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Showing NP-Card for epsilon,epsilon-Carotene-3,3'-dione (NP0333987)

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Record Information
Version2.0
Created at2024-09-09 21:33:45 UTC
Updated at2024-09-09 21:33:45 UTC
NP-MRD IDNP0333987
Secondary Accession NumbersNone
Natural Product Identification
Common Nameepsilon,epsilon-Carotene-3,3'-dione
DescriptionConstituent of Sebastes flavidus and other fishand is) also found in chitons Carotene-3,3'-dione is a carotenoid found in human fluids.; Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds and crustacea. Animals are unable to synthesise carotenoids de novo, and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important. (PMID: 1416048 , 15003396 )
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0333987 (epsilon,epsilon-Carotene-3,3'-dione)


  Mrv2104 05252300062D          

 56 57  0  0  0  0            999 V2000
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M  END
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3D MOL for NP0333987 (epsilon,epsilon-Carotene-3,3'-dione)

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3D SDF for NP0333987 (epsilon,epsilon-Carotene-3,3'-dione)

  Mrv2104 05252300062D          

 56 57  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0333987

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])/C(/[H])=C(/C)\C(\[H])=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])C1C(C)=CC(=O)CC1(C)C)\C(\[H])=C(/C)\C(\[H])=C(/[H])\C(\[H])=C(\C)C([H])=C([H])C1C(C)=CC(=O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1/C40H52O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-26,37-38H,27-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15-,30-16+,31-19+,32-20-

> <INCHI_KEY>
IMFOMPZKWQBDLQ-NRERWQMGNA-N

> <FORMULA>
C40H52O2

> <MOLECULAR_WEIGHT>
564.854

> <EXACT_MASS>
564.396730914

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
71.69415897171075

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5,5-trimethyl-4-[(3Z,5E,7E,9E,11Z,13E,15E,17E)-3,7,12,16-tetramethyl-18-(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>
9.572451591333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.061422914011064

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.459362922683106

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5058655287530005

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
193.38120000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3,5,5-trimethyl-4-[(3Z,5E,7E,9E,11Z,13E,15E,17E)-3,7,12,16-tetramethyl-18-(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>
1

$$$$

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3D-SDF for NP0333987 (epsilon,epsilon-Carotene-3,3'-dione)
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PDB for NP0333987 (epsilon,epsilon-Carotene-3,3'-dione)
HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0      -1.334  26.950   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  30.030   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  22.330   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  34.650   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  17.710   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  39.270   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.344  21.970   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.324  21.970   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.991  35.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.011  35.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  25.410   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  26.950   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  25.410   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  31.570   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  24.640   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  27.720   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  24.640   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  30.030   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335  24.640   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  32.340   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001  22.330   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  34.650   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001  20.790   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334  36.190   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334  17.710   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.001  39.270   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000  20.020   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.335  36.960   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334  25.410   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  29.260   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.335  23.100   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000  33.880   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.667  18.480   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667  38.500   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000  18.480   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.335  38.500   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.667  20.020   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.667  36.960   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.334  20.790   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.001  36.190   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       1.334  17.710   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -6.668  39.270   0.000  0.00  0.00           O+0
HETATM   43  H   UNK     0       2.667  24.640   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.000  27.720   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.001  26.950   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.667  32.340   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.000  23.100   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.001  26.950   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.667  23.100   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.000  29.260   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0      -6.668  25.410   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.334  31.570   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.001  23.870   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.887  33.213   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.335  20.020   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.000  36.960   0.000  0.00  0.00           H+0
CONECT    1   29                                                            
CONECT    2   30                                                            
CONECT    3   31                                                            
CONECT    4   32                                                            
CONECT    5   33                                                            
CONECT    6   34                                                            
CONECT    7   39                                                            
CONECT    8   39                                                            
CONECT    9   40                                                            
CONECT   10   40                                                            
CONECT   11   43   12   15                                                  
CONECT   12   11   44   16                                                  
CONECT   13   45   17   19                                                  
CONECT   14   46   18   20                                                  
CONECT   15   11   47   29                                                  
CONECT   16   12   48   30                                                  
CONECT   17   13   49   29                                                  
CONECT   18   14   50   30                                                  
CONECT   19   13   51   31                                                  
CONECT   20   14   52   32                                                  
CONECT   21   53   23   31                                                  
CONECT   22   54   24   32                                                  
CONECT   23   21   55   37                                                  
CONECT   24   22   56   38                                                  
CONECT   25   33   35                                                       
CONECT   26   34   36                                                       
CONECT   27   35   39                                                       
CONECT   28   36   40                                                       
CONECT   29    1   15   17                                                  
CONECT   30    2   16   18                                                  
CONECT   31    3   19   21                                                  
CONECT   32    4   20   22                                                  
CONECT   33    5   25   37                                                  
CONECT   34    6   26   38                                                  
CONECT   35   25   27   41                                                  
CONECT   36   26   28   42                                                  
CONECT   37   23   33   39                                                  
CONECT   38   24   34   40                                                  
CONECT   39    7    8   27   37                                             
CONECT   40    9   10   28   38                                             
CONECT   41   35                                                            
CONECT   42   36                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  114    0
END

Download
3D PDB for NP0333987 (epsilon,epsilon-Carotene-3,3'-dione)
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SMILES for NP0333987 (epsilon,epsilon-Carotene-3,3'-dione)
[H]\C(=C(\[H])/C(/[H])=C(/C)\C(\[H])=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])C1C(C)=CC(=O)CC1(C)C)\C(\[H])=C(/C)\C(\[H])=C(/[H])\C(\[H])=C(\C)C([H])=C([H])C1C(C)=CC(=O)CC1(C)C
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INCHI for NP0333987 (epsilon,epsilon-Carotene-3,3'-dione)
InChI=1/C40H52O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-26,37-38H,27-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15-,30-16+,31-19+,32-20-
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View in JSmol
SynonymsNot Available
Chemical FormulaC40H52O2
Average Mass564.8540 Da
Monoisotopic Mass564.39673 Da
IUPAC Name3,5,5-trimethyl-4-[(3Z,5E,7E,9E,11Z,13E,15E,17E)-3,7,12,16-tetramethyl-18-(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
Traditional Name3,5,5-trimethyl-4-[(3Z,5E,7E,9E,11Z,13E,15E,17E)-3,7,12,16-tetramethyl-18-(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
CAS Registry NumberNot Available
SMILES
[H]\C(=C(\[H])/C(/[H])=C(/C)\C(\[H])=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])C1C(C)=CC(=O)CC1(C)C)\C(\[H])=C(/C)\C(\[H])=C(/[H])\C(\[H])=C(\C)C([H])=C([H])C1C(C)=CC(=O)CC1(C)C
InChI Identifier
InChI=1/C40H52O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-26,37-38H,27-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15-,30-16+,31-19+,32-20-
InChI KeyIMFOMPZKWQBDLQ-NRERWQMGNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTetraterpenoids  
Direct ParentXanthophylls  
Alternative Parents
Substituents
  • Xanthophyll
    • 

  • Cyclohexenone
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Enone
    • 

  • Acryloyl-group
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.57ChemAxon
pKa (Strongest Acidic)18.46ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity193.38 m³·mol⁻¹ChemAxon
Polarizability71.69 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Khachik F, Beecher GR, Goli MB, Lusby WR, Smith JC Jr: Separation and identification of carotenoids and their oxidation products in the extracts of human plasma. Anal Chem. 1992 Sep 15;64(18):2111-22. doi: 10.1021/ac00042a016. [PubMed:1416048  ] 
  2. Nagao A, Maoka T, Ono H, Kotake-Nara E, Kobayashi M, Tomita M: A 3-hydroxy beta-end group in xanthophylls is preferentially oxidized to a 3-oxo epsilon-end group in mammals. J Lipid Res. 2015 Feb;56(2):449-62. doi: 10.1194/jlr.P055459. Epub 2014 Dec 12. [PubMed:25502844  ] 
  3. Yonekura L, Kobayashi M, Terasaki M, Nagao A: Keto-carotenoids are the major metabolites of dietary lutein and fucoxanthin in mouse tissues. J Nutr. 2010 Oct;140(10):1824-31. doi: 10.3945/jn.110.126466. Epub 2010 Aug 25. [PubMed:20739451  ] 
  4. Hudon J, Anciaes M, Bertacche V, Stradi R: Plumage carotenoids of the Pin-tailed Manakin (Ilicura militaris): evidence for the endogenous production of rhodoxanthin from a colour variant. Comp Biochem Physiol B Biochem Mol Biol. 2007 Jul;147(3):402-11. doi:  10.1016/j.cbpb.2007.02.004. Epub 2007 Feb 24. [PubMed:17400013  ] 
  5. Khachik F, de Moura FF, Chew EY, Douglass LW, Ferris FL 3rd, Kim J, Thompson DJ: The effect of lutein and zeaxanthin supplementation on metabolites of these carotenoids in the serum of persons aged 60 or older. Invest Ophthalmol Vis Sci. 2006 Dec;47(12):5234-42. doi: 10.1167/iovs.06-0504. [PubMed:17122108  ]