NP-MRD: Showing NP-Card for 4-Oxoretinol (NP0092031)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 18:55:15 UTC

Updated at

2022-05-11 18:55:15 UTC

NP-MRD ID

NP0092031

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Oxoretinol

Description

4-Oxoretinol, also known as 4-oxo-rol or 4-oxovitamin A1, 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. 4-Oxoretinol is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Oxoretinol can be biosynthesized from vitamin a through the action of the enzyme cytochrome P450 26A1. In humans, 4-oxoretinol is involved in retinol metabolism. 4-Oxoretinol was first documented in 1996 (PMID: 9110564). A retinoid that is all-trans-retinol in which the hydrogens at position 4 have been replaced by an oxo group (PMID: 9581846).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 50 50  0  0  0  0  0  0  0  0999 V2000
   -3.5148    2.4460   -1.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0482    1.1616   -0.9511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1692    0.2531   -0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7715    0.6248   -0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7233   -0.0126   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6593    0.4852   -0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0298    1.7719   -0.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6396   -0.2785    0.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0523    0.1700    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0210   -0.5863    0.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524   -0.2764    0.7039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9783    0.9683    0.1569 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2548   -1.1834    1.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7056   -1.0315    1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1638    0.1521    0.7785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8127   -0.9476    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9929   -2.1180    0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6078   -0.5256    1.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8502   -1.4994   -0.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9453   -0.4933   -1.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4684    0.8846   -0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3042    1.7982   -0.7645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9675    2.9864   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3757    3.0499   -1.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8052    2.2960   -2.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5284    1.6108   -0.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8721   -0.9686    0.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2331    2.4572   -0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7297    1.5630   -1.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6857    2.3336    0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4049   -1.2333    0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2961    1.1203   -0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6722   -1.5503    1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6649    0.8598   -0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1164    1.5475   -0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4700    1.6273    0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8087   -2.1219    1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0837   -1.0918    2.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1709   -1.9084    0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0887    0.0431    0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592   -2.4928   -0.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273   -3.0109    0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5285   -2.0863    1.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0430   -0.8990    2.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5599   -1.0789    1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7429    0.5730    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3097   -1.6807   -1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2266   -2.4699   -0.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3659   -0.5743   -2.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7615   -0.6641   -0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  6  2  0
  6  7  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 21  1  0
 21 22  2  0
 21 20  1  0
 20 19  1  0
 19 16  1  0
 16 17  1  0
 16 18  1  0
 16  3  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 10 33  1  0
  9 32  1  0
  8 31  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  5 27  1  0
  4 26  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 20 49  1  0
 20 50  1  0
 19 47  1  0
 19 48  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
M  END


  Mrv0541 02231216232D          

 22 22  0  0  0  0            999 V2000
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    0.7145   -1.2375    0.0000 O   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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  2 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0092031

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,21H,11,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-12+

> <INCHI_KEY>
PLIUCYCUYQIBDZ-RMWYGNQTSA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.4351

> <EXACT_MASS>
300.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.69054164246209

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(1E,3E,5E,7E)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

> <ALOGPS_LOGP>
5.31

> <JCHEM_LOGP>
4.026809811666666

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.890472282116395

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.435617288805766

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1707943115512176

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
98.61659999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-oxoretinol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   10   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    2   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
4-Ketoretinol	ChEBI
4-oxo-ROL	ChEBI
3,7-Dimethyl-9-(3-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraen-1-ol	HMDB
4-Ketovitamin a(1)	HMDB
4-Ketovitamin-a-alcohol	HMDB
4-Ketovitamin-alpha-alcohol	HMDB
4-oxo-Retinol	HMDB
4-OxoROL	HMDB
4-Oxovitamin a1	HMDB
4-Oxovitamin-a-alcohol	HMDB
4-Oxovitamin-alpha-alcohol	HMDB
4OVA1	HMDB
all-trans-4-Oxoretinol	HMDB
OXR	HMDB

Chemical Formula

C₂₀H₂₈O₂

Average Mass

300.4351 Da

Monoisotopic Mass

300.20893 Da

IUPAC Name

3-[(1E,3E,5E,7E)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

Traditional Name

4-oxoretinol

CAS Registry Number

Not Available

SMILES

C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C

InChI Identifier

InChI=1S/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,21H,11,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-12+

InChI Key

PLIUCYCUYQIBDZ-RMWYGNQTSA-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

Retinoid skeleton
Diterpenoid
Fatty alcohol
Cyclohexenone
Fatty acyl
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinoid (CHEBI:44597 )
Retinoids (C16683 )

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	5.31	ALOGPS
logP	4.03	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	16.44	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.62 m³·mol⁻¹	ChemAxon
Polarizability	36.69 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012329

DrugBank ID

DB02699

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028948

KNApSAcK ID

Not Available

Chemspider ID

4451124

KEGG Compound ID

C16683

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5289090

PDB ID

OXR

ChEBI ID

44597

Good Scents ID

Not Available

References

General References

Ross SA, De Luca LM: A new metabolite of retinol: all-trans-4-oxo-retinol as a receptor activator and differentiation agent. Nutr Rev. 1996 Nov;54(11 Pt 1):355-6. doi: 10.1111/j.1753-4887.1996.tb03802.x. [PubMed:9110564 ]
Faria TN, Rivi R, Derguini F, Pandolfi PP, Gudas LJ: 4-Oxoretinol, a metabolite of retinol in the human promyelocytic leukemia cell line NB4, induces cell growth arrest and granulocytic differentiation. Cancer Res. 1998 May 1;58(9):2007-13. [PubMed:9581846 ]

Showing NP-Card for 4-Oxoretinol (NP0092031)

MOL for NP0092031 (4-Oxoretinol)

3D MOL for NP0092031 (4-Oxoretinol)

3D SDF for NP0092031 (4-Oxoretinol)

3D-SDF for NP0092031 (4-Oxoretinol)

PDB for NP0092031 (4-Oxoretinol)

3D PDB for NP0092031 (4-Oxoretinol)

SMILES for NP0092031 (4-Oxoretinol)

INCHI for NP0092031 (4-Oxoretinol)

Structure for NP0092031 (4-Oxoretinol)

3D Structure for NP0092031 (4-Oxoretinol)