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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:51 UTC

Update Date

2022-03-07 02:52:11 UTC

HMDB ID

HMDB0029510

Secondary Accession Numbers

HMDB29510

Metabolite Identification

Common Name

Garcinone B

Description

Garcinone B belongs to the class of organic compounds known as 2-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 2-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. Garcinone B has been detected, but not quantified in, fruits and purple mangosteens (Garcinia mangostana). This could make garcinone b a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Garcinone B.

Structure

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


  Mrv1652309272007462D          

 29 32  0  0  0  0            999 V2000
 9993.6088 9993.4324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0385 9993.4324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4695 9995.9076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4695 9994.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1839 9994.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8984 9994.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6128 9994.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8984 9993.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7523 9995.9076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.9417 9993.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.4717 9992.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0392 9995.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7536 9995.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7536 9994.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0392 9994.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1810 9995.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4665 9995.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6096 9995.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3241 9995.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3241 9994.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6096 9994.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8952 9994.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8952 9995.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4673 9994.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1818 9994.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1818 9993.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4673 9993.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7528 9993.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7528 9994.2572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 17 16  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  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
 24 29  1  0  0  0  0
 28 29  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 13  3  1  0  0  0  0
 14  4  1  0  0  0  0
 15  2  1  0  0  0  0
 17  9  1  0  0  0  0
  1 21  2  0  0  0  0
 15 20  1  0  0  0  0
 19 12  1  0  0  0  0
 16 23  2  0  0  0  0
 28 11  1  0  0  0  0
 28 10  1  0  0  0  0
 24 17  2  0  0  0  0
 22 25  2  0  0  0  0
M  END

HMDB0029510
     RDKit          3D
Garcinone B
 51 54  0  0  0  0  0  0  0  0999 V2000
   -7.0809   -0.1460   -0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2388    0.9507    0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8578    1.9039    1.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9745    1.1501   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2527    0.2811   -1.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0174   -0.3292   -0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1166   -1.3873    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948   -1.8657    0.7447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9873   -1.9631    1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7185   -1.4999    0.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3392   -2.0495    1.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5722   -1.6517    1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6402   -2.2934    1.6681 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044   -1.8548    1.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0044   -2.4841    2.0171 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1368   -0.7881    0.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0414   -0.1622   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381   -0.5877    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565    0.0212   -0.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7027    0.9758   -1.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6142   -0.4434   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7501    0.1339   -0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5887    1.1846   -1.5833 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2574    0.9361   -0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5093    1.3192   -1.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6920    0.6883   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6948    0.2590   -1.6738 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4440    1.7291    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4074   -0.3612    0.2714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1781    0.1158   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9675   -0.3013   -1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9593   -1.1068    0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0454    2.8825    0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1194    2.0891    1.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8352    1.5324    1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    1.9802    0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0592    0.8085   -1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9660   -0.5509   -1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4823   -2.6294    1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210   -2.7873    1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326   -3.1208    2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9480   -2.1862    1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633    1.7089   -2.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5141    1.4663   -1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7188    2.1491   -1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6138    0.8256   -1.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2128    0.4492   -2.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8665   -0.8251   -1.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7837    2.5601   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3419    1.2061    0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8217    2.0682    1.1076 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 17 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 22  6  1  0
 21 10  1  0
 18 12  1  0
 29 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  0
 15 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
 27 46  1  0
 27 47  1  0
 27 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
M  END


  Mrv1652309272007462D          

 29 32  0  0  0  0            999 V2000
 9993.6088 9993.4324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0385 9993.4324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4695 9995.9076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4695 9994.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1839 9994.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8984 9994.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6128 9994.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8984 9993.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7523 9995.9076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.9417 9993.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.4717 9992.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0392 9995.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7536 9995.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7536 9994.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0392 9994.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1810 9995.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4665 9995.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6096 9995.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3241 9995.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3241 9994.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6096 9994.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8952 9994.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8952 9995.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4673 9994.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1818 9994.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1818 9993.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4673 9993.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7528 9993.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7528 9994.2572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 17 16  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  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
 24 29  1  0  0  0  0
 28 29  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 13  3  1  0  0  0  0
 14  4  1  0  0  0  0
 15  2  1  0  0  0  0
 17  9  1  0  0  0  0
  1 21  2  0  0  0  0
 15 20  1  0  0  0  0
 19 12  1  0  0  0  0
 16 23  2  0  0  0  0
 28 11  1  0  0  0  0
 28 10  1  0  0  0  0
 24 17  2  0  0  0  0
 22 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029510

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C2=C(OC3=CC(O)=C4OC(C)(C)C=CC4=C3C2=O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O6/c1-11(2)5-6-12-14(24)9-17-19(20(12)26)21(27)18-13-7-8-23(3,4)29-22(13)15(25)10-16(18)28-17/h5,7-10,24-26H,6H2,1-4H3

> <INCHI_KEY>
HVXHJNVYRXRHNX-UHFFFAOYSA-N

> <FORMULA>
C23H22O6

> <MOLECULAR_WEIGHT>
394.4172

> <EXACT_MASS>
394.141638436

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
42.074365015552054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,8,12-trihydroxy-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)-2,5-dihydro-1,10-dioxatetraphen-5-one

> <ALOGPS_LOGP>
4.38

> <JCHEM_LOGP>
5.328134656666668

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.949791033626961

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.236364036989298

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7433080035342807

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
111.3952

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,8,12-trihydroxy-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)-1,10-dioxatetraphen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029510
     RDKit          3D
Garcinone B
 51 54  0  0  0  0  0  0  0  0999 V2000
   -7.0809   -0.1460   -0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2388    0.9507    0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8578    1.9039    1.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9745    1.1501   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2527    0.2811   -1.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0174   -0.3292   -0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1166   -1.3873    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948   -1.8657    0.7447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9873   -1.9631    1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7185   -1.4999    0.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3392   -2.0495    1.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5722   -1.6517    1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6402   -2.2934    1.6681 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044   -1.8548    1.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0044   -2.4841    2.0171 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1368   -0.7881    0.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0414   -0.1622   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381   -0.5877    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565    0.0212   -0.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7027    0.9758   -1.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6142   -0.4434   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7501    0.1339   -0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5887    1.1846   -1.5833 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2574    0.9361   -0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5093    1.3192   -1.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6920    0.6883   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6948    0.2590   -1.6738 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4440    1.7291    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4074   -0.3612    0.2714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1781    0.1158   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9675   -0.3013   -1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9593   -1.1068    0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0454    2.8825    0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1194    2.0891    1.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8352    1.5324    1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    1.9802    0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0592    0.8085   -1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9660   -0.5509   -1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4823   -2.6294    1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210   -2.7873    1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326   -3.1208    2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9480   -2.1862    1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633    1.7089   -2.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5141    1.4663   -1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7188    2.1491   -1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6138    0.8256   -1.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2128    0.4492   -2.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8665   -0.8251   -1.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7837    2.5601   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3419    1.2061    0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8217    2.0682    1.1076 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 17 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 22  6  1  0
 21 10  1  0
 18 12  1  0
 29 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  0
 15 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
 27 46  1  0
 27 47  1  0
 27 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8654.7378654.407   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8657.4058654.407   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8660.0768659.028   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8660.0768655.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8661.4108656.716   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.7448655.947   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.0778656.716   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.7448654.407   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8649.4048659.028   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8647.8918654.677   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8648.8818652.960   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8657.4078659.026   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8658.7408658.256   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8658.7408656.716   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8657.4078655.946   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8652.0718659.026   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8650.7378658.256   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    8654.7388659.027   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8656.0728658.257   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8656.0728656.716   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8654.7388655.947   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8653.4048656.716   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8653.4048658.257   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8650.7398656.717   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8652.0738655.947   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8652.0738654.407   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8650.7398653.637   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8649.4058654.407   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0    8649.4058655.947   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   15                                                            
CONECT    3   13                                                            
CONECT    4    5   14                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9   17                                                            
CONECT   10   28                                                            
CONECT   11   28                                                            
CONECT   12   13   19                                                       
CONECT   13   12   14    3                                                  
CONECT   14   13   15    4                                                  
CONECT   15   14    2   20                                                  
CONECT   16   17   23                                                       
CONECT   17   16    9   24                                                  
CONECT   18   19   23                                                       
CONECT   19   20   18   12                                                  
CONECT   20   19   21   15                                                  
CONECT   21   20   22    1                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   18   16                                                  
CONECT   24   25   29   17                                                  
CONECT   25   24   26   22                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   11   10                                             
CONECT   29   24   28                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0029510
HETATM    1  C1  UNL     1      -7.081  -0.146  -0.305  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.239   0.951   0.229  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.858   1.904   1.204  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.974   1.150  -0.095  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.253   0.281  -1.042  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.017  -0.329  -0.431  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.117  -1.387   0.447  1.00  0.00           C  
HETATM    8  O1  UNL     1      -4.395  -1.866   0.745  1.00  0.00           O  
HETATM    9  C8  UNL     1      -1.987  -1.963   1.020  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.719  -1.500   0.734  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.339  -2.050   1.279  1.00  0.00           O  
HETATM   12  C10 UNL     1       1.572  -1.652   1.045  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.640  -2.293   1.668  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.904  -1.855   1.402  1.00  0.00           C  
HETATM   15  O3  UNL     1       5.004  -2.484   2.017  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.137  -0.788   0.527  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.041  -0.162  -0.085  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.738  -0.588   0.167  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.656   0.021  -0.430  1.00  0.00           C  
HETATM   20  O4  UNL     1       0.703   0.976  -1.225  1.00  0.00           O  
HETATM   21  C17 UNL     1      -0.614  -0.443  -0.142  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.750   0.134  -0.717  1.00  0.00           C  
HETATM   23  O5  UNL     1      -1.589   1.185  -1.583  1.00  0.00           O  
HETATM   24  C19 UNL     1       3.257   0.936  -0.992  1.00  0.00           C  
HETATM   25  C20 UNL     1       4.509   1.319  -1.217  1.00  0.00           C  
HETATM   26  C21 UNL     1       5.692   0.688  -0.595  1.00  0.00           C  
HETATM   27  C22 UNL     1       6.695   0.259  -1.674  1.00  0.00           C  
HETATM   28  C23 UNL     1       6.444   1.729   0.267  1.00  0.00           C  
HETATM   29  O6  UNL     1       5.407  -0.361   0.271  1.00  0.00           O  
HETATM   30  H1  UNL     1      -8.178   0.116  -0.195  1.00  0.00           H  
HETATM   31  H2  UNL     1      -6.968  -0.301  -1.401  1.00  0.00           H  
HETATM   32  H3  UNL     1      -6.959  -1.107   0.217  1.00  0.00           H  
HETATM   33  H4  UNL     1      -7.045   2.883   0.692  1.00  0.00           H  
HETATM   34  H5  UNL     1      -6.119   2.089   1.989  1.00  0.00           H  
HETATM   35  H6  UNL     1      -7.835   1.532   1.575  1.00  0.00           H  
HETATM   36  H7  UNL     1      -4.405   1.980   0.334  1.00  0.00           H  
HETATM   37  H8  UNL     1      -4.059   0.809  -1.976  1.00  0.00           H  
HETATM   38  H9  UNL     1      -4.966  -0.551  -1.330  1.00  0.00           H  
HETATM   39  H10 UNL     1      -4.482  -2.629   1.377  1.00  0.00           H  
HETATM   40  H11 UNL     1      -2.121  -2.787   1.700  1.00  0.00           H  
HETATM   41  H12 UNL     1       2.433  -3.121   2.345  1.00  0.00           H  
HETATM   42  H13 UNL     1       5.948  -2.186   1.843  1.00  0.00           H  
HETATM   43  H14 UNL     1      -2.263   1.709  -2.074  1.00  0.00           H  
HETATM   44  H15 UNL     1       2.514   1.466  -1.496  1.00  0.00           H  
HETATM   45  H16 UNL     1       4.719   2.149  -1.899  1.00  0.00           H  
HETATM   46  H17 UNL     1       7.614   0.826  -1.552  1.00  0.00           H  
HETATM   47  H18 UNL     1       6.213   0.449  -2.676  1.00  0.00           H  
HETATM   48  H19 UNL     1       6.866  -0.825  -1.523  1.00  0.00           H  
HETATM   49  H20 UNL     1       6.784   2.560  -0.386  1.00  0.00           H  
HETATM   50  H21 UNL     1       7.342   1.206   0.638  1.00  0.00           H  
HETATM   51  H22 UNL     1       5.822   2.068   1.108  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    4    4
CONECT    3   33   34   35
CONECT    4    5   36
CONECT    5    6   37   38
CONECT    6    7    7   22
CONECT    7    8    9
CONECT    8   39
CONECT    9   10   10   40
CONECT   10   11   21
CONECT   11   12
CONECT   12   13   13   18
CONECT   13   14   41
CONECT   14   15   16   16
CONECT   15   42
CONECT   16   17   29
CONECT   17   18   18   24
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   22   22
CONECT   22   23
CONECT   23   43
CONECT   24   25   25   44
CONECT   25   26   45
CONECT   26   27   28   29
CONECT   27   46   47   48
CONECT   28   49   50   51
END

HMDB0029510
     RDKit          3D
Garcinone B
 51 54  0  0  0  0  0  0  0  0999 V2000
   -7.0809   -0.1460   -0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2388    0.9507    0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8578    1.9039    1.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9745    1.1501   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2527    0.2811   -1.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0174   -0.3292   -0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1166   -1.3873    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948   -1.8657    0.7447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9873   -1.9631    1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7185   -1.4999    0.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3392   -2.0495    1.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5722   -1.6517    1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6402   -2.2934    1.6681 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044   -1.8548    1.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0044   -2.4841    2.0171 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1368   -0.7881    0.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0414   -0.1622   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381   -0.5877    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565    0.0212   -0.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7027    0.9758   -1.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6142   -0.4434   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7501    0.1339   -0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5887    1.1846   -1.5833 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2574    0.9361   -0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5093    1.3192   -1.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6920    0.6883   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6948    0.2590   -1.6738 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4440    1.7291    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4074   -0.3612    0.2714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1781    0.1158   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9675   -0.3013   -1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9593   -1.1068    0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0454    2.8825    0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1194    2.0891    1.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8352    1.5324    1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    1.9802    0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0592    0.8085   -1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9660   -0.5509   -1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4823   -2.6294    1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210   -2.7873    1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326   -3.1208    2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9480   -2.1862    1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633    1.7089   -2.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5141    1.4663   -1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7188    2.1491   -1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6138    0.8256   -1.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2128    0.4492   -2.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8665   -0.8251   -1.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7837    2.5601   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3419    1.2061    0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8217    2.0682    1.1076 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 17 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 22  6  1  0
 21 10  1  0
 18 12  1  0
 29 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  0
 15 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
 27 46  1  0
 27 47  1  0
 27 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,9,11-Trihydroxy-3,3-dimethyl-10-(3-methyl-2-butenyl)pyrano[3,2-a]xanthen-12(3H)-one, 9ci	HMDB
Garcinone b	MeSH

Chemical Formula

C₂₃H₂₂O₆

Average Molecular Weight

394.4172

Monoisotopic Molecular Weight

394.141638436

IUPAC Name

6,8,12-trihydroxy-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)-2,5-dihydro-1,10-dioxatetraphen-5-one

Traditional Name

6,8,12-trihydroxy-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)-1,10-dioxatetraphen-5-one

CAS Registry Number

76996-28-6

SMILES

CC(C)=CCC1=C(O)C=C2OC3=C(C(=O)C2=C1O)C1=C(OC(C)(C)C=C1)C(O)=C3

InChI Identifier

InChI=1S/C23H22O6/c1-11(2)5-6-12-14(24)9-17-19(20(12)26)21(27)18-13-7-8-23(3,4)29-22(13)15(25)10-16(18)28-17/h5,7-10,24-26H,6H2,1-4H3

InChI Key

HVXHJNVYRXRHNX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 2-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2-prenylated xanthones

Alternative Parents

Substituents

2-prenylated xanthone
Pyranoxanthone
2,2-dimethyl-1-benzopyran
Chromone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Ether
Polyol
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029510)
Cell membrane (HMDB: HMDB0029510)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029510)

Source

Endogenous

Endogenous (HMDB: HMDB0029510)

Plant

Plant (HMDB: HMDB0029510)

Exogenous

Food

Food (HMDB: HMDB0029510)

Fruit

Tropical fruit

Purple mangosteen (FooDB: FOOD00406)

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0029510)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	190 - 192 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0007 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	4.38	ALOGPS
logP	5.33	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.24	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	111.4 m³·mol⁻¹	ChemAxon
Polarizability	42.07 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	192.474	30932474
DeepCCS	[M-H]-	190.078	30932474
DeepCCS	[M-2H]-	223.445	30932474
DeepCCS	[M+Na]+	198.651	30932474
AllCCS	[M+H]+	195.6	32859911
AllCCS	[M+H-H2O]+	192.8	32859911
AllCCS	[M+NH4]+	198.3	32859911
AllCCS	[M+Na]+	199.0	32859911
AllCCS	[M-H]-	195.1	32859911
AllCCS	[M+Na-2H]-	194.7	32859911
AllCCS	[M+HCOO]-	194.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.43 minutes	32390414
Predicted by Siyang on May 30, 2022	14.4659 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.18 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3219.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	266.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	192.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	154.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	155.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	696.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	703.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1363.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	581.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1354.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	460.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	457.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	257.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	255.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Garcinone B	CC(C)=CCC1=C(O)C=C2OC3=C(C(=O)C2=C1O)C1=C(OC(C)(C)C=C1)C(O)=C3	4801.2	Standard polar	33892256
Garcinone B	CC(C)=CCC1=C(O)C=C2OC3=C(C(=O)C2=C1O)C1=C(OC(C)(C)C=C1)C(O)=C3	3275.3	Standard non polar	33892256
Garcinone B	CC(C)=CCC1=C(O)C=C2OC3=C(C(=O)C2=C1O)C1=C(OC(C)(C)C=C1)C(O)=C3	3531.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Garcinone B,1TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC3=CC(O)=C4OC(C)(C)C=CC4=C3C(=O)C2=C1O	3425.9	Semi standard non polar	33892256
Garcinone B,1TMS,isomer #2	CC(C)=CCC1=C(O)C=C2OC3=CC(O)=C4OC(C)(C)C=CC4=C3C(=O)C2=C1O[Si](C)(C)C	3389.3	Semi standard non polar	33892256
Garcinone B,1TMS,isomer #3	CC(C)=CCC1=C(O)C=C2OC3=CC(O[Si](C)(C)C)=C4OC(C)(C)C=CC4=C3C(=O)C2=C1O	3426.3	Semi standard non polar	33892256
Garcinone B,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC3=CC(O[Si](C)(C)C)=C4OC(C)(C)C=CC4=C3C(=O)C2=C1O	3349.0	Semi standard non polar	33892256
Garcinone B,2TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC3=CC(O)=C4OC(C)(C)C=CC4=C3C(=O)C2=C1O[Si](C)(C)C	3338.4	Semi standard non polar	33892256
Garcinone B,2TMS,isomer #3	CC(C)=CCC1=C(O)C=C2OC3=CC(O[Si](C)(C)C)=C4OC(C)(C)C=CC4=C3C(=O)C2=C1O[Si](C)(C)C	3308.4	Semi standard non polar	33892256
Garcinone B,3TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC3=CC(O[Si](C)(C)C)=C4OC(C)(C)C=CC4=C3C(=O)C2=C1O[Si](C)(C)C	3285.5	Semi standard non polar	33892256
Garcinone B,1TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=CC(O)=C4OC(C)(C)C=CC4=C3C(=O)C2=C1O	3634.8	Semi standard non polar	33892256
Garcinone B,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C=C2OC3=CC(O)=C4OC(C)(C)C=CC4=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3617.6	Semi standard non polar	33892256
Garcinone B,1TBDMS,isomer #3	CC(C)=CCC1=C(O)C=C2OC3=CC(O[Si](C)(C)C(C)(C)C)=C4OC(C)(C)C=CC4=C3C(=O)C2=C1O	3642.2	Semi standard non polar	33892256
Garcinone B,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=CC(O[Si](C)(C)C(C)(C)C)=C4OC(C)(C)C=CC4=C3C(=O)C2=C1O	3802.9	Semi standard non polar	33892256
Garcinone B,2TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=CC(O)=C4OC(C)(C)C=CC4=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3791.7	Semi standard non polar	33892256
Garcinone B,2TBDMS,isomer #3	CC(C)=CCC1=C(O)C=C2OC3=CC(O[Si](C)(C)C(C)(C)C)=C4OC(C)(C)C=CC4=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3755.3	Semi standard non polar	33892256
Garcinone B,3TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=CC(O[Si](C)(C)C(C)(C)C)=C4OC(C)(C)C=CC4=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3939.5	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 - Garcinone B GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ufu-2159000000-0b110967eb75f8e35f12	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Garcinone B GC-MS (3 TMS) - 70eV, Positive	splash10-0002-1000090000-2aee2126006740a7bdfe	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Garcinone B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Garcinone B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Garcinone B 10V, Positive-QTOF	splash10-0002-0009000000-a75e3c3a708430291b72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone B 20V, Positive-QTOF	splash10-000j-2009000000-bb7bc1a144d31d330f44	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone B 40V, Positive-QTOF	splash10-01b9-9536000000-acd444094fe53f5f3c5a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone B 10V, Negative-QTOF	splash10-0006-0009000000-2e02070e09768cffd09a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone B 20V, Negative-QTOF	splash10-0006-0009000000-eb7ef11861c5d373eab5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone B 40V, Negative-QTOF	splash10-0a4i-3449000000-62ae11ae587cc35aa9a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone B 10V, Negative-QTOF	splash10-0006-0009000000-fec432cdadbaee13fde1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone B 20V, Negative-QTOF	splash10-0006-0009000000-b62c1b0b150581331583	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone B 40V, Negative-QTOF	splash10-004r-0229000000-d362acb888d6e9fa363c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone B 10V, Positive-QTOF	splash10-000j-0009000000-1b2d3af25f8e659e7f53	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone B 20V, Positive-QTOF	splash10-000i-0009000000-1fe4148e01885e61f22e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone B 40V, Positive-QTOF	splash10-00a2-0098000000-f347a3293925b0526f7e	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

FDB000645

KNApSAcK ID

C00030356

Chemspider ID

4593096

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5495928

PDB ID

Not Available

ChEBI ID

657231

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1810081

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 Garcinone B (HMDB0029510)

MOL for HMDB0029510 (Garcinone B)

3D MOL for HMDB0029510 (Garcinone B)

3D SDF for HMDB0029510 (Garcinone B)

3D-SDF for HMDB0029510 (Garcinone B)

PDB for HMDB0029510 (Garcinone B)

3D PDB for HMDB0029510 (Garcinone B)

SMILES for HMDB0029510 (Garcinone B)

INCHI for HMDB0029510 (Garcinone B)

Structure for HMDB0029510 (Garcinone B)

3D Structure for HMDB0029510 (Garcinone B)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra