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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:36 UTC

Update Date

2022-03-07 02:52:35 UTC

HMDB ID

HMDB0030556

Secondary Accession Numbers

HMDB30556

Metabolite Identification

Common Name

Tovophyllin B

Description

Tovophyllin B belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-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. Tovophyllin B has been detected, but not quantified in, fruits and purple mangosteens (Garcinia mangostana). This could make tovophyllin b a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Tovophyllin B.

Structure

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

  Mrv0541 05061305202D          

 34 38  0  0  0  0            999 V2000
    3.2542   -2.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6413   -2.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5569    1.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2628    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    2.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3110    1.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6505   -1.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2450   -0.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8118    2.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4524    2.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6045    2.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6597    2.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8211    0.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2174    1.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6505    1.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0468   -0.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4155    1.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0284    0.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4432    1.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8303    1.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4247    2.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542    0.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0376    1.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6413    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0560    0.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8026    1.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652    1.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2266    2.9085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6597   -0.5237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    2.5653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4339    0.1627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2082    0.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2634    1.0780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17  8  1  0  0  0  0
 18 13  2  0  0  0  0
 18 15  1  0  0  0  0
 19 13  1  0  0  0  0
 20 16  2  0  0  0  0
 21 19  2  0  0  0  0
 22 15  2  0  0  0  0
 22 21  1  0  0  0  0
 23 17  1  0  0  0  0
 24 20  1  0  0  0  0
 24 21  1  0  0  0  0
 25 17  2  0  0  0  0
 25 20  1  0  0  0  0
 26 16  1  0  0  0  0
 26 23  2  0  0  0  0
 27  3  1  0  0  0  0
 27  4  1  0  0  0  0
 27 11  1  0  0  0  0
 28  5  1  0  0  0  0
 28  6  1  0  0  0  0
 28 12  1  0  0  0  0
 29 22  1  0  0  0  0
 30 23  1  0  0  0  0
 31 24  2  0  0  0  0
 32 19  1  0  0  0  0
 32 25  1  0  0  0  0
 33 18  1  0  0  0  0
 33 27  1  0  0  0  0
 34 26  1  0  0  0  0
 34 28  1  0  0  0  0
M  END

HMDB0030556
     RDKit          3D
Tovophyllin B
 62 66  0  0  0  0  0  0  0  0999 V2000
   -4.1496   -2.0048    3.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4975   -0.6584    3.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228    0.4437    4.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5210   -0.5532    2.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8096    0.6915    2.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8074    0.8505    0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797    1.2710    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1050    1.6103    0.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8192    1.3928   -1.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333    1.0759   -1.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233    0.6435   -1.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6448    0.3294   -1.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406    0.3897   -3.0148 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7239   -0.0995   -1.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -0.4358   -1.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0581   -0.3372   -2.9582 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0073   -0.8633   -0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8552   -0.9517    0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6327   -0.6113    1.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610   -0.1853    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207    0.1286    0.8996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362    0.5399    0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9262   -1.3754    1.2834 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1968   -1.7422    0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4405   -3.1729    1.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2857   -0.8821    1.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2855   -1.6229   -0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2890   -1.2228   -1.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5741    1.2027   -3.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6561    1.6195   -3.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9209    1.9623   -3.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953    3.3399   -3.6948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9772    0.9774   -3.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9183    1.8211   -1.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6230   -2.7903    3.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2071   -1.9863    3.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0675   -2.2885    4.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857    1.4365    4.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1554    0.4001    4.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7199    0.3578    5.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1910   -1.4848    2.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2020    1.5802    2.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414    0.5828    2.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2551    1.5649    1.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256   -0.5271   -3.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5373   -0.6888    2.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6126   -3.8295    0.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4959   -3.1544    2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4259   -3.4995    0.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6556   -1.3541    2.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1380   -0.8760    0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9200    0.1234    1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2299   -1.8822   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4052   -1.1497   -2.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7424    0.9922   -3.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548    1.7296   -5.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6036    4.0999   -3.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2942    3.5748   -3.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6544    3.2376   -4.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5616   -0.0449   -3.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2109    1.1963   -4.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9352    1.1092   -3.2214 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
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 27 28  2  0
 10 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
 22  6  1  0
 34  9  1  0
 22 11  2  0
 20 14  1  0
 28 17  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  8 44  1  0
 16 45  1  0
 19 46  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  0
 29 55  1  0
 30 56  1  0
 32 57  1  0
 32 58  1  0
 32 59  1  0
 33 60  1  0
 33 61  1  0
 33 62  1  0
M  END

