NP-MRD: Showing NP-Card for japonicone D (NP0333277)

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Record Information

Version

2.0

Created at

2024-05-20 09:50:13 UTC

Updated at

2024-11-01 00:37:32 UTC

NP-MRD ID

NP0333277

Natural Product DOI

https://doi.org/10.57994/2627

Secondary Accession Numbers

None

Natural Product Identification

Common Name

japonicone D

Description

Japonicone D belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. japonicone D was first documented in 2024 (PMID: 38982404). Based on a literature review very few articles have been published on japonicone D.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02012312262D          

 48 53  0  0  1  0            999 V2000
    3.7737    5.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3533    4.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1690    4.6030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2190    3.6652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4748    3.9187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3564    2.9418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8633    2.2909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5531    1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599    0.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7359    1.4129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8403    4.6583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7904    4.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6607    5.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    3.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851    3.0147    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8832    2.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269    2.3332    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3029    1.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5147    2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    2.6568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0729    2.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4145    3.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0680    3.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1899    4.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2395    3.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958    3.0231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8535    3.4818    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7128    4.2947    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071    3.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9517    3.2859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5388    3.8655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7472    3.0672    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3343    3.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5426    2.8486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2926    3.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0115    2.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3072    2.7709    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1600    2.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9555    2.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1639    1.4707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9594    1.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5768    0.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7852    0.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1980   -0.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4064   -1.2849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8193   -1.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0277   -2.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0238   -1.6459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  5 11  1  1  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 15 14  1  6  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 20 19  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  2  0  0  0  0
 22 25  2  0  0  0  0
 20 26  1  1  0  0  0
 20 27  1  0  0  0  0
 27 23  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 14 29  1  0  0  0  0
  4 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31  3  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 34 33  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  6  0  0  0
 30 37  1  1  0  0  0
 30 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 40 39  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  2  0  0  0  0
M  END


  Mrv2104 02012312262D          

 48 53  0  0  1  0            999 V2000
    3.7737    5.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3533    4.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1690    4.6030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2190    3.6652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4748    3.9187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3564    2.9418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8633    2.2909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5531    1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599    0.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7359    1.4129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8403    4.6583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7904    4.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6607    5.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    3.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851    3.0147    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8832    2.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269    2.3332    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3029    1.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5147    2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    2.6568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0729    2.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4145    3.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0680    3.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1899    4.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2395    3.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958    3.0231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8535    3.4818    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7128    4.2947    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071    3.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9517    3.2859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5388    3.8655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7472    3.0672    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3343    3.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5426    2.8486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2926    3.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0115    2.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3072    2.7709    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1600    2.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9555    2.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1639    1.4707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9594    1.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5768    0.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7852    0.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1980   -0.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4064   -1.2849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8193   -1.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0277   -2.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0238   -1.6459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  5 11  1  1  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 15 14  1  6  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 20 19  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  2  0  0  0  0
 22 25  2  0  0  0  0
 20 26  1  1  0  0  0
 20 27  1  0  0  0  0
 27 23  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 14 29  1  0  0  0  0
  4 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31  3  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 34 33  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  6  0  0  0
 30 37  1  1  0  0  0
 30 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 40 39  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333277

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@](C)(O)C(=C[C@]1([H])[C@]1(C[C@@]34[C@@H](OC(C)=O)[C@]1([H])C(C)=C3C[C@]1([H])C(=C)C(=O)O[C@@]1([H])C[C@@H]4C)C(=O)O2)[C@@H](C)CCCOC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H44O9/c1-16(9-8-10-40-20(5)35)23-13-25-27(14-32(23,7)39)43-31(38)34(25)15-33-17(2)11-26-22(18(3)30(37)42-26)12-24(33)19(4)28(34)29(33)41-21(6)36/h13,16-17,22,25-29,39H,3,8-12,14-15H2,1-2,4-7H3/t16-,17-,22+,25-,26-,27+,28-,29-,32-,33?,34-/m0/s1

> <INCHI_KEY>
NEJMSJPMPBCXQF-CAGFCGRDSA-N

> <FORMULA>
C34H44O9

> <MOLECULAR_WEIGHT>
596.717

> <EXACT_MASS>
596.298532997

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
63.806172023758315

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-4-[(1'S,2'S,3S,3aR,4'S,6S,7aR,8'R,12'R,15'S)-15'-(acetyloxy)-6-hydroxy-2',6,11'-trimethyl-7'-methylidene-2,6'-dioxo-3a,6,7,7a-tetrahydro-2H-5'-oxaspiro[1-benzofuran-3,13'-tetracyclo[10.2.1.0^{1,10}.0^{4,8}]pentadecan]-10'-en-5-yl]pentyl acetate

> <JCHEM_LOGP>
2.874580282333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.3578194589425

