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Showing NP-Card for 2-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-1,5-dioxatetraphen-10-one (NP0319823)

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Record Information
Version2.0
Created at2022-09-11 21:03:36 UTC
Updated at2022-09-11 21:03:36 UTC
NP-MRD IDNP0319823
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-1,5-dioxatetraphen-10-one
DescriptionNIGROLINEAXANTHONE S 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. 2-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-1,5-dioxatetraphen-10-one is found in Garcinia nigrolineata. It was first documented in 2002 (PMID: 31593387). Based on a literature review a significant number of articles have been published on NIGROLINEAXANTHONE S (PMID: 27253005) (PMID: 27583328) (PMID: 36127157) (PMID: 14695790).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0319823 (2-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-1,5-dioxatetraphen-10-one)


  Mrv1652309112223032D          

 33 36  0  0  0  0            999 V2000
   -1.9893   -5.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4689   -5.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7631   -4.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6543   -5.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1339   -4.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6807   -4.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2011   -4.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9069   -3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0157   -4.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5361   -3.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2418   -2.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414   -1.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926    0.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -0.0357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -3.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    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  1  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  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
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 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
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 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 16 32  2  0  0  0  0
 21 32  1  0  0  0  0
 17 33  1  0  0  0  0
 12 33  1  0  0  0  0
M  END
Download

3D MOL for NP0319823 (2-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-1,5-dioxatetraphen-10-one)

Download
3D SDF for NP0319823 (2-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-1,5-dioxatetraphen-10-one)

  Mrv1652309112223032D          

 33 36  0  0  0  0            999 V2000
   -1.9893   -5.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4689   -5.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7631   -4.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6543   -5.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1339   -4.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6807   -4.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2011   -4.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9069   -3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0157   -4.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5361   -3.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2418   -2.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414   -1.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926    0.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -0.0357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -3.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    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  1  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  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 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
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 24 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 16 32  2  0  0  0  0
 21 32  1  0  0  0  0
 17 33  1  0  0  0  0
 12 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319823

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CCC1(C)OC2=CC(O)=C3C(=O)C4=CC=CC(O)=C4OC3=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O5/c1-17(2)8-5-9-18(3)10-7-14-28(4)15-13-19-23(33-28)16-22(30)24-25(31)20-11-6-12-21(29)26(20)32-27(19)24/h6,8,10-13,15-16,29-30H,5,7,9,14H2,1-4H3/b18-10+

> <INCHI_KEY>
RBHZFZSVMMGEQW-VCHYOVAHSA-N

> <FORMULA>
C28H30O5

> <MOLECULAR_WEIGHT>
446.543

> <EXACT_MASS>
446.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
50.878246610988796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-2,10-dihydro-1,5-dioxatetraphen-10-one

> <JCHEM_LOGP>
7.300515258999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.652597217752213

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.794302781143284

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7850589695581314

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
132.69969999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-1,5-dioxatetraphen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0319823 (2-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-1,5-dioxatetraphen-10-one)
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PDB for NP0319823 (2-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-1,5-dioxatetraphen-10-one)
HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.713 -10.824   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.742  -9.629   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.291  -8.190   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.221  -9.872   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.250  -8.677   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.271  -8.921   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.242  -7.726   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.693  -6.287   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.763  -7.970   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.734  -6.775   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.185  -5.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.811  -3.392   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.677  -0.940   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.189  -0.649   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.693   0.807   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.709  -1.522   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.213  -0.067   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.717  -6.760   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.701  -4.432   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.660  -2.686   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                                                       
CONECT   12   11   13   14   33                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   32                                                  
CONECT   17   16   18   33                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   32                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   24   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   16   21                                                  
CONECT   33   17   12                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

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3D PDB for NP0319823 (2-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-1,5-dioxatetraphen-10-one)
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SMILES for NP0319823 (2-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-1,5-dioxatetraphen-10-one)
CC(C)=CCC\C(C)=C\CCC1(C)OC2=CC(O)=C3C(=O)C4=CC=CC(O)=C4OC3=C2C=C1
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INCHI for NP0319823 (2-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-1,5-dioxatetraphen-10-one)
InChI=1S/C28H30O5/c1-17(2)8-5-9-18(3)10-7-14-28(4)15-13-19-23(33-28)16-22(30)24-25(31)20-11-6-12-21(29)26(20)32-27(19)24/h6,8,10-13,15-16,29-30H,5,7,9,14H2,1-4H3/b18-10+
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SynonymsNot Available
Chemical FormulaC28H30O5
Average Mass446.5430 Da
Monoisotopic Mass446.20932 Da
IUPAC Name2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-2,10-dihydro-1,5-dioxatetraphen-10-one
Traditional Name2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-6,11-dihydroxy-2-methyl-1,5-dioxatetraphen-10-one
CAS Registry NumberNot Available
SMILES
CC(C)=CCC\C(C)=C\CCC1(C)OC2=CC(O)=C3C(=O)C4=CC=CC(O)=C4OC3=C2C=C1
InChI Identifier
InChI=1S/C28H30O5/c1-17(2)8-5-9-18(3)10-7-14-28(4)15-13-19-23(33-28)16-22(30)24-25(31)20-11-6-12-21(29)26(20)32-27(19)24/h6,8,10-13,15-16,29-30H,5,7,9,14H2,1-4H3/b18-10+
InChI KeyRBHZFZSVMMGEQW-VCHYOVAHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Garcinia nigrolineataLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzopyrans  
Sub Class1-benzopyrans  
Direct ParentPyranoxanthones  
Alternative Parents
Substituents
  • Pyranoxanthone
    • 

  • Pyranochromene
    • 

  • Chromone
    • 

  • Aromatic monoterpenoid
    • 

  • Monoterpenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.3ChemAxon
pKa (Strongest Acidic)7.79ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity132.7 m³·mol⁻¹ChemAxon
Polarizability50.88 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00044967  
Chemspider ID9457255  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11282258  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005  ] 
  2. Authors unspecified: Childhood Esophageal Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31593387  ] 
  3. Authors unspecified: Financial Toxicity and Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:27583328  ] 
  4. Gadot R, Najera R, Hirani S, Anand A, Storch E, Goodman WK, Shofty B, Sheth SA: Efficacy of deep brain stimulation for treatment-resistant obsessive-compulsive disorder: systematic review and meta-analysis. J Neurol Neurosurg Psychiatry. 2022 Sep 20. pii: jnnp-2021-328738. doi: 10.1136/jnnp-2021-328738. [PubMed:36127157  ] 
  5. Rukachaisirikul V, Kamkaew M, Sukavisit D, Phongpaichit S, Sawangchote P, Taylor WC: Antibacterial xanthones from the leaves of Garcinia nigrolineata. J Nat Prod. 2003 Dec;66(12):1531-5. doi: 10.1021/np0303254. [PubMed:14695790  ] 
  6. LOTUS database [Link]