  Mrv0541 05061305202D          

 34 38  0  0  0  0            999 V2000
    3.2542   -2.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6413   -2.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5569    1.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2628    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    2.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3110    1.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6505   -1.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2450   -0.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8118    2.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4524    2.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6045    2.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6597    2.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8211    0.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2174    1.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6505    1.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0468   -0.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4155    1.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0284    0.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4432    1.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8303    1.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4247    2.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542    0.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0376    1.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6413    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0560    0.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8026    1.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652    1.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2266    2.9085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6597   -0.5237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    2.5653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4339    0.1627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2082    0.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2634    1.0780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17  8  1  0  0  0  0
 18 13  2  0  0  0  0
 18 15  1  0  0  0  0
 19 13  1  0  0  0  0
 20 16  2  0  0  0  0
 21 19  2  0  0  0  0
 22 15  2  0  0  0  0
 22 21  1  0  0  0  0
 23 17  1  0  0  0  0
 24 20  1  0  0  0  0
 24 21  1  0  0  0  0
 25 17  2  0  0  0  0
 25 20  1  0  0  0  0
 26 16  1  0  0  0  0
 26 23  2  0  0  0  0
 27  3  1  0  0  0  0
 27  4  1  0  0  0  0
 27 11  1  0  0  0  0
 28  5  1  0  0  0  0
 28  6  1  0  0  0  0
 28 12  1  0  0  0  0
 29 22  1  0  0  0  0
 30 23  1  0  0  0  0
 31 24  2  0  0  0  0
 32 19  1  0  0  0  0
 32 25  1  0  0  0  0
 33 18  1  0  0  0  0
 33 27  1  0  0  0  0
 34 26  1  0  0  0  0
 34 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030556

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C2OC3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=C2C=CC(C)(C)OC2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O6/c1-14(2)7-8-17-23(30)26-16(10-12-28(5,6)34-26)20-24(31)21-19(32-25(17)20)13-18-15(22(21)29)9-11-27(3,4)33-18/h7,9-13,29-30H,8H2,1-6H3

> <INCHI_KEY>
NKTLGMPGRFCLNF-UHFFFAOYSA-N

> <FORMULA>
C28H28O6

> <MOLECULAR_WEIGHT>
460.5183

> <EXACT_MASS>
460.188588628

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
51.529596516657705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10,22-dihydroxy-7,7,18,18-tetramethyl-11-(3-methylbut-2-en-1-yl)-8,13,17-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3,5,9,11,15,19,21-octaen-2-one

> <ALOGPS_LOGP>
5.72

> <JCHEM_LOGP>
6.532323380333333

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.486465808993598

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.664917424218311

> <JCHEM_PKA_STRONGEST_BASIC>
-4.302963454910338

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
133.80769999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10,22-dihydroxy-7,7,18,18-tetramethyl-11-(3-methylbut-2-en-1-yl)-8,13,17-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3,5,9,11,15,19,21-octaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030556
     RDKit          3D
Tovophyllin B
 62 66  0  0  0  0  0  0  0  0999 V2000
   -4.1496   -2.0048    3.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4975   -0.6584    3.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228    0.4437    4.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5210   -0.5532    2.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8096    0.6915    2.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8074    0.8505    0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797    1.2710    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1050    1.6103    0.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8192    1.3928   -1.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333    1.0759   -1.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233    0.6435   -1.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6448    0.3294   -1.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406    0.3897   -3.0148 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7239   -0.0995   -1.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -0.4358   -1.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0581   -0.3372   -2.9582 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0073   -0.8633   -0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8552   -0.9517    0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6327   -0.6113    1.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610   -0.1853    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207    0.1286    0.8996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362    0.5399    0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9262   -1.3754    1.2834 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1968   -1.7422    0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4405   -3.1729    1.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2857   -0.8821    1.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2855   -1.6229   -0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2890   -1.2228   -1.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5741    1.2027   -3.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6561    1.6195   -3.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9209    1.9623   -3.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953    3.3399   -3.6948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9772    0.9774   -3.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9183    1.8211   -1.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6230   -2.7903    3.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2071   -1.9863    3.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0675   -2.2885    4.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857    1.4365    4.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1554    0.4001    4.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7199    0.3578    5.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1910   -1.4848    2.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2020    1.5802    2.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414    0.5828    2.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2551    1.5649    1.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256   -0.5271   -3.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5373   -0.6888    2.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6126   -3.8295    0.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4959   -3.1544    2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4259   -3.4995    0.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6556   -1.3541    2.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1380   -0.8760    0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9200    0.1234    1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2299   -1.8822   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4052   -1.1497   -2.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7424    0.9922   -3.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548    1.7296   -5.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6036    4.0999   -3.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2942    3.5748   -3.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6544    3.2376   -4.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5616   -0.0449   -3.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2109    1.1963   -4.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9352    1.1092   -3.2214 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
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 27 28  2  0
 10 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
 22  6  1  0
 34  9  1  0
 22 11  2  0
 20 14  1  0
 28 17  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  8 44  1  0
 16 45  1  0
 19 46  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  0
 29 55  1  0
 30 56  1  0
 32 57  1  0
 32 58  1  0
 32 59  1  0
 33 60  1  0
 33 61  1  0
 33 62  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.075  -5.462   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.664  -4.822   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.840   3.277   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.291   1.375   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.996   4.785   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.447   2.883   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.814  -2.900   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.924  -1.832   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.582   4.575   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.444   4.148   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.062   4.148   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.965   4.575   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.733   0.944   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.184  -4.395   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.472   3.507   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.814   2.653   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.554  -0.337   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.842   2.012   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.253   1.371   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.294   2.226   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.883   2.866   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.993   3.934   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.075   0.090   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.404   3.294   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.664   0.731   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.705   1.585   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.432   2.653   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.855   3.507   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.623   5.429   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.965  -0.978   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.034   4.789   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      10.143   0.304   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      15.322   1.585   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.225   2.012   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   27                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   28                                                            
CONECT    7    8   14                                                       
CONECT    8    7   17                                                       
CONECT    9   11   15                                                       
CONECT   10   12   16                                                       
CONECT   11    9   27                                                       
CONECT   12   10   28                                                       
CONECT   13   18   19                                                       
CONECT   14    1    2    7                                                  
CONECT   15    9   18   22                                                  
CONECT   16   10   20   26                                                  
CONECT   17    8   23   25                                                  
CONECT   18   13   15   33                                                  
CONECT   19   13   21   32                                                  
CONECT   20   16   24   25                                                  
CONECT   21   19   22   24                                                  
CONECT   22   15   21   29                                                  
CONECT   23   17   26   30                                                  
CONECT   24   20   21   31                                                  
CONECT   25   17   20   32                                                  
CONECT   26   16   23   34                                                  
CONECT   27    3    4   11   33                                             
CONECT   28    5    6   12   34                                             
CONECT   29   22                                                            
CONECT   30   23                                                            
CONECT   31   24                                                            
CONECT   32   19   25                                                       
CONECT   33   18   27                                                       
CONECT   34   26   28                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

COMPND    HMDB0030556
HETATM    1  C1  UNL     1      -4.150  -2.005   3.848  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.497  -0.658   3.599  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.023   0.444   4.402  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.521  -0.553   2.738  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.810   0.691   2.404  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.807   0.851   0.925  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.880   1.271   0.221  1.00  0.00           C  
HETATM    8  O1  UNL     1      -4.105   1.610   0.818  1.00  0.00           O  
HETATM    9  C8  UNL     1      -2.819   1.393  -1.174  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.633   1.076  -1.852  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.523   0.644  -1.148  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.645   0.329  -1.795  1.00  0.00           C  
HETATM   13  O2  UNL     1       0.841   0.390  -3.015  1.00  0.00           O  
HETATM   14  C12 UNL     1       1.724  -0.100  -1.027  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.937  -0.436  -1.600  1.00  0.00           C  
HETATM   16  O3  UNL     1       3.058  -0.337  -2.958  1.00  0.00           O  
HETATM   17  C14 UNL     1       4.007  -0.863  -0.818  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.855  -0.952   0.541  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.633  -0.611   1.103  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.561  -0.185   0.340  1.00  0.00           C  
HETATM   21  O4  UNL     1       0.421   0.129   0.900  1.00  0.00           O  
HETATM   22  C18 UNL     1      -0.636   0.540   0.234  1.00  0.00           C  
HETATM   23  O5  UNL     1       4.926  -1.375   1.283  1.00  0.00           O  
HETATM   24  C19 UNL     1       6.197  -1.742   0.836  1.00  0.00           C  
HETATM   25  C20 UNL     1       6.441  -3.173   1.294  1.00  0.00           C  
HETATM   26  C21 UNL     1       7.286  -0.882   1.491  1.00  0.00           C  
HETATM   27  C22 UNL     1       6.285  -1.623  -0.625  1.00  0.00           C  
HETATM   28  C23 UNL     1       5.289  -1.223  -1.378  1.00  0.00           C  
HETATM   29  C24 UNL     1      -1.574   1.203  -3.288  1.00  0.00           C  
HETATM   30  C25 UNL     1      -2.656   1.620  -3.927  1.00  0.00           C  
HETATM   31  C26 UNL     1      -3.921   1.962  -3.250  1.00  0.00           C  
HETATM   32  C27 UNL     1      -4.395   3.340  -3.695  1.00  0.00           C  
HETATM   33  C28 UNL     1      -4.977   0.977  -3.779  1.00  0.00           C  
HETATM   34  O6  UNL     1      -3.918   1.821  -1.872  1.00  0.00           O  
HETATM   35  H1  UNL     1      -3.623  -2.790   3.266  1.00  0.00           H  
HETATM   36  H2  UNL     1      -5.207  -1.986   3.572  1.00  0.00           H  
HETATM   37  H3  UNL     1      -4.068  -2.289   4.917  1.00  0.00           H  
HETATM   38  H4  UNL     1      -3.686   1.436   4.099  1.00  0.00           H  
HETATM   39  H5  UNL     1      -5.155   0.400   4.477  1.00  0.00           H  
HETATM   40  H6  UNL     1      -3.720   0.358   5.492  1.00  0.00           H  
HETATM   41  H7  UNL     1      -2.191  -1.485   2.203  1.00  0.00           H  
HETATM   42  H8  UNL     1      -2.202   1.580   2.885  1.00  0.00           H  
HETATM   43  H9  UNL     1      -0.741   0.583   2.770  1.00  0.00           H  
HETATM   44  H10 UNL     1      -4.255   1.565   1.804  1.00  0.00           H  
HETATM   45  H11 UNL     1       3.826  -0.527  -3.547  1.00  0.00           H  
HETATM   46  H12 UNL     1       2.537  -0.689   2.172  1.00  0.00           H  
HETATM   47  H13 UNL     1       5.613  -3.830   0.956  1.00  0.00           H  
HETATM   48  H14 UNL     1       6.496  -3.154   2.420  1.00  0.00           H  
HETATM   49  H15 UNL     1       7.426  -3.499   0.942  1.00  0.00           H  
HETATM   50  H16 UNL     1       7.656  -1.354   2.423  1.00  0.00           H  
HETATM   51  H17 UNL     1       8.138  -0.876   0.777  1.00  0.00           H  
HETATM   52  H18 UNL     1       6.920   0.123   1.721  1.00  0.00           H  
HETATM   53  H19 UNL     1       7.230  -1.882  -1.094  1.00  0.00           H  
HETATM   54  H20 UNL     1       5.405  -1.150  -2.472  1.00  0.00           H  
HETATM   55  H21 UNL     1      -0.742   0.992  -3.880  1.00  0.00           H  
HETATM   56  H22 UNL     1      -2.655   1.730  -5.013  1.00  0.00           H  
HETATM   57  H23 UNL     1      -3.604   4.100  -3.619  1.00  0.00           H  
HETATM   58  H24 UNL     1      -5.294   3.575  -3.098  1.00  0.00           H  
HETATM   59  H25 UNL     1      -4.654   3.238  -4.770  1.00  0.00           H  
HETATM   60  H26 UNL     1      -4.562  -0.045  -3.667  1.00  0.00           H  
HETATM   61  H27 UNL     1      -5.211   1.196  -4.844  1.00  0.00           H  
HETATM   62  H28 UNL     1      -5.935   1.109  -3.221  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3    4    4
CONECT    3   38   39   40
CONECT    4    5   41
CONECT    5    6   42   43
CONECT    6    7    7   22
CONECT    7    8    9
CONECT    8   44
CONECT    9   10   10   34
CONECT   10   11   29
CONECT   11   12   22   22
CONECT   12   13   13   14
CONECT   14   15   15   20
CONECT   15   16   17
CONECT   16   45
CONECT   17   18   18   28
CONECT   18   19   23
CONECT   19   20   20   46
CONECT   20   21
CONECT   21   22
CONECT   23   24
CONECT   24   25   26   27
CONECT   25   47   48   49
CONECT   26   50   51   52
CONECT   27   28   28   53
CONECT   28   54
CONECT   29   30   30   55
CONECT   30   31   56
CONECT   31   32   33   34
CONECT   32   57   58   59
CONECT   33   60   61   62
END

HMDB0030556
     RDKit          3D
Tovophyllin B
 62 66  0  0  0  0  0  0  0  0999 V2000
   -4.1496   -2.0048    3.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4975   -0.6584    3.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228    0.4437    4.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5210   -0.5532    2.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8096    0.6915    2.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8074    0.8505    0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797    1.2710    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1050    1.6103    0.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8192    1.3928   -1.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333    1.0759   -1.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233    0.6435   -1.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6448    0.3294   -1.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406    0.3897   -3.0148 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7239   -0.0995   -1.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -0.4358   -1.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0581   -0.3372   -2.9582 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0073   -0.8633   -0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8552   -0.9517    0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6327   -0.6113    1.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610   -0.1853    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207    0.1286    0.8996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362    0.5399    0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9262   -1.3754    1.2834 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1968   -1.7422    0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4405   -3.1729    1.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2857   -0.8821    1.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2855   -1.6229   -0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2890   -1.2228   -1.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5741    1.2027   -3.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6561    1.6195   -3.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9209    1.9623   -3.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953    3.3399   -3.6948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9772    0.9774   -3.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9183    1.8211   -1.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6230   -2.7903    3.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2071   -1.9863    3.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0675   -2.2885    4.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857    1.4365    4.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1554    0.4001    4.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7199    0.3578    5.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1910   -1.4848    2.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2020    1.5802    2.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414    0.5828    2.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2551    1.5649    1.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256   -0.5271   -3.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5373   -0.6888    2.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6126   -3.8295    0.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4959   -3.1544    2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4259   -3.4995    0.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6556   -1.3541    2.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1380   -0.8760    0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9200    0.1234    1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2299   -1.8822   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4052   -1.1497   -2.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7424    0.9922   -3.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548    1.7296   -5.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6036    4.0999   -3.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2942    3.5748   -3.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6544    3.2376   -4.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5616   -0.0449   -3.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2109    1.1963   -4.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9352    1.1092   -3.2214 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
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 27 28  2  0
 10 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
 22  6  1  0
 34  9  1  0
 22 11  2  0
 20 14  1  0
 28 17  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  8 44  1  0
 16 45  1  0
 19 46  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  0
 29 55  1  0
 30 56  1  0
 32 57  1  0
 32 58  1  0
 32 59  1  0
 33 60  1  0
 33 61  1  0
 33 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,13-Dihydroxy-3,3,10,10-tetramethyl-6-(3-methyl-2-butenyl)-2H-dipyrano[2,3-a:2',3'-i]xanthen-14-one	HMDB

Chemical Formula

C₂₈H₂₈O₆

Average Molecular Weight

460.5183

Monoisotopic Molecular Weight

460.188588628

IUPAC Name

10,22-dihydroxy-7,7,18,18-tetramethyl-11-(3-methylbut-2-en-1-yl)-8,13,17-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3,5,9,11,15,19,21-octaen-2-one

Traditional Name

10,22-dihydroxy-7,7,18,18-tetramethyl-11-(3-methylbut-2-en-1-yl)-8,13,17-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3,5,9,11,15,19,21-octaen-2-one

CAS Registry Number

40738-45-2

SMILES

CC(C)=CCC1=C2OC3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=C2C=CC(C)(C)OC2=C1O

InChI Identifier

InChI=1S/C28H28O6/c1-14(2)7-8-17-23(30)26-16(10-12-28(5,6)34-26)20-24(31)21-19(32-25(17)20)13-18-15(22(21)29)9-11-27(3,4)33-18/h7,9-13,29-30H,8H2,1-6H3

InChI Key

NKTLGMPGRFCLNF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-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

4-prenylated xanthones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030556)
Cell membrane (HMDB: HMDB0030556)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030556)

Source

Endogenous

Endogenous (HMDB: HMDB0030556)

Plant

Plant (HMDB: HMDB0030556)

Exogenous

Food

Food (HMDB: HMDB0030556)

Fruit

Tropical fruit

Purple mangosteen (FooDB: FOOD00406)

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030556)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	190 - 191 °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	0.0036 g/L	ALOGPS
logP	5.72	ALOGPS
logP	6.53	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	7.66	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	133.81 m³·mol⁻¹	ChemAxon
Polarizability	51.53 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	208.919	31661259
DarkChem	[M-H]-	201.966	31661259
DeepCCS	[M+H]+	207.314	30932474
DeepCCS	[M-H]-	204.918	30932474
DeepCCS	[M-2H]-	237.975	30932474
DeepCCS	[M+Na]+	213.227	30932474
AllCCS	[M+H]+	212.0	32859911
AllCCS	[M+H-H2O]+	209.7	32859911
AllCCS	[M+NH4]+	214.2	32859911
AllCCS	[M+Na]+	214.8	32859911
AllCCS	[M-H]-	210.1	32859911
AllCCS	[M+Na-2H]-	210.3	32859911
AllCCS	[M+HCOO]-	210.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tovophyllin B	CC(C)=CCC1=C2OC3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=C2C=CC(C)(C)OC2=C1O	4830.0	Standard polar	33892256
Tovophyllin B	CC(C)=CCC1=C2OC3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=C2C=CC(C)(C)OC2=C1O	3742.1	Standard non polar	33892256
Tovophyllin B	CC(C)=CCC1=C2OC3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=C2C=CC(C)(C)OC2=C1O	3787.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tovophyllin B,1TMS,isomer #1	CC(C)=CCC1=C(O)C2=C(C=CC(C)(C)O2)C2=C1OC1=CC3=C(C=CC(C)(C)O3)C(O[Si](C)(C)C)=C1C2=O	3544.9	Semi standard non polar	33892256
Tovophyllin B,1TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C2=C(C=CC(C)(C)O2)C2=C1OC1=CC3=C(C=CC(C)(C)O3)C(O)=C1C2=O	3514.6	Semi standard non polar	33892256
Tovophyllin B,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C2=C(C=CC(C)(C)O2)C2=C1OC1=CC3=C(C=CC(C)(C)O3)C(O[Si](C)(C)C)=C1C2=O	3450.8	Semi standard non polar	33892256
Tovophyllin B,1TBDMS,isomer #1	CC(C)=CCC1=C(O)C2=C(C=CC(C)(C)O2)C2=C1OC1=CC3=C(C=CC(C)(C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	3779.0	Semi standard non polar	33892256
Tovophyllin B,1TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C2=C(C=CC(C)(C)O2)C2=C1OC1=CC3=C(C=CC(C)(C)O3)C(O)=C1C2=O	3733.3	Semi standard non polar	33892256
Tovophyllin B,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C2=C(C=CC(C)(C)O2)C2=C1OC1=CC3=C(C=CC(C)(C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	3872.1	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 - Tovophyllin B GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-1001900000-8731ae595831bc3fe857	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tovophyllin B GC-MS (2 TMS) - 70eV, Positive	splash10-000l-1001090000-f4b2fb0ba3c6db7a8609	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tovophyllin 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 - Tovophyllin B 10V, Positive-QTOF	splash10-03di-0000900000-9bab741f1299ca999dd8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tovophyllin B 20V, Positive-QTOF	splash10-0n29-2002900000-969a1e14921d22c54ebc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tovophyllin B 40V, Positive-QTOF	splash10-02ti-6019300000-55bf2214c1cbad53397f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tovophyllin B 10V, Negative-QTOF	splash10-0a4i-0000900000-b3ee393d737d3014613e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tovophyllin B 20V, Negative-QTOF	splash10-0a4i-0002900000-ea1524f36fcb40fd8db7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tovophyllin B 40V, Negative-QTOF	splash10-05bf-1139300000-532dc7334af1af63b248	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tovophyllin B 10V, Positive-QTOF	splash10-08fr-0000900000-600119a2754381df95d9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tovophyllin B 20V, Positive-QTOF	splash10-0a4i-0001900000-e2eccd3a719fb95ae180	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tovophyllin B 40V, Positive-QTOF	splash10-0w29-1108900000-d7d94ef340a982968315	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tovophyllin B 10V, Negative-QTOF	splash10-0a4i-0000900000-759ce675f29f7b362abf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tovophyllin B 20V, Negative-QTOF	splash10-0a4i-0000900000-be0d217baa38d6bfb91f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tovophyllin B 40V, Negative-QTOF	splash10-014l-0121900000-af6968848ddbc02894a3	2021-09-25	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

FDB002437

KNApSAcK ID

C00032367

Chemspider ID

444609

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

509268

PDB ID

Not Available

ChEBI ID

191764

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1821001

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 Tovophyllin B (HMDB0030556)

MOL for HMDB0030556 (Tovophyllin B)

3D MOL for HMDB0030556 (Tovophyllin B)

3D SDF for HMDB0030556 (Tovophyllin B)

3D-SDF for HMDB0030556 (Tovophyllin B)

PDB for HMDB0030556 (Tovophyllin B)

3D PDB for HMDB0030556 (Tovophyllin B)

SMILES for HMDB0030556 (Tovophyllin B)

INCHI for HMDB0030556 (Tovophyllin B)

Structure for HMDB0030556 (Tovophyllin B)

3D Structure for HMDB0030556 (Tovophyllin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra