NP-MRD: Showing NP-Card for 4-Oxoretinal (NP0339092)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 19:38:46 UTC

Updated at

2024-09-11 19:38:47 UTC

NP-MRD ID

NP0339092

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Oxoretinal

Description

4-Oxoretinal, also known as 4OVA, 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-Oxoretinal is an extremely weak basic (essentially neutral) compound (based on its pKa). They induced a moderate response for epidermal inflammation, compared with retinal, whereas neither 4-oxoretinal nor 4-oxoretinol prevented menadione-induced epidermal lipid peroxidation, unlike retinal and retinol. As analyzed in vivo and in vitro, 4-oxoretinal and 4-oxoretinol were not converted into retinoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303262014172D          

 22 22  0  0  0  0            999 V2000
   11.6199  -15.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0324  -14.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8574  -14.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2698  -15.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8574  -16.0649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6199  -13.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0324  -13.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6199  -12.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0324  -11.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8574  -11.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6199  -11.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7950  -11.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3825  -10.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7950   -9.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6199   -9.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3825   -8.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5575   -8.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1451   -9.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3201   -9.6345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5575  -10.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8430  -10.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5575  -11.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 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
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339092

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCC(=O)C1(C)C)=C/C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O2/c1-15(7-6-8-16(2)13-14-21)9-11-18-17(3)10-12-19(22)20(18,4)5/h6-9,11,13-14H,10,12H2,1-5H3/b8-6+,11-9+,15-7+,16-13+

> <INCHI_KEY>
ZORDCCAUKPDLPN-ZBSJWCJSSA-N

> <FORMULA>
C20H26O2

> <MOLECULAR_WEIGHT>
298.4192

> <EXACT_MASS>
298.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.762863124329385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

> <ALOGPS_LOGP>
5.47

> <JCHEM_LOGP>
4.188468097333335

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.83826678218938

> <JCHEM_PKA_STRONGEST_BASIC>
-4.061166896614546

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
97.55859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0      21.690 -28.654   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.460 -27.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.000 -27.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.770 -28.654   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      24.000 -29.988   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      21.690 -25.986   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.460 -24.653   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.690 -23.319   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.460 -21.985   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.000 -21.985   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.690 -20.652   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.151 -20.652   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.381 -19.318   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.151 -17.984   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.690 -17.984   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.381 -16.651   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.841 -16.651   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.071 -17.984   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      15.531 -17.984   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      17.841 -19.318   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.507 -20.088   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.841 -20.858   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   13   18   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
3,7-Dimethyl-9-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-all-trans-2,4,6,8-nonatetraenal	HMDB
4-Ketoretinal	HMDB
4-oxo-all-trans-Retinal	HMDB
4OVA	HMDB

Chemical Formula

C₂₀H₂₆O₂

Average Mass

298.4192 Da

Monoisotopic Mass

298.19328 Da

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

Traditional Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCC(=O)C1(C)C)=C/C=O

InChI Identifier

InChI=1S/C20H26O2/c1-15(7-6-8-16(2)13-14-21)9-11-18-17(3)10-12-19(22)20(18,4)5/h6-9,11,13-14H,10,12H2,1-5H3/b8-6+,11-9+,15-7+,16-13+

InChI Key

ZORDCCAUKPDLPN-ZBSJWCJSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Cyclohexenone
Enal
Alpha,beta-unsaturated aldehyde
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

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	5.47	ALOGPS
logP	4.19	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	19.84	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.56 m³·mol⁻¹	ChemAxon
Polarizability	35.76 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

HMDB0012794

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029176

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481523

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 4-Oxoretinal (NP0339092)

MOL for NP0339092 (4-Oxoretinal)

3D MOL for NP0339092 (4-Oxoretinal)

3D SDF for NP0339092 (4-Oxoretinal)

3D-SDF for NP0339092 (4-Oxoretinal)

PDB for NP0339092 (4-Oxoretinal)

3D PDB for NP0339092 (4-Oxoretinal)

SMILES for NP0339092 (4-Oxoretinal)

INCHI for NP0339092 (4-Oxoretinal)

Structure for NP0339092 (4-Oxoretinal)

3D Structure for NP0339092 (4-Oxoretinal)