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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 05:48:35 UTC

Update Date

2021-09-23 05:48:35 UTC

HMDB ID

HMDB0302026

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Apo-13-zeaxanthinone

Description

Apo-13-zeaxanthinone is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Apo-13-zeaxanthinone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Apo-13-zeaxanthinone can be found in a number of food items such as red bell pepper, italian sweet red pepper, pepper (c. annuum), and orange bell pepper, which makes apo-13-zeaxanthinone a potential biomarker for the consumption of these food products.

Structure

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

HMDB0302026
     RDKit          3D
Apo-13-zeaxanthinone
 46 46  0  0  0  0  0  0  0  0999 V2000
    6.3166   -2.6527    1.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2020   -3.5274    1.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5011   -4.6207    2.5505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8053   -3.2057    1.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4240   -2.0779    1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190   -1.7666    0.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6652   -0.6100    0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7584    0.2688   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -0.2934    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1024    0.8107   -0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5091    1.1898   -0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6588    2.3594   -1.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4606    3.2045   -1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9810    2.9104   -1.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0632    2.3331   -0.7073 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2899    2.6533   -1.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9507    0.8546   -0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6150    0.2945   -0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695    0.0061    1.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4645   -1.0775   -0.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2672   -3.2152    1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1731   -2.1609    0.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4779   -1.8223    2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0259   -3.8854    2.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2152   -1.4163    0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -2.4535    1.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3062    0.5284    0.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5380   -0.2963   -0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4833    1.1508   -0.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4767   -1.0461    0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6612    1.4939   -0.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1379    2.7329   -2.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1237    3.4563   -0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8448    4.1600   -2.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2971    2.6802   -2.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0437    4.0146   -1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0515    2.8009    0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0525    2.1934   -0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3167    0.3517   -1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6836    0.4947    0.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226    0.5143    1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5519    0.3991    1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318   -1.0801    1.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4639   -1.9120   -0.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5334   -1.0451   -1.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768   -1.1773   -1.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  1
 16 38  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END

  Mrv0541 02241212172D          

 20 20  0  0  0  0            999 V2000
   -4.5836    1.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2981    1.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2981    0.7620    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5836    0.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8691    0.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8691    1.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1547    1.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4402    1.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7257    1.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0113    1.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2968    1.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4177    1.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5836    2.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0125    0.3495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1547    0.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8691   -0.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7257    2.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1322    1.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8466    1.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1322    2.8246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  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
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  1 13  1  0  0  0  0
  3 14  1  6  0  0  0
  5 15  1  0  0  0  0
  5 16  1  0  0  0  0
  9 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302026

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1CC(C)=C(\C=C\C(\C)=C\C=C\C(C)=O)C(C)(C)C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H26O2/c1-13(7-6-8-15(3)19)9-10-17-14(2)11-16(20)12-18(17,4)5/h6-10,16,20H,11-12H2,1-5H3/b8-6+,10-9+,13-7+/t16-/m1/s1

> <INCHI_KEY>
JLNMEHQAHDSEEE-YSAUQHOWSA-N

> <FORMULA>
C18H26O2

> <MOLECULAR_WEIGHT>
274.3978

> <EXACT_MASS>
274.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.44732641845722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,5E,7E)-8-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-6-methylocta-3,5,7-trien-2-one

> <ALOGPS_LOGP>
4.79

> <JCHEM_LOGP>
3.186697761666667

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.72671706614393

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.907213404525137

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0896573487155785

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
88.4108

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E,5E,7E)-8-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-6-methylocta-3,5,7-trien-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302026
     RDKit          3D
Apo-13-zeaxanthinone
 46 46  0  0  0  0  0  0  0  0999 V2000
    6.3166   -2.6527    1.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2020   -3.5274    1.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5011   -4.6207    2.5505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8053   -3.2057    1.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4240   -2.0779    1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190   -1.7666    0.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6652   -0.6100    0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7584    0.2688   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -0.2934    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1024    0.8107   -0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5091    1.1898   -0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6588    2.3594   -1.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4606    3.2045   -1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9810    2.9104   -1.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0632    2.3331   -0.7073 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2899    2.6533   -1.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9507    0.8546   -0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6150    0.2945   -0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695    0.0061    1.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4645   -1.0775   -0.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2672   -3.2152    1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1731   -2.1609    0.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4779   -1.8223    2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0259   -3.8854    2.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2152   -1.4163    0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -2.4535    1.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3062    0.5284    0.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5380   -0.2963   -0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4833    1.1508   -0.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4767   -1.0461    0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6612    1.4939   -0.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1379    2.7329   -2.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1237    3.4563   -0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8448    4.1600   -2.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2971    2.6802   -2.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0437    4.0146   -1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0515    2.8009    0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0525    2.1934   -0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3167    0.3517   -1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6836    0.4947    0.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226    0.5143    1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5519    0.3991    1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318   -1.0801    1.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4639   -1.9120   -0.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5334   -1.0451   -1.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768   -1.1773   -1.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  1
 16 38  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -8.556   3.733   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.890   2.963   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.890   1.422   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.556   0.652   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.222   1.422   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.222   2.963   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.889   3.733   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.555   2.963   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.221   3.733   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.888   2.963   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.554   3.733   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.780   2.963   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.556   5.273   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0     -11.223   0.652   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.889   0.652   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.222  -0.118   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.221   5.273   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.113   3.733   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.447   2.963   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.113   5.273   0.000  0.00  0.00           O+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15   16                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   18                                                       
CONECT   13    1                                                            
CONECT   14    3                                                            
CONECT   15    5                                                            
CONECT   16    5                                                            
CONECT   17    9                                                            
CONECT   18   12   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0302026
HETATM    1  C1  UNL     1       6.317  -2.653   1.602  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.202  -3.527   1.988  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.501  -4.621   2.550  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.805  -3.206   1.762  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.424  -2.078   1.179  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.019  -1.767   0.957  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.665  -0.610   0.360  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.758   0.269  -0.031  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.267  -0.293   0.138  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.102   0.811  -0.431  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.509   1.190  -0.686  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.659   2.359  -1.272  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.461   3.204  -1.635  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.981   2.910  -1.597  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.063   2.333  -0.707  1.00  0.00           C  
HETATM   16  O2  UNL     1      -5.290   2.653  -1.290  1.00  0.00           O  
HETATM   17  C15 UNL     1      -3.951   0.855  -0.632  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.615   0.294  -0.303  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.570   0.006   1.198  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.465  -1.077  -0.997  1.00  0.00           C  
HETATM   21  H1  UNL     1       7.267  -3.215   1.530  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.173  -2.161   0.621  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.478  -1.822   2.337  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.026  -3.885   2.066  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.215  -1.416   0.887  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.243  -2.453   1.266  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.306   0.528   0.931  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.538  -0.296  -0.647  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.483   1.151  -0.588  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.477  -1.046   0.484  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.661   1.494  -0.736  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.138   2.733  -2.434  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.124   3.456  -0.727  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.845   4.160  -2.026  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.297   2.680  -2.652  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.044   4.015  -1.499  1.00  0.00           H  
HETATM   37  H17 UNL     1      -4.052   2.801   0.297  1.00  0.00           H  
HETATM   38  H18 UNL     1      -6.052   2.193  -0.857  1.00  0.00           H  
HETATM   39  H19 UNL     1      -4.317   0.352  -1.572  1.00  0.00           H  
HETATM   40  H20 UNL     1      -4.684   0.495   0.148  1.00  0.00           H  
HETATM   41  H21 UNL     1      -1.723   0.514   1.678  1.00  0.00           H  
HETATM   42  H22 UNL     1      -3.552   0.399   1.615  1.00  0.00           H  
HETATM   43  H23 UNL     1      -2.632  -1.080   1.386  1.00  0.00           H  
HETATM   44  H24 UNL     1      -2.464  -1.912  -0.313  1.00  0.00           H  
HETATM   45  H25 UNL     1      -1.533  -1.045  -1.578  1.00  0.00           H  
HETATM   46  H26 UNL     1      -3.277  -1.177  -1.770  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3    4
CONECT    4    5    5   24
CONECT    5    6   25
CONECT    6    7    7   26
CONECT    7    8    9
CONECT    8   27   28   29
CONECT    9   10   10   30
CONECT   10   11   31
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   32   33   34
CONECT   14   15   35   36
CONECT   15   16   17   37
CONECT   16   38
CONECT   17   18   39   40
CONECT   18   19   20
CONECT   19   41   42   43
CONECT   20   44   45   46
END

HMDB0302026
     RDKit          3D
Apo-13-zeaxanthinone
 46 46  0  0  0  0  0  0  0  0999 V2000
    6.3166   -2.6527    1.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2020   -3.5274    1.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5011   -4.6207    2.5505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8053   -3.2057    1.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4240   -2.0779    1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190   -1.7666    0.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6652   -0.6100    0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7584    0.2688   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -0.2934    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1024    0.8107   -0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5091    1.1898   -0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6588    2.3594   -1.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4606    3.2045   -1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9810    2.9104   -1.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0632    2.3331   -0.7073 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2899    2.6533   -1.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9507    0.8546   -0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6150    0.2945   -0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695    0.0061    1.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4645   -1.0775   -0.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2672   -3.2152    1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1731   -2.1609    0.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4779   -1.8223    2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0259   -3.8854    2.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2152   -1.4163    0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -2.4535    1.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3062    0.5284    0.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5380   -0.2963   -0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4833    1.1508   -0.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4767   -1.0461    0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6612    1.4939   -0.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1379    2.7329   -2.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1237    3.4563   -0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8448    4.1600   -2.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2971    2.6802   -2.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0437    4.0146   -1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0515    2.8009    0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0525    2.1934   -0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3167    0.3517   -1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6836    0.4947    0.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226    0.5143    1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5519    0.3991    1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318   -1.0801    1.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4639   -1.9120   -0.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5334   -1.0451   -1.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768   -1.1773   -1.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  1
 16 38  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₂₆O₂

Average Molecular Weight

274.3978

Monoisotopic Molecular Weight

274.193280076

IUPAC Name

(3E,5E,7E)-8-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-6-methylocta-3,5,7-trien-2-one

Traditional Name

(3E,5E,7E)-8-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-6-methylocta-3,5,7-trien-2-one

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC(C)=C(\C=C\C(\C)=C\C=C\C(C)=O)C(C)(C)C1

InChI Identifier

InChI=1S/C18H26O2/c1-13(7-6-8-15(3)19)9-10-17-14(2)11-16(20)12-18(17,4)5/h6-10,16,20H,11-12H2,1-5H3/b8-6+,10-9+,13-7+/t16-/m1/s1

InChI Key

JLNMEHQAHDSEEE-YSAUQHOWSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Cyclofarsesane sesquiterpenoid
Sesquiterpenoid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302026)

Food

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Orange bell pepper (FooDB: FOOD00879)

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
logP	4.79	ALOGPS
logP	3.19	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	18.91	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.41 m³·mol⁻¹	ChemAxon
Polarizability	33.45 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	170.226	32859911
AllCCS	[M+H-H2O]+	166.848	32859911
AllCCS	[M+Na]+	174.262	32859911
AllCCS	[M+NH4]+	173.361	32859911
AllCCS	[M-H]-	174.069	32859911
AllCCS	[M+Na-2H]-	174.761	32859911
AllCCS	[M+HCOO]-	175.656	32859911
DeepCCS	[M+H]+	179.202	30932474
DeepCCS	[M-H]-	176.844	30932474
DeepCCS	[M-2H]-	210.963	30932474
DeepCCS	[M+Na]+	186.227	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Apo-13-zeaxanthinone,2TMS,isomer #1	C=C(/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C)CC1(C)C)O[Si](C)(C)C	2480.2	Semi standard non polar	33892256
Apo-13-zeaxanthinone,2TMS,isomer #1	C=C(/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C)CC1(C)C)O[Si](C)(C)C	2492.4	Standard non polar	33892256
Apo-13-zeaxanthinone,2TMS,isomer #1	C=C(/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C)CC1(C)C)O[Si](C)(C)C	2487.6	Standard polar	33892256
Apo-13-zeaxanthinone,2TBDMS,isomer #1	C=C(/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)O[Si](C)(C)C(C)(C)C	2926.9	Semi standard non polar	33892256
Apo-13-zeaxanthinone,2TBDMS,isomer #1	C=C(/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)O[Si](C)(C)C(C)(C)C	2980.0	Standard non polar	33892256
Apo-13-zeaxanthinone,2TBDMS,isomer #1	C=C(/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)O[Si](C)(C)C(C)(C)C	2697.3	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apo-13-zeaxanthinone 10V, Positive-QTOF	splash10-0a6r-0190000000-506e3f41ebe174898f1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apo-13-zeaxanthinone 20V, Positive-QTOF	splash10-0pbi-1970000000-dc581aff4ec8aa2a5179	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apo-13-zeaxanthinone 40V, Positive-QTOF	splash10-0pb9-7910000000-d6c222e5e578cfb3f091	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apo-13-zeaxanthinone 10V, Negative-QTOF	splash10-00di-0090000000-ec132398821939c56a98	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apo-13-zeaxanthinone 20V, Negative-QTOF	splash10-05fr-0090000000-be9a95d20347013d13b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apo-13-zeaxanthinone 40V, Negative-QTOF	splash10-0a4l-2490000000-79643309565d460a7108	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apo-13-zeaxanthinone 10V, Positive-QTOF	splash10-05rc-3490000000-e5b9c98ba79c8b23c5a2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apo-13-zeaxanthinone 20V, Positive-QTOF	splash10-0079-3950000000-15109db717daaaea30a3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apo-13-zeaxanthinone 40V, Positive-QTOF	splash10-0007-9700000000-b2df25f02f070b79d8a1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apo-13-zeaxanthinone 10V, Negative-QTOF	splash10-00di-0090000000-7ffc806ec17f932c3ea6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apo-13-zeaxanthinone 20V, Negative-QTOF	splash10-05fr-1590000000-dfaba96bb9a2bbf383c7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apo-13-zeaxanthinone 40V, Negative-QTOF	splash10-0gb9-5950000000-1e81cda2abc74f1eb33c	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB001762

KNApSAcK ID

Not Available

Chemspider ID

59696245

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44482347

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for Apo-13-zeaxanthinone (HMDB0302026)

MOL for HMDB0302026 (Apo-13-zeaxanthinone)

3D MOL for HMDB0302026 (Apo-13-zeaxanthinone)

3D SDF for HMDB0302026 (Apo-13-zeaxanthinone)

3D-SDF for HMDB0302026 (Apo-13-zeaxanthinone)

PDB for HMDB0302026 (Apo-13-zeaxanthinone)

3D PDB for HMDB0302026 (Apo-13-zeaxanthinone)

SMILES for HMDB0302026 (Apo-13-zeaxanthinone)

INCHI for HMDB0302026 (Apo-13-zeaxanthinone)

Structure for HMDB0302026 (Apo-13-zeaxanthinone)

3D Structure for HMDB0302026 (Apo-13-zeaxanthinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra