NP-MRD: Showing NP-Card for Retinol acetate (NP0331898)

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Record Information

Version

2.0

Created at

2023-10-02 16:00:38 UTC

Updated at

2024-09-03 04:17:20 UTC

NP-MRD ID

NP0331898

Natural Product DOI

https://doi.org/10.57994/1004

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Retinol acetate

Description

Retinol acetate, also known as crystalets or davitan a 650, 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. Retinol acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Retinol acetate is a potentially toxic compound. Retinol acetate belongs to the family of Retinoids.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308172D          

 24 24  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    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
    5.0013   -0.4125    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
    5.0013   -1.2375    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
    4.2868    0.0000    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
    4.2868   -2.4750    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  1  0  0  0  0
 13 12  2  0  0  0  0
 15  8  1  0  0  0  0
 16 14  1  0  0  0  0
 17  1  1  0  0  0  0
 17  9  2  0  0  0  0
 17 12  1  0  0  0  0
 18  2  1  0  0  0  0
 18 10  1  0  0  0  0
 18 14  2  0  0  0  0
 19  3  1  0  0  0  0
 19 11  1  0  0  0  0
 20  4  1  0  0  0  0
 21 13  1  0  0  0  0
 21 19  2  0  0  0  0
 22  5  1  0  0  0  0
 22  6  1  0  0  0  0
 22 15  1  0  0  0  0
 22 21  1  0  0  0  0
 23 20  2  0  0  0  0
 24 16  1  0  0  0  0
 24 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331898

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC\C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3/b10-7+,13-12+,17-9-,18-14+

> <INCHI_KEY>
QGNJRVVDBSJHIZ-AQDFTDIISA-N

> <FORMULA>
C22H32O2

> <MOLECULAR_WEIGHT>
328.4883

> <EXACT_MASS>
328.240230268

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
40.515645291880475

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate

> <ALOGPS_LOGP>
6.56

> <JCHEM_LOGP>
5.135218583333335

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.004456796498005

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
107.0749

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.38e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5   22                                                            
CONECT    6   22                                                            
CONECT    7    9   10                                                       
CONECT    8   11   15                                                       
CONECT    9    7   17                                                       
CONECT   10    7   18                                                       
CONECT   11    8   19                                                       
CONECT   12   13   17                                                       
CONECT   13   12   21                                                       
CONECT   14   16   18                                                       
CONECT   15    8   22                                                       
CONECT   16   14   24                                                       
CONECT   17    1    9   12                                                  
CONECT   18    2   10   14                                                  
CONECT   19    3   11   21                                                  
CONECT   20    4   23   24                                                  
CONECT   21   13   19   22                                                  
CONECT   22    5    6   15   21                                             
CONECT   23   20                                                            
CONECT   24   16   20                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

View in JSmol

Synonyms

Value	Source
Retinol acetic acid	Generator
13-cis-Retinyl acetate	HMDB
Acetateall-trans-retinol	HMDB
Acetic acid, retinyl ester	HMDB
all-trans-Retinol acetate	HMDB
all-trans-Retinyl acetate	HMDB
all-trans-Retinylacetate	HMDB
all-trans-Vitamin a acetate	HMDB
Crystalets	HMDB
Davitan a 650	HMDB
Myvak	HMDB
Myvax	HMDB
O(15)-Acetylretinol	HMDB
O~15~-acetyl-retinol	HMDB
O~15~-acetylretinol	HMDB
Retinol acetate (JP15)	HMDB
RETINOL acetATE (see retinoidprojects 1 and 3)	HMDB
Retinol, acetate	HMDB
Retinol, acetate, all-trans- (8ci)	HMDB
Retinol, acetate, labeled with tritium	HMDB
Retinyl acetate	HMDB
trans-Retinyl acetate	HMDB
trans-Vitamin a acetate	HMDB
Vitamin a acetate	HMDB
Vitamin a acetate (tritiated)	HMDB
Vitamin a alcohol acetate	HMDB
Vitamin a ester	HMDB
Vitamin a, acetate	HMDB
Vitamin a1 acetate	HMDB
Dagravit a forte	HMDB
RetiNit	HMDB
Retinol acetate, (9,13-cis)-isomer	HMDB
Vitamin a dispersa	HMDB
Dif vitamin a masivo	HMDB
Vitamin-a-saar	HMDB
(2E,4E,6Z)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetic acid	Generator
9-cis-Retinyl acetate	MeSH
Retinol acetate	MeSH
Zuretinol acetic acid	Generator

Chemical Formula

C₂₂H₃₂O₂

Average Mass

328.4883 Da

Monoisotopic Mass

328.24023 Da

IUPAC Name

(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate

Traditional Name

(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC\C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3/b10-7+,13-12+,17-9-,18-14+

InChI Key

QGNJRVVDBSJHIZ-AQDFTDIISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-02	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-02	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-02	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

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
Fatty alcohol ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6.56	ALOGPS
logP	5.14	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	107.07 m³·mol⁻¹	ChemAxon
Polarizability	40.52 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon