NP-MRD: Showing NP-Card for (2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate (NP0200194)

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Record Information

Version

2.0

Created at

2022-09-04 18:59:06 UTC

Updated at

2022-09-04 18:59:07 UTC

NP-MRD ID

NP0200194

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate

Description

19'-Butanoyloxyfucoxanthin 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. Thus, 19'-butanoyloxyfucoxanthin is considered to be an isoprenoid. (2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate is found in Pelagococcus subviridis. (2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate was first documented in 2014 (PMID: 26988788). Based on a literature review a small amount of articles have been published on 19'-butanoyloxyfucoxanthin (PMID: 35550295) (PMID: 34910557) (PMID: 29469573) (PMID: 31358270).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309042220592D          

 54 56  0  0  1  0            999 V2000
   -3.3000  -13.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855  -13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711  -13.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566  -13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566  -12.4480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421  -13.6855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2724  -13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868  -13.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868  -14.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2724  -14.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421  -15.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421  -16.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3704  -16.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1599  -16.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566  -16.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711  -16.1605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5855  -16.5730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000  -16.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145  -16.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000  -15.3355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5439  -14.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7693  -14.1945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013  -13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013  -12.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158  -12.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158  -11.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013  -10.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1302  -10.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1302   -9.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -9.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -8.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5592   -8.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2737   -8.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5592   -7.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2737   -7.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2737   -6.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9881   -5.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026   -6.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9881   -5.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2737   -4.6105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026   -4.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026   -3.7855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8776   -3.7855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2901   -3.0710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5756   -2.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026   -2.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5276   -2.3565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9401   -1.6421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9401   -3.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5276   -3.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2272   -4.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5564   -4.6100    0.0000 C   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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  1  0  0  0
  8 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 44 43  1  1  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  1  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  1  0  0  0
 49 51  1  0  0  0  0
 51 52  1  0  0  0  0
 44 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
M  END

     RDKit          3D

118120  0  0  0  0  0  0  0  0999 V2000
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  -10.0563   -4.1662   -2.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.5679   -1.6999    2.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2247   -0.7731    1.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9152    0.2007    0.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.0440    0.0214    2.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6996   -1.4023    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9519    1.0040   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3604    2.3257    0.2246 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.0691    3.4240   -0.2584 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5241    4.3865    0.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2877    5.5922    0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2869    4.2513    1.8725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9327    2.3173   -0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0997    1.3066    0.4049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0365    0.8172   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4002    1.9362    1.4254 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7211    1.0463    1.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8475    0.9190    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072    2.0669    1.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1605    0.6223   -0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.2773    1.4810    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6296    1.0452   -0.5166 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8564    0.9156   -1.8587 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3529    2.0284   -1.2325 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6876    3.3795   -1.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7823    2.1759   -0.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4717    0.8604   -0.8110 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.7633    1.0721   -0.3058 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7830   -0.1924   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

  Mrv1652309042220592D          

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M  END
> <DATABASE_ID>
NP0200194

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C46H64O8/c1-12-17-41(50)52-31-36(24-25-40-42(6,7)28-38(53-35(5)47)29-44(40,10)51)23-16-21-33(3)19-14-13-18-32(2)20-15-22-34(4)39(49)30-46-43(8,9)26-37(48)27-45(46,11)54-46/h13-16,18-24,37-38,48,51H,12,17,26-31H2,1-11H3/b14-13+,20-15+,21-16+,32-18+,33-19+,34-22+,36-23-/t25?,37-,38-,44+,45+,46-/m0/s1

> <INCHI_KEY>
NEKQVGDUHFTLGS-MFFPCINUSA-N

> <FORMULA>
C46H64O8

> <MOLECULAR_WEIGHT>
745.01

> <EXACT_MASS>
744.460119021

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
118

> <JCHEM_AVERAGE_POLARIZABILITY>
87.44779234343741

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,4E,6E,8E,10E,12E,14E)-2-{2-[(2R,4S)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate

> <JCHEM_LOGP>
7.133160362333331

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.127797470420603

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.030958148011738

> <JCHEM_PKA_STRONGEST_BASIC>
-2.737175756069491

> <JCHEM_POLAR_SURFACE_AREA>
122.66000000000001

> <JCHEM_REFRACTIVITY>
222.91330000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4E,6E,8E,10E,12E,14E)-2-{2-[(2R,4S)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.160 -25.546   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.826 -24.776   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.493 -25.546   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.159 -24.776   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.159 -23.236   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -0.825 -25.546   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.508 -24.776   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.842 -25.546   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.842 -27.086   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.508 -27.856   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.825 -28.626   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.825 -30.166   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.691 -29.899   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.299 -31.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.159 -30.936   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.493 -30.166   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.826 -30.936   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.160 -30.166   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -7.494 -30.936   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.160 -28.626   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.493 -28.626   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.159 -27.856   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.882 -26.496   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.436 -26.496   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.176 -24.776   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.176 -23.236   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.509 -22.466   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.509 -20.926   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.176 -20.156   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.843 -20.156   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.843 -18.616   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.177 -17.846   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.177 -16.306   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.510 -15.536   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.844 -16.306   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.510 -13.996   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.844 -13.226   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.844 -11.686   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.178 -10.916   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.512 -11.686   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.178  -9.376   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       9.844  -8.606   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      12.512  -8.606   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      12.512  -7.066   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      10.972  -7.066   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      11.742  -5.733   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      10.408  -4.963   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      12.512  -4.399   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      14.052  -4.399   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      14.822  -3.065   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      14.822  -5.733   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      14.052  -7.066   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      15.358  -7.882   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      14.105  -8.605   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22                                                       
CONECT   22   21   11   23   24                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    8   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45   46   52                                             
CONECT   45   44   46                                                       
CONECT   46   45   44   47   48                                             
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51   44   53   54                                             
CONECT   53   52                                                            
CONECT   54   52                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₆H₆₄O₈

Average Mass

745.0100 Da

Monoisotopic Mass

744.46012 Da

IUPAC Name

(2Z,4E,6E,8E,10E,12E,14E)-2-{2-[(2R,4S)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C46H64O8/c1-12-17-41(50)52-31-36(24-25-40-42(6,7)28-38(53-35(5)47)29-44(40,10)51)23-16-21-33(3)19-14-13-18-32(2)20-15-22-34(4)39(49)30-46-43(8,9)26-37(48)27-45(46,11)54-46/h13-16,18-24,37-38,48,51H,12,17,26-31H2,1-11H3/b14-13+,20-15+,21-16+,32-18+,33-19+,34-22+,36-23-/t25?,37-,38-,44+,45+,46-/m0/s1

InChI Key

NEKQVGDUHFTLGS-MFFPCINUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pelagococcus subviridis	LOTUS Database	35616633

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
Fatty alcohol ester
Fatty acid ester
Oxepane
Dicarboxylic acid or derivatives
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Acryloyl-group
Cyclic alcohol
Enone
Alpha,beta-unsaturated ketone
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Ketone
Organoheterocyclic compound
Ether
Oxirane
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

C40 isoprenoids (tetraterpenes) (LMPR01070059 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	7.13	ChemAxon
pKa (Strongest Acidic)	14.03	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	122.66 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	222.91 m³·mol⁻¹	ChemAxon
Polarizability	87.45 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

113385806

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14160128

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang QC, Liu C, Wang JX, Kong FZ, Niu Z, Xiang L, Yu RC: Intense blooms of Phaeocystis globosa in the South China Sea are caused by a unique "giant-colony" ecotype. Harmful Algae. 2022 May;114:102227. doi: 10.1016/j.hal.2022.102227. Epub 2022 Mar 23. [PubMed:35550295 ]
Wang JX, Kong FZ, Geng HX, Zhao Y, Guan WB, He C, Kang ZJ, Guo W, Zhou ZX, Zhang QC, Yu RC: Pigment Characterization of the Giant-Colony-Forming Haptophyte Phaeocystis globosa in the Beibu Gulf Reveals Blooms of Different Origins. Appl Environ Microbiol. 2022 Feb 22;88(4):e0165421. doi: 10.1128/AEM.01654-21. Epub 2021 Dec 15. [PubMed:34910557 ]
Staleva-Musto H, Kuznetsova V, West RG, Kesan G, Minofar B, Fuciman M, Bina D, Litvin R, Polivka T: Nonconjugated Acyloxy Group Deactivates the Intramolecular Charge-Transfer State in the Carotenoid Fucoxanthin. J Phys Chem B. 2018 Mar 22;122(11):2922-2930. doi: 10.1021/acs.jpcb.8b00743. Epub 2018 Mar 13. [PubMed:29469573 ]
Yao P, Lei L, Zhao B, Wang J, Chen L: Spatial-temporal variation of Aureococcus anophagefferens blooms in relation to environmental factors in the coastal waters of Qinhuangdao, China. Harmful Algae. 2019 Jun;86:106-118. doi: 10.1016/j.hal.2019.05.011. Epub 2019 May 31. [PubMed:31358270 ]
van Leeuwe MA, Visser RJ, Stefels J: The pigment composition of Phaeocystis antarctica (Haptophyceae) under various conditions of light, temperature, salinity, and iron. J Phycol. 2014 Dec;50(6):1070-80. doi: 10.1111/jpy.12238. Epub 2014 Oct 27. [PubMed:26988788 ]
LOTUS database [Link]

Showing NP-Card for (2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate (NP0200194)

MOL for NP0200194 ((2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate)

3D MOL for NP0200194 ((2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate)

3D SDF for NP0200194 ((2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate)

3D-SDF for NP0200194 ((2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate)

PDB for NP0200194 ((2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate)

3D PDB for NP0200194 ((2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate)

SMILES for NP0200194 ((2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate)

INCHI for NP0200194 ((2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate)

Structure for NP0200194 ((2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate)

3D Structure for NP0200194 ((2z,4e,6e,8e,10e,12e,14e)-2-{2-[(2r,4s)-4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl butanoate)