MiMeDB: Showing metabocard for Neoxanthin (MMDBc0053508)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:26:39 UTC

Update Date

2024-04-30 20:49:36 UTC

Metabolite ID

MMDBc0053508

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 SDF PDB SMILES InChI


  Mrv1652306222023482D          

 59 61  0  0  1  0            999 V2000
   -5.1711   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6461   -4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8518   -4.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9333   -5.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9333   -7.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5211   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6961   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9961   -4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9336   -4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1711   -4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4086   -5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6461   -6.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4711   -6.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5336   -5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5336   -7.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7586   -4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2336   -5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9461   -6.3197    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.2961   -6.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7086   -5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7086   -7.0342    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.7711   -6.3197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8518   -7.8466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9336   -2.7474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -4.1763    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4086   -4.1763    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -2.7474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5211   -4.8908    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6961   -2.0329    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7586   -5.6052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -1.3184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9961   -6.3197    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -0.6039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2336   -7.0342    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1587   -0.9887    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3586   -7.0342    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  2  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 18 14  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 22 21  2  0  0  0  0
 24 23  2  0  0  0  0
 29  1  1  0  0  0  0
 29 15  2  0  0  0  0
 29 17  1  0  0  0  0
 30  2  1  0  0  0  0
 30 16  2  0  0  0  0
 30 18  1  0  0  0  0
 31  3  1  0  0  0  0
 31 19  2  0  0  0  0
 31 21  1  0  0  0  0
 32  4  1  0  0  0  0
 32 20  2  0  0  0  0
 32 23  1  0  0  0  0
 33 25  1  0  0  0  0
 33 27  1  0  0  0  0
 34 26  1  0  0  0  0
 34 28  1  0  0  0  0
 35 22  2  0  0  0  0
 36  5  1  0  0  0  0
 36  6  1  0  0  0  0
 36 25  1  0  0  0  0
 36 35  1  0  0  0  0
 37  7  1  0  0  0  0
 37  8  1  0  0  0  0
 37 26  1  0  0  0  0
 38  9  1  1  0  0  0
 38 27  1  0  0  0  0
 38 35  1  0  0  0  0
 39 10  1  1  0  0  0
 39 28  1  0  0  0  0
 40 24  1  1  0  0  0
 40 37  1  0  0  0  0
 40 39  1  0  0  0  0
 33 41  1  1  0  0  0
 34 42  1  1  0  0  0
 38 43  1  6  0  0  0
 44 39  1  0  0  0  0
 44 40  1  0  0  0  0
 45 11  1  0  0  0  0
 46 12  1  0  0  0  0
 47 13  1  0  0  0  0
 48 14  1  0  0  0  0
 49 15  1  0  0  0  0
 50 16  1  0  0  0  0
 51 17  1  0  0  0  0
 52 18  1  0  0  0  0
 53 19  1  0  0  0  0
 54 20  1  0  0  0  0
 55 21  1  0  0  0  0
 56 23  1  0  0  0  0
 57 24  1  0  0  0  0
 33 58  1  6  0  0  0
 34 59  1  6  0  0  0
M  END


  Mrv1652306222023482D          

 59 61  0  0  1  0            999 V2000
   -5.1711   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6461   -4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8518   -4.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9333   -5.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9333   -7.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5211   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6961   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9961   -4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9336   -4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1711   -4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4086   -5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6461   -6.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4711   -6.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5336   -5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5336   -7.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7586   -4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2336   -5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9461   -6.3197    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.2961   -6.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7086   -5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7086   -7.0342    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.7711   -6.3197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8518   -7.8466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9336   -2.7474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -4.1763    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4086   -4.1763    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -2.7474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5211   -4.8908    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6961   -2.0329    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7586   -5.6052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -1.3184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9961   -6.3197    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.2336   -7.0342    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1587   -0.9887    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3586   -7.0342    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  2  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 18 14  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 22 21  2  0  0  0  0
 24 23  2  0  0  0  0
 29  1  1  0  0  0  0
 29 15  2  0  0  0  0
 29 17  1  0  0  0  0
 30  2  1  0  0  0  0
 30 16  2  0  0  0  0
 30 18  1  0  0  0  0
 31  3  1  0  0  0  0
 31 19  2  0  0  0  0
 31 21  1  0  0  0  0
 32  4  1  0  0  0  0
 32 20  2  0  0  0  0
 32 23  1  0  0  0  0
 33 25  1  0  0  0  0
 33 27  1  0  0  0  0
 34 26  1  0  0  0  0
 34 28  1  0  0  0  0
 35 22  2  0  0  0  0
 36  5  1  0  0  0  0
 36  6  1  0  0  0  0
 36 25  1  0  0  0  0
 36 35  1  0  0  0  0
 37  7  1  0  0  0  0
 37  8  1  0  0  0  0
 37 26  1  0  0  0  0
 38  9  1  1  0  0  0
 38 27  1  0  0  0  0
 38 35  1  0  0  0  0
 39 10  1  1  0  0  0
 39 28  1  0  0  0  0
 40 24  1  1  0  0  0
 40 37  1  0  0  0  0
 40 39  1  0  0  0  0
 33 41  1  1  0  0  0
 34 42  1  1  0  0  0
 38 43  1  6  0  0  0
 44 39  1  0  0  0  0
 44 40  1  0  0  0  0
 45 11  1  0  0  0  0
 46 12  1  0  0  0  0
 47 13  1  0  0  0  0
 48 14  1  0  0  0  0
 49 15  1  0  0  0  0
 50 16  1  0  0  0  0
 51 17  1  0  0  0  0
 52 18  1  0  0  0  0
 53 19  1  0  0  0  0
 54 20  1  0  0  0  0
 55 21  1  0  0  0  0
 56 23  1  0  0  0  0
 57 24  1  0  0  0  0
 33 58  1  6  0  0  0
 34 59  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0053508

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(=C=C1C(C)(C)C[C@]([H])(O)C[C@@]1(C)O)C(\C)=C(/[H])\C(\[H])=C(/[H])\C(\C)=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])[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-CLONMANBSA-N

> <FORMULA>
C40H56O4

> <MOLECULAR_WEIGHT>
600.884

> <EXACT_MASS>
600.417860283

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
74.2626980304669

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S)-6-[(3E,5E,7E,9E,11E,13E,15E,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>
194.03109999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.77e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
neoxanthin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0      -9.653  -6.462   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.953  -6.462   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.273  -9.129   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.795   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -18.390  -8.947   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -16.675  -9.936   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.991  -0.410   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.011  -0.410   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -16.675 -13.657   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.897   4.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.573  -6.462   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.033  -6.462   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -11.193  -9.129   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.413  -3.795   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.343  -7.796   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.263  -5.128   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.653  -9.129   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.953  -3.795   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -11.963 -10.463   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.357  -2.461   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -14.273 -11.797   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -15.813 -11.797   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -1.127   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.897   0.206   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -19.663 -10.463   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -19.663 -13.131   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.883  -7.796   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.723  -5.128   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -13.503 -10.463   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.897  -2.461   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -20.433 -11.797   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -17.353 -11.797   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -18.123 -10.463   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -18.123 -13.131   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0     -21.973 -11.797   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0     -18.390 -14.647   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   45  H   UNK     0      -7.343  -5.128   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.263  -7.796   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0     -11.963  -7.796   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.357  -5.128   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.573  -9.129   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.033  -3.795   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0      -8.883 -10.463   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.723  -2.461   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0     -11.193 -11.797   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.413  -1.127   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0     -13.503 -13.131   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.030  -1.846   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.357   0.206   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0     -21.203 -13.131   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.335   4.620   0.000  0.00  0.00           H+0
CONECT    1   29                                                            
CONECT    2   30                                                            
CONECT    3   31                                                            
CONECT    4   32                                                            
CONECT    5   36                                                            
CONECT    6   36                                                            
CONECT    7   37                                                            
CONECT    8   37                                                            
CONECT    9   38                                                            
CONECT   10   39                                                            
CONECT   11   12   15   45                                                  
CONECT   12   11   16   46                                                  
CONECT   13   17   19   47                                                  
CONECT   14   18   20   48                                                  
CONECT   15   11   29   49                                                  
CONECT   16   12   30   50                                                  
CONECT   17   13   29   51                                                  
CONECT   18   14   30   52                                                  
CONECT   19   13   31   53                                                  
CONECT   20   14   32   54                                                  
CONECT   21   22   31   55                                                  
CONECT   22   21   35                                                       
CONECT   23   24   32   56                                                  
CONECT   24   23   40   57                                                  
CONECT   25   33   36                                                       
CONECT   26   34   37                                                       
CONECT   27   33   38                                                       
CONECT   28   34   39                                                       
CONECT   29    1   15   17                                                  
CONECT   30    2   16   18                                                  
CONECT   31    3   19   21                                                  
CONECT   32    4   20   23                                                  
CONECT   33   25   27   41   58                                             
CONECT   34   26   28   42   59                                             
CONECT   35   22   36   38                                                  
CONECT   36    5    6   25   35                                             
CONECT   37    7    8   26   40                                             
CONECT   38    9   27   35   43                                             
CONECT   39   10   28   40   44                                             
CONECT   40   24   37   39   44                                             
CONECT   41   33                                                            
CONECT   42   34                                                            
CONECT   43   38                                                            
CONECT   44   39   40                                                       
CONECT   45   11                                                            
CONECT   46   12                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   15                                                            
CONECT   50   16                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   20                                                            
CONECT   55   21                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
CONECT   58   33                                                            
CONECT   59   34                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  122    0
END

Synonyms

Value	Source
all-trans-Neoxanthin	Kegg
6,7-Didehydro-5',6'-epoxy-5,5',6,6'-tetrahydro-b,b-carotene-3,3',5-triol	HMDB
Foliaxanthin	HMDB
Trolliflor	HMDB
Trollixanthin	HMDB
9'-cis-Neoxanthin	HMDB
Neoxanthin, (trans)-isomer	HMDB

Molecular Formula

C₄₀H₅₆O₄

Average Mass

600.884

Monoisotopic Mass

600.417860283

IUPAC Name

(1R,3S)-6-[(3E,5E,7E,9E,11E,13E,15E,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

neoxanthin

CAS Registry Number

Not Available

SMILES

[H]C(=C=C1C(C)(C)C[C@]([H])(O)C[C@@]1(C)O)C(\C)=C(/[H])\C(\[H])=C(/[H])\C(\C)=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])[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-CLONMANBSA-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
Oxepane
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

C40 isoprenoids (tetraterpenes) (C08606 )
Carotenoids (C08606 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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	74.26 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-053l-0000090000-eba564ea5bff8d75c3ce	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-4100019000-8db432e3b230dd9950bc	2017-10-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QIT 20V, positive	splash10-0162-0000090000-2be2bfdecc95ed083ef9	2020-07-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0001291000-3182e203a68c515d6a55	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02cr-0221920000-38690bfbd04703cb9af0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01p9-1394310000-2cc8d5afd284c382306b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000t-0300090000-443389e01a5be8228352	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001j-0200190000-b6a19dc5634b7ed96e54	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052k-1600390000-452d15111fa201e6baee	2016-08-03	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0003020

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Neoxanthin

METLIN ID

3673

PubChem Compound

5281247

PDB ID

Not Available

ChEBI ID

25501

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1093/jn/134.9.2237. [PubMed:15333710 ]
Czeczuga-Semeniuk E, Wolczynski S: Identification of carotenoids in ovarian tissue in women. Oncol Rep. 2005 Nov;14(5):1385-92. [PubMed:16211314 ]

Showing metabocard for Neoxanthin (MMDBc0053508)

MOL for #<Metabolite:0x00007fdb441f0230>

3D MOL for #<Metabolite:0x00007fdb441f0230>

3D SDF for #<Metabolite:0x00007fdb441f0230>

3D-SDF for #<Metabolite:0x00007fdb441f0230>

PDB for #<Metabolite:0x00007fdb441f0230>

3D PDB for #<Metabolite:0x00007fdb441f0230>

SMILES for #<Metabolite:0x00007fdb441f0230>

INCHI for #<Metabolite:0x00007fdb441f0230>

Structure for #<Metabolite:0x00007fdb441f0230>

3D Structure for #<Metabolite:0x00007fdb441f0230>