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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:02:08 UTC

Update Date

2021-09-14 15:41:21 UTC

HMDB ID

HMDB0012517

Secondary Accession Numbers

HMDB12517

Metabolite Identification

Common Name

11'-Carboxy-gamma-chromanol

Description

11'-Carboxy-gamma-tocopherol is a dehydrogenation carboxylate product of 11'-hydroxy-r-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. r-Tocopherol provides different antioxidant activities in food and in-vitro studies and showed higher activity in trapping lipophilic electrophiles and reactive nitrogen and oxygen species. From the metabolism end product, only that of r-tocopherol (2,7,8-trimethyl-2-(b-carboxyethyl)-6-hydroxychroman), but not that of a-tocopherol, was identified to provide natriuretic activity. Only the r-tocopherol plasma level served as biomarker for cancer and cardiovascular risk.

Structure

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

  Mrv0541 02251208062D          

 29 30  0  0  1  0            999 V2000
   11.7407  -13.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5657  -13.8199    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9782  -13.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5657  -12.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9782  -11.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5657  -10.9621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7407  -10.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9782  -10.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8032  -10.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2157   -9.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0408   -9.5331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8032   -8.8186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9782  -14.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8032  -14.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2157  -15.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0408  -15.2489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6282  -15.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0408  -14.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7552  -14.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4697  -14.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1842  -14.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8986  -14.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6132  -14.0114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8986  -15.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6132  -15.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1842  -15.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1842  -16.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4697  -15.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7552  -15.6614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 16 29  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 28  2  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

HMDB0012517
     RDKit          3D
11'-Carboxy-gamma-chromanol
 69 70  0  0  0  0  0  0  0  0999 V2000
    6.7972    0.4387   -2.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1311   -0.1884   -1.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6182   -1.3525   -1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7437   -1.9610   -1.7262 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9812   -1.8962   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8690   -1.3137    0.4808 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3578   -0.1484   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0167    0.3804   -1.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5041    1.6336   -1.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2363    0.4742    0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3539   -0.3343    1.2420 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8084   -1.4454    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3739    0.4344    2.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4456    1.3608    1.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5876    1.0235    0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7335    0.1683    0.7176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4863   -1.2623    1.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8068    0.7562    1.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4350    2.0123    1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0962    1.8394   -0.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2048    0.8171   -0.2505 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3019    1.1896    0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7808    0.7165   -1.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8974   -0.2505   -1.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5709   -1.6569   -1.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4764   -2.5155   -1.5731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3004   -2.0549   -1.1571 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3143   -0.9872    2.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2392   -1.9646    1.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0981    0.5513   -3.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412   -0.2078   -3.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2288    1.3973   -2.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1343   -2.8152   -1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4145   -2.8178    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6178    1.9944   -1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2998    2.4039   -1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3627    1.4456   -2.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6185   -2.1503    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308   -2.1164    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2582   -1.1920   -0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9096   -0.2895    2.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015    1.0724    2.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1293    2.1114    0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0582    2.1122    2.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0232    2.0298    0.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    0.6655   -0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735    0.0650   -0.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0106   -1.8405    0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4813   -1.8144    1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0130   -1.4099    2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484    0.9765    2.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6044   -0.0061    1.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6459    2.7806    0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485    2.4334    1.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3891    1.5808   -1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5327    2.8335   -0.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8137   -0.1648    0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0088    0.3206    0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8990    2.0498    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9333    1.3230    1.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1539    1.7102   -1.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9864    0.4392   -2.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1497   -0.2281   -2.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8457    0.0750   -1.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2199   -2.6282   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9107   -0.1327    2.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7245   -1.3783    3.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8362   -2.9599    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0946   -2.1325    2.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 11 28  1  0
 28 29  1  0
  8  2  1  0
 29  6  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  6
 17 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  1
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
M  END

  Mrv0541 02251208062D          

 29 30  0  0  1  0            999 V2000
   11.7407  -13.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5657  -13.8199    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9782  -13.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5657  -12.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9782  -11.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5657  -10.9621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7407  -10.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9782  -10.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8032  -10.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2157   -9.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0408   -9.5331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8032   -8.8186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9782  -14.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8032  -14.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2157  -15.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0408  -15.2489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6282  -15.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0408  -14.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7552  -14.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4697  -14.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1842  -14.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8986  -14.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6132  -14.0114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8986  -15.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6132  -15.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1842  -15.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1842  -16.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4697  -15.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7552  -15.6614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 16 29  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 28  2  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012517

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H](CCC[C@@H](C)CCC(O)=O)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O4/c1-17(8-6-9-18(2)11-12-23(27)28)10-7-14-25(5)15-13-21-16-22(26)19(3)20(4)24(21)29-25/h16-18,26H,6-15H2,1-5H3,(H,27,28)/t17-,18+,25+/m0/s1

> <INCHI_KEY>
IITULCXNOMOXAH-YYULODDRSA-N

> <FORMULA>
C25H40O4

> <MOLECULAR_WEIGHT>
404.5827

> <EXACT_MASS>
404.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
48.93518741593094

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,8S)-11-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundecanoic acid

> <ALOGPS_LOGP>
6.22

> <JCHEM_LOGP>
7.497897679333333

> <ALOGPS_LOGS>
-6.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.470462122847591

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.044404780703179

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852416276880013

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
118.24769999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.38e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,8S)-11-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-4,8-dimethylundecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012517
     RDKit          3D
11'-Carboxy-gamma-chromanol
 69 70  0  0  0  0  0  0  0  0999 V2000
    6.7972    0.4387   -2.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1311   -0.1884   -1.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6182   -1.3525   -1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7437   -1.9610   -1.7262 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9812   -1.8962   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8690   -1.3137    0.4808 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3578   -0.1484   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0167    0.3804   -1.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5041    1.6336   -1.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2363    0.4742    0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3539   -0.3343    1.2420 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8084   -1.4454    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3739    0.4344    2.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4456    1.3608    1.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5876    1.0235    0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7335    0.1683    0.7176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4863   -1.2623    1.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8068    0.7562    1.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4350    2.0123    1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0962    1.8394   -0.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2048    0.8171   -0.2505 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3019    1.1896    0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7808    0.7165   -1.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8974   -0.2505   -1.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5709   -1.6569   -1.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4764   -2.5155   -1.5731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3004   -2.0549   -1.1571 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3143   -0.9872    2.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2392   -1.9646    1.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0981    0.5513   -3.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412   -0.2078   -3.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2288    1.3973   -2.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1343   -2.8152   -1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4145   -2.8178    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6178    1.9944   -1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2998    2.4039   -1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3627    1.4456   -2.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6185   -2.1503    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308   -2.1164    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2582   -1.1920   -0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9096   -0.2895    2.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015    1.0724    2.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1293    2.1114    0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0582    2.1122    2.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0232    2.0298    0.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    0.6655   -0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735    0.0650   -0.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0106   -1.8405    0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4813   -1.8144    1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0130   -1.4099    2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484    0.9765    2.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6044   -0.0061    1.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6459    2.7806    0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485    2.4334    1.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3891    1.5808   -1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5327    2.8335   -0.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8137   -0.1648    0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0088    0.3206    0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8990    2.0498    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9333    1.3230    1.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1539    1.7102   -1.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9864    0.4392   -2.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1497   -0.2281   -2.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8457    0.0750   -1.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2199   -2.6282   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9107   -0.1327    2.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7245   -1.3783    3.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8362   -2.9599    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0946   -2.1325    2.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 11 28  1  0
 28 29  1  0
  8  2  1  0
 29  6  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  6
 17 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  1
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      21.916 -25.797   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.456 -25.797   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.226 -24.464   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.456 -23.130   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.226 -21.796   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.456 -20.463   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.916 -20.463   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.226 -19.129   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.766 -19.129   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.536 -17.795   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      28.076 -17.795   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      25.766 -16.461   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      24.226 -27.131   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.766 -27.131   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.536 -28.465   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.076 -28.465   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.306 -29.798   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.076 -26.925   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.410 -26.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.743 -26.925   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      32.077 -26.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      33.411 -26.925   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      34.745 -26.155   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      33.411 -28.465   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      34.745 -29.235   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      32.077 -29.235   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      32.077 -30.775   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.743 -28.465   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      29.410 -29.235   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   29                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   20   26   29                                                  
CONECT   29   16   28                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

COMPND    HMDB0012517
HETATM    1  C1  UNL     1       6.797   0.439  -2.925  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.131  -0.188  -1.729  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.618  -1.353  -1.175  1.00  0.00           C  
HETATM    4  O1  UNL     1       7.744  -1.961  -1.726  1.00  0.00           O  
HETATM    5  C4  UNL     1       5.981  -1.896  -0.081  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.869  -1.314   0.481  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.358  -0.148  -0.051  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.017   0.380  -1.153  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.504   1.634  -1.761  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.236   0.474   0.484  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.354  -0.334   1.242  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.808  -1.445   0.447  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.374   0.434   2.035  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.446   1.361   1.402  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.588   1.023   0.451  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.733   0.168   0.718  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.486  -1.262   1.118  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.807   0.756   1.605  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.435   2.012   1.066  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.096   1.839  -0.270  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.205   0.817  -0.250  1.00  0.00           C  
HETATM   22  C20 UNL     1      -6.302   1.190   0.723  1.00  0.00           C  
HETATM   23  C21 UNL     1      -5.781   0.716  -1.619  1.00  0.00           C  
HETATM   24  C22 UNL     1      -6.897  -0.251  -1.796  1.00  0.00           C  
HETATM   25  C23 UNL     1      -6.571  -1.657  -1.504  1.00  0.00           C  
HETATM   26  O3  UNL     1      -7.476  -2.515  -1.573  1.00  0.00           O  
HETATM   27  O4  UNL     1      -5.300  -2.055  -1.157  1.00  0.00           O  
HETATM   28  C24 UNL     1       3.314  -0.987   2.296  1.00  0.00           C  
HETATM   29  C25 UNL     1       4.239  -1.965   1.660  1.00  0.00           C  
HETATM   30  H1  UNL     1       6.098   0.551  -3.770  1.00  0.00           H  
HETATM   31  H2  UNL     1       7.641  -0.208  -3.205  1.00  0.00           H  
HETATM   32  H3  UNL     1       7.229   1.397  -2.575  1.00  0.00           H  
HETATM   33  H4  UNL     1       8.134  -2.815  -1.351  1.00  0.00           H  
HETATM   34  H5  UNL     1       6.415  -2.818   0.312  1.00  0.00           H  
HETATM   35  H6  UNL     1       3.618   1.994  -1.238  1.00  0.00           H  
HETATM   36  H7  UNL     1       5.300   2.404  -1.673  1.00  0.00           H  
HETATM   37  H8  UNL     1       4.363   1.446  -2.835  1.00  0.00           H  
HETATM   38  H9  UNL     1       2.618  -2.150   0.066  1.00  0.00           H  
HETATM   39  H10 UNL     1       1.231  -2.116   1.140  1.00  0.00           H  
HETATM   40  H11 UNL     1       1.258  -1.192  -0.474  1.00  0.00           H  
HETATM   41  H12 UNL     1       0.910  -0.290   2.757  1.00  0.00           H  
HETATM   42  H13 UNL     1       2.001   1.072   2.770  1.00  0.00           H  
HETATM   43  H14 UNL     1       1.129   2.111   0.836  1.00  0.00           H  
HETATM   44  H15 UNL     1       0.058   2.112   2.205  1.00  0.00           H  
HETATM   45  H16 UNL     1      -1.023   2.030   0.081  1.00  0.00           H  
HETATM   46  H17 UNL     1      -0.101   0.666  -0.496  1.00  0.00           H  
HETATM   47  H18 UNL     1      -2.274   0.065  -0.286  1.00  0.00           H  
HETATM   48  H19 UNL     1      -1.011  -1.840   0.271  1.00  0.00           H  
HETATM   49  H20 UNL     1      -2.481  -1.814   1.221  1.00  0.00           H  
HETATM   50  H21 UNL     1      -1.013  -1.410   2.085  1.00  0.00           H  
HETATM   51  H22 UNL     1      -2.448   0.976   2.624  1.00  0.00           H  
HETATM   52  H23 UNL     1      -3.604  -0.006   1.705  1.00  0.00           H  
HETATM   53  H24 UNL     1      -2.646   2.781   0.968  1.00  0.00           H  
HETATM   54  H25 UNL     1      -4.149   2.433   1.810  1.00  0.00           H  
HETATM   55  H26 UNL     1      -3.389   1.581  -1.051  1.00  0.00           H  
HETATM   56  H27 UNL     1      -4.533   2.833  -0.536  1.00  0.00           H  
HETATM   57  H28 UNL     1      -4.814  -0.165   0.069  1.00  0.00           H  
HETATM   58  H29 UNL     1      -7.009   0.321   0.744  1.00  0.00           H  
HETATM   59  H30 UNL     1      -6.899   2.050   0.336  1.00  0.00           H  
HETATM   60  H31 UNL     1      -5.933   1.323   1.741  1.00  0.00           H  
HETATM   61  H32 UNL     1      -6.154   1.710  -1.976  1.00  0.00           H  
HETATM   62  H33 UNL     1      -4.986   0.439  -2.367  1.00  0.00           H  
HETATM   63  H34 UNL     1      -7.150  -0.228  -2.899  1.00  0.00           H  
HETATM   64  H35 UNL     1      -7.846   0.075  -1.312  1.00  0.00           H  
HETATM   65  H36 UNL     1      -5.220  -2.628  -0.306  1.00  0.00           H  
HETATM   66  H37 UNL     1       3.911  -0.133   2.677  1.00  0.00           H  
HETATM   67  H38 UNL     1       2.725  -1.378   3.134  1.00  0.00           H  
HETATM   68  H39 UNL     1       3.836  -2.960   1.470  1.00  0.00           H  
HETATM   69  H40 UNL     1       5.095  -2.133   2.381  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    3    8
CONECT    3    4    5
CONECT    4   33
CONECT    5    6    6   34
CONECT    6    7   29
CONECT    7    8    8   10
CONECT    8    9
CONECT    9   35   36   37
CONECT   10   11
CONECT   11   12   13   28
CONECT   12   38   39   40
CONECT   13   14   41   42
CONECT   14   15   43   44
CONECT   15   16   45   46
CONECT   16   17   18   47
CONECT   17   48   49   50
CONECT   18   19   51   52
CONECT   19   20   53   54
CONECT   20   21   55   56
CONECT   21   22   23   57
CONECT   22   58   59   60
CONECT   23   24   61   62
CONECT   24   25   63   64
CONECT   25   26   26   27
CONECT   27   65
CONECT   28   29   66   67
CONECT   29   68   69
END

HMDB0012517
     RDKit          3D
11'-Carboxy-gamma-chromanol
 69 70  0  0  0  0  0  0  0  0999 V2000
    6.7972    0.4387   -2.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1311   -0.1884   -1.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6182   -1.3525   -1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7437   -1.9610   -1.7262 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9812   -1.8962   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8690   -1.3137    0.4808 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3578   -0.1484   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0167    0.3804   -1.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5041    1.6336   -1.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2363    0.4742    0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3539   -0.3343    1.2420 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8084   -1.4454    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3739    0.4344    2.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4456    1.3608    1.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5876    1.0235    0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7335    0.1683    0.7176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4863   -1.2623    1.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8068    0.7562    1.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4350    2.0123    1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0962    1.8394   -0.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2048    0.8171   -0.2505 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3019    1.1896    0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7808    0.7165   -1.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8974   -0.2505   -1.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5709   -1.6569   -1.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4764   -2.5155   -1.5731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3004   -2.0549   -1.1571 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3143   -0.9872    2.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2392   -1.9646    1.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0981    0.5513   -3.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412   -0.2078   -3.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2288    1.3973   -2.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1343   -2.8152   -1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4145   -2.8178    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6178    1.9944   -1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2998    2.4039   -1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3627    1.4456   -2.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6185   -2.1503    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308   -2.1164    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2582   -1.1920   -0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9096   -0.2895    2.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015    1.0724    2.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1293    2.1114    0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0582    2.1122    2.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0232    2.0298    0.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    0.6655   -0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735    0.0650   -0.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0106   -1.8405    0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4813   -1.8144    1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0130   -1.4099    2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484    0.9765    2.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6044   -0.0061    1.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6459    2.7806    0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485    2.4334    1.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3891    1.5808   -1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5327    2.8335   -0.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8137   -0.1648    0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0088    0.3206    0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8990    2.0498    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9333    1.3230    1.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1539    1.7102   -1.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9864    0.4392   -2.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1497   -0.2281   -2.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8457    0.0750   -1.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2199   -2.6282   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9107   -0.1327    2.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7245   -1.3783    3.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8362   -2.9599    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0946   -2.1325    2.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 11 28  1  0
 28 29  1  0
  8  2  1  0
 29  6  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  6
 17 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  1
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11'-Carboxy-gamma-tocopherol	HMDB
(4R,8S)-11-[(2R)-6-Hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundecanoate	Generator

Chemical Formula

C₂₅H₄₀O₄

Average Molecular Weight

404.5827

Monoisotopic Molecular Weight

404.292659768

IUPAC Name

(4R,8S)-11-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundecanoic acid

Traditional Name

(4R,8S)-11-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-4,8-dimethylundecanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](CCC[C@@H](C)CCC(O)=O)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2

InChI Identifier

InChI=1S/C25H40O4/c1-17(8-6-9-18(2)11-12-23(27)28)10-7-14-25(5)15-13-21-16-22(26)19(3)20(4)24(21)29-25/h16-18,26H,6-15H2,1-5H3,(H,27,28)/t17-,18+,25+/m0/s1

InChI Key

IITULCXNOMOXAH-YYULODDRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Long-chain fatty acid
Chromane
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Branched fatty acid
Heterocyclic fatty acid
Methyl-branched fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Benzenoid
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012517)

Source

Endogenous

Endogenous (HMDB: HMDB0012517)

Animal

Animal (HMDB: HMDB0012517)

Exogenous

Food

Food (HMDB: HMDB0012517)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012517)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012517)

Lipid metabolism pathway (HMDB: HMDB0012517)

Cellular process

Cell signaling (HMDB: HMDB0012517)

Biochemical process

Lipid transport (HMDB: HMDB0012517)

Role

Biological role

Energy source (HMDB: HMDB0012517)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00024 g/L	ALOGPS
logP	6.22	ALOGPS
logP	7.5	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	5.04	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	118.25 m³·mol⁻¹	ChemAxon
Polarizability	48.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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]+	197.894	31661259
DarkChem	[M-H]-	192.612	31661259
DeepCCS	[M+H]+	202.329	30932474
DeepCCS	[M-H]-	199.971	30932474
DeepCCS	[M-2H]-	233.036	30932474
DeepCCS	[M+Na]+	208.422	30932474
AllCCS	[M+H]+	207.3	32859911
AllCCS	[M+H-H2O]+	204.9	32859911
AllCCS	[M+NH4]+	209.4	32859911
AllCCS	[M+Na]+	210.0	32859911
AllCCS	[M-H]-	207.1	32859911
AllCCS	[M+Na-2H]-	209.0	32859911
AllCCS	[M+HCOO]-	211.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11'-Carboxy-gamma-chromanol	C[C@@H](CCC[C@@H](C)CCC(O)=O)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2	4397.3	Standard polar	33892256
11'-Carboxy-gamma-chromanol	C[C@@H](CCC[C@@H](C)CCC(O)=O)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2	3090.3	Standard non polar	33892256
11'-Carboxy-gamma-chromanol	C[C@@H](CCC[C@@H](C)CCC(O)=O)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2	3245.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
11'-Carboxy-gamma-chromanol,1TMS,isomer #1	CC1=C(O)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCC(=O)O[Si](C)(C)C)OC2=C1C	3072.7	Semi standard non polar	33892256
11'-Carboxy-gamma-chromanol,1TMS,isomer #2	CC1=C(O[Si](C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCC(=O)O)OC2=C1C	3084.9	Semi standard non polar	33892256
11'-Carboxy-gamma-chromanol,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCC(=O)O[Si](C)(C)C)OC2=C1C	3063.9	Semi standard non polar	33892256
11'-Carboxy-gamma-chromanol,1TBDMS,isomer #1	CC1=C(O)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCC(=O)O[Si](C)(C)C(C)(C)C)OC2=C1C	3339.5	Semi standard non polar	33892256
11'-Carboxy-gamma-chromanol,1TBDMS,isomer #2	CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCC(=O)O)OC2=C1C	3353.0	Semi standard non polar	33892256
11'-Carboxy-gamma-chromanol,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCC(=O)O[Si](C)(C)C(C)(C)C)OC2=C1C	3572.7	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 - 11'-Carboxy-gamma-chromanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-01px-3789000000-b9cb7dc2edc9c0dc3149	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11'-Carboxy-gamma-chromanol GC-MS (2 TMS) - 70eV, Positive	splash10-001i-4388590000-bdc6d60eb866d7a8b7ef	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11'-Carboxy-gamma-chromanol 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 - 11'-Carboxy-gamma-chromanol 10V, Positive-QTOF	splash10-052r-0529200000-08553bc979f15487e787	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-gamma-chromanol 20V, Positive-QTOF	splash10-0udi-0911000000-9e630eaf829f03921b29	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-gamma-chromanol 40V, Positive-QTOF	splash10-0udi-1910000000-f8b7aad184832fe318dc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-gamma-chromanol 10V, Negative-QTOF	splash10-0udi-0103900000-dda02cca2ec6a1b6c1cc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-gamma-chromanol 20V, Negative-QTOF	splash10-0k9b-2719500000-fa011191e66ab5e1d820	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-gamma-chromanol 40V, Negative-QTOF	splash10-0a4v-9715000000-067f230061e510e29e79	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-gamma-chromanol 10V, Negative-QTOF	splash10-0zfr-0007900000-c691010f380fd137af49	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-gamma-chromanol 20V, Negative-QTOF	splash10-0a4l-6209300000-6d88fde92393398bc7d4	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-gamma-chromanol 40V, Negative-QTOF	splash10-006x-1913000000-242862c102afa2200c76	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-gamma-chromanol 10V, Positive-QTOF	splash10-0a4i-0139000000-4a4c307e44e7b68aa3a3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-gamma-chromanol 20V, Positive-QTOF	splash10-0a5d-2492000000-d883fbb7be140d78fd9c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11'-Carboxy-gamma-chromanol 40V, Positive-QTOF	splash10-006x-3920000000-54856887377167d10023	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

FDB029110

KNApSAcK ID

Not Available

Chemspider ID

30776628

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481453

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

CE5718

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
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Showing metabocard for 11'-Carboxy-gamma-chromanol (HMDB0012517)

MOL for HMDB0012517 (11'-Carboxy-gamma-chromanol)

3D MOL for HMDB0012517 (11'-Carboxy-gamma-chromanol)

3D SDF for HMDB0012517 (11'-Carboxy-gamma-chromanol)

3D-SDF for HMDB0012517 (11'-Carboxy-gamma-chromanol)

PDB for HMDB0012517 (11'-Carboxy-gamma-chromanol)

3D PDB for HMDB0012517 (11'-Carboxy-gamma-chromanol)

SMILES for HMDB0012517 (11'-Carboxy-gamma-chromanol)

INCHI for HMDB0012517 (11'-Carboxy-gamma-chromanol)

Structure for HMDB0012517 (11'-Carboxy-gamma-chromanol)

3D Structure for HMDB0012517 (11'-Carboxy-gamma-chromanol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra