NP-MRD: Showing NP-Card for (2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol (NP0065851)

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Record Information

Version

2.0

Created at

2022-04-28 10:03:03 UTC

Updated at

2022-04-28 10:03:03 UTC

NP-MRD ID

NP0065851

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol

Description

Bacterioruberin 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, bacterioruberin is considered to be an isoprenoid. (2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol is found in Bacterium, Haloferax volcanii and Kocuria rosea. (2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol was first documented in 2021 (PMID: 34951666). Based on a literature review a small amount of articles have been published on bacterioruberin (PMID: 35390753) (PMID: 34942349) (PMID: 34870747) (PMID: 34822465).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212032D          

 54 53  0  0  1  0            999 V2000
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.3750    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.6125    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4375    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500    8.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6750    8.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0875    9.2881    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.6750   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2625   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3895   10.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9605    9.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9125    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3250   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1500   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9750   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1500   10.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1500    9.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7750    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4125   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2375   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 20 34  1  0  0  0  0
 16 35  1  0  0  0  0
 12 36  1  0  0  0  0
  7 37  1  0  0  0  0
  3 38  1  0  0  0  0
  1 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 43 42  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 44 47  1  0  0  0  0
 43 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 50 53  1  0  0  0  0
 40 54  1  0  0  0  0
M  END

     RDKit          3D

130129  0  0  0  0  0  0  0  0999 V2000
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   -2.2984    8.4627    0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2907    7.8055    0.9907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3795    8.1239    1.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0485    6.9924    2.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1137    6.8976    3.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8019    8.1441    3.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4742    5.5455    3.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4446    5.0426    4.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4555    3.6047    4.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2840    2.8113    4.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4238    3.4386    5.5877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0275    1.3799    4.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7610    0.4190    5.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3802   -1.0012    5.3619 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.7622   -1.7044    4.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0787   -0.9838    2.9455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3011   -1.6513    1.6003 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.7331   -1.7412    1.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5817   -0.6798    0.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6661   -2.8558    1.5090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3644   -1.7118    6.6432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3838   -1.0145    7.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8300   -3.1354    6.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5817   -1.8040    7.3082 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3584   -3.8804   -4.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2834   -6.1454   -3.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0114   -5.6503   -2.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2535   -5.5026   -1.2273 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7319   -4.9620    0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9201   -6.8199   -0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5280   -0.9656   -3.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
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 52125  1  0
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 53127  1  0
 53128  1  0
 53129  1  0
 54130  1  0
M  END


  Mrv1652304282212032D          

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  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
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  8  9  1  0  0  0  0
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 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 50 53  1  0  0  0  0
 40 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0065851

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H](CCC(C)(C)O)C(C)(C)O)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@H](CCC(C)(C)O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C50H76O4/c1-39(23-17-25-41(3)27-19-29-43(5)31-33-45(49(11,12)53)35-37-47(7,8)51)21-15-16-22-40(2)24-18-26-42(4)28-20-30-44(6)32-34-46(50(13,14)54)36-38-48(9,10)52/h15-34,45-46,51-54H,35-38H2,1-14H3/b16-15+,23-17+,24-18+,27-19+,28-20+,33-31+,34-32+,39-21+,40-22+,41-25+,42-26+,43-29+,44-30+/t45-,46-/m1/s1

> <INCHI_KEY>
UVCQMCCIAHQDAF-RNTVPSGKSA-N

> <FORMULA>
C50H76O4

> <MOLECULAR_WEIGHT>
741.154

> <EXACT_MASS>
740.574360927

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
130

> <JCHEM_AVERAGE_POLARIZABILITY>
96.43497948975363

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S,6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E,28E,30E,32S)-5,32-bis(2-hydroxypropan-2-yl)-2,8,12,16,21,25,29,35-octamethylhexatriaconta-6,8,10,12,14,16,18,20,22,24,26,28,30-tridecaene-2,35-diol

> <ALOGPS_LOGP>
8.19

> <JCHEM_LOGP>
10.106084564

> <ALOGPS_LOGS>
-6.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.518142973357126

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.518142973357126

> <JCHEM_PKA_STRONGEST_BASIC>
-0.45516418825913096

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
251.33000000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.50e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E,28E,30E,32S)-5,32-bis(2-hydroxypropan-2-yl)-2,8,12,16,21,25,29,35-octamethylhexatriaconta-6,8,10,12,14,16,18,20,22,24,26,28,30-tridecaene-2,35-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.780   5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.090   6.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.400   8.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.170   9.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.710   9.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.020  10.669   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.790  12.003   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.330  12.003   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.100  13.337   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.640  13.337   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.410  14.670   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.950  14.670   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.720  16.004   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      29.260  16.004   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      30.030  17.338   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.260  18.672   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      28.490  20.005   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      30.594  19.442   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      27.926  17.902   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      31.570  17.338   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      32.340  18.672   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      33.880  18.672   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      35.420  18.672   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      33.880  20.212   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      33.880  17.132   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      27.720  13.337   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      23.100  10.669   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      18.480   8.002   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.780   8.002   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.160   5.335   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -3.850  -1.334   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -2.310  -2.874   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -2.310   0.206   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       0.000  -5.335   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       0.770  -6.668   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -1.334  -6.105   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       1.334  -4.565   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
CONECT    1    2   39                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   37                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   36                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   35                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   34                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24                                                            
CONECT   28   23   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   20                                                            
CONECT   35   16                                                            
CONECT   36   12                                                            
CONECT   37    7                                                            
CONECT   38    3                                                            
CONECT   39    1   40                                                       
CONECT   40   39   41   54                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   48                                                  
CONECT   44   43   45   46   47                                             
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   44                                                            
CONECT   48   43   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   52   53                                             
CONECT   51   50                                                            
CONECT   52   50                                                            
CONECT   53   50                                                            
CONECT   54   40                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  106    0
END

View in JSmol

Synonyms

Value	Source
(2S,2's)-2,2'-Bis(3-hydroxy-3-methylbutyl)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-gamma,gamma-carotene-1,1'-diol	ChEBI
(5S,,6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E,28E,30E,32S)-5,32-Bis(2-hydroxypropan-2-yl)-2,8,12,16,21,25,29,35-octamethylhexatriaconta-6,8,10,12,14,16,18,20,22,24,26,28,30-tridecaene-2,35-diol	ChEBI
(2S,2's)-2,2'-Bis(3-hydroxy-3-methylbutyl)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-g,g-carotene-1,1'-diol	Generator
(2S,2's)-2,2'-Bis(3-hydroxy-3-methylbutyl)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-γ,γ-carotene-1,1'-diol	Generator

Chemical Formula

C₅₀H₇₆O₄

Average Mass

741.1540 Da

Monoisotopic Mass

740.57436 Da

IUPAC Name

(5S,6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E,28E,30E,32S)-5,32-bis(2-hydroxypropan-2-yl)-2,8,12,16,21,25,29,35-octamethylhexatriaconta-6,8,10,12,14,16,18,20,22,24,26,28,30-tridecaene-2,35-diol

Traditional Name

(5S,6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E,28E,30E,32S)-5,32-bis(2-hydroxypropan-2-yl)-2,8,12,16,21,25,29,35-octamethylhexatriaconta-6,8,10,12,14,16,18,20,22,24,26,28,30-tridecaene-2,35-diol

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H](CCC(C)(C)O)C(C)(C)O)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@H](CCC(C)(C)O)C(C)(C)O

InChI Identifier

InChI=1S/C50H76O4/c1-39(23-17-25-41(3)27-19-29-43(5)31-33-45(49(11,12)53)35-37-47(7,8)51)21-15-16-22-40(2)24-18-26-42(4)28-20-30-44(6)32-34-46(50(13,14)54)36-38-48(9,10)52/h15-34,45-46,51-54H,35-38H2,1-14H3/b16-15+,23-17+,24-18+,27-19+,28-20+,33-31+,34-32+,39-21+,40-22+,41-25+,42-26+,43-29+,44-30+/t45-,46-/m1/s1

InChI Key

UVCQMCCIAHQDAF-RNTVPSGKSA-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
Bacterium; sewage; soil	LOTUS Database	35616633
Haloferax volcanii	Archaea	KNApSAcK
Kocuria rosea	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
Tertiary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tertiary alcohol (CHEBI:49388 )
tetrol (CHEBI:49388 )
C50 carotenoid (CHEBI:49388 )

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	8.19	ALOGPS
logP	10.11	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	18.52	ChemAxon
pKa (Strongest Basic)	-0.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	251.33 m³·mol⁻¹	ChemAxon
Polarizability	96.43 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	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

C00023099

Chemspider ID

4945706

KEGG Compound ID

Not Available

BioCyc ID

CPD-18004

BiGG ID

Not Available

Wikipedia Link

Halobacterium

METLIN ID

Not Available

PubChem Compound

6441558

PDB ID

Not Available

ChEBI ID

49388

Good Scents ID

rw1416391

References

General References

Culka A, Jehlicka J, Oren A, Rousaki A, Vandenabeele P: Fast outdoor screening and discrimination of carotenoids of halophilic microorganisms using miniaturized Raman spectrometers. Spectrochim Acta A Mol Biomol Spectrosc. 2022 Aug 5;276:121156. doi: 10.1016/j.saa.2022.121156. Epub 2022 Mar 18. [PubMed:35390753 ]
Flegler A, Lipski A: The C50 carotenoid bacterioruberin regulates membrane fluidity in pink-pigmented Arthrobacter species. Arch Microbiol. 2021 Dec 24;204(1):70. doi: 10.1007/s00203-021-02719-3. [PubMed:34951666 ]
Serrano S, Mendo S, Caetano T: Haloarchaea have a high genomic diversity for the biosynthesis of carotenoids of biotechnological interest. Res Microbiol. 2022 Mar-Apr;173(3):103919. doi: 10.1016/j.resmic.2021.103919. Epub 2021 Dec 20. [PubMed:34942349 ]
Sahli K, Gomri MA, Esclapez J, Gomez-Villegas P, Bonete MJ, Leon R, Kharroub K: Characterization and biological activities of carotenoids produced by three haloarchaeal strains isolated from Algerian salt lakes. Arch Microbiol. 2021 Dec 4;204(1):6. doi: 10.1007/s00203-021-02611-0. [PubMed:34870747 ]
Giani M, Montoyo-Pujol YG, Peiro G, Martinez-Espinosa RM: Halophilic Carotenoids and Breast Cancer: From Salt Marshes to Biomedicine. Mar Drugs. 2021 Oct 21;19(11). pii: md19110594. doi: 10.3390/md19110594. [PubMed:34822465 ]

Showing NP-Card for (2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol (NP0065851)

MOL for NP0065851 ((2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol)

3D MOL for NP0065851 ((2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol)

3D SDF for NP0065851 ((2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol)

3D-SDF for NP0065851 ((2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol)

PDB for NP0065851 ((2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol)

3D PDB for NP0065851 ((2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol)

SMILES for NP0065851 ((2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol)

INCHI for NP0065851 ((2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol)

Structure for NP0065851 ((2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol)

3D Structure for NP0065851 ((2S,2'S)-3,3',4,4'-Tetradehydro-2,2'-bis(3-hydroxy-3-methylbutyl)-psi,psi-carotene-1,1'-diol)