NP-MRD: Showing NP-Card for Fischeriolide B (NP0043874)

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Record Information

Version

1.0

Created at

2021-06-22 17:26:59 UTC

Updated at

2021-06-22 17:26:59 UTC

NP-MRD ID

NP0043874

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fischeriolide B

Description

Fischeriolide B belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Fischeriolide B is found in Euphorbia fischeriana. It was first documented in 2016 (PMID: 26702644). Based on a literature review a significant number of articles have been published on Fischeriolide B (PMID: 34154027) (PMID: 34153984) (PMID: 34153980) (PMID: 34153975).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

NP0043874
     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
    5.5065   -0.8633   -1.3528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125   -0.0807   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4487    0.1806   -0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4268   -0.0995   -1.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7943   -0.3188   -2.6988 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0324   -0.1181   -1.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6958    0.1155    0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7686    0.2890    1.1880 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2051   -1.0136    1.5085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9471    1.0237    0.6335 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0171    1.0748    1.5015 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1578    0.4716    0.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3115    0.3881    1.3721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7161    0.2312    0.6283 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9346    1.6456    1.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9650   -0.6537    1.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3766   -0.4115    2.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4196   -0.5445    1.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0836   -0.1440   -0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682   -1.1542   -1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6451    1.2143   -0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255   -0.2722   -0.4307 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2512    0.3039   -1.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0178   -0.4187   -2.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4152    0.8248    2.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6431    2.0315    0.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5156    2.3847    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7355   -1.4020   -0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1064   -2.0378   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9640   -0.6679   -2.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8561    1.8867   -0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1749    1.6991    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4219    1.1541   -1.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4362   -1.3865   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0556    0.2138   -2.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9849    1.3845   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3770   -0.1321   -3.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1959   -1.5041   -2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 12  2  1  0
 22 14  1  0
 10  3  1  0
 24  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  8 28  1  1
  9 29  1  0
 10 30  1  6
 15 31  1  0
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 16 35  1  0
 17 36  1  0
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 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  6
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
M  END


  Mrv1652306222119272D          

 24 27  0  0  1  0            999 V2000
    5.2939    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114    2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751    1.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.2463   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830    1.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5902   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7927   -0.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 13 20  1  1  0  0  0
  5 21  1  6  0  0  0
  4 22  1  6  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0043874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2[C@H](OC1=O)[C@H](O)C1=C(CC[C@@H]3C(C)(C)CCC[C@@]13C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O4/c1-10-13-15(21)11-6-7-12-19(2,3)8-5-9-20(12,4)14(11)16(22)17(13)24-18(10)23/h12,16-17,22H,5-9H2,1-4H3/t12-,16-,17+,20-/m1/s1

> <INCHI_KEY>
QRIJKODYPMIMSS-IZZHEETASA-N

> <FORMULA>
C20H26O4

> <MOLECULAR_WEIGHT>
330.424

> <EXACT_MASS>
330.183109317

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.52006691661333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,7R,16S,17R)-17-hydroxy-2,6,6,13-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-1(10),12-diene-11,14-dione

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
3.457897657666667

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.121657579927344

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.083752948514219

> <JCHEM_PKA_STRONGEST_BASIC>
-3.488180764445185

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
90.65679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,7R,16S,17R)-17-hydroxy-2,6,6,13-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-1(10),12-diene-11,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043874
     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
    5.5065   -0.8633   -1.3528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125   -0.0807   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4487    0.1806   -0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4268   -0.0995   -1.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7943   -0.3188   -2.6988 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0324   -0.1181   -1.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6958    0.1155    0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7686    0.2890    1.1880 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2051   -1.0136    1.5085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9471    1.0237    0.6335 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0171    1.0748    1.5015 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1578    0.4716    0.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3115    0.3881    1.3721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7161    0.2312    0.6283 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9346    1.6456    1.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9650   -0.6537    1.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3766   -0.4115    2.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4196   -0.5445    1.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0836   -0.1440   -0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682   -1.1542   -1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6451    1.2143   -0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255   -0.2722   -0.4307 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2512    0.3039   -1.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0178   -0.4187   -2.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8561    1.8867   -0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1749    1.6991    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4219    1.1541   -1.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4362   -1.3865   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0556    0.2138   -2.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9849    1.3845   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3770   -0.1321   -3.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1959   -1.5041   -2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 12  2  1  0
 22 14  1  0
 10  3  1  0
 24  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  8 28  1  1
  9 29  1  0
 10 30  1  6
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  6
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0       9.882   3.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.928   4.480   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.896   3.938   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.380   3.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.088   2.521   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.017   3.453   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.842  -0.136   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.835  -1.314   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.090  -0.539   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.813  -0.198   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12    6   14   20                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   13                                                            
CONECT   21    5                                                            
CONECT   22    4   23                                                       
CONECT   23   22    2   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    NP0043874
HETATM    1  C1  UNL     1       5.507  -0.863  -1.353  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.713  -0.081  -0.359  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.449   0.181  -0.520  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.427  -0.100  -1.511  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.794  -0.319  -2.699  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.032  -0.118  -1.105  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.696   0.116   0.141  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.769   0.289   1.188  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.205  -1.014   1.509  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.947   1.024   0.634  1.00  0.00           C  
HETATM   11  O3  UNL     1       4.017   1.075   1.501  1.00  0.00           O  
HETATM   12  C9  UNL     1       5.158   0.472   0.934  1.00  0.00           C  
HETATM   13  O4  UNL     1       6.311   0.388   1.372  1.00  0.00           O  
HETATM   14  C10 UNL     1      -0.716   0.231   0.628  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.935   1.646   1.039  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.965  -0.654   1.831  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.377  -0.411   2.280  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.420  -0.544   1.252  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.084  -0.144  -0.132  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.768  -1.154  -1.075  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.645   1.214  -0.520  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.626  -0.272  -0.431  1.00  0.00           C  
HETATM   23  C19 UNL     1      -1.251   0.304  -1.776  1.00  0.00           C  
HETATM   24  C20 UNL     1       0.018  -0.419  -2.173  1.00  0.00           C  
HETATM   25  H1  UNL     1       6.067  -0.199  -2.042  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.880  -1.609  -1.878  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.267  -1.464  -0.784  1.00  0.00           H  
HETATM   28  H4  UNL     1       1.415   0.825   2.073  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.061  -1.607   0.733  1.00  0.00           H  
HETATM   30  H6  UNL     1       2.643   2.031   0.236  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.516   2.385   0.308  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.367   1.803   2.004  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.980   1.899   1.293  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.753  -1.719   1.629  1.00  0.00           H  
HETATM   35  H11 UNL     1      -0.293  -0.335   2.652  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.575  -1.144   3.111  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.416   0.591   2.795  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.304   0.086   1.573  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.833  -1.597   1.299  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.736  -1.402  -0.607  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.106  -2.038  -1.199  1.00  0.00           H  
HETATM   42  H18 UNL     1      -3.964  -0.668  -2.058  1.00  0.00           H  
HETATM   43  H19 UNL     1      -2.856   1.887  -0.938  1.00  0.00           H  
HETATM   44  H20 UNL     1      -4.175   1.699   0.353  1.00  0.00           H  
HETATM   45  H21 UNL     1      -4.422   1.154  -1.311  1.00  0.00           H  
HETATM   46  H22 UNL     1      -1.436  -1.386  -0.509  1.00  0.00           H  
HETATM   47  H23 UNL     1      -2.056   0.214  -2.517  1.00  0.00           H  
HETATM   48  H24 UNL     1      -0.985   1.385  -1.624  1.00  0.00           H  
HETATM   49  H25 UNL     1       0.377  -0.132  -3.170  1.00  0.00           H  
HETATM   50  H26 UNL     1      -0.196  -1.504  -2.078  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3   12
CONECT    3    4   10
CONECT    4    5    5    6
CONECT    6    7    7   24
CONECT    7    8   14
CONECT    8    9   10   28
CONECT    9   29
CONECT   10   11   30
CONECT   11   12
CONECT   12   13   13
CONECT   14   15   16   22
CONECT   15   31   32   33
CONECT   16   17   34   35
CONECT   17   18   36   37
CONECT   18   19   38   39
CONECT   19   20   21   22
CONECT   20   40   41   42
CONECT   21   43   44   45
CONECT   22   23   46
CONECT   23   24   47   48
CONECT   24   49   50
END

NP0043874
     RDKit          3D

50 53  0  0  0  0  0  0  0  0999 V2000
    5.5065   -0.8633   -1.3528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125   -0.0807   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4487    0.1806   -0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4268   -0.0995   -1.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7943   -0.3188   -2.6988 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0324   -0.1181   -1.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6958    0.1155    0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7686    0.2890    1.1880 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2051   -1.0136    1.5085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9471    1.0237    0.6335 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0171    1.0748    1.5015 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1578    0.4716    0.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3115    0.3881    1.3721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7161    0.2312    0.6283 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9346    1.6456    1.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9650   -0.6537    1.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3766   -0.4115    2.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4196   -0.5445    1.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0836   -0.1440   -0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682   -1.1542   -1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6451    1.2143   -0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255   -0.2722   -0.4307 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2512    0.3039   -1.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0178   -0.4187   -2.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0670   -0.1986   -2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8804   -1.6087   -1.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2674   -1.4637   -0.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4152    0.8248    2.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0611   -1.6071    0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6431    2.0315    0.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5156    2.3847    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3668    1.8028    2.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796    1.8988    1.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7532   -1.7192    1.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2932   -0.3345    2.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5748   -1.1444    3.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4162    0.5907    2.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3035    0.0861    1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8332   -1.5967    1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7355   -1.4020   -0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1064   -2.0378   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9640   -0.6679   -2.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8561    1.8867   -0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1749    1.6991    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4219    1.1541   -1.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4362   -1.3865   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0556    0.2138   -2.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9849    1.3845   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3770   -0.1321   -3.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1959   -1.5041   -2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 12  2  1  0
 22 14  1  0
 10  3  1  0
 24  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  8 28  1  1
  9 29  1  0
 10 30  1  6
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  6
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₄

Average Mass

330.4240 Da

Monoisotopic Mass

330.18311 Da

IUPAC Name

(2R,7R,16S,17R)-17-hydroxy-2,6,6,13-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-1(10),12-diene-11,14-dione

Traditional Name

(2R,7R,16S,17R)-17-hydroxy-2,6,6,13-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-1(10),12-diene-11,14-dione

CAS Registry Number

Not Available

SMILES

CC1=C2[C@H](OC1=O)[C@H](O)C1=C(CC[C@@H]3C(C)(C)CCC[C@@]13C)C2=O

InChI Identifier

InChI=1S/C20H26O4/c1-10-13-15(21)11-6-7-12-19(2,3)8-5-9-20(12,4)14(11)16(22)17(13)24-18(10)23/h12,16-17,22H,5-9H2,1-4H3/t12-,16-,17+,20-/m1/s1

InChI Key

QRIJKODYPMIMSS-IZZHEETASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia fischeriana	Linigton's dataset	26702644

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
Naphthofuran
Cyclohexenone
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organooxygen compound
Carbonyl group
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	2.99	ALOGPS
logP	3.46	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.08	ChemAxon
pKa (Strongest Basic)	-3.5	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	0	ChemAxon
Refractivity	90.66 m³·mol⁻¹	ChemAxon
Polarizability	36.52 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

58920823

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

127041906

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee JW, Lee C, Jin Q, Jang H, Lee D, Lee HJ, Shin JW, Han SB, Hong JT, Kim Y, Lee MK, Hwang BY: Diterpenoids from the Roots of Euphorbia fischeriana with Inhibitory Effects on Nitric Oxide Production. J Nat Prod. 2016 Jan 22;79(1):126-31. doi: 10.1021/acs.jnatprod.5b00789. Epub 2015 Dec 24. [PubMed:26702644 ]
Liu W, Zhang J, Yang Y, Jin Y, Li Z, You L, Luo J, Su X: Effect of Adrenocorticotropic Hormone Stimulation During Simultaneous Bilateral Adrenal Vein Sampling in Primary Aldosteronism. Horm Metab Res. 2021 Jun;53(6):364-370. doi: 10.1055/a-1498-6958. Epub 2021 Jun 21. [PubMed:34154027 ]
Oberbauer R, Meyer TW: Precision medicine in transplantation and hemodialysis. Nephrol Dial Transplant. 2021 Jun 22;36(Supplement_2):31-36. doi: 10.1093/ndt/gfaa367. [PubMed:34153984 ]
Rosenkranz AR, Tesar V: Lupus nephritis and ANCA-associated vasculitis: towards precision medicine? Nephrol Dial Transplant. 2021 Jun 22;36(Supplement_2):37-43. doi: 10.1093/ndt/gfab166. [PubMed:34153980 ]
Chen RE, Winkler ES, Case JB, Aziati ID, Bricker TL, Joshi A, Darling TL, Ying B, Errico JM, Shrihari S, VanBlargan LA, Xie X, Gilchuk P, Zost SJ, Droit L, Liu Z, Stumpf S, Wang D, Handley SA, Stine WB Jr, Shi PY, Davis-Gardner ME, Suthar MS, Knight MG, Andino R, Chiu CY, Ellebedy AH, Fremont DH, Whelan SPJ, Crowe JE Jr, Purcell L, Corti D, Boon ACM, Diamond MS: In vivo monoclonal antibody efficacy against SARS-CoV-2 variant strains. Nature. 2021 Aug;596(7870):103-108. doi: 10.1038/s41586-021-03720-y. Epub 2021 Jun 21. [PubMed:34153975 ]

Showing NP-Card for Fischeriolide B (NP0043874)

MOL for NP0043874 (Fischeriolide B)

3D MOL for NP0043874 (Fischeriolide B)

3D SDF for NP0043874 (Fischeriolide B)

3D-SDF for NP0043874 (Fischeriolide B)

PDB for NP0043874 (Fischeriolide B)

3D PDB for NP0043874 (Fischeriolide B)

SMILES for NP0043874 (Fischeriolide B)

INCHI for NP0043874 (Fischeriolide B)

Structure for NP0043874 (Fischeriolide B)

3D Structure for NP0043874 (Fischeriolide B)