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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 15:12:26 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0003020

Secondary Accession Numbers

HMDB0036920
HMDB03020
HMDB36920

Metabolite Identification

Common Name

Neoxanthin

Description

Neoxanthin 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. Xanthophylls arise by oxygenation of the carotene backbone. Neoxanthin is an intermediate in the synthesis of abscisic acid from violaxanthin. Neoxanthin has been detected, but not quantified in, several different foods, such as apples, paprikas, Valencia oranges, kiwis, globe artichokes, sparkleberries, hard wheat, and cinnamon. This could make neoxanthin a potential biomarker for the consumption of these foods. Neoxanthin has been shown to exhibit apoptotic and anti-proliferative functions (PMID: 15333710 , 15333710 ).

Structure

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


  Mrv1652304232000272D          

 45 47  0  0  1  0            999 V2000
   -5.9112    1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1968    0.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1968   -0.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4823   -0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9113   -0.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9111    1.8971    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1967    1.4845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1966    3.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6255    3.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9109    3.5470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9109    4.3721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4506    2.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6256    2.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0382    1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1966    2.3095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3997    2.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9326    1.1814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5199   -0.5790    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  6  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
  6 15  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
 15  8  1  0  0  0  0
 15  7  1  0  0  0  0
 13  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 13 12  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  6  0  0  0
  4 17  1  0  0  0  0
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  3  4  2  0  0  0  0
 33 34  2  0  0  0  0
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 39 44  1  6  0  0  0
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 41 40  1  0  0  0  0
 41 42  1  0  0  0  0
 32 33  2  0  0  0  0
 32 45  1  1  0  0  0
M  END

HMDB0003020
     RDKit          3D
Neoxanthin
100102  0  0  0  0  0  0  0  0999 V2000
   -7.8486    2.2803   -4.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2860    1.8429   -3.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
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 43 97  1  0
 44 98  1  0
 44 99  1  0
 44100  1  0
M  END


  Mrv1652304232000272D          

 45 47  0  0  1  0            999 V2000
   -5.9112    1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1968    0.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1968   -0.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4823   -0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9113   -0.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9111    1.8971    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1967    1.4845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1966    3.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6255    3.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9109    3.5470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9109    4.3721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4506    2.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6256    2.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0382    1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1966    2.3095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3997    2.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7677   -0.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0535   -0.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3390   -0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6245   -0.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3389    0.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9101   -0.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1957   -0.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5188   -0.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2332   -0.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9477   -0.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2331   -1.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6621   -0.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3767   -0.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0910   -0.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0909   -1.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8055   -0.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8056    0.6584    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8056    1.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0913    2.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5203    2.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8059    3.1334    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8060    3.9583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5202    1.8959    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6787    1.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0913    1.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2664    1.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9326    1.1814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3452    1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5199   -0.5790    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  6  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
  6 15  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
 15  8  1  0  0  0  0
 15  7  1  0  0  0  0
 13  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 13 12  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  6  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 32 30  1  6  0  0  0
 30 31  1  0  0  0  0
  3  4  2  0  0  0  0
 33 34  2  0  0  0  0
 34 41  1  0  0  0  0
 34 39  1  0  0  0  0
 41 35  1  0  0  0  0
 35 37  1  0  0  0  0
 39 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 39 44  1  6  0  0  0
 39 43  1  1  0  0  0
 41 40  1  0  0  0  0
 41 42  1  0  0  0  0
 32 33  2  0  0  0  0
 32 45  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0003020

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C(=[C@@]=C1C(C)(C)C[C@H](O)C[C@@]1(C)O)C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-22-35-36(5,6)25-33(41)27-38(35,9)43)15-11-12-16-30(2)18-14-20-32(4)23-24-40-37(7,8)26-34(42)28-39(40,10)44-40/h11-21,23-24,33-34,41-43H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,24-23+,29-15+,30-16+,31-19+,32-20-/t22-,33-,34-,38+,39+,40-/m0/s1

> <INCHI_KEY>
PGYAYSRVSAJXTE-OQASCVKESA-N

> <FORMULA>
C40H56O4

> <MOLECULAR_WEIGHT>
600.8702

> <EXACT_MASS>
600.41786028

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
72.71092519202969

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S)-6-[(1M,3E,5E,7E,9E,11E,13E,15Z,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,3-diol

> <ALOGPS_LOGP>
7.85

> <JCHEM_LOGP>
6.691937891

> <ALOGPS_LOGS>
-5.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.930480509146975

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.005124919564018

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7377022034819802

> <JCHEM_POLAR_SURFACE_AREA>
73.22

> <JCHEM_REFRACTIVITY>
194.0311000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.77e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9'-cis-neoxanthin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003020
     RDKit          3D
Neoxanthin
100102  0  0  0  0  0  0  0  0999 V2000
   -7.8486    2.2803   -4.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2860    1.8429   -3.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9906    1.7434   -2.9861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2416    1.3441   -1.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9335    1.2552   -1.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1441    0.8606   -0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8444    0.4889    0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356    0.8187   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9993    0.4107    0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3251    0.4513    0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3236    0.1128    1.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294    0.2159    0.9683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9002    0.6952   -0.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6791   -0.1593    1.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9506   -0.0260    1.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0415   -0.3913    2.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3072   -0.1820    2.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4817    0.4339    0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4761   -0.4703    2.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4574   -1.0106    2.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4177   -1.5469    1.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2795   -0.6481    0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3650    0.6845    1.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7184   -0.3714   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6907   -1.1946    0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8435   -2.6213    1.0028 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9004   -3.1614    0.2271 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6401   -3.4888    0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4414   -3.0138    1.5467 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2109   -3.6937    1.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6914   -3.3313    2.8854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1472    1.5338   -1.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4671    1.6067   -1.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2961    1.2701   -0.7726 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.7055    2.0849    0.3537 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1420    2.0376   -0.0431 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.6150    3.4419   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9168    1.3701    1.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6026    0.1509    0.5451 C   0  0  1  0  0  0  0  0  0  0  0  0
  -13.7047    0.4827   -0.2425 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6569   -0.7571   -0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3057   -0.1984   -0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7514   -0.9907   -1.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3966   -0.5080    0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1338    3.0579   -4.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7994    2.8183   -4.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9453    1.4218   -5.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3978    2.0007   -3.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7576    1.1120   -0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4145    1.4879   -2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7675   -0.1204    0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2577   -0.1514    1.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1142    1.4105    1.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3777    1.0263   -1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3648    0.0588    1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6458    0.7881   -0.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0773   -0.2231    2.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3713    0.0429   -1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9638    0.7355   -0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4293    1.7041   -0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4127   -0.5628    2.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025    0.3826    0.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9221   -0.8254    3.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8454    1.3648    0.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2348   -0.3011   -0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5119    0.8143    0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7377   -0.3423    3.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8648    0.5883    2.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8043    1.4345    0.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4165    0.9847    1.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4231    0.6951   -0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5161   -0.5804   -1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8233   -0.9899   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3757   -0.5875    1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9788   -1.0739   -0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1243   -2.6884    2.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8348   -2.7591   -0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4532   -3.5077   -0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8947   -4.5088    1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4656   -2.8671    0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3681   -4.3557    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7341   -4.2809    1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6094   -3.6041    3.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7134    1.2233   -1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9464    1.9298   -2.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7106    3.4877   -0.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1278    4.2259    0.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5989    3.6849   -1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3143    1.1069    1.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7373    2.0299    1.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0379   -0.3871    1.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5256    1.2116   -0.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1331   -1.1576   -1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4995   -1.6905    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7396   -0.2964   -2.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4317   -1.7988   -1.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7098   -1.3136   -1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9538   -0.9879    1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5596   -1.1833    0.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9112    0.4636    1.0499 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  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  1
  2 32  1  0
 32 33  2  0
 34 33  1  6
 34 35  1  0
 35 36  1  0
 36 37  1  6
 36 38  1  0
 38 39  1  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 42 43  1  0
 42 44  1  0
 29 21  1  0
 36 34  1  0
 42 34  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  3 48  1  0
  4 49  1  0
  5 50  1  0
  7 51  1  0
  7 52  1  0
  7 53  1  0
  8 54  1  0
  9 55  1  0
 10 56  1  0
 11 57  1  0
 13 58  1  0
 13 59  1  0
 13 60  1  0
 14 61  1  0
 15 62  1  0
 16 63  1  0
 18 64  1  0
 18 65  1  0
 18 66  1  0
 19 67  1  0
 23 68  1  0
 23 69  1  0
 23 70  1  0
 24 71  1  0
 24 72  1  0
 24 73  1  0
 25 74  1  0
 25 75  1  0
 26 76  1  1
 27 77  1  0
 28 78  1  0
 28 79  1  0
 30 80  1  0
 30 81  1  0
 30 82  1  0
 31 83  1  0
 32 84  1  0
 33 85  1  0
 37 86  1  0
 37 87  1  0
 37 88  1  0
 38 89  1  0
 38 90  1  0
 39 91  1  1
 40 92  1  0
 41 93  1  0
 41 94  1  0
 43 95  1  0
 43 96  1  0
 43 97  1  0
 44 98  1  0
 44 99  1  0
 44100  1  0
M  END

HEADER    PROTEIN                                 23-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-20         0                                  
HETATM    1  C   UNK     0     -11.034   2.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.701   1.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.701  -0.309   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.367  -1.079   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -11.034  -1.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -11.034   3.541   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -9.701   2.771   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -9.700   5.851   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.368   5.851   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -11.034   6.621   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -11.034   8.161   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -13.908   4.311   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -12.368   4.311   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -13.138   2.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.700   4.311   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.213   3.913   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.033  -0.309   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.700  -1.079   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.366  -0.309   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.032  -1.079   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.366   1.231   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.699  -0.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.365  -1.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.968  -0.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.302  -1.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.636  -0.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.302  -2.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.969  -1.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.303  -0.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.637  -1.081   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.636  -2.621   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.970  -0.311   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.970   1.229   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.970   2.769   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.637   5.079   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.305   5.079   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.971   5.849   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.971   7.389   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      10.304   3.539   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.867   2.206   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.637   3.539   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.097   3.539   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      11.074   2.205   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      11.844   3.539   0.000  0.00  0.00           C+0
HETATM   45  H   UNK     0      10.304  -1.081   0.000  0.00  0.00           H+0
CONECT    1    6    2                                                       
CONECT    2    1    3                                                       
CONECT    3    2    5    4                                                  
CONECT    4   17    3                                                       
CONECT    5    3                                                            
CONECT    6    1   15    7   13                                             
CONECT    7    6   15                                                       
CONECT    8   15   10                                                       
CONECT    9   13   10                                                       
CONECT   10    8    9   11                                                  
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13    6    9   12   14                                             
CONECT   14   13                                                            
CONECT   15    6    8    7   16                                             
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   22                                                       
CONECT   21   19                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   28                                                       
CONECT   27   25                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   32   31                                                  
CONECT   31   30                                                            
CONECT   32   30   33   45                                                  
CONECT   33   34   32                                                       
CONECT   34   33   41   39                                                  
CONECT   35   41   37                                                       
CONECT   36   39   37                                                       
CONECT   37   35   36   38                                                  
CONECT   38   37                                                            
CONECT   39   34   36   44   43                                             
CONECT   40   41                                                            
CONECT   41   34   35   40   42                                             
CONECT   42   41                                                            
CONECT   43   39                                                            
CONECT   44   39                                                            
CONECT   45   32                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   94    0
END

COMPND    HMDB0003020
HETATM    1  C1  UNL     1      -7.849   2.280  -4.405  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.286   1.843  -3.075  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.991   1.743  -2.986  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.242   1.344  -1.811  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.933   1.255  -1.798  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.144   0.861  -0.630  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.844   0.489   0.616  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.836   0.819  -0.695  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.999   0.411   0.490  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.325   0.451   0.317  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.324   0.113   1.283  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.629   0.216   0.968  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.900   0.695  -0.415  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.679  -0.159   1.906  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.951  -0.026   1.611  1.00  0.00           C  
HETATM   16  C16 UNL     1       6.042  -0.391   2.512  1.00  0.00           C  
HETATM   17  C17 UNL     1       7.307  -0.182   2.124  1.00  0.00           C  
HETATM   18  C18 UNL     1       7.482   0.434   0.762  1.00  0.00           C  
HETATM   19  C19 UNL     1       8.476  -0.470   2.870  1.00  0.00           C  
HETATM   20  C20 UNL     1       9.457  -1.011   2.152  1.00  0.00           C  
HETATM   21  C21 UNL     1      10.418  -1.547   1.455  1.00  0.00           C  
HETATM   22  C22 UNL     1      11.280  -0.648   0.738  1.00  0.00           C  
HETATM   23  C23 UNL     1      11.365   0.685   1.468  1.00  0.00           C  
HETATM   24  C24 UNL     1      10.718  -0.371  -0.655  1.00  0.00           C  
HETATM   25  C25 UNL     1      12.691  -1.195   0.589  1.00  0.00           C  
HETATM   26  C26 UNL     1      12.843  -2.621   1.003  1.00  0.00           C  
HETATM   27  O1  UNL     1      13.900  -3.161   0.227  1.00  0.00           O  
HETATM   28  C27 UNL     1      11.640  -3.489   0.739  1.00  0.00           C  
HETATM   29  C28 UNL     1      10.441  -3.014   1.547  1.00  0.00           C  
HETATM   30  C29 UNL     1       9.211  -3.694   1.050  1.00  0.00           C  
HETATM   31  O2  UNL     1      10.691  -3.331   2.885  1.00  0.00           O  
HETATM   32  C30 UNL     1      -8.147   1.534  -1.954  1.00  0.00           C  
HETATM   33  C31 UNL     1      -9.467   1.607  -1.961  1.00  0.00           C  
HETATM   34  C32 UNL     1     -10.296   1.270  -0.773  1.00  0.00           C  
HETATM   35  O3  UNL     1      -9.705   2.085   0.354  1.00  0.00           O  
HETATM   36  C33 UNL     1     -11.142   2.038  -0.043  1.00  0.00           C  
HETATM   37  C34 UNL     1     -11.615   3.442  -0.334  1.00  0.00           C  
HETATM   38  C35 UNL     1     -11.917   1.370   1.058  1.00  0.00           C  
HETATM   39  C36 UNL     1     -12.603   0.151   0.545  1.00  0.00           C  
HETATM   40  O4  UNL     1     -13.705   0.483  -0.242  1.00  0.00           O  
HETATM   41  C37 UNL     1     -11.657  -0.757  -0.147  1.00  0.00           C  
HETATM   42  C38 UNL     1     -10.306  -0.198  -0.452  1.00  0.00           C  
HETATM   43  C39 UNL     1      -9.751  -0.991  -1.635  1.00  0.00           C  
HETATM   44  C40 UNL     1      -9.397  -0.508   0.740  1.00  0.00           C  
HETATM   45  H1  UNL     1      -7.134   3.058  -4.787  1.00  0.00           H  
HETATM   46  H2  UNL     1      -8.799   2.818  -4.273  1.00  0.00           H  
HETATM   47  H3  UNL     1      -7.945   1.422  -5.089  1.00  0.00           H  
HETATM   48  H4  UNL     1      -5.398   2.001  -3.881  1.00  0.00           H  
HETATM   49  H5  UNL     1      -5.758   1.112  -0.903  1.00  0.00           H  
HETATM   50  H6  UNL     1      -3.415   1.488  -2.714  1.00  0.00           H  
HETATM   51  H7  UNL     1      -4.768  -0.120   0.376  1.00  0.00           H  
HETATM   52  H8  UNL     1      -3.258  -0.151   1.290  1.00  0.00           H  
HETATM   53  H9  UNL     1      -4.114   1.411   1.169  1.00  0.00           H  
HETATM   54  H10 UNL     1      -1.378   1.026  -1.624  1.00  0.00           H  
HETATM   55  H11 UNL     1      -1.365   0.059   1.382  1.00  0.00           H  
HETATM   56  H12 UNL     1       0.646   0.788  -0.665  1.00  0.00           H  
HETATM   57  H13 UNL     1       1.077  -0.223   2.270  1.00  0.00           H  
HETATM   58  H14 UNL     1       2.371   0.043  -1.163  1.00  0.00           H  
HETATM   59  H15 UNL     1       3.964   0.735  -0.607  1.00  0.00           H  
HETATM   60  H16 UNL     1       2.429   1.704  -0.494  1.00  0.00           H  
HETATM   61  H17 UNL     1       3.413  -0.563   2.869  1.00  0.00           H  
HETATM   62  H18 UNL     1       5.202   0.383   0.622  1.00  0.00           H  
HETATM   63  H19 UNL     1       5.922  -0.825   3.479  1.00  0.00           H  
HETATM   64  H20 UNL     1       6.845   1.365   0.695  1.00  0.00           H  
HETATM   65  H21 UNL     1       7.235  -0.301  -0.005  1.00  0.00           H  
HETATM   66  H22 UNL     1       8.512   0.814   0.633  1.00  0.00           H  
HETATM   67  H23 UNL     1       8.738  -0.342   3.883  1.00  0.00           H  
HETATM   68  H24 UNL     1      10.865   0.588   2.466  1.00  0.00           H  
HETATM   69  H25 UNL     1      10.804   1.435   0.900  1.00  0.00           H  
HETATM   70  H26 UNL     1      12.417   0.985   1.666  1.00  0.00           H  
HETATM   71  H27 UNL     1      10.423   0.695  -0.745  1.00  0.00           H  
HETATM   72  H28 UNL     1      11.516  -0.580  -1.428  1.00  0.00           H  
HETATM   73  H29 UNL     1       9.823  -0.990  -0.791  1.00  0.00           H  
HETATM   74  H30 UNL     1      13.376  -0.588   1.198  1.00  0.00           H  
HETATM   75  H31 UNL     1      12.979  -1.074  -0.484  1.00  0.00           H  
HETATM   76  H32 UNL     1      13.124  -2.688   2.086  1.00  0.00           H  
HETATM   77  H33 UNL     1      13.835  -2.759  -0.699  1.00  0.00           H  
HETATM   78  H34 UNL     1      11.453  -3.508  -0.350  1.00  0.00           H  
HETATM   79  H35 UNL     1      11.895  -4.509   1.115  1.00  0.00           H  
HETATM   80  H36 UNL     1       8.466  -2.867   0.827  1.00  0.00           H  
HETATM   81  H37 UNL     1       9.368  -4.356   0.187  1.00  0.00           H  
HETATM   82  H38 UNL     1       8.734  -4.281   1.868  1.00  0.00           H  
HETATM   83  H39 UNL     1      11.609  -3.604   3.062  1.00  0.00           H  
HETATM   84  H40 UNL     1      -7.713   1.223  -1.018  1.00  0.00           H  
HETATM   85  H41 UNL     1      -9.946   1.930  -2.863  1.00  0.00           H  
HETATM   86  H42 UNL     1     -12.711   3.488  -0.086  1.00  0.00           H  
HETATM   87  H43 UNL     1     -11.128   4.226   0.274  1.00  0.00           H  
HETATM   88  H44 UNL     1     -11.599   3.685  -1.432  1.00  0.00           H  
HETATM   89  H45 UNL     1     -11.314   1.107   1.953  1.00  0.00           H  
HETATM   90  H46 UNL     1     -12.737   2.030   1.472  1.00  0.00           H  
HETATM   91  H47 UNL     1     -13.038  -0.387   1.436  1.00  0.00           H  
HETATM   92  H48 UNL     1     -13.526   1.212  -0.886  1.00  0.00           H  
HETATM   93  H49 UNL     1     -12.133  -1.158  -1.091  1.00  0.00           H  
HETATM   94  H50 UNL     1     -11.499  -1.690   0.470  1.00  0.00           H  
HETATM   95  H51 UNL     1      -9.740  -0.296  -2.509  1.00  0.00           H  
HETATM   96  H52 UNL     1     -10.432  -1.799  -1.882  1.00  0.00           H  
HETATM   97  H53 UNL     1      -8.710  -1.314  -1.431  1.00  0.00           H  
HETATM   98  H54 UNL     1      -9.954  -0.988   1.554  1.00  0.00           H  
HETATM   99  H55 UNL     1      -8.560  -1.183   0.465  1.00  0.00           H  
HETATM  100  H56 UNL     1      -8.911   0.464   1.050  1.00  0.00           H  
CONECT    1    2   45   46   47
CONECT    2    3    3   32
CONECT    3    4   48
CONECT    4    5    5   49
CONECT    5    6   50
CONECT    6    7    8    8
CONECT    7   51   52   53
CONECT    8    9   54
CONECT    9   10   10   55
CONECT   10   11   56
CONECT   11   12   12   57
CONECT   12   13   14
CONECT   13   58   59   60
CONECT   14   15   15   61
CONECT   15   16   62
CONECT   16   17   17   63
CONECT   17   18   19
CONECT   18   64   65   66
CONECT   19   20   20   67
CONECT   20   21   21
CONECT   21   22   29
CONECT   22   23   24   25
CONECT   23   68   69   70
CONECT   24   71   72   73
CONECT   25   26   74   75
CONECT   26   27   28   76
CONECT   27   77
CONECT   28   29   78   79
CONECT   29   30   31
CONECT   30   80   81   82
CONECT   31   83
CONECT   32   33   33   84
CONECT   33   34   85
CONECT   34   35   36   42
CONECT   35   36
CONECT   36   37   38
CONECT   37   86   87   88
CONECT   38   39   89   90
CONECT   39   40   41   91
CONECT   40   92
CONECT   41   42   93   94
CONECT   42   43   44
CONECT   43   95   96   97
CONECT   44   98   99  100
END

HMDB0003020
     RDKit          3D
Neoxanthin
100102  0  0  0  0  0  0  0  0999 V2000
   -7.8486    2.2803   -4.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2860    1.8429   -3.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9906    1.7434   -2.9861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2416    1.3441   -1.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9335    1.2552   -1.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1441    0.8606   -0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8444    0.4889    0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356    0.8187   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9993    0.4107    0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3251    0.4513    0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3236    0.1128    1.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294    0.2159    0.9683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9002    0.6952   -0.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6791   -0.1593    1.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9506   -0.0260    1.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0415   -0.3913    2.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3072   -0.1820    2.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4817    0.4339    0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4761   -0.4703    2.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4574   -1.0106    2.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4177   -1.5469    1.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2795   -0.6481    0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3650    0.6845    1.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7184   -0.3714   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6907   -1.1946    0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8435   -2.6213    1.0028 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9004   -3.1614    0.2271 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6401   -3.4888    0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4414   -3.0138    1.5467 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2109   -3.6937    1.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6914   -3.3313    2.8854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1472    1.5338   -1.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4671    1.6067   -1.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2961    1.2701   -0.7726 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.7055    2.0849    0.3537 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1420    2.0376   -0.0431 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.6150    3.4419   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9168    1.3701    1.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6026    0.1509    0.5451 C   0  0  1  0  0  0  0  0  0  0  0  0
  -13.7047    0.4827   -0.2425 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6569   -0.7571   -0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3057   -0.1984   -0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7514   -0.9907   -1.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3966   -0.5080    0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1338    3.0579   -4.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7994    2.8183   -4.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9453    1.4218   -5.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3978    2.0007   -3.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7576    1.1120   -0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4145    1.4879   -2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7675   -0.1204    0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2577   -0.1514    1.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1142    1.4105    1.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3777    1.0263   -1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3648    0.0588    1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6458    0.7881   -0.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0773   -0.2231    2.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3713    0.0429   -1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9638    0.7355   -0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4293    1.7041   -0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4127   -0.5628    2.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025    0.3826    0.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9221   -0.8254    3.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8454    1.3648    0.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2348   -0.3011   -0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5119    0.8143    0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7377   -0.3423    3.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8648    0.5883    2.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8043    1.4345    0.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4165    0.9847    1.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4231    0.6951   -0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5161   -0.5804   -1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8233   -0.9899   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3757   -0.5875    1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9788   -1.0739   -0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1243   -2.6884    2.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8348   -2.7591   -0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4532   -3.5077   -0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8947   -4.5088    1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4656   -2.8671    0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3681   -4.3557    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7341   -4.2809    1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6094   -3.6041    3.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7134    1.2233   -1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9464    1.9298   -2.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7106    3.4877   -0.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1278    4.2259    0.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5989    3.6849   -1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3143    1.1069    1.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7373    2.0299    1.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0379   -0.3871    1.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5256    1.2116   -0.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1331   -1.1576   -1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4995   -1.6905    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7396   -0.2964   -2.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4317   -1.7988   -1.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7098   -1.3136   -1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9538   -0.9879    1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5596   -1.1833    0.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9112    0.4636    1.0499 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  2  0
 12 13  1  0
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 29 30  1  0
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  2 32  1  0
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 34 33  1  6
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  1 46  1  0
  1 47  1  0
  3 48  1  0
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 44100  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3S,5R,6R,3's,5'r,6's)-9'-cis-6,7-Didehydro-5,6,5',6'-tetrahydro-5',6'-epoxy-beta,beta-carotene-3,5,3'-triol	ChEBI
(3S,5R,6R,3's,5'r,6's)-9'-cis-6,7-Didehydro-5,6,5',6'-tetrahydro-5',6'-epoxy-b,b-carotene-3,5,3'-triol	Generator
(3S,5R,6R,3's,5'r,6's)-9'-cis-6,7-Didehydro-5,6,5',6'-tetrahydro-5',6'-epoxy-β,β-carotene-3,5,3'-triol	Generator
(3S,3'S,5R,5'R,6R,6'S,9'-cis)-6,7-Didehydro-5',6'-epoxy-5',6'-dihydro-beta,beta-carotene-3,3',5(6H)-triol	HMDB
(3S,3'S,5R,5'R,6R,6'S,9'-cis)-6,7-Didehydro-5',6'-epoxy-5',6'-dihydro-β,β-carotene-3,3',5(6H)-triol	HMDB
(3S,3’S,5R,5’R,6R,6’S,9’-cis)-6,7-Didehydro-5’,6’-epoxy-5’,6’-dihydro-β,β-carotene-3,3’,5(6H)-triol	HMDB
(9'Z)-Neoxanthin	HMDB
(9’Z)-Neoxanthin	HMDB
9'-cis-Neoxanthin	HMDB
9'Z-(6R)-neoxanthin	HMDB
9-cis-Neoxanthin	HMDB
9’-cis-Neoxanthin	HMDB
9’Z-(6R)-neoxanthin	HMDB
Foliaxanthin	HMDB
Neoxanthin	HMDB
Neoxanthine	HMDB
cis-Neoxanthin	HMDB

Chemical Formula

C₄₀H₅₆O₄

Average Molecular Weight

600.8702

Monoisotopic Molecular Weight

600.41786028

IUPAC Name

(1R,3S)-6-[(1M,3E,5E,7E,9E,11E,13E,15Z,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,3-diol

Traditional Name

9'-cis-neoxanthin

CAS Registry Number

14660-91-4

SMILES

[H]C(=[C@@]=C1C(C)(C)C[C@H](O)C[C@@]1(C)O)C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C

InChI Identifier

InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-22-35-36(5,6)25-33(41)27-38(35,9)43)15-11-12-16-30(2)18-14-20-32(4)23-24-40-37(7,8)26-34(42)28-39(40,10)44-40/h11-21,23-24,33-34,41-43H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,24-23+,29-15+,30-16+,31-19+,32-20-/t22-,33-,34-,38+,39+,40-/m0/s1

InChI Key

PGYAYSRVSAJXTE-OQASCVKESA-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

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	200 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.0e-08 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00088 g/L	ALOGPS
logP	7.85	ALOGPS
logP	6.69	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	14.01	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.22 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	194.03 m³·mol⁻¹	ChemAxon
Polarizability	72.71 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	280.197	30932474
DeepCCS	[M+Na]+	254.519	30932474
AllCCS	[M+H]+	266.1	32859911
AllCCS	[M+H-H2O]+	264.6	32859911
AllCCS	[M+NH4]+	267.6	32859911
AllCCS	[M+Na]+	268.0	32859911
AllCCS	[M-H]-	240.3	32859911
AllCCS	[M+Na-2H]-	244.9	32859911
AllCCS	[M+HCOO]-	250.0	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 × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.33 minutes	32390414
Predicted by Siyang on May 30, 2022	23.8097 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.22 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	4659.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	318.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	275.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	206.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	164.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1396.2 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	771.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	115.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2154.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	856.3 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	1608.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	889.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	562.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	123.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	501.4 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	10.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Neoxanthin	[H]C(=[C@@]=C1C(C)(C)C[C@H](O)C[C@@]1(C)O)C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C	6535.9	Standard polar	33892256
Neoxanthin	[H]C(=[C@@]=C1C(C)(C)C[C@H](O)C[C@@]1(C)O)C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C	4863.0	Standard non polar	33892256
Neoxanthin	[H]C(=[C@@]=C1C(C)(C)C[C@H](O)C[C@@]1(C)O)C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C	4711.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Neoxanthin,1TMS,isomer #1	CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O[Si](C)(C)C)C[C@@]1(C)O)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C	4686.1	Semi standard non polar	33892256
Neoxanthin,1TMS,isomer #2	CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O)C[C@@]1(C)O[Si](C)(C)C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C	4706.1	Semi standard non polar	33892256
Neoxanthin,1TMS,isomer #3	CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O)C[C@@]1(C)O)/C=C/[C@@]12O[C@]1(C)C[C@@H](O[Si](C)(C)C)CC2(C)C	4669.6	Semi standard non polar	33892256
Neoxanthin,2TMS,isomer #1	CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O[Si](C)(C)C)C[C@@]1(C)O[Si](C)(C)C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C	4612.4	Semi standard non polar	33892256
Neoxanthin,2TMS,isomer #2	CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O[Si](C)(C)C)C[C@@]1(C)O)/C=C/[C@@]12O[C@]1(C)C[C@@H](O[Si](C)(C)C)CC2(C)C	4593.0	Semi standard non polar	33892256
Neoxanthin,2TMS,isomer #3	CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O)C[C@@]1(C)O[Si](C)(C)C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O[Si](C)(C)C)CC2(C)C	4610.4	Semi standard non polar	33892256
Neoxanthin,3TMS,isomer #1	CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O[Si](C)(C)C)C[C@@]1(C)O[Si](C)(C)C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O[Si](C)(C)C)CC2(C)C	4530.2	Semi standard non polar	33892256
Neoxanthin,1TBDMS,isomer #1	CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]1(C)O)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C	4909.9	Semi standard non polar	33892256
Neoxanthin,1TBDMS,isomer #2	CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O)C[C@@]1(C)O[Si](C)(C)C(C)(C)C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C	4920.3	Semi standard non polar	33892256
Neoxanthin,1TBDMS,isomer #3	CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O)C[C@@]1(C)O)/C=C/[C@@]12O[C@]1(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC2(C)C	4905.1	Semi standard non polar	33892256
Neoxanthin,2TBDMS,isomer #1	CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]1(C)O[Si](C)(C)C(C)(C)C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C	5058.5	Semi standard non polar	33892256
Neoxanthin,2TBDMS,isomer #2	CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]1(C)O)/C=C/[C@@]12O[C@]1(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC2(C)C	5034.8	Semi standard non polar	33892256
Neoxanthin,2TBDMS,isomer #3	CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O)C[C@@]1(C)O[Si](C)(C)C(C)(C)C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC2(C)C	5059.5	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Neoxanthin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

35306

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1589021

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Czeczuga-Semeniuk E, Wolczynski S: Identification of carotenoids in ovarian tissue in women. Oncol Rep. 2005 Nov;14(5):1385-92. [PubMed:16211314 ]
Asai A, Terasaki M, Nagao A: An epoxide-furanoid rearrangement of spinach neoxanthin occurs in the gastrointestinal tract of mice and in vitro: formation and cytostatic activity of neochrome stereoisomers. J Nutr. 2004 Sep;134(9):2237-43. [PubMed:15333710 ]

Showing metabocard for Neoxanthin (HMDB0003020)

MOL for HMDB0003020 (Neoxanthin)

3D MOL for HMDB0003020 (Neoxanthin)

3D SDF for HMDB0003020 (Neoxanthin)

3D-SDF for HMDB0003020 (Neoxanthin)

PDB for HMDB0003020 (Neoxanthin)

3D PDB for HMDB0003020 (Neoxanthin)

SMILES for HMDB0003020 (Neoxanthin)

INCHI for HMDB0003020 (Neoxanthin)

Structure for HMDB0003020 (Neoxanthin)

3D Structure for HMDB0003020 (Neoxanthin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized