NP-MRD: Showing NP-Card for (2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid (NP0174444)

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Record Information

Version

2.0

Created at

2022-09-03 11:42:03 UTC

Updated at

2022-09-03 11:42:03 UTC

NP-MRD ID

NP0174444

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid

Description

Gambogellic Acid, also known as gambogellate, belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system. (2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid is found in Garcinia hanburyi. (2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid was first documented in 2008 (PMID: 18254140). Based on a literature review a small amount of articles have been published on Gambogellic Acid (PMID: 27809607) (PMID: 20605273).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032213422D          

 46 52  0  0  1  0            999 V2000
    9.3596    2.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5060    2.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3098    3.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9657    1.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3748    1.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1575    0.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4411    0.0251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7163   -0.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5728    1.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1699    2.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4534    1.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6974    3.5765    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
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  7  8  1  6  0  0  0
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 43 44  2  0  0  0  0
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 45 46  2  0  0  0  0
M  END

     RDKit          3D

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 39 89  1  0
 42 90  1  0
 32 78  1  0
 32 79  1  0
 32 80  1  0
 33 81  1  0
 33 82  1  0
 33 83  1  0
  3 49  1  0
  3 50  1  0
  3 51  1  0
  1 47  1  0
  1 48  1  0
M  END


  Mrv1652309032213422D          

 46 52  0  0  1  0            999 V2000
    9.3596    2.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5060    2.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3098    3.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9657    1.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3748    1.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1575    0.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4411    0.0251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7163   -0.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5728    1.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1699    2.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4534    1.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8728    2.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1028    3.1596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750    2.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8576    1.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4382    0.7492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3351   -0.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6076   -1.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4144   -1.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6682   -1.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9673   -0.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2361    0.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6452    0.2425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0310    1.1666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2714    1.6342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7080    2.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2582    3.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4631    2.8564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7049    2.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7100    1.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1811    0.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6327   -0.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3352    0.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6101    1.0359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2882    1.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6849    0.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4335    0.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3786   -0.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6383   -1.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0640   -1.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8044   -0.8393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091   -2.0265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8320    2.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417    2.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5033    2.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6974    3.5765    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
  2  4  1  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  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 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  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  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  2  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
  7 23  1  0  0  0  0
 15 24  1  0  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 27  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  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
 25 35  1  0  0  0  0
 35 36  1  0  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
 26 45  1  0  0  0  0
 14 45  1  0  0  0  0
 45 46  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0174444

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2O[C@]3(C)CCC(C(C3)C2=C(O)C2=C1O[C@@]13C4C[C@@H](C=C1C2=O)C(=O)C3(C\C=C(/C)C(O)=O)OC4(C)C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C38H44O8/c1-18(2)9-10-23-31-27(24-17-36(8,44-31)13-12-22(24)19(3)4)30(40)28-29(39)25-15-21-16-26-35(6,7)46-37(33(21)41,14-11-20(5)34(42)43)38(25,26)45-32(23)28/h9,11,15,21-22,24,26,40H,3,10,12-14,16-17H2,1-2,4-8H3,(H,42,43)/b20-11+/t21-,22?,24?,26?,36-,37?,38-/m1/s1

> <INCHI_KEY>
NVYMXCXFPJLTOZ-JGULFVLLSA-N

> <FORMULA>
C38H44O8

> <MOLECULAR_WEIGHT>
628.762

> <EXACT_MASS>
628.303618377

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
68.6515026515693

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-[(2S,8R,19S)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1^{8,12}.0^{2,17}.0^{2,21}.0^{4,15}.0^{6,13}]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid

> <ALOGPS_LOGP>
5.05

> <JCHEM_LOGP>
7.1861799756666676

> <ALOGPS_LOGS>
-5.93

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.120071348090322

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7761908233456

> <JCHEM_PKA_STRONGEST_BASIC>
-4.13039043667311

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
175.21950000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.40e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-[(2S,8R,19S)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1^{8,12}.0^{2,17}.0^{2,21}.0^{4,15}.0^{6,13}]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      17.471   5.067   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.878   4.941   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.512   6.489   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.869   3.634   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.633   2.296   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.227   0.811   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.890   0.047   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.404  -1.488   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.136   2.106   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.384   4.039   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.046   3.276   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.963   4.370   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.392   5.898   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.473   3.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.068   2.493   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.151   1.398   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.959  -0.300   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.468  -1.873   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.973  -2.196   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.447  -3.661   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.006  -1.053   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.641   1.790   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.404   0.453   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.525   2.178   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.107   3.050   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.922   4.508   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.082   5.890   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.598   5.332   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.049   3.812   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.059   2.036   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.071   0.827   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.914  -0.742   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.492   0.171   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.005   1.934   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.271   2.930   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.012   1.083   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.409   0.147   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.307  -1.389   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.925  -2.069   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.586  -2.246   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       8.968  -1.567   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       7.484  -3.783   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       3.420   4.298   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       1.945   4.916   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       8.406   5.118   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       8.768   6.676   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   23                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   45                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16   11   23                                                  
CONECT   23   22    7                                                       
CONECT   24   15   25                                                       
CONECT   25   24   26   30   35                                             
CONECT   26   25   27   45                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   43                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25   31                                                  
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   35                                                       
CONECT   35   34   25   36   43                                             
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   26   14   46                                                  
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  104    0
END

View in JSmol

Synonyms

Value	Source
Gambogellate	Generator

Chemical Formula

C₃₈H₄₄O₈

Average Mass

628.7620 Da

Monoisotopic Mass

628.30362 Da

IUPAC Name

(2E)-4-[(2S,8R,19S)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1^{8,12}.0^{2,17}.0^{2,21}.0^{4,15}.0^{6,13}]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2O[C@]3(C)CCC(C(C3)C2=C(O)C2=C1O[C@@]13C4C[C@@H](C=C1C2=O)C(=O)C3(C\C=C(/C)C(O)=O)OC4(C)C)C(C)=C

InChI Identifier

InChI=1S/C38H44O8/c1-18(2)9-10-23-31-27(24-17-36(8,44-31)13-12-22(24)19(3)4)30(40)28-29(39)25-15-21-16-26-35(6,7)46-37(33(21)41,14-11-20(5)34(42)43)38(25,26)45-32(23)28/h9,11,15,21-22,24,26,40H,3,10,12-14,16-17H2,1-2,4-8H3,(H,42,43)/b20-11+/t21-,22?,24?,26?,36-,37?,38-/m1/s1

InChI Key

NVYMXCXFPJLTOZ-JGULFVLLSA-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 pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranoxanthones

Alternative Parents

Substituents

Pyranoxanthone
Pyranochromene
Chromone
Monoterpenoid
Aromatic monoterpenoid
Aryl ketone
Cyclohexenone
Oxepane
Alkyl aryl ether
Benzenoid
Vinylogous acid
Tetrahydrofuran
Ketone
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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
logP	5.05	ALOGPS
logP	7.19	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	175.22 m³·mol⁻¹	ChemAxon
Polarizability	68.65 Å³	ChemAxon
Number of Rings	7	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

C00047154

Chemspider ID

81409465

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134715174

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li SL, Song JZ, Han QB, Qiao CF, Xu HX: Improved high-performance liquid chromatographic method for simultaneous determination of 12 cytotoxic caged xanthones in gamboges, a potential anticancer resin from Garcinia hanburyi. Biomed Chromatogr. 2008 Jun;22(6):637-44. doi: 10.1002/bmc.981. [PubMed:18254140 ]
Dong B, Zheng YF, Wen HM, Wang XZ, Xiong HW, Wu H, Li W: Two new xanthone epimers from the processed gamboge. Nat Prod Res. 2017 Apr;31(7):817-821. doi: 10.1080/14786419.2016.1247079. Epub 2016 Nov 4. [PubMed:27809607 ]
Wang J, Ma J, You Q, Zhao L, Wang F, Li C, Guo Q: Studies on chemical modification and biology of a natural product, gambogic acid (II): Synthesis and bioevaluation of gambogellic acid and its derivatives from gambogic acid as antitumor agents. Eur J Med Chem. 2010 Sep;45(9):4343-53. doi: 10.1016/j.ejmech.2010.04.037. Epub 2010 May 13. [PubMed:20605273 ]
LOTUS database [Link]

Showing NP-Card for (2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid (NP0174444)

MOL for NP0174444 ((2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid)

3D MOL for NP0174444 ((2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid)

3D SDF for NP0174444 ((2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid)

3D-SDF for NP0174444 ((2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid)

PDB for NP0174444 ((2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid)

3D PDB for NP0174444 ((2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid)

SMILES for NP0174444 ((2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid)

INCHI for NP0174444 ((2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid)

Structure for NP0174444 ((2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid)

3D Structure for NP0174444 ((2e)-4-[(2s,8r,19s)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid)