NP-MRD: Showing NP-Card for (2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid (NP0322739)

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Record Information

Version

2.0

Created at

2022-09-12 01:41:13 UTC

Updated at

2022-09-12 01:41:13 UTC

NP-MRD ID

NP0322739

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid

Description

Gambogenic Acid, also known as neo-gambogic acid or gambogenate, belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. (2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid is found in Garcinia hanburyi. (2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid was first documented in 2019 (PMID: 31377565). Based on a literature review a significant number of articles have been published on Gambogenic Acid (PMID: 36086867) (PMID: 36081284) (PMID: 35994849) (PMID: 34980780) (PMID: 34692693) (PMID: 34331200).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122203412D          

 46 50  0  0  1  0            999 V2000
   12.4147   -0.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6956   -0.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6862   -1.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9859   -0.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2667   -0.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5570   -0.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8379   -0.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8285   -1.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1282   -0.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0504   -0.1206    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
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M  END

     RDKit          3D

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 13 64  1  0
 15 65  1  0
 15 66  1  0
 16 67  1  0
 18 68  1  0
 18 69  1  0
 18 70  1  0
 19 71  1  0
 19 72  1  0
 19 73  1  0
 30 79  1  1
 29 77  1  0
 29 78  1  0
 28 76  1  1
 27 75  1  0
 23 74  1  0
 36 86  1  0
 36 87  1  0
 37 88  1  0
 39 89  1  0
 39 90  1  0
 39 91  1  0
 42 92  1  0
 32 80  1  0
 32 81  1  0
 32 82  1  0
 33 83  1  0
 33 84  1  0
 33 85  1  0
M  END


  Mrv1652309122203412D          

 46 50  0  0  1  0            999 V2000
   12.4147   -0.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6956   -0.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6862   -1.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9859   -0.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2667   -0.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5570   -0.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8379   -0.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8285   -1.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1282   -0.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3840   -0.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5214   -0.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2342    0.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8063    0.9346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4208    0.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4049    1.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8317    2.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4176    2.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8285    3.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5926    2.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8947   -0.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1819   -0.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9953   -1.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2345   -1.9331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6996   -1.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0526   -2.4869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8833   -1.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5301   -2.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7385   -1.9494    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8969   -1.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7739   -0.1984    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1160    0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2687    0.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3910    1.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6432   -0.3433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3906   -0.7820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6620    0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2479    0.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9705    1.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5047    2.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1589    1.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6248    1.2806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815    2.6863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0034   -1.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2887   -2.0337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3842   -0.6937    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0504   -0.1206    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
  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
 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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 14 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 35 43  1  0  0  0  0
 28 43  1  0  0  0  0
 43 44  2  0  0  0  0
 35 45  1  0  0  0  0
 26 45  1  0  0  0  0
 30 45  1  0  0  0  0
 45 46  1  1  0  0  0
 20 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322739

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC1=C(O)C(CC=C(C)C)=C2O[C@@]34[C@H]5C[C@@H](C=C3C(=O)C2=C1O)C(=O)[C@]4(C\C=C(\C)C(O)=O)OC5(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C38H46O8/c1-20(2)10-9-11-22(5)13-15-25-30(39)26(14-12-21(3)4)33-29(31(25)40)32(41)27-18-24-19-28-36(7,8)46-37(34(24)42,38(27,28)45-33)17-16-23(6)35(43)44/h10,12-13,16,18,24,28,39-40H,9,11,14-15,17,19H2,1-8H3,(H,43,44)/b22-13+,23-16-/t24-,28+,37+,38-/m1/s1

> <INCHI_KEY>
RCWNBHCZYXWDOV-VSFMGBBVSA-N

> <FORMULA>
C38H46O8

> <MOLECULAR_WEIGHT>
630.778

> <EXACT_MASS>
630.319268441

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
70.19025178831374

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-4-[(1S,2S,13S,15R)-7-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0^{2,11}.0^{2,15}.0^{4,9}]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid

> <JCHEM_LOGP>
8.230181694333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.567850695656021

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7547395872842135

> <JCHEM_PKA_STRONGEST_BASIC>
-4.209351278750495

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
181.06890000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-4-[(1S,2S,13S,15R)-7-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0^{2,11}.0^{2,15}.0^{4,9}]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      23.174  -0.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.832  -1.140   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.814  -2.680   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.507  -0.355   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.165  -1.110   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.840  -0.325   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.497  -1.079   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.480  -2.619   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.173  -0.294   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.784  -1.075   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.173  -0.883   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.637   0.561   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.705   1.745   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.119   0.818   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.089   2.493   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.886   3.880   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.113   5.212   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.880   6.547   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.573   5.208   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.137  -0.368   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.673  -1.812   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.191  -2.069   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.638  -3.609   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.773  -3.123   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.431  -4.642   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.249  -2.682   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.590  -4.128   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.112  -3.639   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.407  -2.088   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.178  -0.370   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.950   0.638   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.368   1.165   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.463   2.403   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.067  -0.641   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.462  -1.460   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.969   0.550   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.063   1.837   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.545   3.288   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.542   4.461   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.030   3.564   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.033   2.391   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       3.512   5.014   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       3.740  -2.906   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       2.406  -3.796   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       6.317  -1.295   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       7.561  -0.225   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                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14   21   46                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   11   23                                                  
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   45                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   43                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   45                                                  
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   35                                                       
CONECT   35   34   36   43   45                                             
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   35   28   44                                                  
CONECT   44   43                                                            
CONECT   45   35   26   30   46                                             
CONECT   46   45   20                                                       
MASTER        0    0    0    0    0    0    0    0   46    0  100    0
END

View in JSmol

Synonyms

Value	Source
Gambogenate	Generator
Neo-gambogic acid	MeSH
Neogambogic acid	MeSH

Chemical Formula

C₃₈H₄₆O₈

Average Mass

630.7780 Da

Monoisotopic Mass

630.31927 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC1=C(O)C(CC=C(C)C)=C2O[C@@]34[C@H]5C[C@@H](C=C3C(=O)C2=C1O)C(=O)[C@]4(C\C=C(\C)C(O)=O)OC5(C)C

InChI Identifier

InChI=1S/C38H46O8/c1-20(2)10-9-11-22(5)13-15-25-30(39)26(14-12-21(3)4)33-29(31(25)40)32(41)27-18-24-19-28-36(7,8)46-37(34(24)42,38(27,28)45-33)17-16-23(6)35(43)44/h10,12-13,16,18,24,28,39-40H,9,11,14-15,17,19H2,1-8H3,(H,43,44)/b22-13+,23-16-/t24-,28+,37+,38-/m1/s1

InChI Key

RCWNBHCZYXWDOV-VSFMGBBVSA-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 hanburyi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Aromatic monoterpenoid
Monoterpenoid
Aryl ketone
Alkyl aryl ether
Phenol
Oxepane
Cyclohexenone
Benzenoid
Vinylogous acid
Oxolane
Ketone
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00030342

Chemspider ID

8969378

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10794070

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pan LY, Wang YS, Liu XH, Wang N, Xu W, Xiu YF: Pharmacokinetic comparison of five xanthones in rat plasma after oral administration of crude and processed Garcinia hanburyi extracts. J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Sep 15;1126-1127:121737. doi: 10.1016/j.jchromb.2019.121737. Epub 2019 Jul 26. [PubMed:31377565 ]
Wu J, Wang D, Zhou J, Li J, Xie R, Li Y, Huang J, Liu B, Qiu J: Gambogenic acid induces apoptosis and autophagy through ROS-mediated endoplasmic reticulum stress via JNK pathway in prostate cancer cells. Phytother Res. 2023 Jan;37(1):310-328. doi: 10.1002/ptr.7614. Epub 2022 Sep 9. [PubMed:36086867 ]
Wang M, Cheng H, Wu H, Liu C, Li S, Li B, Su J, Luo S, Li Q: Gambogenic acid antagonizes the expression and effects of long non-coding RNA NEAT1 and triggers autophagy and ferroptosis in melanoma. Biomed Pharmacother. 2022 Oct;154:113636. doi: 10.1016/j.biopha.2022.113636. Epub 2022 Sep 5. [PubMed:36081284 ]
Tao S, Yang L, Wu C, Hu Y, Guo F, Ren Q, Ma L, Fu P: Gambogenic acid alleviates kidney fibrosis via epigenetic inhibition of EZH2 to regulate Smad7-dependent mechanism. Phytomedicine. 2022 Nov;106:154390. doi: 10.1016/j.phymed.2022.154390. Epub 2022 Aug 11. [PubMed:35994849 ]
Wang M, Zhan F, Cheng H, Li Q: Gambogenic Acid Inhibits Basal Autophagy of Drug-Resistant Hepatoma Cells and Improves Its Sensitivity to Adriamycin. Biol Pharm Bull. 2022;45(1):63-70. doi: 10.1248/bpb.b21-00511. [PubMed:34980780 ]
Liu C, Xu J, Guo C, Chen X, Qian C, Zhang X, Zhou P, Yang Y: Gambogenic Acid Induces Endoplasmic Reticulum Stress in Colorectal Cancer via the Aurora A Pathway. Front Cell Dev Biol. 2021 Oct 6;9:736350. doi: 10.3389/fcell.2021.736350. eCollection 2021. [PubMed:34692693 ]
Pesonen L, Svartsjo S, Back V, de Thonel A, Mezger V, Saberan-Djoneidi D, Roos-Mattjus P: Gambogic acid and gambogenic acid induce a thiol-dependent heat shock response and disrupt the interaction between HSP90 and HSF1 or HSF2. Cell Stress Chaperones. 2021 Sep;26(5):819-833. doi: 10.1007/s12192-021-01222-4. Epub 2021 Jul 30. [PubMed:34331200 ]
Ding Z, Li Y, Tang Z, Song X, Jing F, Wu H, Lu B: Role of gambogenic acid in regulating PI3K/Akt/NF-kbeta signaling pathways in rat model of acute hepatotoxicity. Biosci Biotechnol Biochem. 2021 Feb 24;85(3):520-527. doi: 10.1093/bbb/zbaa039. [PubMed:33624779 ]
Wang B, Yuan T, Zha L, Liu Y, Chen W, Zhang C, Bao Y, Dong Q: Oral Delivery of Gambogenic Acid by Functional Polydopamine Nanoparticles for Targeted Tumor Therapy. Mol Pharm. 2021 Mar 1;18(3):1470-1479. doi: 10.1021/acs.molpharmaceut.1c00030. Epub 2021 Feb 14. [PubMed:33586444 ]
Jun-Zeng, Huang TY, Wang ZZ, Gong YF, Liu XC, Zhang XM, Huang XY: Scar-reducing effects of gambogenic acid on skin wounds in rabbit ears. Int Immunopharmacol. 2021 Jan;90:107200. doi: 10.1016/j.intimp.2020.107200. Epub 2020 Nov 24. [PubMed:33246825 ]
Zhao Q, Zhong J, Bi Y, Liu Y, Liu Y, Guo J, Pan L, Tan Y, Yu X: Gambogenic acid induces Noxa-mediated apoptosis in colorectal cancer through ROS-dependent activation of IRE1alpha/JNK. Phytomedicine. 2020 Nov;78:153306. doi: 10.1016/j.phymed.2020.153306. Epub 2020 Aug 18. [PubMed:32854039 ]
Zha L, Qian J, Wang B, Liu H, Zhang C, Dong Q, Chen W, Hong L: In vitro/in vivo evaluation of pH-sensitive Gambogenic acid loaded Zein nanoparticles with polydopamine coating. Int J Pharm. 2020 Sep 25;587:119665. doi: 10.1016/j.ijpharm.2020.119665. Epub 2020 Jul 21. [PubMed:32702449 ]
Wang M, Li S, Wang Y, Cheng H, Su J, Li Q: Gambogenic acid induces ferroptosis in melanoma cells undergoing epithelial-to-mesenchymal transition. Toxicol Appl Pharmacol. 2020 Aug 15;401:115110. doi: 10.1016/j.taap.2020.115110. Epub 2020 Jun 10. [PubMed:32533954 ]
Zhou S, Zhao N, Wang J: Gambogenic acid suppresses bladder cancer cells growth and metastasis by regulating NF-kappaB signaling. Chem Biol Drug Des. 2020 Nov;96(5):1272-1279. doi: 10.1111/cbdd.13737. Epub 2020 Jul 26. [PubMed:32491272 ]
Lin TY, Chang JL, Xun Y, Zhao Y, Peng W, Yang W, Ding BJ, Chen WD: Folic acid-modified nonionic surfactant vesicles for gambogenic acid targeting: Preparation, characterization, and in vitro and in vivo evaluation. Kaohsiung J Med Sci. 2020 May;36(5):344-353. doi: 10.1002/kjm2.12162. Epub 2020 Apr 15. [PubMed:32293112 ]
Shen D, Wang Y, Niu H, Liu C: Gambogenic acid exerts anticancer effects in cisplatin‑resistant non‑small cell lung cancer cells. Mol Med Rep. 2020 Mar;21(3):1267-1275. doi: 10.3892/mmr.2020.10909. Epub 2020 Jan 3. [PubMed:31922223 ]
Cheng W, Wang B, Zhang C, Dong Q, Qian J, Zha L, Chen W, Hong L: Preparation and preliminary pharmacokinetics study of GNA-loaded zein nanoparticles. J Pharm Pharmacol. 2019 Nov;71(11):1626-1634. doi: 10.1111/jphp.13151. Epub 2019 Aug 29. [PubMed:31468524 ]
Lin TY, Zhu TT, Xun Y, Tao YS, Yang YQ, Xie JL, Zhang XM, Chen SX, Ding BJ, Chen WD: A novel drug delivery system of mixed micelles based on poly(ethylene glycol)-poly(lactide) and poly(ethylene glycol)-poly(varepsilon-caprolactone) for gambogenic acid. Kaohsiung J Med Sci. 2019 Dec;35(12):757-764. doi: 10.1002/kjm2.12110. Epub 2019 Aug 21. [PubMed:31433556 ]
Wang B, Cheng W, Zhang C, Bao Y, Zha L, Qian J, Hong L, Chen W: Self-assembled micelles based on gambogenic acid-phospholipid complex for sustained-release drug delivery. J Microencapsul. 2019 Sep;36(6):566-575. doi: 10.1080/02652048.2019.1656294. Epub 2019 Sep 4. [PubMed:31411510 ]
Liu H, Chen H, Cao F, Peng D, Chen W, Zhang C: Amphiphilic Block Copolymer Poly (Acrylic Acid)-B-Polycaprolactone as a Novel pH-sensitive Nanocarrier for Anti-Cancer Drugs Delivery: In-vitro and In-vivo Evaluation. Polymers (Basel). 2019 May 7;11(5):820. doi: 10.3390/polym11050820. [PubMed:31067730 ]
LOTUS database [Link]

Showing NP-Card for (2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid (NP0322739)

MOL for NP0322739 ((2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid)

3D MOL for NP0322739 ((2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid)

3D SDF for NP0322739 ((2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid)

3D-SDF for NP0322739 ((2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid)

PDB for NP0322739 ((2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid)

3D PDB for NP0322739 ((2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid)

SMILES for NP0322739 ((2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid)

INCHI for NP0322739 ((2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid)

Structure for NP0322739 ((2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid)

3D Structure for NP0322739 ((2z)-4-[(1s,2s,13s,15r)-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid)