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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:08:51 UTC

Update Date

2021-09-14 15:41:21 UTC

HMDB ID

HMDB0012866

Secondary Accession Numbers

HMDB12866

Metabolite Identification

Common Name

9'-Carboxy-alpha-chromanol

Description

9'-carboxy-alpha-tocopherol is a dehydrogenation carboxylate product of 9'-hydroxy-a-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. The tocopherols ( a-tocopherol , b-tocopherol ,r-tocopherol and d-tocopherol ) and their corresponding tocotrienols are synthesized by plants and have vitamin E antixoidant activity (see pathway vitamin E biosynthesis ). They differ in the number and location of methyl groups on the chromanol ring. The naturally occurring form of a-tocopherol is (2R,4'R,8'R)-a-tocopherol (synonym (R,R,R)-a-tocopherol). Synthetic a-tocopherols are a racemic mixture of eight different R and S stereoisomers. Only the 2R forms are recognized as meeting human requirements. The in vivo function of vitamin E is to scavenge peroxyl radicals via its phenolic (chromanol) hydroxyl group, thus protecting lipids against free radical-catalyzed peroxidation. The tocopheryl radical formed can then be reduced by reductants such as L-ascorbate. Other major products of a-tocopherol oxidation include α-tocopherylquinone and epoxy-a-tocopherols. The metabolites a-tocopheronic acid and its lactone, known as the Simon metabolites, are generally believed to be artefacts. In addition to these oxidation products, the other major class of tocopherol metabolites is the carboxyethyl-hydroxychromans.These metabolites are produced in significant amounts in response to excess vitamin E ingestion. Vitamin E is fat-soluble and its utilization requires intestinal fat absorption mechanisms. It is secreted from the intestine into the lymphatic system in chylomicrons which subsequently enter the plasma. Lipolysis of these chylomicrons can result in delivery of vitamin E to tissues, transfer to high-density lipoproteins (and subsequently to other lipoproteins via the phospholipid exchange protein), or retention in chylomicron remnants. These remnants are taken up by the liver. Natural (R,R,R)-α-tocopherol and synthetic 2R-α-tocopherols are then preferentially secreted from the liver into plasma as a result of the specificity of the α-tocopherol transfer protein. This protein, along with the metabolism of excess vitamin E in the liver and excretion into urine and bile, mediate the supply of a-tocopherol in plasma and tissues.

Structure

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

  Mrv1652303102016462D          

 28 29  0  0  1  0            999 V2000
   11.1953  -12.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9098  -12.7755    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6243  -12.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6243  -11.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3388  -11.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3388  -10.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0532   -9.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6243   -9.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6243   -9.0629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9098  -10.3004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9098  -13.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6243  -14.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6243  -14.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3388  -15.2505    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6243  -15.6630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7513  -14.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5763  -14.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9888  -15.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8138  -15.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2263  -14.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2263  -15.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0513  -15.9649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8138  -16.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2263  -17.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9888  -16.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5763  -17.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5763  -15.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7513  -15.9649    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 11  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  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 14 28  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 27  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0012866
     RDKit          3D
9'-Carboxy-alpha-chromanol
 66 67  0  0  0  0  0  0  0  0999 V2000
   -7.2463   -0.1956    1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0417   -0.3652    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8301    0.0209    0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7125    0.5925    2.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649   -0.1240    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6919   -0.6451   -1.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9288   -1.0283   -1.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9886   -1.5956   -3.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0920   -0.8958   -0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3330   -1.2705   -1.4004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5013   -0.8308   -1.9761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -0.6960   -1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4182    0.5357   -0.2860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9280    1.7179   -1.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458    0.9707    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9070    1.2686   -0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2040    1.7838   -0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0366    0.9809    0.8238 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3870    0.7042    2.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4321   -0.2943    0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2817   -1.1875    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5311   -0.4871    1.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3668   -0.0529    0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167    0.6644    0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7703   -1.1992   -0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9765   -1.5354   -0.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8541   -1.9054   -1.3744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4430    0.2607    0.6864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1621   -0.3461    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1828   -0.9817    2.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2220    0.7853    1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5489    1.6869    2.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7707    0.1786    2.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5725    0.3355    2.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1115   -2.6972   -2.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0434   -1.3450   -3.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8478   -1.1791   -3.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3843   -1.6560   -2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966   -1.8905   -2.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -0.1772   -2.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533   -1.5716   -0.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492   -0.8605   -1.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4100    2.6718   -0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7674    1.6089   -2.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0100    1.9055   -0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4045    1.8480    1.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1279    0.0877    1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0428    0.3568   -1.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5463    2.0357   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    2.7659    0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8895    2.0646   -0.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875    1.5926    0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0340   -0.3202    2.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0909    0.9011    2.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5571    1.4124    2.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -0.8450   -0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0039    0.0169   -0.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6648   -1.4865    1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4594   -2.1314    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0840   -1.2038    2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3397    0.3928    1.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8544    0.7093   -0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4172    0.6614   -0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9175    0.1639    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3024    1.6784    0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1116   -2.3594   -2.2522 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  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 25 27  1  0
 13 28  1  0
  9  2  1  0
 28  5  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  1
 19 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 24 65  1  0
 27 66  1  0
M  END

  Mrv1652303102016462D          

 28 29  0  0  1  0            999 V2000
   11.1953  -12.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9098  -12.7755    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6243  -12.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6243  -11.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3388  -11.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3388  -10.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0532   -9.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6243   -9.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6243   -9.0629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9098  -10.3004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9098  -13.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6243  -14.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6243  -14.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3388  -15.2505    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6243  -15.6630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7513  -14.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5763  -14.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9888  -15.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8138  -15.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2263  -14.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2263  -15.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0513  -15.9649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8138  -16.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2263  -17.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9888  -16.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5763  -17.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5763  -15.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7513  -15.9649    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 11  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  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 14 28  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 27  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012866

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H](CCCC(C)C(O)=O)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O4/c1-15(9-7-11-16(2)23(26)27)10-8-13-24(6)14-12-20-19(5)21(25)17(3)18(4)22(20)28-24/h15-16,25H,7-14H2,1-6H3,(H,26,27)/t15-,16?,24-/m0/s1

> <INCHI_KEY>
CUGVBZDXUTZXJO-GCIQOJCMSA-N

> <FORMULA>
C24H38O4

> <MOLECULAR_WEIGHT>
390.5561

> <EXACT_MASS>
390.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.156150959491015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S)-9-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid

> <ALOGPS_LOGP>
5.67

> <JCHEM_LOGP>
7.378148920666668

> <ALOGPS_LOGS>
-5.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.802178810155162

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.999793180837479

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852614901836805

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
114.11279999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.78e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6S)-9-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012866
     RDKit          3D
9'-Carboxy-alpha-chromanol
 66 67  0  0  0  0  0  0  0  0999 V2000
   -7.2463   -0.1956    1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0417   -0.3652    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8301    0.0209    0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7125    0.5925    2.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649   -0.1240    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6919   -0.6451   -1.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9288   -1.0283   -1.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9886   -1.5956   -3.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0920   -0.8958   -0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3330   -1.2705   -1.4004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5013   -0.8308   -1.9761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -0.6960   -1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4182    0.5357   -0.2860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9280    1.7179   -1.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458    0.9707    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9070    1.2686   -0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2040    1.7838   -0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0366    0.9809    0.8238 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3870    0.7042    2.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4321   -0.2943    0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2817   -1.1875    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5311   -0.4871    1.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3668   -0.0529    0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167    0.6644    0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7703   -1.1992   -0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9765   -1.5354   -0.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8541   -1.9054   -1.3744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4430    0.2607    0.6864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1621   -0.3461    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1828   -0.9817    2.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2220    0.7853    1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5489    1.6869    2.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7707    0.1786    2.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5725    0.3355    2.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1115   -2.6972   -2.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0434   -1.3450   -3.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8478   -1.1791   -3.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3843   -1.6560   -2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966   -1.8905   -2.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -0.1772   -2.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533   -1.5716   -0.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492   -0.8605   -1.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4100    2.6718   -0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7674    1.6089   -2.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0100    1.9055   -0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4045    1.8480    1.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1279    0.0877    1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0428    0.3568   -1.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5463    2.0357   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    2.7659    0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8895    2.0646   -0.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875    1.5926    0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0340   -0.3202    2.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0909    0.9011    2.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5571    1.4124    2.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -0.8450   -0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0039    0.0169   -0.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6648   -1.4865    1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4594   -2.1314    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0840   -1.2038    2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3397    0.3928    1.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8544    0.7093   -0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4172    0.6614   -0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9175    0.1639    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3024    1.6784    0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1116   -2.3594   -2.2522 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  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 25 27  1  0
 13 28  1  0
  9  2  1  0
 28  5  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  1
 19 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 24 65  1  0
 27 66  1  0
M  END

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      20.898 -23.078   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.232 -23.848   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.565 -23.078   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.565 -21.537   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.899 -20.767   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.899 -19.227   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.233 -18.457   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.565 -18.457   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      23.565 -16.917   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      22.232 -19.227   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      22.232 -25.388   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.565 -26.158   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.565 -27.698   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.899 -28.468   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.565 -29.238   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.669 -27.134   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.209 -27.134   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.979 -28.468   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.519 -28.468   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.289 -27.134   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.289 -29.801   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      31.829 -29.801   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      29.519 -31.135   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      30.289 -32.469   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      27.979 -31.135   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      27.209 -32.469   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      27.209 -29.801   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      25.669 -29.801   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   28                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   18   25   28                                                  
CONECT   28   14   27                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

COMPND    HMDB0012866
HETATM    1  C1  UNL     1      -7.246  -0.196   1.215  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.042  -0.365   0.384  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.830   0.021   0.917  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.712   0.593   2.284  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.665  -0.124   0.160  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.692  -0.645  -1.113  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.929  -1.028  -1.632  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.989  -1.596  -3.012  1.00  0.00           C  
HETATM    9  C9  UNL     1      -6.092  -0.896  -0.905  1.00  0.00           C  
HETATM   10  O1  UNL     1      -7.333  -1.270  -1.400  1.00  0.00           O  
HETATM   11  C10 UNL     1      -2.501  -0.831  -1.976  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.267  -0.696  -1.096  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.418   0.536  -0.286  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.928   1.718  -1.087  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.146   0.971   0.412  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.907   1.269  -0.585  1.00  0.00           C  
HETATM   17  C16 UNL     1       2.204   1.784  -0.097  1.00  0.00           C  
HETATM   18  C17 UNL     1       3.037   0.981   0.824  1.00  0.00           C  
HETATM   19  C18 UNL     1       2.387   0.704   2.124  1.00  0.00           C  
HETATM   20  C19 UNL     1       3.432  -0.294   0.086  1.00  0.00           C  
HETATM   21  C20 UNL     1       4.282  -1.188   0.929  1.00  0.00           C  
HETATM   22  C21 UNL     1       5.531  -0.487   1.331  1.00  0.00           C  
HETATM   23  C22 UNL     1       6.367  -0.053   0.183  1.00  0.00           C  
HETATM   24  C23 UNL     1       7.617   0.664   0.734  1.00  0.00           C  
HETATM   25  C24 UNL     1       6.770  -1.199  -0.641  1.00  0.00           C  
HETATM   26  O2  UNL     1       7.976  -1.535  -0.673  1.00  0.00           O  
HETATM   27  O3  UNL     1       5.854  -1.905  -1.374  1.00  0.00           O  
HETATM   28  O4  UNL     1      -2.443   0.261   0.686  1.00  0.00           O  
HETATM   29  H1  UNL     1      -8.162  -0.346   0.636  1.00  0.00           H  
HETATM   30  H2  UNL     1      -7.183  -0.982   2.023  1.00  0.00           H  
HETATM   31  H3  UNL     1      -7.222   0.785   1.749  1.00  0.00           H  
HETATM   32  H4  UNL     1      -4.549   1.687   2.174  1.00  0.00           H  
HETATM   33  H5  UNL     1      -3.771   0.179   2.736  1.00  0.00           H  
HETATM   34  H6  UNL     1      -5.572   0.335   2.904  1.00  0.00           H  
HETATM   35  H7  UNL     1      -5.112  -2.697  -2.941  1.00  0.00           H  
HETATM   36  H8  UNL     1      -4.043  -1.345  -3.572  1.00  0.00           H  
HETATM   37  H9  UNL     1      -5.848  -1.179  -3.576  1.00  0.00           H  
HETATM   38  H10 UNL     1      -7.384  -1.656  -2.330  1.00  0.00           H  
HETATM   39  H11 UNL     1      -2.497  -1.891  -2.368  1.00  0.00           H  
HETATM   40  H12 UNL     1      -2.477  -0.177  -2.852  1.00  0.00           H  
HETATM   41  H13 UNL     1      -1.353  -1.572  -0.376  1.00  0.00           H  
HETATM   42  H14 UNL     1      -0.349  -0.861  -1.639  1.00  0.00           H  
HETATM   43  H15 UNL     1      -1.410   2.672  -0.789  1.00  0.00           H  
HETATM   44  H16 UNL     1      -1.767   1.609  -2.163  1.00  0.00           H  
HETATM   45  H17 UNL     1      -3.010   1.905  -0.929  1.00  0.00           H  
HETATM   46  H18 UNL     1      -0.405   1.848   1.043  1.00  0.00           H  
HETATM   47  H19 UNL     1       0.128   0.088   1.061  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.043   0.357  -1.233  1.00  0.00           H  
HETATM   49  H21 UNL     1       0.546   2.036  -1.352  1.00  0.00           H  
HETATM   50  H22 UNL     1       1.997   2.766   0.455  1.00  0.00           H  
HETATM   51  H23 UNL     1       2.889   2.065  -0.965  1.00  0.00           H  
HETATM   52  H24 UNL     1       3.987   1.593   0.988  1.00  0.00           H  
HETATM   53  H25 UNL     1       2.034  -0.320   2.239  1.00  0.00           H  
HETATM   54  H26 UNL     1       3.091   0.901   2.996  1.00  0.00           H  
HETATM   55  H27 UNL     1       1.557   1.412   2.293  1.00  0.00           H  
HETATM   56  H28 UNL     1       2.555  -0.845  -0.273  1.00  0.00           H  
HETATM   57  H29 UNL     1       4.004   0.017  -0.804  1.00  0.00           H  
HETATM   58  H30 UNL     1       3.665  -1.486   1.827  1.00  0.00           H  
HETATM   59  H31 UNL     1       4.459  -2.131   0.380  1.00  0.00           H  
HETATM   60  H32 UNL     1       6.084  -1.204   2.013  1.00  0.00           H  
HETATM   61  H33 UNL     1       5.340   0.393   1.993  1.00  0.00           H  
HETATM   62  H34 UNL     1       5.854   0.709  -0.438  1.00  0.00           H  
HETATM   63  H35 UNL     1       8.417   0.661  -0.004  1.00  0.00           H  
HETATM   64  H36 UNL     1       7.918   0.164   1.690  1.00  0.00           H  
HETATM   65  H37 UNL     1       7.302   1.678   0.993  1.00  0.00           H  
HETATM   66  H38 UNL     1       6.112  -2.359  -2.252  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    3    9
CONECT    3    4    5
CONECT    4   32   33   34
CONECT    5    6    6   28
CONECT    6    7   11
CONECT    7    8    9    9
CONECT    8   35   36   37
CONECT    9   10
CONECT   10   38
CONECT   11   12   39   40
CONECT   12   13   41   42
CONECT   13   14   15   28
CONECT   14   43   44   45
CONECT   15   16   46   47
CONECT   16   17   48   49
CONECT   17   18   50   51
CONECT   18   19   20   52
CONECT   19   53   54   55
CONECT   20   21   56   57
CONECT   21   22   58   59
CONECT   22   23   60   61
CONECT   23   24   25   62
CONECT   24   63   64   65
CONECT   25   26   26   27
CONECT   27   66
END

HMDB0012866
     RDKit          3D
9'-Carboxy-alpha-chromanol
 66 67  0  0  0  0  0  0  0  0999 V2000
   -7.2463   -0.1956    1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0417   -0.3652    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8301    0.0209    0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7125    0.5925    2.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649   -0.1240    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6919   -0.6451   -1.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9288   -1.0283   -1.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9886   -1.5956   -3.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0920   -0.8958   -0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3330   -1.2705   -1.4004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5013   -0.8308   -1.9761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -0.6960   -1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4182    0.5357   -0.2860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9280    1.7179   -1.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458    0.9707    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9070    1.2686   -0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2040    1.7838   -0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0366    0.9809    0.8238 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3870    0.7042    2.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4321   -0.2943    0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2817   -1.1875    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5311   -0.4871    1.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3668   -0.0529    0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167    0.6644    0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7703   -1.1992   -0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9765   -1.5354   -0.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8541   -1.9054   -1.3744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4430    0.2607    0.6864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1621   -0.3461    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1828   -0.9817    2.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2220    0.7853    1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5489    1.6869    2.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7707    0.1786    2.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5725    0.3355    2.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1115   -2.6972   -2.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0434   -1.3450   -3.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8478   -1.1791   -3.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3843   -1.6560   -2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966   -1.8905   -2.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -0.1772   -2.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533   -1.5716   -0.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492   -0.8605   -1.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4100    2.6718   -0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7674    1.6089   -2.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0100    1.9055   -0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4045    1.8480    1.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1279    0.0877    1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0428    0.3568   -1.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5463    2.0357   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    2.7659    0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8895    2.0646   -0.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875    1.5926    0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0340   -0.3202    2.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0909    0.9011    2.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5571    1.4124    2.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -0.8450   -0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0039    0.0169   -0.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6648   -1.4865    1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4594   -2.1314    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0840   -1.2038    2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3397    0.3928    1.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8544    0.7093   -0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4172    0.6614   -0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9175    0.1639    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3024    1.6784    0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1116   -2.3594   -2.2522 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  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 25 27  1  0
 13 28  1  0
  9  2  1  0
 28  5  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  1
 19 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 24 65  1  0
 27 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9'-Carboxy-alpha-tocopherol	HMDB
(6S)-9-[(2S)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnonanoate	Generator

Chemical Formula

C₂₄H₃₈O₄

Average Molecular Weight

390.5561

Monoisotopic Molecular Weight

390.277009704

IUPAC Name

(6S)-9-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid

Traditional Name

(6S)-9-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](CCCC(C)C(O)=O)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C

InChI Identifier

InChI=1S/C24H38O4/c1-15(9-7-11-16(2)23(26)27)10-8-13-24(6)14-12-20-19(5)21(25)17(3)18(4)22(20)28-24/h15-16,25H,7-14H2,1-6H3,(H,26,27)/t15-,16?,24-/m0/s1

InChI Key

CUGVBZDXUTZXJO-GCIQOJCMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Medium-chain fatty acid
Alkyl aryl ether
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0012866)
Cell membrane (HMDB: HMDB0012866)

Source

Endogenous

Endogenous (HMDB: HMDB0012866)

Process

Not Available

Role

Not Available

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	0.00058 g/L	ALOGPS
logP	5.67	ALOGPS
logP	7.38	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	5	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	9	ChemAxon
Refractivity	114.11 m³·mol⁻¹	ChemAxon
Polarizability	47.16 Å³	ChemAxon
Number of Rings	2	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]+	191.382	31661259
DarkChem	[M-H]-	190.418	31661259
DeepCCS	[M+H]+	199.789	30932474
DeepCCS	[M-H]-	197.431	30932474
DeepCCS	[M-2H]-	231.275	30932474
DeepCCS	[M+Na]+	206.503	30932474
AllCCS	[M+H]+	201.6	32859911
AllCCS	[M+H-H2O]+	199.2	32859911
AllCCS	[M+NH4]+	203.9	32859911
AllCCS	[M+Na]+	204.6	32859911
AllCCS	[M-H]-	204.7	32859911
AllCCS	[M+Na-2H]-	206.2	32859911
AllCCS	[M+HCOO]-	208.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9'-Carboxy-alpha-chromanol	C[C@@H](CCCC(C)C(O)=O)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C	4268.8	Standard polar	33892256
9'-Carboxy-alpha-chromanol	C[C@@H](CCCC(C)C(O)=O)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C	2974.5	Standard non polar	33892256
9'-Carboxy-alpha-chromanol	C[C@@H](CCCC(C)C(O)=O)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C	3069.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9'-Carboxy-alpha-chromanol,1TMS,isomer #1	CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C)O2)C(C)=C1O	2916.3	Semi standard non polar	33892256
9'-Carboxy-alpha-chromanol,1TMS,isomer #2	CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCCC(C)C(=O)O)O2)C(C)=C1O[Si](C)(C)C	2986.1	Semi standard non polar	33892256
9'-Carboxy-alpha-chromanol,2TMS,isomer #1	CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C)O2)C(C)=C1O[Si](C)(C)C	2958.8	Semi standard non polar	33892256
9'-Carboxy-alpha-chromanol,1TBDMS,isomer #1	CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O	3173.1	Semi standard non polar	33892256
9'-Carboxy-alpha-chromanol,1TBDMS,isomer #2	CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCCC(C)C(=O)O)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	3237.2	Semi standard non polar	33892256
9'-Carboxy-alpha-chromanol,2TBDMS,isomer #1	CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	3446.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 9'-Carboxy-alpha-chromanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-056v-4498000000-1a58e6e3c53fa8869307	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9'-Carboxy-alpha-chromanol GC-MS (2 TMS) - 70eV, Positive	splash10-01di-7278590000-3d1f22c3ebefa9b07820	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9'-Carboxy-alpha-chromanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9'-Carboxy-alpha-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 - 9'-Carboxy-alpha-chromanol 10V, Positive-QTOF	splash10-00r6-0419000000-1b909b2af5a45354471e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 20V, Positive-QTOF	splash10-014i-0911000000-7aa69e501c59a2d9b07b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 40V, Positive-QTOF	splash10-016r-1900000000-4d93f14c8f0d69b048f3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 10V, Negative-QTOF	splash10-000i-0009000000-e4ce51bae06f0f67bcc0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 20V, Negative-QTOF	splash10-01pa-0319000000-034afebbf088626f17f7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 40V, Negative-QTOF	splash10-071j-3923000000-da0f980f1619f88b6f01	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 10V, Negative-QTOF	splash10-000i-0009000000-7a0b01839255af1f268e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 20V, Negative-QTOF	splash10-00kp-0209000000-8e7780c46151dc97537a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 40V, Negative-QTOF	splash10-0a70-1393000000-f40ff2e44226a5bc0b86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 10V, Positive-QTOF	splash10-014m-0059000000-76cee7c90212b1d89f7c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 20V, Positive-QTOF	splash10-0002-1193000000-19f0e0d5a180283994c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 40V, Positive-QTOF	splash10-0a4i-5980000000-eae9b1d62f3097886e58	2021-09-22	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

FDB029190

KNApSAcK ID

Not Available

Chemspider ID

35032551

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481534

PDB ID

Not Available

ChEBI ID

175124

Food Biomarker Ontology

Not Available

VMH ID

CE5856

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 9'-Carboxy-alpha-chromanol (HMDB0012866)

MOL for HMDB0012866 (9'-Carboxy-alpha-chromanol)

3D MOL for HMDB0012866 (9'-Carboxy-alpha-chromanol)

3D SDF for HMDB0012866 (9'-Carboxy-alpha-chromanol)

3D-SDF for HMDB0012866 (9'-Carboxy-alpha-chromanol)

PDB for HMDB0012866 (9'-Carboxy-alpha-chromanol)

3D PDB for HMDB0012866 (9'-Carboxy-alpha-chromanol)

SMILES for HMDB0012866 (9'-Carboxy-alpha-chromanol)

INCHI for HMDB0012866 (9'-Carboxy-alpha-chromanol)

Structure for HMDB0012866 (9'-Carboxy-alpha-chromanol)

3D Structure for HMDB0012866 (9'-Carboxy-alpha-chromanol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra