NP-MRD: Showing NP-Card for 5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate (NP0301842)

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Record Information

Version

1.0

Created at

2022-09-10 15:02:08 UTC

Updated at

2022-09-10 15:02:08 UTC

NP-MRD ID

NP0301842

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate

Description

5-(Acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-6,10,14-trimethyl-11-(prop-2-enoyloxy)-3-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]Pentadecan-4-yl butanoate belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton. 5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate is found in Klyxum simplex. 5-(Acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-6,10,14-trimethyl-11-(prop-2-enoyloxy)-3-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]Pentadecan-4-yl butanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251510532D          

 44 46  0  0  0  0            999 V2000
   -1.0726   -8.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4239   -7.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9531   -7.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3043   -6.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1265   -6.3130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8335   -5.7046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1848   -4.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7139   -4.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1082   -4.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5790   -3.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4594   -5.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3595   -3.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583   -3.2855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5118   -2.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7002   -2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4777   -5.5666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7707   -6.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6511   -4.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  8 12  1  0  0  0  0
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  7 40  1  0  0  0  0
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 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
M  END

     RDKit          3D

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 29 80  1  0
  2 47  1  0
  1 45  1  0
  1 46  1  0
M  END


  Mrv1533004251510532D          

 44 46  0  0  0  0            999 V2000
   -1.0726   -8.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4239   -7.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9531   -7.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3043   -6.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1265   -6.3130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8335   -5.7046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1848   -4.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7139   -4.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1082   -4.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5790   -3.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4594   -5.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0652   -3.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3595   -3.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583   -3.2855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5118   -2.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7002   -2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3805   -1.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026   -1.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5689   -0.5592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6748   -0.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8527   -1.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282   -1.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0398   -2.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7334   -2.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6746   -2.7588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3891   -2.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3891   -1.5213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1036   -2.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8181   -2.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5325   -2.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8632   -0.1318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6530    0.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2544   -0.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8414    0.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6312    1.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8873   -3.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3581   -4.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0323   -4.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9435   -3.5613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0069   -4.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4777   -5.5666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998   -5.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7707   -6.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6511   -4.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 20 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 15 36  1  0  0  0  0
 12 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  1  0  0  0  0
  7 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301842

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)OC1C(OC(C)=O)C(C)(O)C2C3CC(C)(O)C(CCC(C)(OC(=O)CCC)C(O3)C2C1C(C)C)OC(=O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C33H52O11/c1-10-13-23(36)43-28-25(18(4)5)26-27(33(9,39)30(28)40-19(6)34)20-17-31(7,38)21(42-22(35)12-3)15-16-32(8,29(26)41-20)44-24(37)14-11-2/h12,18,20-21,25-30,38-39H,3,10-11,13-17H2,1-2,4-9H3

> <INCHI_KEY>
IAZCISKNKJSEDU-UHFFFAOYSA-N

> <FORMULA>
C33H52O11

> <MOLECULAR_WEIGHT>
624.768

> <EXACT_MASS>
624.350962494

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
67.62284451762405

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-6,10,14-trimethyl-11-(prop-2-enoyloxy)-3-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate

> <ALOGPS_LOGP>
3.73

> <JCHEM_LOGP>
3.867649085666666

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.118554236230459

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.459404919835961

> <JCHEM_PKA_STRONGEST_BASIC>
-3.259034962883499

> <JCHEM_POLAR_SURFACE_AREA>
154.89

> <JCHEM_REFRACTIVITY>
158.0698

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -2.002 -15.965   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.658 -14.571   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.779 -13.307   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.435 -11.913   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.969 -11.784   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -1.556 -10.649   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.212  -9.255   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.333  -7.991   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.202  -8.120   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.081  -6.855   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.858  -9.513   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.988  -6.597   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.671  -5.799   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.722  -6.133   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.689  -5.462   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.040  -3.963   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.444  -2.543   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.978  -2.414   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.795  -1.044   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.126  -1.745   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.592  -1.874   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.426  -2.880   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.074  -4.380   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.369  -3.843   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.259  -5.150   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.593  -4.380   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.593  -2.840   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.927  -5.150   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.260  -4.380   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.594  -5.150   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.478  -0.246   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.952   0.199   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.075  -0.855   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -5.304   1.698   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.778   2.144   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.523  -6.468   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.402  -7.733   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.660  -8.621   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.495  -6.648   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -3.746  -9.126   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -4.625 -10.391   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -6.160 -10.262   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -7.039 -11.527   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -6.815  -8.869   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   40                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13   36                                                  
CONECT   13   12   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   36                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21   31                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   13   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   20   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36   15   12   37                                                  
CONECT   37   36   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37    7   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

View in JSmol

Synonyms

Value	Source
5-(Acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-6,10,14-trimethyl-11-(prop-2-enoyloxy)-3-(propan-2-yl)-15-oxatricyclo[6.6.1.0,]pentadecan-4-yl butanoic acid	Generator
5-(Acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-6,10,14-trimethyl-11-(prop-2-enoyloxy)-3-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoic acid	Generator

Chemical Formula

C₃₃H₅₂O₁₁

Average Mass

624.7680 Da

Monoisotopic Mass

624.35096 Da

IUPAC Name

5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-6,10,14-trimethyl-11-(prop-2-enoyloxy)-3-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate

Traditional Name

5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)OC1C(OC(C)=O)C(C)(O)C2C3CC(C)(O)C(CCC(C)(OC(=O)CCC)C(O3)C2C1C(C)C)OC(=O)C=C

InChI Identifier

InChI=1S/C33H52O11/c1-10-13-23(36)43-28-25(18(4)5)26-27(33(9,39)30(28)40-19(6)34)20-17-31(7,38)21(42-22(35)12-3)15-16-32(8,29(26)41-20)44-24(37)14-11-2/h12,18,20-21,25-30,38-39H,3,10-11,13-17H2,1-2,4-9H3

InChI Key

IAZCISKNKJSEDU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Klyxum simplex	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Eunicellane and asbestinane diterpenoids

Alternative Parents

Substituents

Eunicellane-type diterpenoid
Cladiellane diterpenoid
Tetracarboxylic acid or derivatives
Fatty acid ester
Cyclitol or derivatives
Acrylic acid ester
Fatty acyl
Cyclic alcohol
Acrylic acid or derivatives
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
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	3.73	ALOGPS
logP	3.87	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.46	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	154.89 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	158.07 m³·mol⁻¹	ChemAxon
Polarizability	67.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

56656979

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate (NP0301842)

MOL for NP0301842 (5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate)

3D MOL for NP0301842 (5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate)

3D SDF for NP0301842 (5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate)

3D-SDF for NP0301842 (5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate)

PDB for NP0301842 (5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate)

3D PDB for NP0301842 (5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate)

SMILES for NP0301842 (5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate)

INCHI for NP0301842 (5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate)

Structure for NP0301842 (5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate)

3D Structure for NP0301842 (5-(acetyloxy)-14-(butanoyloxy)-6,10-dihydroxy-3-isopropyl-6,10,14-trimethyl-11-(prop-2-enoyloxy)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-4-yl butanoate)