NP-MRD: Showing NP-Card for (+)-Sargachromanol E (NP0078712)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 23:45:29 UTC

Updated at

2022-04-28 23:45:29 UTC

NP-MRD ID

NP0078712

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Sargachromanol E

Description

Sargachromanol E belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocopherols that contain a saturated trimethyltridecyl chain. (+)-Sargachromanol E is found in Sargassum siliquastrum . (+)-Sargachromanol E was first documented in 2011 (PMID: 21600262). Based on a literature review a small amount of articles have been published on Sargachromanol E (PMID: 23973192) (PMID: 35251696) (PMID: 23278330).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201452D          

 31 32  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1933    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6305    1.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4550    1.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8921    2.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7166    2.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1538    3.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9783    3.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4155    3.7278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2400    3.6990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6772    4.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5017    4.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9389    5.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8890    3.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6273    2.9705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0282    4.4562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3656    2.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8423    0.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   -0.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
  9 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  6  0  0  0
 20 27  1  6  0  0  0
 19 28  1  0  0  0  0
 15 29  1  0  0  0  0
  9 30  1  1  0  0  0
  2 31  1  0  0  0  0
M  END

     RDKit          3D

 71 72  0  0  0  0  0  0  0  0999 V2000
   -8.7750    0.8181   -0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3805    1.3052   -0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1541    2.7708   -0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3731    0.4757   -0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5848   -0.9900   -0.4800 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9412   -1.2477    0.8254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3513   -1.7152   -0.9439 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0837   -1.3914   -2.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2037   -1.2386   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2489   -1.4945    1.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1922   -0.6107   -0.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0464   -0.1223    0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8110   -0.8219   -0.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3547   -0.3276    0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7101    1.0910    0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -1.1829    1.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101   -0.7402    1.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4755   -1.4348    1.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9710   -1.2018    0.1973 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0131   -1.6666   -0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2685   -1.9899   -0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4346   -1.3162    0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5829    0.0679    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7834    0.6782   -0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8743    1.9651   -0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1057    2.5950   -0.7660 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7124    2.6384   -0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4764    2.0602   -0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2036    2.7651   -1.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4392    0.7587   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2116    0.1820   -0.0204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9943   -0.0330   -0.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5060    1.6506   -0.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8694    0.5003    0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9649    3.3335   -0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1698    2.9819   -0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0681    3.0325   -1.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3776    0.8448   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4267   -1.3176   -1.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7768   -0.4915    1.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4251   -2.7993   -0.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4305   -0.4833   -2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4496   -0.6096    1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0354   -2.2582    1.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994   -1.9624    1.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2400   -0.4640   -1.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9123    0.9813    0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2069   -0.3615    1.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8747   -1.9077   -0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6727   -0.5640   -1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    1.3288    0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071    1.4812    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0332    1.6558   -0.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7900   -2.2278    1.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0080   -0.9278    3.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4228    0.3632    1.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885   -2.5398    1.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2783   -1.0359    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557   -2.0088   -1.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5160   -0.7541   -1.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3168   -2.4520   -0.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1687   -3.0051    0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4760   -2.1064   -1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3437   -1.8858    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2859   -1.2902    1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6804    0.1352    0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9613    2.1250   -0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7532    3.6621   -1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7056    3.0444   -0.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4858    2.0553   -1.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3865    3.6310   -1.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 19 18  1  1
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 31 19  1  0
 30 23  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  6
  6 40  1  0
  7 41  1  6
  8 42  1  0
 10 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 15 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  0
 18 58  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 24 66  1  0
 26 67  1  0
 27 68  1  0
 29 69  1  0
 29 70  1  0
 29 71  1  0
M  END


  Mrv1652304292201452D          

 31 32  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1933    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6305    1.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4550    1.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8921    2.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7166    2.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1538    3.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9783    3.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4155    3.7278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2400    3.6990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6772    4.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5017    4.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9389    5.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8890    3.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6273    2.9705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0282    4.4562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3656    2.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8423    0.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   -0.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
  9 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  6  0  0  0
 20 27  1  6  0  0  0
 19 28  1  0  0  0  0
 15 29  1  0  0  0  0
  9 30  1  1  0  0  0
  2 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078712

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C[C@H](O)[C@@H](O)C(\C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O4/c1-18(2)15-24(29)25(30)20(4)11-7-9-19(3)10-8-13-27(6)14-12-22-17-23(28)16-21(5)26(22)31-27/h10-11,15-17,24-25,28-30H,7-9,12-14H2,1-6H3/b19-10+,20-11+/t24-,25-,27+/m0/s1

> <INCHI_KEY>
YIWOAJFKIIOXPS-BXYCSXDPSA-N

> <FORMULA>
C27H40O4

> <MOLECULAR_WEIGHT>
428.613

> <EXACT_MASS>
428.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.35325948059978

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,5S,6E,10E)-13-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-triene-4,5-diol

> <ALOGPS_LOGP>
5.50

> <JCHEM_LOGP>
6.1143288233333335

> <ALOGPS_LOGS>
-5.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.359185326919569

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.141411387548668

> <JCHEM_PKA_STRONGEST_BASIC>
-3.337998625169279

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
130.56470000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.91e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5S,6E,10E)-13-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-triene-4,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.817   0.536   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.094   1.896   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.910   3.202   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.449   3.148   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.265   4.454   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.804   4.400   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.620   5.706   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.160   5.652   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.976   6.958   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.515   6.905   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.331   8.211   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.870   8.157   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.686   9.463   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.593   6.797   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.238   5.545   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      11.253   8.318   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.883   4.293   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.172   1.788   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.540  -0.716   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   12   30                                             
CONECT   10    9   11                                                       
CONECT   11   10    4                                                       
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   29                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21                                                            
CONECT   27   20                                                            
CONECT   28   19                                                            
CONECT   29   15                                                            
CONECT   30    9                                                            
CONECT   31    2                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₀O₄

Average Mass

428.6130 Da

Monoisotopic Mass

428.29266 Da

IUPAC Name

(4S,5S,6E,10E)-13-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-triene-4,5-diol

Traditional Name

(4S,5S,6E,10E)-13-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6,10-triene-4,5-diol

CAS Registry Number

Not Available

SMILES

CC(C)=C[C@H](O)[C@@H](O)C(\C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1

InChI Identifier

InChI=1S/C27H40O4/c1-18(2)15-24(29)25(30)20(4)11-7-9-19(3)10-8-13-27(6)14-12-22-17-23(28)16-21(5)26(22)31-27/h10-11,15-17,24-25,28-30H,7-9,12-14H2,1-6H3/b19-10+,20-11+/t24-,25-,27+/m0/s1

InChI Key

YIWOAJFKIIOXPS-BXYCSXDPSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Sargassum siliquastrum	Chromalveolata	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocopherols that contain a saturated trimethyltridecyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Tocotrienols

Alternative Parents

Substituents

Tocotrienol
Diterpenoid
Chromane
Benzopyran
1-benzopyran
Fatty alcohol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Benzenoid
Secondary alcohol
1,2-diol
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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
logP	5.5	ALOGPS
logP	6.11	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	10.14	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	130.56 m³·mol⁻¹	ChemAxon
Polarizability	51.35 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00042951

Chemspider ID

9514329

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11339386

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee JH, Ko JY, Samarakoon K, Oh JY, Heo SJ, Kim CY, Nah JW, Jang MK, Lee JS, Jeon YJ: Preparative isolation of sargachromanol E from Sargassum siliquastrum by centrifugal partition chromatography and its anti-inflammatory activity. Food Chem Toxicol. 2013 Dec;62:54-60. doi: 10.1016/j.fct.2013.08.010. Epub 2013 Aug 20. [PubMed:23973192 ]
Natarajan PM, Umapathy VR, Murali A, Swamikannu B: Computational simulations of identified marine-derived natural bioactive compounds as potential inhibitors of oral cancer. Future Sci OA. 2022 Jan 24;8(3):FSO782. doi: 10.2144/fsoa-2021-0148. eCollection 2022 Mar. [PubMed:35251696 ]
Kim JA, Ahn BN, Kong CS, Kim SK: The chromene sargachromanol E inhibits ultraviolet A-induced ageing of skin in human dermal fibroblasts. Br J Dermatol. 2013 May;168(5):968-76. doi: 10.1111/bjd.12187. Epub 2013 Apr 2. [PubMed:23278330 ]
Heo SJ, Kim KN, Yoon WJ, Oh C, Choi YU, Affan A, Lee YJ, Lee HS, Kang DH: Chromene induces apoptosis via caspase-3 activation in human leukemia HL-60 cells. Food Chem Toxicol. 2011 Sep;49(9):1998-2004. doi: 10.1016/j.fct.2011.05.011. Epub 2011 May 11. [PubMed:21600262 ]

Showing NP-Card for (+)-Sargachromanol E (NP0078712)

MOL for NP0078712 ((+)-Sargachromanol E)

3D MOL for NP0078712 ((+)-Sargachromanol E)

3D SDF for NP0078712 ((+)-Sargachromanol E)

3D-SDF for NP0078712 ((+)-Sargachromanol E)

PDB for NP0078712 ((+)-Sargachromanol E)

3D PDB for NP0078712 ((+)-Sargachromanol E)

SMILES for NP0078712 ((+)-Sargachromanol E)

INCHI for NP0078712 ((+)-Sargachromanol E)

Structure for NP0078712 ((+)-Sargachromanol E)

3D Structure for NP0078712 ((+)-Sargachromanol E)