NP-MRD: Showing NP-Card for Apo-15-zeaxanthinal (NP0045774)

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Record Information

Version

2.0

Created at

2022-03-17 19:37:11 UTC

Updated at

2022-03-17 19:37:12 UTC

NP-MRD ID

NP0045774

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apo-15-zeaxanthinal

Description

Apo-15-zeaxanthinal 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. Thus, apo-15-zeaxanthinal is considered to be an isoprenoid lipid molecule. Apo-15-zeaxanthinal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

 
  Mrv1652302041919222D          

 22 22  0  0  1  0            999 V2000
   14.7477  -16.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7477  -17.0169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.4621  -17.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1766  -17.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1766  -16.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4621  -15.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0332  -17.4294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0454  -15.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8788  -15.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9021  -15.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6123  -16.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3090  -15.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0126  -16.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7126  -15.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4145  -16.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1154  -15.7829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8168  -16.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5179  -15.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2193  -16.1879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9021  -17.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3089  -14.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1154  -14.9545    0.0000 C   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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  1  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 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
  4 20  1  0  0  0  0
 12 21  1  0  0  0  0
 16 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045774

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C)=C/C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-15(7-6-8-16(2)11-12-21)9-10-19-17(3)13-18(22)14-20(19,4)5/h6-12,18,22H,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-11+/t18-/m1/s1

> <INCHI_KEY>
QPRQNCDEPWLQRO-ZCEAMUHZSA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.4351

> <EXACT_MASS>
300.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.5911536566155

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-9-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenal

> <ALOGPS_LOGP>
5.41

> <JCHEM_LOGP>
3.4690329316666664

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.907213404525137

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0893213750655364

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
98.53489999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E,8E)-9-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenal

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-FEB-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-FEB-19         0                                  
HETATM    1  C   UNK     0      27.529 -30.225   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.529 -31.765   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.863 -32.535   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.196 -31.765   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.196 -30.225   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.863 -29.455   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      26.195 -32.535   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      29.951 -28.366   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.774 -28.366   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.551 -29.443   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.876 -30.208   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.177 -29.457   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.490 -30.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.797 -29.460   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      38.107 -30.217   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      39.415 -29.461   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      40.725 -30.217   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      42.033 -29.462   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      43.343 -30.217   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      31.551 -32.547   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      34.177 -27.915   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      39.415 -27.915   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1    8    9                                             
CONECT    7    2                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20    4                                                            
CONECT   21   12                                                            
CONECT   22   16                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
(-)-(R)-all-trans-3-Hydroxyretinal	ChEBI

Chemical Formula

C₂₀H₂₈O₂

Average Mass

300.4351 Da

Monoisotopic Mass

300.20893 Da

IUPAC Name

(2E,4E,6E,8E)-9-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenal

Traditional Name

(2E,4E,6E,8E)-9-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenal

CAS Registry Number

60046-53-9

SMILES

C\C(\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C)=C/C=O

InChI Identifier

InChI=1S/C20H28O2/c1-15(7-6-8-16(2)11-12-21)9-10-19-17(3)13-18(22)14-20(19,4)5/h6-12,18,22H,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-11+/t18-/m1/s1

InChI Key

QPRQNCDEPWLQRO-ZCEAMUHZSA-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
Capsicum annuum	FooDB	KNAPSACK

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
Enal
Alpha,beta-unsaturated aldehyde
Secondary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinoid (CHEBI:52228 )
Retinoids (LMPR01090049 )

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	5.41	ALOGPS
logP	3.47	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	18.91	ChemAxon
pKa (Strongest Basic)	-1.1	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	98.53 m³·mol⁻¹	ChemAxon
Polarizability	36.59 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001761

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C18196

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

52228

Good Scents ID

Not Available

References

General References

Showing NP-Card for Apo-15-zeaxanthinal (NP0045774)

MOL for NP0045774 (Apo-15-zeaxanthinal)

3D MOL for NP0045774 (Apo-15-zeaxanthinal)

3D SDF for NP0045774 (Apo-15-zeaxanthinal)

3D-SDF for NP0045774 (Apo-15-zeaxanthinal)

PDB for NP0045774 (Apo-15-zeaxanthinal)

3D PDB for NP0045774 (Apo-15-zeaxanthinal)

SMILES for NP0045774 (Apo-15-zeaxanthinal)

INCHI for NP0045774 (Apo-15-zeaxanthinal)

Structure for NP0045774 (Apo-15-zeaxanthinal)

3D Structure for NP0045774 (Apo-15-zeaxanthinal)