NP-MRD: Showing NP-Card for (1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione (NP0155127)

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Record Information

Version

2.0

Created at

2022-09-02 12:08:03 UTC

Updated at

2022-09-02 12:08:03 UTC

NP-MRD ID

NP0155127

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione

Description

Guttiferone A belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione is found in Garcinia intermedia, Garcinia macrophylla and Symphonia globulifera. (1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione was first documented in 2020 (PMID: 33158263). Based on a literature review a small amount of articles have been published on Guttiferone A (PMID: 33480950) (PMID: 31983232).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022214082D          

 44 46  0  0  1  0            999 V2000
   -2.4120    1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8652    2.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9953    1.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3408    1.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4214    1.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5291    0.7325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2888    0.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2134   -0.0297    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6116   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0241   -0.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6116   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0241   -2.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2134   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5291   -0.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2913   -1.1076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2913   -1.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769   -2.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769   -3.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1376   -3.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2913   -3.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535   -0.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6369   -1.3753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3692   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6067    0.6848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6067   -0.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4317   -0.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8442   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4317   -2.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8442   -2.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6067   -2.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942   -2.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535    0.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6369    1.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2913    1.0482    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2913    1.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058    2.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058    3.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203    3.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2913    3.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0219   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3544    0.4552    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 27 34  1  0  0  0  0
 24 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 37 43  1  0  0  0  0
 16 43  1  0  0  0  0
 43 44  2  0  0  0  0
M  END


  Mrv1652309022214082D          

 44 46  0  0  1  0            999 V2000
   -2.4120    1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8652    2.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9953    1.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3408    1.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4214    1.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5291    0.7325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2888    0.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2134   -0.0297    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6116   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0241   -0.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6116   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0241   -2.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2134   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5291   -0.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2913   -1.1076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2913   -1.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769   -2.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769   -3.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1376   -3.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2913   -3.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535   -0.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6369   -1.3753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3692   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6067    0.6848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6067   -0.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4317   -0.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8442   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4317   -2.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8442   -2.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6067   -2.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942   -2.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535    0.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6369    1.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2913    1.0482    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2913    1.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058    2.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058    3.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203    3.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2913    3.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0219   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3544    0.4552    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 27 34  1  0  0  0  0
 24 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 37 43  1  0  0  0  0
 16 43  1  0  0  0  0
 43 44  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0155127

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC[C@@]1(C)[C@H](CC=C(C)C)C[C@]2(CC=C(C)C)C(=O)\C(=C(\O)C3=CC=C(O)C(O)=C3)C(=O)[C@@]1(CC=C(C)C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C38H50O6/c1-23(2)11-10-18-36(9)28(14-12-24(3)4)22-37(19-16-25(5)6)33(42)31(32(41)27-13-15-29(39)30(40)21-27)34(43)38(36,35(37)44)20-17-26(7)8/h11-13,15-17,21,28,39-41H,10,14,18-20,22H2,1-9H3/b32-31-/t28-,36+,37-,38+/m1/s1

> <INCHI_KEY>
SHBMQWRFQJLYJU-XVQCXYMJSA-N

> <FORMULA>
C38H50O6

> <MOLECULAR_WEIGHT>
602.812

> <EXACT_MASS>
602.36073933

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
68.90288083201231

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3Z,5R,6S,7R)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione

> <ALOGPS_LOGP>
6.27

> <JCHEM_LOGP>
9.717411320999997

> <ALOGPS_LOGS>
-5.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.511515768195133

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.94190048102118

> <JCHEM_PKA_STRONGEST_BASIC>
-6.319325197844557

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
181.61560000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3Z,5R,6S,7R)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.502   2.198   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.281   3.135   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.482   4.662   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.858   2.546   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.636   3.483   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.787   2.894   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.988   1.367   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.539   1.568   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.398  -0.055   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.142  -0.055   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.912  -1.389   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.142  -2.723   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.912  -4.056   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.398  -2.723   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.988  -1.478   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.410  -2.068   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.410  -3.608   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.077  -4.378   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.077  -5.918   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.257  -6.688   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.410  -6.688   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.833  -1.478   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.922  -2.567   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.423  -0.055   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.963  -0.055   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.733   1.278   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.733  -1.389   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.273  -1.389   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.043  -2.723   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.273  -4.056   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.043  -5.390   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.733  -4.056   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.963  -5.390   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.963  -2.723   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.833   1.367   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.922   2.456   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.410   1.957   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.410   3.497   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.744   4.267   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.744   5.807   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.078   6.577   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.410   6.577   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.907  -0.055   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       0.662   0.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   37                                             
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16                                                       
CONECT   16   15   17   22   43                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   35                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   27                                                       
CONECT   35   24   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    7   38   43                                             
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   37   16   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₈H₅₀O₆

Average Mass

602.8120 Da

Monoisotopic Mass

602.36074 Da

IUPAC Name

(1S,3Z,5R,6S,7R)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione

Traditional Name

(1S,3Z,5R,6S,7R)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione

CAS Registry Number

Not Available

SMILES

CC(C)=CCC[C@@]1(C)[C@H](CC=C(C)C)C[C@]2(CC=C(C)C)C(=O)\C(=C(\O)C3=CC=C(O)C(O)=C3)C(=O)[C@@]1(CC=C(C)C)C2=O

InChI Identifier

InChI=1S/C38H50O6/c1-23(2)11-10-18-36(9)28(14-12-24(3)4)22-37(19-16-25(5)6)33(42)31(32(41)27-13-15-29(39)30(40)21-27)34(43)38(36,35(37)44)20-17-26(7)8/h11-13,15-17,21,28,39-41H,10,14,18-20,22H2,1-9H3/b32-31-/t28-,36+,37-,38+/m1/s1

InChI Key

SHBMQWRFQJLYJU-XVQCXYMJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Garcinia intermedia	LOTUS Database	35616633
Garcinia macrophylla	LOTUS Database	35616633
Symphonia globulifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Aromatic monoterpenoid
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	6.27	ALOGPS
logP	9.72	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	5.94	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	181.62 m³·mol⁻¹	ChemAxon
Polarizability	68.9 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

C00034855

Chemspider ID

21185469

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139071568

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Menelle P, Quintin J, Cottet K, Fromentin Y, Dupont J, Lallemand MC, Buisson D: Biotransformation of guttiferones, Symphonia globulifera metabolites, by Bipolaris cactivora, an endophytic fungus isolated from its leaves. Org Biomol Chem. 2021 Feb 18;19(6):1378-1385. doi: 10.1039/d0ob02443k. [PubMed:33480950 ]
da Silva CA, Rosa IA, de Souza TC, Dos Santos MH: Evaluating four modes of extraction to analyze bioactive compounds in Garcinia brasiliensis (bacupari) by high-performance liquid chromatography diode-array detection (HPLC-DAD). Nat Prod Res. 2021 Nov;35(21):4073-4077. doi: 10.1080/14786419.2020.1716344. Epub 2020 Jan 25. [PubMed:31983232 ]
Duval R, Cottet K, Blaud M, Merckx A, Houze S, Grellier P, Lallemand MC, Michel S: A Photoalkylative Fluorogenic Probe of Guttiferone A for Live Cell Imaging and Proteome Labeling in Plasmodium falciparum. Molecules. 2020 Nov 4;25(21):5139. doi: 10.3390/molecules25215139. [PubMed:33158263 ]
LOTUS database [Link]

Showing NP-Card for (1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione (NP0155127)

MOL for NP0155127 ((1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D MOL for NP0155127 ((1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D SDF for NP0155127 ((1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D-SDF for NP0155127 ((1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

PDB for NP0155127 ((1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D PDB for NP0155127 ((1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

SMILES for NP0155127 ((1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

INCHI for NP0155127 ((1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

Structure for NP0155127 ((1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D Structure for NP0155127 ((1s,3z,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)