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Showing NP-Card for 5,8-Epoxy-5,8-dihydro-3-hydroxy-8'-apo-b,y-carotenal (NP0337062)

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Record Information
Version2.0
Created at2024-09-11 09:06:18 UTC
Updated at2024-09-11 09:06:18 UTC
NP-MRD IDNP0337062
Secondary Accession NumbersNone
Natural Product Identification
Common Name5,8-Epoxy-5,8-dihydro-3-hydroxy-8'-apo-b,y-carotenal
Description5,8-Epoxy-5,8-dihydro-3-hydroxy-8'-apo-b,y-carotenal belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 5,8-Epoxy-5,8-dihydro-3-hydroxy-8'-apo-b,y-carotenal was first documented in 2024 (PMID: 39002916). Based on a literature review very few articles have been published on 5,8-Epoxy-5,8-dihydro-3-hydroxy-8'-apo-b,y-carotenal.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337062 (5,8-Epoxy-5,8-dihydro-3-hydroxy-8'-apo-b,y-carotenal)


  Mrv2104 05262311382D          

 33 34  0  0  0  0            999 V2000
   -3.9991   -0.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4990    0.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9153    0.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7488    0.5826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3324   -1.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1650   -1.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3317   -0.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7488   -0.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4984    0.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1670    0.9160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329    0.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1656    0.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657   -0.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990   -0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486    0.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9983   -0.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8316   -0.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4146   -0.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1650   -0.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7480   -1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9161   -0.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7486   -1.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3323   -1.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2487    2.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6657    1.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9161    1.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3323    1.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827    1.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004    0.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2493   -0.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4976   -0.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9147    0.5826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7480   -2.1656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  8  1  0  0  0  0
  1 22  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 25  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5 22  1  0  0  0  0
  6  7  1  0  0  0  0
  6 33  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 10 29  2  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
 14 16  1  0  0  0  0
 16 17  2  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
 19 31  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
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3D MOL for NP0337062 (5,8-Epoxy-5,8-dihydro-3-hydroxy-8'-apo-b,y-carotenal)

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3D SDF for NP0337062 (5,8-Epoxy-5,8-dihydro-3-hydroxy-8'-apo-b,y-carotenal)

  Mrv2104 05262311382D          

 33 34  0  0  0  0            999 V2000
   -3.9991   -0.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4990    0.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9153    0.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7488    0.5826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3324   -1.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1650   -1.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3317   -0.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7488   -0.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4984    0.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1670    0.9160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329    0.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1656    0.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657   -0.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990   -0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486    0.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9983   -0.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8316   -0.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4146   -0.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1650   -0.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7480   -1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9161   -0.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7486   -1.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3323   -1.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2487    2.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6657    1.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9161    1.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3323    1.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827    1.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004    0.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2493   -0.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4976   -0.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9147    0.5826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7480   -2.1656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  8  1  0  0  0  0
  1 22  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 25  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5 22  1  0  0  0  0
  6  7  1  0  0  0  0
  6 33  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 10 29  2  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
 14 16  1  0  0  0  0
 16 17  2  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
 19 31  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0337062

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(C=O)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(\C)C1OC2(C)CC(O)CC(C)(C)C2=C1

> <INCHI_IDENTIFIER>
InChI=1/C30H40O3/c1-22(14-10-16-24(3)21-31)12-8-9-13-23(2)15-11-17-25(4)27-18-28-29(5,6)19-26(32)20-30(28,7)33-27/h8-18,21,26-27,32H,19-20H2,1-7H3/b9-8+,14-10+,15-11+,22-12+,23-13+,24-16-,25-17-

> <INCHI_KEY>
DFTUPAXJLNIGJB-UUVOACAKNA-N

> <FORMULA>
C30H40O3

> <MOLECULAR_WEIGHT>
448.647

> <EXACT_MASS>
448.297745148

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.9771217981977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,4E,6E,8E,10E,12E,14Z)-15-(6-hydroxy-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-yl)-2,6,11-trimethylhexadeca-2,4,6,8,10,12,14-heptaenal

> <JCHEM_LOGP>
5.399139331666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.128958926789299

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7423933654223616

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
147.01130000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4E,6E,8E,10E,12E,14Z)-15-(6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl)-2,6,11-trimethylhexadeca-2,4,6,8,10,12,14-heptaenal

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0337062 (5,8-Epoxy-5,8-dihydro-3-hydroxy-8'-apo-b,y-carotenal)
Download
PDB for NP0337062 (5,8-Epoxy-5,8-dihydro-3-hydroxy-8'-apo-b,y-carotenal)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -7.465  -0.933   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.531   0.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.309   1.555   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -8.864   1.088   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -8.087  -3.420   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.641  -2.954   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.953  -1.555   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.864  -0.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.264   0.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.312   1.710   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.621   0.621   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.176   0.933   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.109  -0.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.665  -0.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.131   1.555   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.597  -1.088   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.152  -0.776   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.241  -1.865   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.641  -1.555   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.730  -2.798   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.443  -1.865   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.997  -2.332   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.220  -3.731   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.931   4.042   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.843   2.954   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.443   3.265   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.354   2.177   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.954   2.488   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.867   1.399   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.332  -0.154   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.262  -0.154   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.174   1.088   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -10.730  -4.042   0.000  0.00  0.00           O+0
CONECT    1    2    8   22                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    8                                                       
CONECT    5    6   22                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8                                                       
CONECT    8    1    4    7    9                                             
CONECT    9    8                                                            
CONECT   10   11   29                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   31                                                  
CONECT   20   19                                                            
CONECT   21   22                                                            
CONECT   22    1    5   21   23                                             
CONECT   23   22                                                            
CONECT   24   25                                                            
CONECT   25    3   24   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   10   28   30                                                  
CONECT   30   29                                                            
CONECT   31   19   32                                                       
CONECT   32   31                                                            
CONECT   33    6                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

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3D PDB for NP0337062 (5,8-Epoxy-5,8-dihydro-3-hydroxy-8'-apo-b,y-carotenal)
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SMILES for NP0337062 (5,8-Epoxy-5,8-dihydro-3-hydroxy-8'-apo-b,y-carotenal)
C\C(C=O)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(\C)C1OC2(C)CC(O)CC(C)(C)C2=C1
Download
INCHI for NP0337062 (5,8-Epoxy-5,8-dihydro-3-hydroxy-8'-apo-b,y-carotenal)
InChI=1/C30H40O3/c1-22(14-10-16-24(3)21-31)12-8-9-13-23(2)15-11-17-25(4)27-18-28-29(5,6)19-26(32)20-30(28,7)33-27/h8-18,21,26-27,32H,19-20H2,1-7H3/b9-8+,14-10+,15-11+,22-12+,23-13+,24-16-,25-17-
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View in JSmol
SynonymsNot Available
Chemical FormulaC30H40O3
Average Mass448.6470 Da
Monoisotopic Mass448.29775 Da
IUPAC Name(2Z,4E,6E,8E,10E,12E,14Z)-15-(6-hydroxy-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-yl)-2,6,11-trimethylhexadeca-2,4,6,8,10,12,14-heptaenal
Traditional Name(2Z,4E,6E,8E,10E,12E,14Z)-15-(6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl)-2,6,11-trimethylhexadeca-2,4,6,8,10,12,14-heptaenal
CAS Registry NumberNot Available
SMILES
C\C(C=O)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(\C)C1OC2(C)CC(O)CC(C)(C)C2=C1
InChI Identifier
InChI=1/C30H40O3/c1-22(14-10-16-24(3)21-31)12-8-9-13-23(2)15-11-17-25(4)27-18-28-29(5,6)19-26(32)20-30(28,7)33-27/h8-18,21,26-27,32H,19-20H2,1-7H3/b9-8+,14-10+,15-11+,22-12+,23-13+,24-16-,25-17-
InChI KeyDFTUPAXJLNIGJB-UUVOACAKNA-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 triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTriterpenoids  
Direct ParentTriterpenoids  
Alternative Parents
Substituents
  • Triterpenoid
    • 

  • Benzofuran
    • 

  • Alpha,beta-unsaturated aldehyde
    • 

  • Cyclic alcohol
    • 

  • Dihydrofuran
    • 

  • Enal
    • 

  • Secondary alcohol
    • 

  • Ether
    • 

  • Organoheterocyclic compound
    • 

  • Dialkyl ether
    • 

  • Oxacycle
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Aldehyde
    • 

  • Organic oxide
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP5.4ChemAxon
pKa (Strongest Acidic)15.13ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity147.01 m³·mol⁻¹ChemAxon
Polarizability54.98 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
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. Zhang C, Li L, Lin J, Luo J, Liu L, Peng X: Barley polysaccharides inhibit colorectal cancer by two relatively independent pathways. Int J Biol Macromol. 2024 Oct;277(Pt 3):133820. doi:  10.1016/j.ijbiomac.2024.133820. Epub 2024 Jul 11. [PubMed:39002916  ]