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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:53:16 UTC

Update Date

2022-03-07 02:53:59 UTC

HMDB ID

HMDB0034095

Secondary Accession Numbers

HMDB34095

Metabolite Identification

Common Name

Gambogic acid

Description

Gambogic acid, also known as gambogate or b-guttiferin, 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. Gambogic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Gambogic acid is a xanthonoid that is derived from the brownish or orange resin from Garcinia hanburyi. Outside of the human body, gambogic acid has been detected, but not quantified in, fruits and herbs and spices. This could make gambogic acid a potential biomarker for the consumption of these foods. At the highest level of 120 mg/kg the primary toxic target organs were the liver and kidneys. For the same length of exposure, the higher the concentration of gambogic acid that was administered, the greater the effect on inhibiting cell growth. The ratio of relative tumor volume (RTV) for the treated group of mice to the control group indicates the gambogic acid was having an impact on tumor size while having no adverse effects on body weight or mortality.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241215292D          

 46 51  0  0  0  0            999 V2000
   -0.3972   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972   -1.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161   -1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0280   -1.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0280   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118    0.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8266   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8266   -1.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118   -1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4533   -1.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4533   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -0.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1666   -1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5412    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 44 46  2  0  0  0  0
M  END

HMDB0034095
     RDKit          3D
Gambogic acid
 90 95  0  0  0  0  0  0  0  0999 V2000
    8.4173    2.6091    0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7615    1.2485    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9400    0.4906    1.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0660    0.7854   -0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3607   -0.4821   -0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0842    0.1654   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5135    1.6399   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241215292D          

 46 51  0  0  0  0            999 V2000
   -0.3972   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972   -1.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161   -1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0280   -1.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0280   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118    0.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8266   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8266   -1.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118   -1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4533   -1.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4533   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -0.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1666   -1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8785   -1.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8785   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1666   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161    0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3986    1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3986    2.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1132    2.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161    2.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5412    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9706    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5412   -0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161   -2.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -2.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5932    0.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -0.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6853   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4000    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6853   -1.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1721    0.9119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9418    1.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7287    2.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3541    2.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1251    0.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4519    0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4519    1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7373    1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7373    2.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225    1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078    1.6486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225    0.4116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  2  0  0  0  0
  3 28  1  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  2  0  0  0  0
  5 14  1  0  0  0  0
  6 19  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 24  1  0  0  0  0
  8 27  1  0  0  0  0
  9 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 29  2  0  0  0  0
 12 13  1  0  0  0  0
 12 15  2  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 13 39  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 31  1  0  0  0  0
 17 18  1  0  0  0  0
 17 30  2  0  0  0  0
 18 35  1  0  0  0  0
 18 40  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 32  2  0  0  0  0
 31 39  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034095

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCCC1(C)OC2=C(C=C1)C(O)=C1C(=O)C3=CC4CC5C(C)(C)OC(C\C=C(\C)C(O)=O)(C4=O)C35OC1=C2CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/b22-13-

> <INCHI_KEY>
GEZHEQNLKAOMCA-XKZIYDEJSA-N

> <FORMULA>
C38H44O8

> <MOLECULAR_WEIGHT>
628.7512

> <EXACT_MASS>
628.303618384

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
68.09938568736706

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-4-[12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4,6(11),9,12,15-pentaen-19-yl]-2-methylbut-2-enoic acid

> <ALOGPS_LOGP>
5.57

> <JCHEM_LOGP>
7.783757148666668

> <ALOGPS_LOGS>
-5.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.776651867350122

