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Showing NP-Card for 20-acetoxy-clavulone iii (NP0327073)

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Record Information
Version2.0
Created at2022-09-12 09:17:32 UTC
Updated at2022-09-12 09:17:32 UTC
NP-MRD IDNP0327073
Secondary Accession NumbersNone
Natural Product Identification
Common Name20-acetoxy-clavulone iii
Description20-Acetoxy-clavulone iii belongs to the class of organic compounds known as clavulones and derivatives. These are ester derivatives of prostanoids. Thus, 20-acetoxy-clavulone III is considered to be an eicosanoid. 20-acetoxy-clavulone iii is found in Clavularia viridis. Based on a literature review very few articles have been published on 20-acetoxy-clavulone iii.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0327073 (20-acetoxy-clavulone iii)


  Mrv1652309122211172D          

 36 36  0  0  1  0            999 V2000
   -1.2288   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -5.8458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0087   -6.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -7.2747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8337   -6.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2462   -7.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712   -7.2747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4837   -7.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3087   -7.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7212   -8.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5462   -8.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0312   -8.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7762   -7.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8158   -8.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8158   -9.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0312   -9.3711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1942  -10.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9761  -10.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5950   -9.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4319   -9.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0508   -8.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8327   -8.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4515   -8.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2334   -8.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8523   -7.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6342   -8.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2530   -7.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7972   -9.0501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4239   -9.9295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6039  -10.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3911  -10.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9966  -11.2931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4837   -6.5603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2462   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4837   -5.1313    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  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
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 16 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
  7 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END
Download

3D MOL for NP0327073 (20-acetoxy-clavulone iii)

Download
3D SDF for NP0327073 (20-acetoxy-clavulone iii)

  Mrv1652309122211172D          

 36 36  0  0  1  0            999 V2000
   -1.2288   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -5.8458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0087   -6.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -7.2747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8337   -6.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2462   -7.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712   -7.2747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4837   -7.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3087   -7.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7212   -8.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5462   -8.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0312   -8.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7762   -7.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8158   -8.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8158   -9.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0312   -9.3711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1942  -10.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9761  -10.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5950   -9.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4319   -9.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0508   -8.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8327   -8.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4515   -8.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2334   -8.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8523   -7.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6342   -8.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2530   -7.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7972   -9.0501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4239   -9.9295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6039  -10.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3911  -10.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9966  -11.2931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4837   -6.5603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2462   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4837   -5.1313    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  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
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 16 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
  7 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0327073

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC[C@@H](OC(C)=O)\C=C\C=C1/C(=O)C=C[C@]1(C\C=C/CCCCCOC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O9/c1-20(28)34-19-10-8-6-5-7-9-17-27(36-22(3)30)18-16-25(31)24(27)13-11-12-23(35-21(2)29)14-15-26(32)33-4/h7,9,11-13,16,18,23H,5-6,8,10,14-15,17,19H2,1-4H3/b9-7-,12-11+,24-13+/t23-,27-/m0/s1

> <INCHI_KEY>
LHIPZWGSDUHLAW-KAJQFPCGSA-N

> <FORMULA>
C27H36O9

> <MOLECULAR_WEIGHT>
504.576

> <EXACT_MASS>
504.235932739

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.51664976336435

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (4R,5E)-4-(acetyloxy)-7-[(1Z,2S)-2-(acetyloxy)-2-[(2Z)-8-(acetyloxy)oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate

> <JCHEM_LOGP>
3.255538029666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.37965567772995

> <JCHEM_POLAR_SURFACE_AREA>
122.27000000000001

> <JCHEM_REFRACTIVITY>
135.49219999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
20-acetoxy-clavulone III

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0327073 (20-acetoxy-clavulone iii)
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PDB for NP0327073 (20-acetoxy-clavulone iii)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.294 -10.912   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.754 -10.912   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.016 -12.246   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.754 -13.580   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.556 -12.246   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.326 -13.580   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.866 -13.580   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.636 -14.913   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.176 -14.913   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.946 -16.247   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.486 -16.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.392 -15.001   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.916 -13.536   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.856 -15.477   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.856 -17.017   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.392 -17.493   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.696 -19.002   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.155 -19.494   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.311 -18.475   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.006 -16.966   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.161 -15.947   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.621 -16.438   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.776 -15.420   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.236 -15.911   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      18.391 -14.893   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      19.850 -15.384   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.006 -14.365   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      20.155 -16.893   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.258 -18.535   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.594 -20.038   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.063 -20.499   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.460 -21.080   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       4.636 -12.246   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.866 -10.912   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.326 -10.912   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.636  -9.578   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   33                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17   29                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   16   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    7   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

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3D PDB for NP0327073 (20-acetoxy-clavulone iii)
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SMILES for NP0327073 (20-acetoxy-clavulone iii)
COC(=O)CC[C@@H](OC(C)=O)\C=C\C=C1/C(=O)C=C[C@]1(C\C=C/CCCCCOC(C)=O)OC(C)=O
Download
INCHI for NP0327073 (20-acetoxy-clavulone iii)
InChI=1S/C27H36O9/c1-20(28)34-19-10-8-6-5-7-9-17-27(36-22(3)30)18-16-25(31)24(27)13-11-12-23(35-21(2)29)14-15-26(32)33-4/h7,9,11-13,16,18,23H,5-6,8,10,14-15,17,19H2,1-4H3/b9-7-,12-11+,24-13+/t23-,27-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC27H36O9
Average Mass504.5760 Da
Monoisotopic Mass504.23593 Da
IUPAC Namemethyl (4R,5E)-4-(acetyloxy)-7-[(1Z,2S)-2-(acetyloxy)-2-[(2Z)-8-(acetyloxy)oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate
Traditional Name20-acetoxy-clavulone III
CAS Registry NumberNot Available
SMILES
COC(=O)CC[C@@H](OC(C)=O)\C=C\C=C1/C(=O)C=C[C@]1(C\C=C/CCCCCOC(C)=O)OC(C)=O
InChI Identifier
InChI=1S/C27H36O9/c1-20(28)34-19-10-8-6-5-7-9-17-27(36-22(3)30)18-16-25(31)24(27)13-11-12-23(35-21(2)29)14-15-26(32)33-4/h7,9,11-13,16,18,23H,5-6,8,10,14-15,17,19H2,1-4H3/b9-7-,12-11+,24-13+/t23-,27-/m0/s1
InChI KeyLHIPZWGSDUHLAW-KAJQFPCGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Clavularia viridisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as clavulones and derivatives. These are ester derivatives of prostanoids.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassEicosanoids  
Direct ParentClavulones and derivatives  
Alternative Parents
Substituents
  • Clavulone
    • 

  • Clavulone-skeleton
    • 

  • Tetracarboxylic acid or derivatives
    • 

  • Fatty alcohol ester
    • 

  • Fatty acid ester
    • 

  • Fatty acid methyl ester
    • 

  • Methyl ester
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.26ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area122.27 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity135.49 m³·mol⁻¹ChemAxon
Polarizability54.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4446342  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283221  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]