NP-MRD: Showing NP-Card for (1r,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-1,5,6-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione (NP0263599)

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Record Information

Version

2.0

Created at

2022-09-08 06:49:41 UTC

Updated at

2022-09-08 06:49:42 UTC

NP-MRD ID

NP0263599

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Guttiferone G belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1r,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-1,5,6-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione is found in Garcinia macrophylla. (1r,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-1,5,6-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione was first documented in 2003 (PMID: 14598218). Based on a literature review very few articles have been published on Guttiferone G (PMID: 17516596).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082208492D          

 47 49  0  0  1  0            999 V2000
   -4.9956   -2.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5831   -1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9956   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7581   -1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3456   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5206   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1081   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5206    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2831   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8706    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456    0.2293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2701   -0.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -0.8486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0323   -1.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178   -2.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178   -2.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3966   -3.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -3.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7945   -0.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779   -1.1162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1102    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477    0.9438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5852   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727   -1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0323    1.3072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.7628    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0954    0.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2701    0.9915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3133    1.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    2.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6831    2.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4696    3.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4800    2.7416    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
  2  4  2  0  0  0  0
  4  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
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  2  0  0  0  0
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 21 22  2  0  0  0  0
 22 23  1  4  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
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 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 34 40  1  0  0  0  0
 13 40  1  0  0  0  0
 40 41  2  0  0  0  0
 34 42  1  0  0  0  0
 11 42  1  0  0  0  0
 42 43  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
M  END

     RDKit          3D

101103  0  0  0  0  0  0  0  0999 V2000
    7.7715   -0.2047   -1.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6942    1.2306   -1.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8344    0.2211    1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 48  1  0
  1 49  1  0
  1 50  1  0
  3 51  1  0
  3 52  1  0
  3 53  1  0
  4 54  1  0
  5 55  1  0
  5 56  1  0
  6 57  1  0
  6 58  1  0
  8 59  1  0
  8 60  1  0
  8 61  1  0
  9 62  1  0
 10 63  1  0
 10 64  1  0
 11 65  1  6
 12 66  1  0
 12 67  1  0
 14 68  1  0
 14 69  1  0
 15 70  1  0
 17 71  1  0
 17 72  1  0
 17 73  1  0
 18 74  1  0
 18 75  1  0
 18 76  1  0
 23 77  1  0
 25 78  1  0
 26 79  1  0
 28 80  1  0
 30 81  1  0
 31 82  1  0
 35 83  1  0
 35 84  1  0
 36 85  1  0
 38 86  1  0
 38 87  1  0
 38 88  1  0
 39 89  1  0
 39 90  1  0
 39 91  1  0
 42 92  1  1
 43 93  1  0
 43 94  1  0
 44 95  1  0
 46 96  1  0
 46 97  1  0
 46 98  1  0
 47 99  1  0
 47100  1  0
 47101  1  0
M  END


  Mrv1652309082208492D          

 47 49  0  0  1  0            999 V2000
   -4.9956   -2.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5831   -1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9956   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7581   -1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3456   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5206   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1081   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5206    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2831   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8706    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456    0.2293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2701   -0.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -0.8486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0323   -1.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178   -2.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178   -2.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3966   -3.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -3.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7945   -0.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779   -1.1162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1102    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477    0.9438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5852   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727   -1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5852   -2.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352   -2.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7945    0.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779    1.5749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323    1.3072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0323    2.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7468    2.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7468    3.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4612    3.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323    3.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7628    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0954    0.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2701    0.9915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3133    1.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    2.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6831    2.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4696    3.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4800    2.7416    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
  2  4  2  0  0  0  0
  4  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
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  4  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 34 40  1  0  0  0  0
 13 40  1  0  0  0  0
 40 41  2  0  0  0  0
 34 42  1  0  0  0  0
 11 42  1  0  0  0  0
 42 43  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0263599

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C41H54O6/c1-25(2)11-10-12-29(9)14-15-31-24-40(21-19-27(5)6)37(45)35(36(44)30-16-18-33(42)34(43)23-30)38(46)41(39(40)47,22-20-28(7)8)32(31)17-13-26(3)4/h11,13-14,16,18-20,23,31-32,42-44H,10,12,15,17,21-22,24H2,1-9H3/b29-14+,36-35?/t31-,32+,40-,41+/m1/s1

> <INCHI_KEY>
WVVJNGUTZLKXSY-FFNRHCHASA-N

> <FORMULA>
C41H54O6

> <MOLECULAR_WEIGHT>
642.877

> <EXACT_MASS>
642.392039459

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
101

> <JCHEM_AVERAGE_POLARIZABILITY>
74.31712709146368

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
10.632509811

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.511895146846623

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.0237804978206215

> <JCHEM_PKA_STRONGEST_BASIC>
-6.319325148814262

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
196.34210000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.325  -4.907   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.555  -3.573   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.325  -2.239   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.015  -3.573   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.245  -2.239   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.705  -2.239   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.935  -0.906   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.705   0.428   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.395  -0.906   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.625   0.428   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.085   0.428   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.504  -0.995   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.927  -1.584   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.927  -3.124   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.593  -3.894   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.593  -5.434   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.740  -6.204   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.927  -6.204   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.350  -0.995   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.439  -2.084   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.939   0.428   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.479   0.428   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.249   1.762   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.249  -0.906   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.789  -0.906   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.559  -2.239   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.789  -3.573   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.559  -4.907   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.249  -3.573   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.479  -4.907   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.479  -2.239   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.350   1.851   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.439   2.940   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.927   2.440   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.927   3.980   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.261   4.750   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.261   6.290   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.594   7.060   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.927   7.060   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.424   0.428   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.178   1.333   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       0.504   1.851   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.585   2.940   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -0.186   4.427   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -1.275   5.516   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -0.877   7.004   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -2.763   5.118   0.000  0.00  0.00           C+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                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   42                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19   40                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   13   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   32                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24                                                       
CONECT   32   21   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   40   42                                             
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   34   13   41                                                  
CONECT   41   40                                                            
CONECT   42   34   11   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
MASTER        0    0    0    0    0    0    0    0   47    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₁H₅₄O₆

Average Mass

642.8770 Da

Monoisotopic Mass

642.39204 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C41H54O6/c1-25(2)11-10-12-29(9)14-15-31-24-40(21-19-27(5)6)37(45)35(36(44)30-16-18-33(42)34(43)23-30)38(46)41(39(40)47,22-20-28(7)8)32(31)17-13-26(3)4/h11,13-14,16,18-20,23,31-32,42-44H,10,12,15,17,21-22,24H2,1-9H3/b29-14+,36-35?/t31-,32+,40-,41+/m1/s1

InChI Key

WVVJNGUTZLKXSY-FFNRHCHASA-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
Garcinia macrophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00055904

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

132598259

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gey C, Kyrylenko S, Hennig L, Nguyen LH, Buttner A, Pham HD, Giannis A: Phloroglucinol derivatives guttiferone G, aristoforin, and hyperforin: inhibitors of human sirtuins SIRT1 and SIRT2. Angew Chem Int Ed Engl. 2007;46(27):5219-22. doi: 10.1002/anie.200605207. [PubMed:17516596 ]
Williams RB, Hoch J, Glass TE, Evans R, Miller JS, Wisse JH, Kingston DG: A novel cytotoxic guttiferone analogue from Garcinia macrophylla from the Suriname rainforest. Planta Med. 2003 Sep;69(9):864-6. doi: 10.1055/s-2003-43204. [PubMed:14598218 ]
LOTUS database [Link]

Showing NP-Card for (1r,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-1,5,6-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione (NP0263599)

MOL for NP0263599 ((1r,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-1,5,6-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D MOL for NP0263599 ((1r,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-1,5,6-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D SDF for NP0263599 ((1r,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-1,5,6-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D-SDF for NP0263599 ((1r,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-1,5,6-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

PDB for NP0263599 ((1r,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-1,5,6-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D PDB for NP0263599 ((1r,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-1,5,6-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

SMILES for NP0263599 ((1r,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-1,5,6-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

INCHI for NP0263599 ((1r,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-1,5,6-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

Structure for NP0263599 ((1r,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-1,5,6-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D Structure for NP0263599 ((1r,5r,6s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-1,5,6-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)