5-8,10H2,1-4H3/t12-,13+,17+,19-,20-/m1/s1

> <INCHI_KEY>
GQJIWGTZFBKKGB-ICLIJLJDSA-N

> <FORMULA>
C20H26O4

> <MOLECULAR_WEIGHT>
330.424

> <EXACT_MASS>
330.183109317

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
35.655752374129946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,7R,10S,11S)-2,6,6,10-tetramethyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-14-ene-5,9,13-trione

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
3.7073174759999996

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.844762509731346

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.397028741907813

> <JCHEM_PKA_STRONGEST_BASIC>
-6.6787005450966435

> <JCHEM_POLAR_SURFACE_AREA>
60.440000000000005

> <JCHEM_REFRACTIVITY>
89.47129999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,7R,10S,11S)-2,6,6,10-tetramethyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-14-ene-5,9,13-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
   -1.5818   -3.7660   -2.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197   -3.6204   -1.0720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9578   -4.0917   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2679   -4.5951   -1.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472   -5.7540   -0.6082 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5885   -4.1343   -1.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9729   -2.7728   -1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9163   -1.6618   -1.2937 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8842   -1.4121   -2.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4481   -2.1679   -0.7024 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5250   -1.0991   -0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1771    0.1042   -0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0173    0.5627    0.7097 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2010    0.7471   -0.2600 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5298    1.5150    1.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0868    1.7233   -1.4524 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6863    2.8911   -1.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0535    4.0078   -1.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3248    5.1583   -1.2921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3983    3.6085   -1.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4066    2.2784   -1.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5390    1.3584   -2.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622    0.3199   -0.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3303   -0.3420   -0.4922 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3799   -3.0333   -2.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742   -3.6839   -3.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342   -4.7603   -2.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409   -4.0490    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696   -3.4877   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2654   -5.1301   -0.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5311   -4.1371   -2.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3564   -4.8635   -1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1208   -2.8714    0.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9466   -2.5014   -1.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2453   -0.5776   -3.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8888   -1.2116   -3.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5349   -2.2734   -3.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2672   -2.2175    0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5044   -1.4500   -0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433   -0.7944   -1.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    0.8294    1.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2244    2.2760    1.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4981    2.0223    1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3890    1.2506   -2.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1908    4.3064   -2.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4815    1.9136   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3892    0.8743   -3.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3991   -0.4328   -1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115    0.8229   -0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636   -0.7243    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0
 21 16  1  0
  6  4  1  0
  6  7  1  0
  4  2  1  0
  8 24  1  0
 10 11  1  0
 16 17  1  0
 17 18  1  0
 18 20  1  0
 20 21  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 18 19  2  0
 24 14  1  0
  2  1  1  6
  2 10  1  0
  8  9  1  6
  8  7  1  0
 16 44  1  6
  8 10  1  0
  2  3  1  0
 10 38  1  1
 24 23  1  0
 24 50  1  1
 14 16  1  0
 14 15  1  1
 21 22  1  0
  4  5  2  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
 11 39  1  0
 11 40  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 20 45  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.582  -3.766  -2.451  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.920  -3.620  -1.072  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.958  -4.092  -0.018  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.268  -4.595  -1.009  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.147  -5.754  -0.608  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.589  -4.134  -1.572  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.973  -2.773  -1.014  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.916  -1.662  -1.294  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.884  -1.412  -2.814  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.448  -2.168  -0.702  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.525  -1.099  -0.906  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.177   0.104  -0.066  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.017   0.563   0.710  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.201   0.747  -0.260  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.530   1.515   1.052  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.087   1.723  -1.452  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.686   2.891  -1.157  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.054   4.008  -1.403  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.325   5.158  -1.292  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.398   3.608  -1.815  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.407   2.278  -1.831  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.539   1.358  -2.091  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.662   0.320  -0.970  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.330  -0.342  -0.492  0.00  0.00           C+0
HETATM   25  H   UNK     0      -2.380  -3.033  -2.603  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.874  -3.684  -3.276  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.034  -4.760  -2.558  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.541  -4.049   0.995  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.870  -3.488  -0.037  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.265  -5.130  -0.192  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.531  -4.137  -2.664  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.356  -4.864  -1.288  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.121  -2.871   0.069  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.947  -2.501  -1.436  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.245  -0.578  -3.098  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.889  -1.212  -3.199  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.535  -2.273  -3.379  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.267  -2.217   0.385  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.504  -1.450  -0.567  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.643  -0.794  -1.948  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.555   0.829   1.908  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.224   2.276   1.283  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.498   2.022   1.006  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.389   1.251  -2.316  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.191   4.306  -2.016  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.482   1.914  -2.169  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.389   0.874  -3.059  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.399  -0.433  -1.264  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.111   0.823  -0.102  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.564  -0.724   0.515  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    4    1   10    3                                             
CONECT    3    2   28   29   30                                             
CONECT    4    6    2    5                                                  
CONECT    5    4                                                            
CONECT    6    4    7   31   32                                             
CONECT    7    6    8   33   34                                             
CONECT    8   24    9    7   10                                             
CONECT    9    8   35   36   37                                             
CONECT   10   11    2    8   38                                             
CONECT   11   10   12   39   40                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   24   16   15                                             
CONECT   15   14   41   42   43                                             
CONECT   16   21   17   44   14                                             
CONECT   17   16   18                                                       
CONECT   18   17   20   19                                                  
CONECT   19   18                                                            
CONECT   20   18   21   45                                                  
CONECT   21   16   20   22                                                  
CONECT   22   23   21   46   47                                             
CONECT   23   22   24   48   49                                             
CONECT   24    8   14   23   50                                             
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    3                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    6                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    7                                                            
CONECT   35    9                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   20                                                            
CONECT   46   22                                                            
CONECT   47   22                                                            
CONECT   48   23                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
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
   -1.5818   -3.7660   -2.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197   -3.6204   -1.0720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9578   -4.0917   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2679   -4.5951   -1.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472   -5.7540   -0.6082 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5885   -4.1343   -1.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9729   -2.7728   -1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9163   -1.6618   -1.2937 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8842   -1.4121   -2.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4481   -2.1679   -0.7024 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5250   -1.0991   -0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1771    0.1042   -0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0173    0.5627    0.7097 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2010    0.7471   -0.2600 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5298    1.5150    1.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0868    1.7233   -1.4524 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6863    2.8911   -1.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0535    4.0078   -1.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3248    5.1583   -1.2921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3983    3.6085   -1.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4066    2.2784   -1.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5390    1.3584   -2.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622    0.3199   -0.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3303   -0.3420   -0.4922 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3799   -3.0333   -2.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742   -3.6839   -3.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342   -4.7603   -2.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409   -4.0490    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696   -3.4877   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2654   -5.1301   -0.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5311   -4.1371   -2.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3564   -4.8635   -1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1208   -2.8714    0.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9466   -2.5014   -1.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2453   -0.5776   -3.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8888   -1.2116   -3.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5349   -2.2734   -3.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2672   -2.2175    0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5044   -1.4500   -0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433   -0.7944   -1.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    0.8294    1.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2244    2.2760    1.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4981    2.0223    1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3890    1.2506   -2.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1908    4.3064   -2.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4815    1.9136   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3892    0.8743   -3.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3991   -0.4328   -1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115    0.8229   -0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636   -0.7243    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0
 21 16  1  0
  6  4  1  0
  6  7  1  0
  4  2  1  0
  8 24  1  0
 10 11  1  0
 16 17  1  0
 17 18  1  0
 18 20  1  0
 20 21  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 18 19  2  0
 24 14  1  0
  2  1  1  6
  2 10  1  0
  8  9  1  6
  8  7  1  0
 16 44  1  6
  8 10  1  0
  2  3  1  0
 10 38  1  1
 24 23  1  0
 24 50  1  1
 14 16  1  0
 14 15  1  1
 21 22  1  0
  4  5  2  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
 11 39  1  0
 11 40  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 20 45  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
3b,6,6,9a-Tetramethyl-5a,6,8,9,9a,9b,10,11-octahydrophenanthro(1,2-b)furan-2,4,7(3ah,3BH,5H)-trione	MeSH

Chemical Formula

C₂₀H₂₆O₄

Average Mass

330.4240 Da

Monoisotopic Mass

330.18311 Da

IUPAC Name

(1R,2S,7R,10S,11S)-2,6,6,10-tetramethyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-14-ene-5,9,13-trione

Traditional Name

(1R,2S,7R,10S,11S)-2,6,6,10-tetramethyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-14-ene-5,9,13-trione

CAS Registry Number

Not Available

SMILES

[H]C1=C2C([H])([H])C([H])([H])[C@@]3([H])[C@@](C(=O)C([H])([H])[C@@]4([H])C(C(=O)C([H])([H])C([H])([H])[C@]34C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])[C@@]2([H])OC1=O

InChI Identifier

InChI=1S/C20H26O4/c1-18(2)13-10-15(22)20(4)12(19(13,3)8-7-14(18)21)6-5-11-9-16(23)24-17(11)20/h9,12-13,17H,5-8,10H2,1-4H3/t12-,13+,17+,19-,20-/m1/s1

InChI Key

GQJIWGTZFBKKGB-ICLIJLJDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Amomum krervanh	JEOL database	Yin, H., et al, J. Nat. Prod. 76, 237 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
3-oxosteroid
16-oxosteroid
Oxosteroid
7-oxosteroid
3-oxo-5-alpha-steroid
15-oxasteroid
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.59	ALOGPS
logP	3.71	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	5.4	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.47 m³·mol⁻¹	ChemAxon
Polarizability	35.66 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

29419712

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71578894

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:29437326 ]
Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
Zhong Z, Zhao G, Xu D, Dong B, Song D, Xie X, She X: Bioinspired Total Syntheses of Isospongian-type Diterpenoids (-)-Kravanhins A and C. Chem Asian J. 2016 May 20;11(10):1542-7. doi: 10.1002/asia.201600398. Epub 2016 May 3. [PubMed:27124237 ]
Yin H, Luo JG, Kong LY: Tetracyclic diterpenoids with isomerized isospongian skeleton and labdane diterpenoids from the fruits of Amomum kravanh. J Nat Prod. 2013 Feb 22;76(2):237-42. doi: 10.1021/np3007217. Epub 2013 Feb 8. [PubMed:23394284 ]
Yin, H., et al. (2013). Yin, H., et al, J. Nat. Prod. 76, 237 (2013). J. Nat. Prod..

Showing NP-Card for kravanhin C (NP0043220)

MOL for NP0043220 (kravanhin C)

3D MOL for NP0043220 (kravanhin C)

3D SDF for NP0043220 (kravanhin C)

3D-SDF for NP0043220 (kravanhin C)

PDB for NP0043220 (kravanhin C)

3D PDB for NP0043220 (kravanhin C)

SMILES for NP0043220 (kravanhin C)

INCHI for NP0043220 (kravanhin C)

Structure for NP0043220 (kravanhin C)

3D Structure for NP0043220 (kravanhin C)