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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 00:54:54 UTC

Update Date

2022-03-07 03:17:43 UTC

HMDB ID

HMDB0060340

Secondary Accession Numbers

HMDB60340

Metabolite Identification

Common Name

15,15'-Dihydroxy-beta-carotene

Description

15,15'-Dihydroxy-beta-carotene, also known as retinal-pinacol, belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. 15,15'-Dihydroxy-beta-carotene is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv0541 05161317542D          

 42 43  0  0  0  0            999 V2000
   16.4328    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4354    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7591    5.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8197    5.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3947    6.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3341    6.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2920    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5788    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0065    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8644    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4354    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4354    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5788    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1499    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1499    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8644    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 11  2  0  0  0  0
 18 12  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 23 21  2  0  0  0  0
 24 22  2  0  0  0  0
 25 13  1  0  0  0  0
 26 14  1  0  0  0  0
 29  1  1  0  0  0  0
 29 15  2  0  0  0  0
 29 21  1  0  0  0  0
 30  2  1  0  0  0  0
 30 16  2  0  0  0  0
 30 22  1  0  0  0  0
 31  3  1  0  0  0  0
 31 17  1  0  0  0  0
 31 27  2  0  0  0  0
 32  4  1  0  0  0  0
 32 18  1  0  0  0  0
 32 28  2  0  0  0  0
 33  5  1  0  0  0  0
 33 19  1  0  0  0  0
 34  6  1  0  0  0  0
 34 20  1  0  0  0  0
 35 23  1  0  0  0  0
 35 33  2  0  0  0  0
 36 24  1  0  0  0  0
 36 34  2  0  0  0  0
 37 27  1  0  0  0  0
 38 28  1  0  0  0  0
 38 37  1  0  0  0  0
 39  7  1  0  0  0  0
 39  8  1  0  0  0  0
 39 25  1  0  0  0  0
 39 35  1  0  0  0  0
 40  9  1  0  0  0  0
 40 10  1  0  0  0  0
 40 26  1  0  0  0  0
 40 36  1  0  0  0  0
 41 37  1  0  0  0  0
 42 38  1  0  0  0  0
M  END

HMDB0060340
     RDKit          3D
15,15'-Dihydroxy-beta-carotene
100101  0  0  0  0  0  0  0  0999 V2000
   11.9704   -2.2852    0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3557   -0.9130    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0207   -0.4776    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9164    0.2022    0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5937   -1.9084    0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1567   -0.2484    0.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434    0.5743    0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7924    0.0144    0.9950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6506   -1.4435    1.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7580    0.8051    1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    0.3686    1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2412    1.2906    2.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
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 42100  1  0
M  END


  Mrv0541 05161317542D          

 42 43  0  0  0  0            999 V2000
   16.4328    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4354    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7591    5.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8197    5.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3947    6.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3341    6.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2920    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5788    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0065    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8644    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4354    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4354    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5788    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.1486    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1499    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1499    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8644    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 16 12  1  0  0  0  0
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 29  1  1  0  0  0  0
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 32  4  1  0  0  0  0
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 32 28  2  0  0  0  0
 33  5  1  0  0  0  0
 33 19  1  0  0  0  0
 34  6  1  0  0  0  0
 34 20  1  0  0  0  0
 35 23  1  0  0  0  0
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 37 27  1  0  0  0  0
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 38 37  1  0  0  0  0
 39  7  1  0  0  0  0
 39  8  1  0  0  0  0
 39 25  1  0  0  0  0
 39 35  1  0  0  0  0
 40  9  1  0  0  0  0
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 40 36  1  0  0  0  0
 41 37  1  0  0  0  0
 42 38  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060340

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)C(O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H58O2/c1-29(21-23-35-33(5)19-13-25-39(35,7)8)15-11-17-31(3)27-37(41)38(42)28-32(4)18-12-16-30(2)22-24-36-34(6)20-14-26-40(36,9)10/h11-12,15-18,21-24,27-28,37-38,41-42H,13-14,19-20,25-26H2,1-10H3/b17-11+,18-12+,23-21+,24-22+,29-15+,30-16+,31-27+,32-28+

> <INCHI_KEY>
LAMXZCLZRAUDED-WDJSDFAOSA-N

> <FORMULA>
C40H58O2

> <MOLECULAR_WEIGHT>
570.8873

> <EXACT_MASS>
570.4436811

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
73.82111770567016

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1E,3E,5E,7E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-1,18-bis(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,11,13,15,17-octaene-9,10-diol

> <ALOGPS_LOGP>
8.10

> <JCHEM_LOGP>
9.336195542666669

> <ALOGPS_LOGS>
-6.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.894920282547133

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.455249791386734

> <JCHEM_PKA_STRONGEST_BASIC>
-3.342803221144017

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
193.2182

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.71e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E,3E,5E,7E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-1,18-bis(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,11,13,15,17-octaene-9,10-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060340
     RDKit          3D
15,15'-Dihydroxy-beta-carotene
100101  0  0  0  0  0  0  0  0999 V2000
   11.9704   -2.2852    0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3557   -0.9130    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3723   -0.0169   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0207   -0.4776    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9164    0.2022    0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6256   -0.4763    0.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5937   -1.9084    0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5087    0.1944    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1567   -0.2484    0.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434    0.5743    0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7924    0.0144    0.9950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6506   -1.4435    1.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7580    0.8051    1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    0.3686    1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2412    1.2906    2.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259    0.4372   -0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0960    0.3212   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2049   -0.3005    0.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4400    0.1654   -0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6405   -0.0989   -0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2387   -1.5326    1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.2459    0.4901   -0.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3368    1.5987    0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6532   -1.8362    1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1882    1.3602   -0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853   -1.2978   -1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
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 25 70  1  0
 25 71  1  0
 26 72  1  0
 27 73  1  0
 30 74  1  0
 30 75  1  0
 30 76  1  0
 31 77  1  0
 31 78  1  0
 32 79  1  0
 32 80  1  0
 33 81  1  0
 33 82  1  0
 35 83  1  0
 35 84  1  0
 35 85  1  0
 36 86  1  0
 36 87  1  0
 36 88  1  0
 38 89  1  0
 38 90  1  0
 38 91  1  0
 39 92  1  0
 39 93  1  0
 39 94  1  0
 40 95  1  0
 40 96  1  0
 41 97  1  0
 41 98  1  0
 42 99  1  0
 42100  1  0
M  END

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0      30.675  13.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      48.013   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      36.009  13.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      42.678   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.341   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      49.346  16.170   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.684  10.420   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.663  10.420   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      53.003  11.910   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      51.024  11.910   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.342  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      45.345  10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.340   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      53.347  15.400   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.008  10.780   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      46.679  11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      34.676  10.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      44.011  11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.674   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      52.014  16.170   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      29.341  10.780   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      49.346  11.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      29.341   9.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      49.346  13.090   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      25.340   8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      53.347  13.860   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      37.343  10.780   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      41.344  11.550   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.675  11.550   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      48.013  10.780   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      36.009  11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      42.678  10.780   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      28.007   6.930   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      50.680  15.400   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      28.007   8.470   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      50.680  13.860   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      38.677  11.550   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      40.010  10.780   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      26.674   9.240   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      52.014  13.090   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      38.677  13.090   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      40.010   9.240   0.000  0.00  0.00           O+0
CONECT    1   29                                                            
CONECT    2   30                                                            
CONECT    3   31                                                            
CONECT    4   32                                                            
CONECT    5   33                                                            
CONECT    6   34                                                            
CONECT    7   39                                                            
CONECT    8   39                                                            
CONECT    9   40                                                            
CONECT   10   40                                                            
CONECT   11   15   17                                                       
CONECT   12   16   18                                                       
CONECT   13   19   25                                                       
CONECT   14   20   26                                                       
CONECT   15   11   29                                                       
CONECT   16   12   30                                                       
CONECT   17   11   31                                                       
CONECT   18   12   32                                                       
CONECT   19   13   33                                                       
CONECT   20   14   34                                                       
CONECT   21   23   29                                                       
CONECT   22   24   30                                                       
CONECT   23   21   35                                                       
CONECT   24   22   36                                                       
CONECT   25   13   39                                                       
CONECT   26   14   40                                                       
CONECT   27   31   37                                                       
CONECT   28   32   38                                                       
CONECT   29    1   15   21                                                  
CONECT   30    2   16   22                                                  
CONECT   31    3   17   27                                                  
CONECT   32    4   18   28                                                  
CONECT   33    5   19   35                                                  
CONECT   34    6   20   36                                                  
CONECT   35   23   33   39                                                  
CONECT   36   24   34   40                                                  
CONECT   37   27   38   41                                                  
CONECT   38   28   37   42                                                  
CONECT   39    7    8   25   35                                             
CONECT   40    9   10   26   36                                             
CONECT   41   37                                                            
CONECT   42   38                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

COMPND    HMDB0060340
HETATM    1  C1  UNL     1      11.970  -2.285   0.577  1.00  0.00           C  
HETATM    2  C2  UNL     1      12.356  -0.913   0.133  1.00  0.00           C  
HETATM    3  C3  UNL     1      11.372  -0.017  -0.027  1.00  0.00           C  
HETATM    4  C4  UNL     1      10.021  -0.478   0.245  1.00  0.00           C  
HETATM    5  C5  UNL     1       8.916   0.202   0.182  1.00  0.00           C  
HETATM    6  C6  UNL     1       7.626  -0.476   0.497  1.00  0.00           C  
HETATM    7  C7  UNL     1       7.594  -1.908   0.810  1.00  0.00           C  
HETATM    8  C8  UNL     1       6.509   0.194   0.481  1.00  0.00           C  
HETATM    9  C9  UNL     1       5.157  -0.248   0.740  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.143   0.574   0.724  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.792   0.014   0.995  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.651  -1.443   1.182  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.758   0.805   1.028  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.318   0.369   1.299  1.00  0.00           C  
HETATM   15  O1  UNL     1      -0.241   1.291   2.197  1.00  0.00           O  
HETATM   16  C15 UNL     1      -0.326   0.437  -0.042  1.00  0.00           C  
HETATM   17  O2  UNL     1       0.258  -0.590  -0.836  1.00  0.00           O  
HETATM   18  C16 UNL     1      -1.726   0.610  -0.220  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.725  -0.058   0.272  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.617  -1.198   1.172  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.096   0.321  -0.134  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.205  -0.300   0.306  1.00  0.00           C  
HETATM   23  C21 UNL     1      -6.440   0.165  -0.179  1.00  0.00           C  
HETATM   24  C22 UNL     1      -7.641  -0.099  -0.098  1.00  0.00           C  
HETATM   25  C23 UNL     1      -7.239  -1.533   1.042  1.00  0.00           C  
HETATM   26  C24 UNL     1      -8.984  -0.395  -0.006  1.00  0.00           C  
HETATM   27  C25 UNL     1      -9.829   0.585  -0.434  1.00  0.00           C  
HETATM   28  C26 UNL     1     -11.246   0.490  -0.451  1.00  0.00           C  
HETATM   29  C27 UNL     1     -11.898   1.650  -0.804  1.00  0.00           C  
HETATM   30  C28 UNL     1     -11.087   2.843  -1.133  1.00  0.00           C  
HETATM   31  C29 UNL     1     -13.374   1.728  -0.757  1.00  0.00           C  
HETATM   32  C30 UNL     1     -14.025   0.599  -1.493  1.00  0.00           C  
HETATM   33  C31 UNL     1     -13.279  -0.661  -1.367  1.00  0.00           C  
HETATM   34  C32 UNL     1     -12.153  -0.647  -0.304  1.00  0.00           C  
HETATM   35  C33 UNL     1     -12.743  -0.803   1.076  1.00  0.00           C  
HETATM   36  C34 UNL     1     -11.436  -1.960  -0.646  1.00  0.00           C  
HETATM   37  C35 UNL     1      11.693   1.312  -0.504  1.00  0.00           C  
HETATM   38  C36 UNL     1      11.445   1.367  -2.037  1.00  0.00           C  
HETATM   39  C37 UNL     1      10.919   2.463   0.059  1.00  0.00           C  
HETATM   40  C38 UNL     1      13.159   1.686  -0.260  1.00  0.00           C  
HETATM   41  C39 UNL     1      14.135   0.640  -0.641  1.00  0.00           C  
HETATM   42  C40 UNL     1      13.782  -0.703  -0.105  1.00  0.00           C  
HETATM   43  H1  UNL     1      12.848  -2.938   0.761  1.00  0.00           H  
HETATM   44  H2  UNL     1      11.327  -2.814  -0.152  1.00  0.00           H  
HETATM   45  H3  UNL     1      11.481  -2.165   1.588  1.00  0.00           H  
HETATM   46  H4  UNL     1       9.888  -1.561   0.534  1.00  0.00           H  
HETATM   47  H5  UNL     1       8.914   1.213  -0.120  1.00  0.00           H  
HETATM   48  H6  UNL     1       8.027  -2.534  -0.018  1.00  0.00           H  
HETATM   49  H7  UNL     1       6.657  -2.308   1.181  1.00  0.00           H  
HETATM   50  H8  UNL     1       8.338  -2.120   1.655  1.00  0.00           H  
HETATM   51  H9  UNL     1       6.608   1.268   0.221  1.00  0.00           H  
HETATM   52  H10 UNL     1       5.009  -1.323   0.959  1.00  0.00           H  
HETATM   53  H11 UNL     1       4.337   1.599   0.525  1.00  0.00           H  
HETATM   54  H12 UNL     1       1.653  -1.836   1.262  1.00  0.00           H  
HETATM   55  H13 UNL     1       3.250  -1.967   0.350  1.00  0.00           H  
HETATM   56  H14 UNL     1       3.231  -1.740   2.106  1.00  0.00           H  
HETATM   57  H15 UNL     1       1.923   1.873   0.852  1.00  0.00           H  
HETATM   58  H16 UNL     1       0.409  -0.585   1.804  1.00  0.00           H  
HETATM   59  H17 UNL     1      -0.575   0.803   2.951  1.00  0.00           H  
HETATM   60  H18 UNL     1       0.188   1.360  -0.587  1.00  0.00           H  
HETATM   61  H19 UNL     1      -0.385  -1.298  -1.006  1.00  0.00           H  
HETATM   62  H20 UNL     1      -2.038   1.457  -0.890  1.00  0.00           H  
HETATM   63  H21 UNL     1      -2.754  -2.194   0.695  1.00  0.00           H  
HETATM   64  H22 UNL     1      -3.340  -1.123   2.042  1.00  0.00           H  
HETATM   65  H23 UNL     1      -1.632  -1.233   1.645  1.00  0.00           H  
HETATM   66  H24 UNL     1      -4.228   1.122  -0.827  1.00  0.00           H  
HETATM   67  H25 UNL     1      -5.062  -1.100   0.989  1.00  0.00           H  
HETATM   68  H26 UNL     1      -6.355   1.117  -0.914  1.00  0.00           H  
HETATM   69  H27 UNL     1      -6.773  -0.914   1.760  1.00  0.00           H  
HETATM   70  H28 UNL     1      -8.262  -1.699   1.276  1.00  0.00           H  
HETATM   71  H29 UNL     1      -6.708  -2.053   0.310  1.00  0.00           H  
HETATM   72  H30 UNL     1      -9.424  -1.267   0.367  1.00  0.00           H  
HETATM   73  H31 UNL     1      -9.318   1.498  -0.801  1.00  0.00           H  
HETATM   74  H32 UNL     1     -10.544   2.721  -2.070  1.00  0.00           H  
HETATM   75  H33 UNL     1     -10.351   3.104  -0.319  1.00  0.00           H  
HETATM   76  H34 UNL     1     -11.793   3.728  -1.180  1.00  0.00           H  
HETATM   77  H35 UNL     1     -13.748   1.833   0.289  1.00  0.00           H  
HETATM   78  H36 UNL     1     -13.669   2.681  -1.286  1.00  0.00           H  
HETATM   79  H37 UNL     1     -15.038   0.481  -1.055  1.00  0.00           H  
HETATM   80  H38 UNL     1     -14.218   0.912  -2.567  1.00  0.00           H  
HETATM   81  H39 UNL     1     -12.715  -0.799  -2.337  1.00  0.00           H  
HETATM   82  H40 UNL     1     -13.848  -1.583  -1.196  1.00  0.00           H  
HETATM   83  H41 UNL     1     -12.338  -0.003   1.724  1.00  0.00           H  
HETATM   84  H42 UNL     1     -12.388  -1.756   1.512  1.00  0.00           H  
HETATM   85  H43 UNL     1     -13.854  -0.827   1.048  1.00  0.00           H  
HETATM   86  H44 UNL     1     -10.616  -1.826  -1.352  1.00  0.00           H  
HETATM   87  H45 UNL     1     -12.178  -2.660  -1.169  1.00  0.00           H  
HETATM   88  H46 UNL     1     -11.191  -2.518   0.266  1.00  0.00           H  
HETATM   89  H47 UNL     1      11.188   0.325  -2.408  1.00  0.00           H  
HETATM   90  H48 UNL     1      10.618   2.048  -2.299  1.00  0.00           H  
HETATM   91  H49 UNL     1      12.382   1.669  -2.524  1.00  0.00           H  
HETATM   92  H50 UNL     1      10.514   2.284   1.052  1.00  0.00           H  
HETATM   93  H51 UNL     1      10.160   2.846  -0.644  1.00  0.00           H  
HETATM   94  H52 UNL     1      11.630   3.370   0.177  1.00  0.00           H  
HETATM   95  H53 UNL     1      13.341   2.560  -0.949  1.00  0.00           H  
HETATM   96  H54 UNL     1      13.234   2.087   0.753  1.00  0.00           H  
HETATM   97  H55 UNL     1      15.125   0.927  -0.167  1.00  0.00           H  
HETATM   98  H56 UNL     1      14.340   0.627  -1.726  1.00  0.00           H  
HETATM   99  H57 UNL     1      14.156  -1.479  -0.828  1.00  0.00           H  
HETATM  100  H58 UNL     1      14.305  -0.923   0.875  1.00  0.00           H  
CONECT    1    2   43   44   45
CONECT    2    3    3   42
CONECT    3    4   37
CONECT    4    5    5   46
CONECT    5    6   47
CONECT    6    7    8    8
CONECT    7   48   49   50
CONECT    8    9   51
CONECT    9   10   10   52
CONECT   10   11   53
CONECT   11   12   13   13
CONECT   12   54   55   56
CONECT   13   14   57
CONECT   14   15   16   58
CONECT   15   59
CONECT   16   17   18   60
CONECT   17   61
CONECT   18   19   19   62
CONECT   19   20   21
CONECT   20   63   64   65
CONECT   21   22   22   66
CONECT   22   23   67
CONECT   23   24   24   68
CONECT   24   25   26
CONECT   25   69   70   71
CONECT   26   27   27   72
CONECT   27   28   73
CONECT   28   29   29   34
CONECT   29   30   31
CONECT   30   74   75   76
CONECT   31   32   77   78
CONECT   32   33   79   80
CONECT   33   34   81   82
CONECT   34   35   36
CONECT   35   83   84   85
CONECT   36   86   87   88
CONECT   37   38   39   40
CONECT   38   89   90   91
CONECT   39   92   93   94
CONECT   40   41   95   96
CONECT   41   42   97   98
CONECT   42   99  100
END

HMDB0060340
     RDKit          3D
15,15'-Dihydroxy-beta-carotene
100101  0  0  0  0  0  0  0  0999 V2000
   11.9704   -2.2852    0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3557   -0.9130    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3723   -0.0169   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0207   -0.4776    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9164    0.2022    0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6256   -0.4763    0.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5937   -1.9084    0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5087    0.1944    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1567   -0.2484    0.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434    0.5743    0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7924    0.0144    0.9950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6506   -1.4435    1.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7580    0.8051    1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    0.3686    1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2412    1.2906    2.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259    0.4372   -0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2582   -0.5899   -0.8360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7258    0.6098   -0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7250   -0.0579    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6167   -1.1982    1.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0960    0.3212   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2049   -0.3005    0.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4400    0.1654   -0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6405   -0.0989   -0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2387   -1.5326    1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9837   -0.3953   -0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8292    0.5852   -0.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2459    0.4901   -0.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8978    1.6505   -0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0866    2.8431   -1.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3740    1.7282   -0.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0252    0.5994   -1.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2790   -0.6614   -1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1526   -0.6475   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7425   -0.8026    1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4361   -1.9605   -0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6933    1.3118   -0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4454    1.3666   -2.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9193    2.4628    0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1592    1.6862   -0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1346    0.6396   -0.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7816   -0.7033   -0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8480   -2.9378    0.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3273   -2.8138   -0.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4809   -2.1652    1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8883   -1.5605    0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9138    1.2132   -0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0273   -2.5336   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6569   -2.3082    1.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3376   -2.1198    1.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6079    1.2682    0.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0093   -1.3231    0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3368    1.5987    0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6532   -1.8362    1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2499   -1.9669    0.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2310   -1.7396    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    1.8735    0.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4088   -0.5845    1.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5754    0.8029    2.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1882    1.3602   -0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853   -1.2978   -1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0379    1.4575   -0.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539   -2.1944    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3397   -1.1227    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6324   -1.2328    1.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2280    1.1225   -0.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0622   -1.0996    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3555    1.1168   -0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7731   -0.9140    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2618   -1.6990    1.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7075   -2.0525    0.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4245   -1.2674    0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3181    1.4977   -0.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5441    2.7206   -2.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3514    3.1040   -0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7931    3.7285   -1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7480    1.8334    0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6688    2.6808   -1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0381    0.4813   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2178    0.9118   -2.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7154   -0.7990   -2.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8483   -1.5833   -1.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3385   -0.0027    1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3879   -1.7559    1.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8545   -0.8269    1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6162   -1.8258   -1.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1784   -2.6599   -1.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1906   -2.5182    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1878    0.3251   -2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6180    2.0482   -2.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3820    1.6690   -2.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5141    2.2839    1.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1602    2.8458   -0.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6299    3.3703    0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3406    2.5599   -0.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2336    2.0871    0.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1252    0.9267   -0.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3398    0.6268   -1.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1557   -1.4790   -0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3048   -0.9227    0.8753 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
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
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 18 19  2  0
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 22 23  1  0
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  3 37  1  0
 37 38  1  0
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 42100  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
15,15'-Dihydro-15,15'-dihydroxy-beta,beta-carotene	ChEBI
Retinal-pinacol	ChEBI
15,15'-Dihydro-15,15'-dihydroxy-b,b-carotene	Generator
15,15'-Dihydro-15,15'-dihydroxy-β,β-carotene	Generator
15,15'-Dihydroxy-b-carotene	Generator
15,15'-Dihydroxy-β-carotene	Generator

Chemical Formula

C₄₀H₅₈O₂

Average Molecular Weight

570.8873

Monoisotopic Molecular Weight

570.4436811

IUPAC Name

(1E,3E,5E,7E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-1,18-bis(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,11,13,15,17-octaene-9,10-diol

Traditional Name

(1E,3E,5E,7E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-1,18-bis(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,11,13,15,17-octaene-9,10-diol

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)C(O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C40H58O2/c1-29(21-23-35-33(5)19-13-25-39(35,7)8)15-11-17-31(3)27-37(41)38(42)28-32(4)18-12-16-30(2)22-24-36-34(6)20-14-26-40(36,9)10/h11-12,15-18,21-24,27-28,37-38,41-42H,13-14,19-20,25-26H2,1-10H3/b17-11+,18-12+,23-21+,24-22+,29-15+,30-16+,31-27+,32-28+

InChI Key

LAMXZCLZRAUDED-WDJSDFAOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Retinoid skeleton
Fatty alcohol
Fatty acyl
Secondary alcohol
1,2-diol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

carotenol (CHEBI:67228 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060340)

Source

Exogenous

Exogenous (HMDB: HMDB0060340)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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	0.00057 g/L	ALOGPS
logP	8.1	ALOGPS
logP	9.34	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	13.46	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	193.22 m³·mol⁻¹	ChemAxon
Polarizability	73.82 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]+	248.619	31661259
DarkChem	[M-H]-	242.967	31661259
DeepCCS	[M+H]+	263.969	30932474
DeepCCS	[M-H]-	262.144	30932474
DeepCCS	[M-2H]-	295.386	30932474
DeepCCS	[M+Na]+	269.575	30932474
AllCCS	[M+H]+	257.7	32859911
AllCCS	[M+H-H2O]+	256.0	32859911
AllCCS	[M+NH4]+	259.2	32859911
AllCCS	[M+Na]+	259.7	32859911
AllCCS	[M-H]-	235.8	32859911
AllCCS	[M+Na-2H]-	240.0	32859911
AllCCS	[M+HCOO]-	244.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	5.92 minutes	32390414
Predicted by Siyang on May 30, 2022	40.8071 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.39 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	5567.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	1121.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	418.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	602.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	546.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1646.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1384.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	128.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	3522.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	1185.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2382.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1427.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	823.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	445.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	1021.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	11.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
15,15'-Dihydroxy-beta-carotene	C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)C(O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C	5416.6	Standard polar	33892256
15,15'-Dihydroxy-beta-carotene	C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)C(O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C	4512.4	Standard non polar	33892256
15,15'-Dihydroxy-beta-carotene	C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)C(O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C	4503.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
15,15'-Dihydroxy-beta-carotene,1TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(O)C(/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)CCCC2(C)C)O[Si](C)(C)C)C(C)(C)CCC1	4525.9	Semi standard non polar	33892256
15,15'-Dihydroxy-beta-carotene,2TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(O[Si](C)(C)C)C(/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)CCCC2(C)C)O[Si](C)(C)C)C(C)(C)CCC1	4512.2	Semi standard non polar	33892256
15,15'-Dihydroxy-beta-carotene,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(O)C(/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)CCCC2(C)C)O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1	4735.3	Semi standard non polar	33892256
15,15'-Dihydroxy-beta-carotene,2TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(O[Si](C)(C)C(C)(C)C)C(/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)CCCC2(C)C)O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1	4959.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 15,15'-Dihydroxy-beta-carotene GC-MS (Non-derivatized) - 70eV, Positive	splash10-053i-0090040000-a1d23d6ce14e070e4a46	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15,15'-Dihydroxy-beta-carotene GC-MS (1 TMS) - 70eV, Positive	splash10-056r-4035009000-b3b1d3f80fc236d9f252	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15,15'-Dihydroxy-beta-carotene GC-MS ("15,15'-Dihydroxy-beta-carotene,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15,15'-Dihydroxy-beta-carotene GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15,15'-Dihydroxy-beta-carotene GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15,15'-Dihydroxy-beta-carotene GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-15	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 - 15,15'-Dihydroxy-beta-carotene 10V, Positive-QTOF	splash10-00di-0442390000-76834980e77992eb05bc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15,15'-Dihydroxy-beta-carotene 20V, Positive-QTOF	splash10-001r-0975520000-02f573d03b01b694b72e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15,15'-Dihydroxy-beta-carotene 40V, Positive-QTOF	splash10-0019-1973520000-61617d3d49f54dac793d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15,15'-Dihydroxy-beta-carotene 10V, Negative-QTOF	splash10-014i-0011090000-501e1b74c7642f994cee	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15,15'-Dihydroxy-beta-carotene 20V, Negative-QTOF	splash10-0aor-0092030000-2ac1302ce27833de27fd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15,15'-Dihydroxy-beta-carotene 40V, Negative-QTOF	splash10-0a4r-0190010000-81b56555c2fbde269f38	2017-10-06	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

FDB030264

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C20332

BioCyc ID

CPD-14387

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70678891

PDB ID

Not Available

ChEBI ID

67228

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
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 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Beta,beta-carotene 15,15'-monooxygenase

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Symmetrically cleaves beta-carotene into two molecules of retinal. The reaction proceeds in three stages, epoxidation of the 15,15'-double bond, hydration of the double bond leading to ring opening, and oxidative cleavage of the diol formed.
Gene Name:: BCMO1
Uniprot ID:: Q9HAY6
Molecular weight:: 62636.69

Reactions

beta-Carotene-15,15'-epoxide + Water → 15,15'-Dihydroxy-beta-carotene	details
15,15'-Dihydroxy-beta-carotene + Acceptor → Retinal + Reduced acceptor	details

Showing metabocard for 15,15'-Dihydroxy-beta-carotene (HMDB0060340)

MOL for HMDB0060340 (15,15'-Dihydroxy-beta-carotene)

3D MOL for HMDB0060340 (15,15'-Dihydroxy-beta-carotene)

3D SDF for HMDB0060340 (15,15'-Dihydroxy-beta-carotene)

3D-SDF for HMDB0060340 (15,15'-Dihydroxy-beta-carotene)

PDB for HMDB0060340 (15,15'-Dihydroxy-beta-carotene)

3D PDB for HMDB0060340 (15,15'-Dihydroxy-beta-carotene)

SMILES for HMDB0060340 (15,15'-Dihydroxy-beta-carotene)

INCHI for HMDB0060340 (15,15'-Dihydroxy-beta-carotene)

Structure for HMDB0060340 (15,15'-Dihydroxy-beta-carotene)

3D Structure for HMDB0060340 (15,15'-Dihydroxy-beta-carotene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions