NP-MRD: Showing NP-Card for all-trans-5,6-Epoxyretinoic acid (NP0092150)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 18:58:41 UTC

Updated at

2022-05-11 18:58:41 UTC

NP-MRD ID

NP0092150

Secondary Accession Numbers

None

Natural Product Identification

Common Name

all-trans-5,6-Epoxyretinoic acid

Description

All-trans-5,6-Epoxyretinoic acid, also known as 5,6-epoxy-5,6-dihydro-retinoic acid or 5,6-epoxyretinoic acid, sodium salt, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. All-trans-5,6-Epoxyretinoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. All-trans-5,6-epoxyretinoic acid can be biosynthesized from all-trans-retinoic acid; which is mediated by the enzyme cytochrome P450. A retinoid obtained by epoxidation across the 5,6-double bond of retinoic acid. all-trans-5,6-Epoxyretinoic acid was first documented in 1978 (PMID: 275830). In humans, all-trans-5,6-epoxyretinoic acid is involved in retinol metabolism (PMID: 12703967) (PMID: 15606149) (PMID: 1859380) (PMID: 4091803).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 52  0  0  0  0  0  0  0  0999 V2000
    1.1555   -1.1023    1.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9207   -0.2581    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372    0.0463   -0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5474   -0.3406    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8547    0.1002   -0.1182 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9198    0.3898   -1.4554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4943   -0.7811   -1.0152 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7364   -2.0265   -1.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9703   -0.9648   -0.9594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7116    0.0860   -0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0021    0.3084    1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6700    0.9628    0.7801 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8918    2.3293    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9759    1.2156    2.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9544    0.2160   -0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2970   -0.1138    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    0.3440   -0.5830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7272    0.0878   -0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1175   -0.7303    0.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6613    0.6225   -1.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0612    0.4096   -0.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5264   -0.2619    0.2121 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0304    0.9973   -1.5780 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8833   -1.9337    1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2353   -1.6046    1.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499   -0.5323    2.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5437    0.6801   -0.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4994   -0.9506    1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2276   -2.3499   -2.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873   -1.7809   -1.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8885   -2.8649   -0.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1653   -1.9444   -0.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4085   -1.1097   -1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8666    1.0201   -0.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7156   -0.3519    0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7810   -0.6685    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5585    0.9835    1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6270    2.8922    0.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1861    2.2523   -0.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8877    2.8363    0.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6588    1.7601    2.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1279    1.8884    1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6239    0.2611    2.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7558    0.8318   -1.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4414   -0.7182    0.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1118    0.9697   -1.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7120   -0.0853    1.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7050   -1.6196    0.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2626   -1.0928    1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3662    1.2363   -1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8489    0.4590   -1.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
  2 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 23  1  0
 21 22  2  0
  7  5  1  0
 12  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 23 51  1  0
M  END


  Mrv1652307091917132D          

 23 24  0  0  0  0            999 V2000
    7.8815  -10.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0444  -10.9130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7875  -11.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5017  -11.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2163  -11.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9307  -11.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6451  -11.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3596  -11.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0739  -11.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7884  -11.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5028  -11.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2171  -11.6733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0739  -10.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2163  -10.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5028  -10.4358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3714  -13.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8838  -12.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3585  -11.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6442  -11.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6442  -12.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3585  -12.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0731  -12.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0731  -11.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 14  5  1  0  0  0  0
 15 11  2  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  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  1  0  0  0  0
  2 18  1  0  0  0  0
  1 18  1  0  0  0  0
 22 17  1  0  0  0  0
 22 16  1  0  0  0  0
  2 23  1  0  0  0  0
  3 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0092150

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C12OC1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-15(8-6-9-16(2)14-17(21)22)10-13-20-18(3,4)11-7-12-19(20,5)23-20/h6,8-10,13-14H,7,11-12H2,1-5H3,(H,21,22)/b9-6+,13-10+,15-8+,16-14+

> <INCHI_KEY>
KEEHJLBAOLGBJZ-WEDZBJJJSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.4345

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.19479182962852

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid

> <ALOGPS_LOGP>
5.74

> <JCHEM_LOGP>
4.540570249333333

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.936687619832732

> <JCHEM_PKA_STRONGEST_BASIC>
-4.282240537384268

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
96.5225

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.91e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-19         0                                  
HETATM    1  C   UNK     0      14.712 -19.926   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      16.883 -20.371   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      18.270 -21.020   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.603 -21.790   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.937 -21.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.271 -21.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.604 -21.020   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.938 -21.790   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.271 -21.020   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.605 -21.790   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.939 -21.020   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      30.272 -21.790   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      26.271 -19.480   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.937 -19.480   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      28.939 -19.480   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      17.493 -24.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.450 -23.077   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.603 -21.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.269 -21.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.269 -23.330   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.603 -24.100   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.936 -23.330   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.936 -21.790   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2   18   23                                                       
CONECT    3    4   23                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11                                                            
CONECT   13    9                                                            
CONECT   14    5                                                            
CONECT   15   11                                                            
CONECT   16   22                                                            
CONECT   17   22                                                            
CONECT   18   19   23    2    1                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   17   16                                             
CONECT   23   18   22    2    3                                             
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
all-trans-5,6-Epoxy-5,6-dihydroretinoic acid	ChEBI
all-trans-5,6-Epoxy-5,6-dihydroretinoate	Generator
all-trans-5,6-Epoxyretinoate	Generator
5,6-Epoxy-5,6-dihydro-retinoate	HMDB
5,6-Epoxy-5,6-dihydro-retinoic acid	HMDB
5,6-Epoxyretinoic acid, (13-cis)-isomer	HMDB
5,6-Epoxyretinoic acid, sodium salt	HMDB
5,6-Epoxyretinoic acid	HMDB
5,6-Epoxy-5,6-dihydroretinoic acid	HMDB
5,6-Epoxy-atra	HMDB
all-trans-5,6-Epoxyretinoic acid	HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4345 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid

Traditional Name

(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C12OC1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(O)=O

InChI Identifier

InChI=1S/C20H28O3/c1-15(8-6-9-16(2)14-17(21)22)10-13-20-18(3,4)11-7-12-19(20,5)23-20/h6,8-10,13-14H,7,11-12H2,1-5H3,(H,21,22)/b9-6+,13-10+,15-8+,16-14+

InChI Key

KEEHJLBAOLGBJZ-WEDZBJJJSA-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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents

Substituents

Retinoic acid
Diterpenoid
Retinoid skeleton
Medium-chain fatty acid
Branched fatty acid
Epoxy fatty acid
Heterocyclic fatty acid
Oxepane
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Carboxylic acid derivative
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Ether
Oxacycle
Oxirane
Dialkyl ether
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

retinoid (CHEBI:80658 )
Retinoids (C16680 )

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	5.74	ALOGPS
logP	4.54	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.94	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.52 m³·mol⁻¹	ChemAxon
Polarizability	37.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012451

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029067

KNApSAcK ID

Not Available

Chemspider ID

4515523

KEGG Compound ID

C16680

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5363137

PDB ID

Not Available

ChEBI ID

80658

Good Scents ID

Not Available

References

General References

Panzella L, Manini P, Crescenzi O, Napolitano A, d'Ischia M: Nitrite-induced nitration pathways of retinoic acid, 5,6-epoxyretinoic acid, and their esters under mildly acidic conditions: toward a reappraisal of retinoids as scavengers of reactive nitrogen species. Chem Res Toxicol. 2003 Apr;16(4):502-11. doi: 10.1021/tx0256836. [PubMed:12703967 ]
Panzella L, Manini P, Napolitano A, d'Ischia M: Free radical oxidation of (E)-retinoic acid by the Fenton reagent: competing epoxidation and oxidative breakdown pathways and novel products of 5,6-epoxyretinoic acid transformation. Chem Res Toxicol. 2004 Dec;17(12):1716-24. doi: 10.1021/tx049794b. [PubMed:15606149 ]
Barua AB, Gunning DB, Olson JA: Metabolism in vivo of all-trans-[11-3H]retinoic acid after an oral dose in rats. Characterization of retinoyl beta-glucuronide in the blood and other tissues. Biochem J. 1991 Jul 15;277 ( Pt 2)(Pt 2):527-31. doi: 10.1042/bj2770527. [PubMed:1859380 ]
Napoli JL, McCormick AM, Schnoes HK, DeLuca HF: Identification of 5,8-oxyretinoic acid isolated from small intestine of vitamin A-deficient rats dosed with retinoic acid. Proc Natl Acad Sci U S A. 1978 Jun;75(6):2603-5. doi: 10.1073/pnas.75.6.2603. [PubMed:275830 ]
Iwahashi H, Ikeda A, Kido R: Haemoglobin-catalysed retinoic acid 5,6-epoxidation. Biochem J. 1985 Dec 1;232(2):459-66. doi: 10.1042/bj2320459. [PubMed:4091803 ]

Showing NP-Card for all-trans-5,6-Epoxyretinoic acid (NP0092150)

MOL for NP0092150 (all-trans-5,6-Epoxyretinoic acid)

3D MOL for NP0092150 (all-trans-5,6-Epoxyretinoic acid)

3D SDF for NP0092150 (all-trans-5,6-Epoxyretinoic acid)

3D-SDF for NP0092150 (all-trans-5,6-Epoxyretinoic acid)

PDB for NP0092150 (all-trans-5,6-Epoxyretinoic acid)

3D PDB for NP0092150 (all-trans-5,6-Epoxyretinoic acid)

SMILES for NP0092150 (all-trans-5,6-Epoxyretinoic acid)

INCHI for NP0092150 (all-trans-5,6-Epoxyretinoic acid)

Structure for NP0092150 (all-trans-5,6-Epoxyretinoic acid)

3D Structure for NP0092150 (all-trans-5,6-Epoxyretinoic acid)