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.756826432766361

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9992999746434004

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
179.16160000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.12e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-4-[12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4,6(11),9,12,15-pentaen-19-yl]-2-methylbut-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034095
     RDKit          3D
Gambogic acid
 90 95  0  0  0  0  0  0  0  0999 V2000
    8.4173    2.6091    0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7615    1.2485    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9400    0.4906    1.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0660    0.7854   -0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3607   -0.4821   -0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9120   -0.4804   -1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0842    0.1654   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5135    1.6399   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2897   -0.5090    1.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -1.0104    1.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9120   -0.9530    1.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930   -1.5040    2.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2355   -2.0958    3.3328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3799   -1.3912    1.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6703   -0.7714    0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3903   -0.2298   -0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0781    0.4260   -1.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2465    1.0439   -2.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6705    0.6203   -3.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9369   -0.4897   -4.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465    1.1992   -4.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7012   -0.3173    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499    0.2033   -0.5123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9423   -0.6567   -0.0378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0703   -1.2017    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -1.8643    1.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9508   -2.3440    2.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1895   -2.3550    1.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7271   -3.0762    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6996   -2.2428   -0.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010   -1.2815   -1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5968   -1.8088   -1.9903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3157   -1.1708   -2.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4795   -0.0585   -0.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444   -0.2337    0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9211    1.0770    1.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337    1.9003    1.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8574    2.3629    2.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0916    3.2091    1.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5688    2.1135    3.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3791    2.6430    4.3774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5219    1.3694    4.0365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3840   -0.9439    1.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4512   -0.4257    1.3602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5194   -1.9564    2.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -2.5314    3.4712 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5082    2.4694   -0.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9575    3.1177   -0.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2404    3.2013    0.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1400    0.7440    2.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0119   -0.5841    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9255    0.8401    1.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0243    1.4375   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8336   -1.0189   -1.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6413   -1.1961   -0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5736   -1.5046   -1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.1547   -2.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5869    2.2796    0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0818    1.7364    0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9444    2.0300   -0.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2818   -0.6308    1.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4720   -1.5182    2.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8029   -2.5518    4.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6913    1.2380   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4127   -0.3358   -2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7955    1.8556   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4053   -0.7764   -4.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463   -1.3545   -3.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1253   -0.2446   -4.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4661    0.3980   -4.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036    1.8297   -4.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853    1.8063   -3.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0003   -2.7069    3.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0354   -2.8319    2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5704   -3.3880   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2265   -4.0198    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8986   -2.8588   -0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4042   -2.8134   -2.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8631   -1.1565   -2.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4326   -1.7561   -1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7644   -1.4516   -3.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3886   -1.7636   -2.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9642   -0.1125   -2.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5673    0.9324    2.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406    1.5509    0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5080    2.1830    0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1796    3.3955    0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0922    4.1263    2.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9436    2.5944    2.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8582    1.7613    4.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 16 22  1  0
 22 23  1  0
 15 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 38 40  1  0
 40 41  2  0
 40 42  1  0
 35 43  1  0
 43 44  2  0
 26 45  1  0
 45 46  2  0
 23  7  1  0
 30 25  1  0
 22 11  2  0
 35 25  1  0
 45 14  1  0
 43 28  1  0
  1 47  1  0
  1 48  1  0
  1 49  1  0
  3 50  1  0
  3 51  1  0
  3 52  1  0
  4 53  1  0
  5 54  1  0
  5 55  1  0
  6 56  1  0
  6 57  1  0
  8 58  1  0
  8 59  1  0
  8 60  1  0
  9 61  1  0
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 13 63  1  0
 17 64  1  0
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 21 72  1  0
 27 73  1  0
 28 74  1  0
 29 75  1  0
 29 76  1  0
 30 77  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
 36 84  1  0
 36 85  1  0
 37 86  1  0
 39 87  1  0
 39 88  1  0
 39 89  1  0
 42 90  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.741  -0.768   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.741  -2.308   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.590  -3.077   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.919  -2.308   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.919  -0.768   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.590  -0.001   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.075   0.001   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.410  -0.768   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.410  -2.308   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.075  -3.077   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.250  -3.077   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.579  -2.308   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.579  -0.768   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.250  -0.001   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.911  -3.077   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.240  -2.308   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.240  -0.768   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.911  -0.001   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.590   1.538   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.744   2.308   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.744   3.847   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.078   4.617   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.590   4.617   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.744   0.001   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.078  -0.768   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.412   0.001   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.744  -1.538   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.590  -4.617   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       3.250  -4.617   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.574   0.001   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.080  -1.435   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.746  -0.768   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.080   0.001   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -8.746  -2.308   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.921   1.702   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.358   2.613   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.960   4.101   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.128   3.947   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.567   0.822   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.577   0.768   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.577   2.308   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.243   3.077   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.243   4.617   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.909   2.308   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       0.575   3.077   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       1.909   0.768   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4   28                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6   14                                                  
CONECT    6    1    5   19                                                  
CONECT    7    1    8                                                       
CONECT    8    7    9   24   27                                             
CONECT    9    8   10                                                       
CONECT   10    2    9                                                       
CONECT   11    4   12   29                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14   18   39                                             
CONECT   14    5   13                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17   31                                                  
CONECT   17   16   18   30                                                  
CONECT   18   13   17   35   40                                             
CONECT   19    6   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    8   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   32                                                       
CONECT   27    8                                                            
CONECT   28    3                                                            
CONECT   29   11                                                            
CONECT   30   17                                                            
CONECT   31   16   39                                                       
CONECT   32   26   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   18   36                                                       
CONECT   36   35   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   13   31   36                                                  
CONECT   40   18   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  102    0
END

COMPND    HMDB0034095
HETATM    1  C1  UNL     1       8.417   2.609   0.020  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.761   1.248   0.137  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.940   0.491   1.415  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.066   0.785  -0.882  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.361  -0.482  -0.985  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.912  -0.480  -1.238  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.084   0.165  -0.144  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.514   1.640  -0.001  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.290  -0.509   1.142  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.304  -1.010   1.834  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.912  -0.953   1.407  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.893  -1.504   2.172  1.00  0.00           C  
HETATM   13  O1  UNL     1       1.236  -2.096   3.333  1.00  0.00           O  
HETATM   14  C13 UNL     1      -0.380  -1.391   1.665  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.670  -0.771   0.468  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.390  -0.230  -0.271  1.00  0.00           C  
HETATM   17  C16 UNL     1       0.078   0.426  -1.555  1.00  0.00           C  
HETATM   18  C17 UNL     1       1.246   1.044  -2.191  1.00  0.00           C  
HETATM   19  C18 UNL     1       1.671   0.620  -3.371  1.00  0.00           C  
HETATM   20  C19 UNL     1       0.937  -0.490  -4.030  1.00  0.00           C  
HETATM   21  C20 UNL     1       2.846   1.199  -4.077  1.00  0.00           C  
HETATM   22  C21 UNL     1       1.701  -0.317   0.196  1.00  0.00           C  
HETATM   23  O2  UNL     1       2.750   0.203  -0.512  1.00  0.00           O  
HETATM   24  O3  UNL     1      -1.942  -0.657  -0.038  1.00  0.00           O  
HETATM   25  C22 UNL     1      -3.070  -1.202   0.545  1.00  0.00           C  
HETATM   26  C23 UNL     1      -2.880  -1.864   1.842  1.00  0.00           C  
HETATM   27  C24 UNL     1      -3.951  -2.344   2.448  1.00  0.00           C  
HETATM   28  C25 UNL     1      -5.190  -2.355   1.582  1.00  0.00           C  
HETATM   29  C26 UNL     1      -4.727  -3.076   0.303  1.00  0.00           C  
HETATM   30  C27 UNL     1      -3.700  -2.243  -0.409  1.00  0.00           C  
HETATM   31  C28 UNL     1      -4.301  -1.281  -1.414  1.00  0.00           C  
HETATM   32  C29 UNL     1      -5.597  -1.809  -1.990  1.00  0.00           C  
HETATM   33  C30 UNL     1      -3.316  -1.171  -2.560  1.00  0.00           C  
HETATM   34  O4  UNL     1      -4.479  -0.059  -0.777  1.00  0.00           O  
HETATM   35  C31 UNL     1      -4.244  -0.234   0.558  1.00  0.00           C  
HETATM   36  C32 UNL     1      -3.921   1.077   1.242  1.00  0.00           C  
HETATM   37  C33 UNL     1      -5.134   1.900   1.178  1.00  0.00           C  
HETATM   38  C34 UNL     1      -5.857   2.363   2.152  1.00  0.00           C  
HETATM   39  C35 UNL     1      -7.092   3.209   1.847  1.00  0.00           C  
HETATM   40  C36 UNL     1      -5.569   2.114   3.520  1.00  0.00           C  
HETATM   41  O5  UNL     1      -6.379   2.643   4.377  1.00  0.00           O  
HETATM   42  O6  UNL     1      -4.522   1.369   4.037  1.00  0.00           O  
HETATM   43  C37 UNL     1      -5.384  -0.944   1.176  1.00  0.00           C  
HETATM   44  O7  UNL     1      -6.451  -0.426   1.360  1.00  0.00           O  
HETATM   45  C38 UNL     1      -1.519  -1.956   2.378  1.00  0.00           C  
HETATM   46  O8  UNL     1      -1.325  -2.531   3.471  1.00  0.00           O  
HETATM   47  H1  UNL     1       9.508   2.469  -0.056  1.00  0.00           H  
HETATM   48  H2  UNL     1       7.958   3.118  -0.830  1.00  0.00           H  
HETATM   49  H3  UNL     1       8.240   3.201   0.943  1.00  0.00           H  
HETATM   50  H4  UNL     1       7.140   0.744   2.139  1.00  0.00           H  
HETATM   51  H5  UNL     1       8.012  -0.584   1.170  1.00  0.00           H  
HETATM   52  H6  UNL     1       8.925   0.840   1.853  1.00  0.00           H  
HETATM   53  H7  UNL     1       7.024   1.437  -1.781  1.00  0.00           H  
HETATM   54  H8  UNL     1       6.834  -1.019  -1.880  1.00  0.00           H  
HETATM   55  H9  UNL     1       6.641  -1.196  -0.144  1.00  0.00           H  
HETATM   56  H10 UNL     1       4.574  -1.505  -1.431  1.00  0.00           H  
HETATM   57  H11 UNL     1       4.729   0.155  -2.149  1.00  0.00           H  
HETATM   58  H12 UNL     1       3.587   2.280   0.177  1.00  0.00           H  
HETATM   59  H13 UNL     1       5.082   1.736   0.925  1.00  0.00           H  
HETATM   60  H14 UNL     1       4.944   2.030  -0.913  1.00  0.00           H  
HETATM   61  H15 UNL     1       5.282  -0.631   1.588  1.00  0.00           H  
HETATM   62  H16 UNL     1       3.472  -1.518   2.804  1.00  0.00           H  
HETATM   63  H17 UNL     1       0.803  -2.552   4.063  1.00  0.00           H  
HETATM   64  H18 UNL     1      -0.691   1.238  -1.391  1.00  0.00           H  
HETATM   65  H19 UNL     1      -0.413  -0.336  -2.215  1.00  0.00           H  
HETATM   66  H20 UNL     1       1.796   1.856  -1.750  1.00  0.00           H  
HETATM   67  H21 UNL     1       1.405  -0.776  -4.976  1.00  0.00           H  
HETATM   68  H22 UNL     1       0.946  -1.354  -3.334  1.00  0.00           H  
HETATM   69  H23 UNL     1      -0.125  -0.245  -4.234  1.00  0.00           H  
HETATM   70  H24 UNL     1       3.466   0.398  -4.554  1.00  0.00           H  
HETATM   71  H25 UNL     1       2.504   1.830  -4.945  1.00  0.00           H  
HETATM   72  H26 UNL     1       3.485   1.806  -3.412  1.00  0.00           H  
HETATM   73  H27 UNL     1      -4.000  -2.707   3.458  1.00  0.00           H  
HETATM   74  H28 UNL     1      -6.035  -2.832   2.053  1.00  0.00           H  
HETATM   75  H29 UNL     1      -5.570  -3.388  -0.318  1.00  0.00           H  
HETATM   76  H30 UNL     1      -4.226  -4.020   0.657  1.00  0.00           H  
HETATM   77  H31 UNL     1      -2.899  -2.859  -0.870  1.00  0.00           H  
HETATM   78  H32 UNL     1      -5.404  -2.813  -2.364  1.00  0.00           H  
HETATM   79  H33 UNL     1      -5.863  -1.156  -2.851  1.00  0.00           H  
HETATM   80  H34 UNL     1      -6.433  -1.756  -1.269  1.00  0.00           H  
HETATM   81  H35 UNL     1      -3.764  -1.452  -3.528  1.00  0.00           H  
HETATM   82  H36 UNL     1      -2.389  -1.764  -2.382  1.00  0.00           H  
HETATM   83  H37 UNL     1      -2.964  -0.112  -2.688  1.00  0.00           H  
HETATM   84  H38 UNL     1      -3.567   0.932   2.240  1.00  0.00           H  
HETATM   85  H39 UNL     1      -3.141   1.551   0.571  1.00  0.00           H  
HETATM   86  H40 UNL     1      -5.508   2.183   0.161  1.00  0.00           H  
HETATM   87  H41 UNL     1      -7.180   3.396   0.771  1.00  0.00           H  
HETATM   88  H42 UNL     1      -7.092   4.126   2.458  1.00  0.00           H  
HETATM   89  H43 UNL     1      -7.944   2.594   2.200  1.00  0.00           H  
HETATM   90  H44 UNL     1      -3.858   1.761   4.676  1.00  0.00           H  
CONECT    1    2   47   48   49
CONECT    2    3    4    4
CONECT    3   50   51   52
CONECT    4    5   53
CONECT    5    6   54   55
CONECT    6    7   56   57
CONECT    7    8    9   23
CONECT    8   58   59   60
CONECT    9   10   10   61
CONECT   10   11   62
CONECT   11   12   22   22
CONECT   12   13   14   14
CONECT   13   63
CONECT   14   15   45
CONECT   15   16   16   24
CONECT   16   17   22
CONECT   17   18   64   65
CONECT   18   19   19   66
CONECT   19   20   21
CONECT   20   67   68   69
CONECT   21   70   71   72
CONECT   22   23
CONECT   24   25
CONECT   25   26   30   35
CONECT   26   27   27   45
CONECT   27   28   73
CONECT   28   29   43   74
CONECT   29   30   75   76
CONECT   30   31   77
CONECT   31   32   33   34
CONECT   32   78   79   80
CONECT   33   81   82   83
CONECT   34   35
CONECT   35   36   43
CONECT   36   37   84   85
CONECT   37   38   38   86
CONECT   38   39   40
CONECT   39   87   88   89
CONECT   40   41   41   42
CONECT   42   90
CONECT   43   44   44
CONECT   45   46   46
END