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0796897686585494

> <JCHEM_POLAR_SURFACE_AREA>
125.43

> <JCHEM_REFRACTIVITY>
155.8204

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-[(1'S,2'S,3S,3aR,4'S,6S,7aR,8'R,12'R,15'S)-15'-(acetyloxy)-6-hydroxy-2',6,11'-trimethyl-7'-methylidene-2,6'-dioxo-7,7a-dihydro-3aH-5'-oxaspiro[1-benzofuran-3,13'-tetracyclo[10.2.1.0^{1,10}.0^{4,8}]pentadecan]-10'-en-5-yl]pentyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-FEB-23         0                                  
HETATM    1  O   UNK     0       7.044   9.457   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.126   8.361   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.649   8.592   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.875   6.842   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.486   7.315   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.265   5.491   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.212   4.276   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.632   2.849   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.579   1.634   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.107   2.637   0.000  0.00  0.00           O+0
HETATM   11  H   UNK     0       7.169   8.695   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       5.209   8.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.967   9.691   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.291   7.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.199   5.627   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.249   5.357   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.343   4.355   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.299   2.816   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.827   4.017   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.599   4.959   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.136   4.478   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.774   5.721   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.127   6.970   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.354   8.433   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.314   5.715   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0       2.979   5.643   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       1.593   6.499   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0       1.331   8.017   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0       2.813   7.433   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.243   6.134   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.339   7.216   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      10.728   5.726   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0      11.824   6.807   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.213   5.317   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.613   5.959   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      13.088   4.050   0.000  0.00  0.00           O+0
HETATM   37  H   UNK     0       8.040   5.172   0.000  0.00  0.00           H+0
HETATM   38  C   UNK     0       9.632   4.644   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.117   4.235   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.506   2.745   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      12.991   2.337   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.410   1.663   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      10.799   0.173   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       9.703  -0.908   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      10.092  -2.399   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       8.996  -3.480   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       9.385  -4.971   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       7.511  -3.072   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   31                                                       
CONECT    4    2    5   16   30                                             
CONECT    5    4    6   11   12                                             
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5                                                            
CONECT   12    5   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   29                                                  
CONECT   15   14    6   16   17                                             
CONECT   16   15    4                                                       
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   26   27                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24   27                                                  
CONECT   24   23                                                            
CONECT   25   22                                                            
CONECT   26   20                                                            
CONECT   27   20   23   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   14                                                       
CONECT   30    4   31   37   38                                             
CONECT   31   30    3   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36   39                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   30                                                            
CONECT   38   30   39                                                       
CONECT   39   38   34   40                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  106    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₄O₉

Average Mass

596.7170 Da

Monoisotopic Mass

596.29853 Da

IUPAC Name

(4S)-4-[(1'S,2'S,3S,3aR,4'S,6S,7aR,8'R,12'R,15'S)-15'-(acetyloxy)-6-hydroxy-2',6,11'-trimethyl-7'-methylidene-2,6'-dioxo-3a,6,7,7a-tetrahydro-2H-5'-oxaspiro[1-benzofuran-3,13'-tetracyclo[10.2.1.0^{1,10}.0^{4,8}]pentadecan]-10'-en-5-yl]pentyl acetate

Traditional Name

(4S)-4-[(1'S,2'S,3S,3aR,4'S,6S,7aR,8'R,12'R,15'S)-15'-(acetyloxy)-6-hydroxy-2',6,11'-trimethyl-7'-methylidene-2,6'-dioxo-7,7a-dihydro-3aH-5'-oxaspiro[1-benzofuran-3,13'-tetracyclo[10.2.1.0^{1,10}.0^{4,8}]pentadecan]-10'-en-5-yl]pentyl acetate

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@](C)(O)C(=C[C@]1([H])[C@]1(C[C@@]34[C@@H](OC(C)=O)[C@]1([H])C(C)=C3C[C@]1([H])C(=C)C(=O)O[C@@]1([H])C[C@@H]4C)C(=O)O2)[C@@H](C)CCCOC(C)=O

InChI Identifier

InChI=1S/C34H44O9/c1-16(9-8-10-40-20(5)35)23-13-25-27(14-32(23,7)39)43-31(38)34(25)15-33-17(2)11-26-22(18(3)30(37)42-26)12-24(33)19(4)28(34)29(33)41-21(6)36/h13,16-17,22,25-29,39H,3,8-12,14-15H2,1-2,4-7H3/t16-,17-,22+,25-,26-,27+,28-,29-,32-,33?,34-/m0/s1

InChI Key

NEJMSJPMPBCXQF-CAGFCGRDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	Not Available	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2024-05-20	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	Not Available	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2024-05-20	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	Not Available	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2024-05-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	Not Available	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2024-05-20	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	Not Available	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2024-05-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	Not Available	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2024-05-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
japonica		Not Available

Chemical Taxonomy

Description

This compound 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

Diterpenoid
Diterpene lactone
Xanthanolide-skeleton
Tetracarboxylic acid or derivatives
Fatty alcohol ester
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	2.87	ChemAxon
pKa (Strongest Acidic)	14.36	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	155.82 m³·mol⁻¹	ChemAxon
Polarizability	63.81 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Niu Z, Chen CY, Zhou Y, Liu GK, Zhang BY, Oppong MB, Zhang DQ, Yao T, Qiu F: Characterization of Sesquiterpene Dimers from the Flowers of Inula japonica and the Structural Revisions of Related Compounds. J Nat Prod. 2024 Jul 26;87(7):1754-1762. doi: 10.1021/acs.jnatprod.4c00269. Epub 2024 Jul 9. [PubMed:38982404 ]

Showing NP-Card for japonicone D (NP0333277)

MOL for NP0333277 (japonicone D)

3D MOL for NP0333277 (japonicone D)

3D SDF for NP0333277 (japonicone D)

3D-SDF for NP0333277 (japonicone D)

PDB for NP0333277 (japonicone D)

3D PDB for NP0333277 (japonicone D)

SMILES for NP0333277 (japonicone D)

INCHI for NP0333277 (japonicone D)

Structure for NP0333277 (japonicone D)

3D Structure for NP0333277 (japonicone D)