NP-MRD: Showing NP-Card for (6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one (NP0241672)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 01:48:38 UTC

Updated at

2022-09-07 01:48:38 UTC

NP-MRD ID

NP0241672

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one

Description

Papilioerythrinone 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. (6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one is found in Paralithodes brevipes. (6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one was first documented in 2013 (PMID: 23851380). Based on a literature review a small amount of articles have been published on Papilioerythrinone (PMID: 25421097) (PMID: 24691990) (PMID: 24647990).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072203482D          

 43 44  0  0  1  0            999 V2000
   -2.8579  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8171  -11.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7565  -11.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -12.7875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4315   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3899  -12.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6153  -12.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 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
 36 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 33 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
M  END

     RDKit          3D

 95 96  0  0  0  0  0  0  0  0999 V2000
   11.5519   -0.4358    2.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1784    0.0054    1.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4925   -0.3331    1.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2913    0.0244    0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5612   -0.0707    0.3961 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6766    0.5242   -0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1982    0.4288   -0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7866   -1.0096   -1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5964    1.3766   -1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5990    0.7347    0.5267 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1192    0.7706    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2245    0.0948    1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8033    0.3760    0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4572    1.3220   -0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8823   -0.2822    1.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5220   -0.2594    1.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2933   -0.2807    1.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    0.1492    0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2020    0.9366   -0.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9139   -0.2104    0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7559    0.1189    0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5023   -0.1556    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5979    0.2267   -0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8488   -0.0198   -0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0309   -0.6984    1.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8976    0.1137   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1372    0.0764   -1.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4516    0.0487   -1.5206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3982   -0.0284   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8319   -0.0618    0.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7874   -0.1403   -0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6309   -0.1320    0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0644   -0.2321    0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6479   -0.0694    1.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8220    0.1666    2.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0901    0.0088    1.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7158   -0.4564    2.3144 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7600    0.6658    0.1897 C   0  0  1  0  0  0  0  0  0  0  0  0
  -13.4632    2.0172    0.1886 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2676    0.0401   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9680   -0.6694   -0.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3885   -2.1636   -0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3947   -0.7885   -2.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2216   -1.4955    2.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3528   -0.4835    3.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8176    0.2679    3.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9619   -0.8749    2.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9554    1.5590   -1.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9928   -0.1708   -1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7517   -1.1907   -0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4282   -1.7358   -0.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7645   -1.1287   -2.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3339    1.4415   -2.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4512    2.3459   -1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6662    0.9238   -2.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8662    1.8390    0.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7663    1.5394   -0.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4863   -0.6703    1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3885    1.4330   -0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8211    2.3676   -0.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0346    1.0439   -1.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3209   -1.0160    2.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3636   -0.2228    2.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0688   -1.3242    1.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6364    0.3266   -1.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7696    1.9270   -0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2368    0.9777   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8378   -0.7474    1.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8658    0.6618   -0.8877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6770   -0.6587    1.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3687    0.7408   -1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5717   -1.7276    1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993   -0.8948    1.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6778   -0.1321    2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5478    0.7402   -2.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7997   -0.6553   -2.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8769    0.1200   -2.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7712   -1.0970    1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4862    0.5181    1.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8172    0.4075    0.8067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0964   -0.1982   -1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1614   -0.0457    1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5055    1.2039    2.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0199   -0.5752    2.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5328   -0.0613    3.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.8674    0.5663    0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0452    2.2586   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0797   -0.6639   -1.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2017    0.7976   -1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0913   -2.4947   -1.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7827   -2.1397    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4811   -2.7950   -0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7427   -1.6513   -2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3139   -1.0602   -3.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0987    0.1757   -2.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 34 36  1  0
 36 37  2  0
 36 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 41 42  1  0
 41 43  1  0
  7 10  1  0
 41 33  1  0
 19 65  1  0
 19 66  1  0
 19 67  1  0
 17 64  1  0
 16 63  1  0
 15 62  1  0
 14 59  1  0
 14 60  1  0
 14 61  1  0
 12 58  1  0
 11 57  1  0
 10 56  1  1
  1 44  1  0
  1 45  1  0
  1 46  1  0
  3 47  1  0
  6 48  1  0
  6 49  1  0
  8 50  1  0
  8 51  1  0
  8 52  1  0
  9 53  1  0
  9 54  1  0
  9 55  1  0
 20 68  1  0
 21 69  1  0
 22 70  1  0
 23 71  1  0
 25 72  1  0
 25 73  1  0
 25 74  1  0
 26 75  1  0
 27 76  1  0
 28 77  1  0
 30 78  1  0
 30 79  1  0
 30 80  1  0
 31 81  1  0
 32 82  1  0
 35 83  1  0
 35 84  1  0
 35 85  1  0
 38 86  1  1
 39 87  1  0
 40 88  1  0
 40 89  1  0
 42 90  1  0
 42 91  1  0
 42 92  1  0
 43 93  1  0
 43 94  1  0
 43 95  1  0
M  END


  Mrv1652309072203482D          

 43 44  0  0  1  0            999 V2000
   -2.8579  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8171  -11.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7565  -11.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -12.7875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4315   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3899  -12.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6153  -12.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 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
 36 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 33 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0241672

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=CC(=O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(=O)[C@@H](O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H52O3/c1-28(17-13-19-30(3)21-23-35-32(5)25-34(41)26-39(35,7)8)15-11-12-16-29(2)18-14-20-31(4)22-24-36-33(6)38(43)37(42)27-40(36,9)10/h11-25,35,37,42H,26-27H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,28-15+,29-16+,30-19+,31-20+/t35-,37-/m0/s1

> <INCHI_KEY>
LIMWSSBYWJHLNB-PSHRTHBJSA-N

> <FORMULA>
C40H52O3

> <MOLECULAR_WEIGHT>
580.853

> <EXACT_MASS>
580.391645534

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
72.44274704959054

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S)-6-hydroxy-2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-[(1R)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one

> <JCHEM_LOGP>
8.809917063666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.372727893431264

> <JCHEM_PKA_STRONGEST_BASIC>
-3.510568819413165

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
194.68190000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6S)-6-hydroxy-2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-[(1R)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335 -26.180   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668 -25.410   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002 -26.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336 -25.410   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0     -10.669 -26.180   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -9.336 -23.870   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002 -23.100   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.992 -21.920   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.012 -21.920   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668 -23.870   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334 -23.870   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000 -23.100   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334 -23.870   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668 -23.870   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002 -23.100   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336 -23.870   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336 -25.410   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669 -23.100   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.003 -23.870   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.337 -23.100   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.670 -23.870   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.670 -25.410   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.004 -23.100   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.004 -21.560   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.338 -20.790   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.338 -19.250   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.004 -18.480   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      18.672 -18.480   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      18.672 -16.940   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      20.005 -19.250   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      21.339 -18.480   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      20.005 -20.790   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      18.672 -21.560   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      19.394 -22.920   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      17.949 -22.920   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   41                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   33   42   43                                             
CONECT   42   41                                                            
CONECT   43   41                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₅₂O₃

Average Mass

580.8530 Da

Monoisotopic Mass

580.39165 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=CC(=O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(=O)[C@@H](O)CC1(C)C

InChI Identifier

InChI=1S/C40H52O3/c1-28(17-13-19-30(3)21-23-35-32(5)25-34(41)26-39(35,7)8)15-11-12-16-29(2)18-14-20-31(4)22-24-36-33(6)38(43)37(42)27-40(36,9)10/h11-25,35,37,42H,26-27H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,28-15+,29-16+,30-19+,31-20+/t35-,37-/m0/s1

InChI Key

LIMWSSBYWJHLNB-PSHRTHBJSA-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
Paralithodes brevipes	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
Cyclohexenone
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

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

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

29272853

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101316822

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Garcia-de Blas E, Mateo R, Alonso-Alvarez C: Accumulation of dietary carotenoids, retinoids and tocopherol in the internal tissues of a bird: a hypothesis for the cost of producing colored ornaments. Oecologia. 2015 Jan;177(1):259-71. doi: 10.1007/s00442-014-3163-8. Epub 2014 Nov 25. [PubMed:25421097 ]
Garcia-de Blas E, Mateo R, Guzman Bernardo FJ, Rodriguez Martin-Doimeadios RC, Alonso-Alvarez C: Astaxanthin and papilioerythrinone in the skin of birds: a chromatic convergence of two metabolic routes with different precursors? Naturwissenschaften. 2014 May;101(5):407-16. doi: 10.1007/s00114-014-1169-z. Epub 2014 Apr 2. [PubMed:24691990 ]
Prum RO, LaFountain AM, Berg CJ, Tauber MJ, Frank HA: Mechanism of carotenoid coloration in the brightly colored plumages of broadbills (Eurylaimidae). J Comp Physiol B. 2014 Jul;184(5):651-72. doi: 10.1007/s00360-014-0816-1. Epub 2014 Mar 20. [PubMed:24647990 ]
LaFountain AM, Frank HA, Prum RO: Carotenoids from the crimson and maroon plumages of Old World orioles (Oriolidae). Arch Biochem Biophys. 2013 Nov 15;539(2):126-32. doi: 10.1016/j.abb.2013.07.001. Epub 2013 Jul 12. [PubMed:23851380 ]
LOTUS database [Link]

Showing NP-Card for (6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one (NP0241672)

MOL for NP0241672 ((6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one)

3D MOL for NP0241672 ((6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one)

3D SDF for NP0241672 ((6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one)

3D-SDF for NP0241672 ((6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one)

PDB for NP0241672 ((6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one)

3D PDB for NP0241672 ((6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one)

SMILES for NP0241672 ((6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one)

INCHI for NP0241672 ((6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one)

Structure for NP0241672 ((6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one)

3D Structure for NP0241672 ((6s)-6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one)