HMDB0034095
     RDKit          3D
Gambogic acid
 90 95  0  0  0  0  0  0  0  0999 V2000
    8.4173    2.6091    0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7615    1.2485    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9400    0.4906    1.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0660    0.7854   -0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3607   -0.4821   -0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9120   -0.4804   -1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0842    0.1654   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5135    1.6399   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2897   -0.5090    1.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -1.0104    1.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9120   -0.9530    1.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930   -1.5040    2.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2355   -2.0958    3.3328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3799   -1.3912    1.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6703   -0.7714    0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3903   -0.2298   -0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0781    0.4260   -1.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2465    1.0439   -2.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6705    0.6203   -3.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9369   -0.4897   -4.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465    1.1992   -4.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7012   -0.3173    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499    0.2033   -0.5123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9423   -0.6567   -0.0378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0703   -1.2017    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -1.8643    1.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9508   -2.3440    2.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1895   -2.3550    1.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7271   -3.0762    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6996   -2.2428   -0.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010   -1.2815   -1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5968   -1.8088   -1.9903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3157   -1.1708   -2.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4795   -0.0585   -0.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444   -0.2337    0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9211    1.0770    1.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337    1.9003    1.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8574    2.3629    2.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0916    3.2091    1.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5688    2.1135    3.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3791    2.6430    4.3774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5219    1.3694    4.0365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3840   -0.9439    1.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4512   -0.4257    1.3602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5194   -1.9564    2.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -2.5314    3.4712 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5082    2.4694   -0.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9575    3.1177   -0.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2404    3.2013    0.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1400    0.7440    2.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0119   -0.5841    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9255    0.8401    1.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0243    1.4375   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8336   -1.0189   -1.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6413   -1.1961   -0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5736   -1.5046   -1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.1547   -2.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5869    2.2796    0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0818    1.7364    0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9444    2.0300   -0.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2818   -0.6308    1.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4720   -1.5182    2.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8029   -2.5518    4.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6913    1.2380   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4127   -0.3358   -2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7955    1.8556   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4053   -0.7764   -4.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463   -1.3545   -3.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1253   -0.2446   -4.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4661    0.3980   -4.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036    1.8297   -4.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853    1.8063   -3.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0003   -2.7069    3.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0354   -2.8319    2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5704   -3.3880   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2265   -4.0198    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8986   -2.8588   -0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4042   -2.8134   -2.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8631   -1.1565   -2.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4326   -1.7561   -1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7644   -1.4516   -3.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3886   -1.7636   -2.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9642   -0.1125   -2.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5673    0.9324    2.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406    1.5509    0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5080    2.1830    0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1796    3.3955    0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0922    4.1263    2.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9436    2.5944    2.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8582    1.7613    4.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
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 14 15  1  0
 15 16  2  0
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 17 18  1  0
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 19 20  1  0
 19 21  1  0
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 22 23  1  0
 15 24  1  0
 24 25  1  0
 25 26  1  0
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 26 45  1  0
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  1 47  1  0
  1 48  1  0
  1 49  1  0
  3 50  1  0
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  4 53  1  0
  5 54  1  0
  5 55  1  0
  6 56  1  0
  6 57  1  0
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  8 59  1  0
  8 60  1  0
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 39 87  1  0
 39 88  1  0
 39 89  1  0
 42 90  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Gambogate	Generator
a-Gambogic acid	HMDB
b-Guttiferin	HMDB
b-Guttilactone	HMDB
Guttatic acid	HMDB
Guttic acid	HMDB
Gamboge acid	HMDB
Gambogoic acid	HMDB
(2Z)-4-[12-Hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoate	Generator
Gambogic acid	MeSH

Chemical Formula

C₃₈H₄₄O₈

Average Molecular Weight

628.7512

Monoisotopic Molecular Weight

628.303618384

IUPAC Name

(2Z)-4-[12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4,6(11),9,12,15-pentaen-19-yl]-2-methylbut-2-enoic acid

Traditional Name

CAS Registry Number

2752-65-0

SMILES

CC(C)=CCCC1(C)OC2=C(C=C1)C(O)=C1C(=O)C3=CC4CC5C(C)(C)OC(C\C=C(\C)C(O)=O)(C4=O)C35OC1=C2CC=C(C)C

InChI Identifier

InChI=1S/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/b22-13-

InChI Key

GEZHEQNLKAOMCA-XKZIYDEJSA-N

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0034095)

Cellular substructure

Membrane (HMDB: HMDB0034095)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034095)

Source

Exogenous

Food

Food (HMDB: HMDB0034095)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0034095)

Not Available

Nutrient (HMDB: HMDB0034095)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	86 - 91 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00071 g/L	ALOGPS
logP	5.57	ALOGPS
logP	7.78	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	-4	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	8	ChemAxon
Refractivity	179.16 m³·mol⁻¹	ChemAxon
Polarizability	68.1 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	240.679	31661259
DarkChem	[M-H]-	232.497	31661259
DeepCCS	[M-2H]-	277.649	30932474
DeepCCS	[M+Na]+	251.838	30932474
AllCCS	[M+H]+	246.0	32859911
AllCCS	[M+H-H2O]+	244.8	32859911
AllCCS	[M+NH4]+	247.1	32859911
AllCCS	[M+Na]+	247.4	32859911
AllCCS	[M-H]-	248.5	32859911
AllCCS	[M+Na-2H]-	251.8	32859911
AllCCS	[M+HCOO]-	255.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gambogic acid	CC(C)=CCCC1(C)OC2=C(C=C1)C(O)=C1C(=O)C3=CC4CC5C(C)(C)OC(C\C=C(\C)C(O)=O)(C4=O)C35OC1=C2CC=C(C)C	6134.6	Standard polar	33892256
Gambogic acid	CC(C)=CCCC1(C)OC2=C(C=C1)C(O)=C1C(=O)C3=CC4CC5C(C)(C)OC(C\C=C(\C)C(O)=O)(C4=O)C35OC1=C2CC=C(C)C	4227.5	Standard non polar	33892256
Gambogic acid	CC(C)=CCCC1(C)OC2=C(C=C1)C(O)=C1C(=O)C3=CC4CC5C(C)(C)OC(C\C=C(\C)C(O)=O)(C4=O)C35OC1=C2CC=C(C)C	4305.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gambogic acid,1TMS,isomer #1	CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O)C5=O)C(=O)C1=C2O[Si](C)(C)C	4379.1	Semi standard non polar	33892256
Gambogic acid,1TMS,isomer #2	CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O[Si](C)(C)C)C5=O)C(=O)C1=C2O	4324.7	Semi standard non polar	33892256
Gambogic acid,1TMS,isomer #3	CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O)OC(C)(C)C4C5)C(=O)C1=C2O	4252.4	Semi standard non polar	33892256
Gambogic acid,2TMS,isomer #1	CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O[Si](C)(C)C)C5=O)C(=O)C1=C2O[Si](C)(C)C	4266.3	Semi standard non polar	33892256
Gambogic acid,2TMS,isomer #2	CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O)OC(C)(C)C4C5)C(=O)C1=C2O[Si](C)(C)C	4191.7	Semi standard non polar	33892256
Gambogic acid,2TMS,isomer #3	CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O[Si](C)(C)C)OC(C)(C)C4C5)C(=O)C1=C2O	4148.5	Semi standard non polar	33892256
Gambogic acid,3TMS,isomer #1	CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O[Si](C)(C)C)OC(C)(C)C4C5)C(=O)C1=C2O[Si](C)(C)C	4112.2	Semi standard non polar	33892256
Gambogic acid,3TMS,isomer #1	CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O[Si](C)(C)C)OC(C)(C)C4C5)C(=O)C1=C2O[Si](C)(C)C	4212.5	Standard non polar	33892256
Gambogic acid,1TBDMS,isomer #1	CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O)C5=O)C(=O)C1=C2O[Si](C)(C)C(C)(C)C	4630.9	Semi standard non polar	33892256
Gambogic acid,1TBDMS,isomer #2	CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O[Si](C)(C)C(C)(C)C)C5=O)C(=O)C1=C2O	4576.8	Semi standard non polar	33892256
Gambogic acid,1TBDMS,isomer #3	CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C(C)(C)C)C3(C/C=C(/C)C(=O)O)OC(C)(C)C4C5)C(=O)C1=C2O	4503.1	Semi standard non polar	33892256
Gambogic acid,2TBDMS,isomer #1	CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O[Si](C)(C)C(C)(C)C)C5=O)C(=O)C1=C2O[Si](C)(C)C(C)(C)C	4707.6	Semi standard non polar	33892256
Gambogic acid,2TBDMS,isomer #2	CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C(C)(C)C)C3(C/C=C(/C)C(=O)O)OC(C)(C)C4C5)C(=O)C1=C2O[Si](C)(C)C(C)(C)C	4637.3	Semi standard non polar	33892256
Gambogic acid,2TBDMS,isomer #3	CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C(C)(C)C)C3(C/C=C(/C)C(=O)O[Si](C)(C)C(C)(C)C)OC(C)(C)C4C5)C(=O)C1=C2O	4588.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Gambogic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9000057000-19abde6d758101a01ef7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gambogic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gambogic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gambogic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gambogic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gambogic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gambogic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gambogic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gambogic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gambogic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gambogic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gambogic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gambogic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gambogic acid GC-MS ("Gambogic acid,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-11-02	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gambogic acid 10V, Positive-QTOF	splash10-01t9-0000096000-e56a0ec531207df34ab6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gambogic acid 20V, Positive-QTOF	splash10-0o6r-3001591000-411cf0af71ea4c9389ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gambogic acid 40V, Positive-QTOF	splash10-016r-7153941000-92579129327c5702bfb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gambogic acid 10V, Negative-QTOF	splash10-004i-1001039000-9c55dff29165d33866d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gambogic acid 20V, Negative-QTOF	splash10-057i-1014095000-77a8e0d8dca00f9672ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gambogic acid 40V, Negative-QTOF	splash10-0ab9-2794313000-d45dab05ad38be7aee92	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gambogic acid 10V, Negative-QTOF	splash10-004i-0000009000-312b00b9e28384b5d53e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gambogic acid 20V, Negative-QTOF	splash10-004i-0000059000-d354ba3ab7fc6d3f1462	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gambogic acid 40V, Negative-QTOF	splash10-02t9-2100391000-dcdb58e0da6ce0fbbe96	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gambogic acid 10V, Positive-QTOF	splash10-004i-0000079000-d5501837c889acaa5034	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gambogic acid 20V, Positive-QTOF	splash10-004r-0000093000-23942b0217f9c03ee878	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gambogic acid 40V, Positive-QTOF	splash10-00kg-2000951000-5ee22b87ea31bfe4e09e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gambogic acid

METLIN ID

Not Available

PubChem Compound

5353639

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Gambogic acid (HMDB0034095)

MOL for HMDB0034095 (Gambogic acid)

3D MOL for HMDB0034095 (Gambogic acid)

3D SDF for HMDB0034095 (Gambogic acid)

3D-SDF for HMDB0034095 (Gambogic acid)

PDB for HMDB0034095 (Gambogic acid)

3D PDB for HMDB0034095 (Gambogic acid)

SMILES for HMDB0034095 (Gambogic acid)

INCHI for HMDB0034095 (Gambogic acid)

Structure for HMDB0034095 (Gambogic acid)

3D Structure for HMDB0034095 (Gambogic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra