Vitamin A palmitate

Details

• Internal ID: 2c2bd2fe-f964-4824-a188-4ecbc6f3cac9
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters > Wax esters > Wax monoesters
• IUPAC Name: [(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] hexadecanoate
• SMILES (Canonical): CCCCCCCCCCCCCCCC(=O)OCC=C(C)C=CC=C(C)C=CC1=C(CCCC1(C)C)C
• SMILES (Isomeric): CCCCCCCCCCCCCCCC(=O)OC/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(CCCC1(C)C)C
• InChI: InChI=1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20+,27-26+,31-22+,32-28+
• InChI Key: VYGQUTWHTHXGQB-FFHKNEKCSA-N
• Popularity: 2,644 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₆₀O₂
• Molecular Weight: 524.90 g/mol
• Exact Mass: 524.45933115 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 13.60
• Atomic LogP (AlogP): 11.54
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 20

Synonyms

• VITAMIN A PALMITATE
• 79-81-2
• Retinol palmitate
• Retinol, hexadecanoate
• all-trans-Retinyl palmitate
• Arovit
• Optovit-A
• Retinyl hexadecanoate
• Aquapalm
• Dispatabs Tabs
• Vitazyme A
• Optovit A
• Axerophthol palmitate
• Vitamin A Solubilized
• trans-Retinol palmitate
• trans-Retinyl palmitate
• Retinyl (Vitamin A) Palmitate
• Lutavit A 500 Plus
• all-trans-Retinol palmitate
• [(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] hexadecanoate
• C36H60O2
• Arovit (Roche)
• all-trans-Vitamin A palmitate
• Aquasol A (TN)
• CCRIS 3280
• Retinol, palmitate, all-trans-
• Retinol palmitate [JAN]
• EINECS 201-228-5
• O~15~-hexadecanoylretinol
• UNII-1D1K0N0VVC
• NSC-758478
• BRN 1917366
• 1D1K0N0VVC
• Retinol, palmitate, all-trans
• Retinol palmitate (6CI,7CI)
• Retinol, all-trans-, palmitate
• DTXSID1021241
• CHEBI:17616
• Palmitic acid, ester with retinol
• all-trans-RetinylPalmitate-d5(Major)
• Retinol, palmitate, all-trans- (8CI)
• NCGC00095056-03
• EC 201-228-5
• (2E,4E,6E,8E)-Hexadecanoic acid 3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2, 4,6,8,tetraenyl ester
• DTXCID101241
• Retinyl (palmitate)
• CAS-79-81-2
• (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl hexadecanoate
• SMR000112463
• retinylpalmitate
• retinol-palmitate
• retinyl-palmitate
• Vitamin A palmitate;Retinol palmitate
• 1331666-45-5
• Palmitic acid retinol
• Retinyl palmitic acid
• Vitamin- A palmitate
• Retinol, hexadecanoato
• O~15~-palmitoylretinol
• Retinyl hexadecanoic acid
• Spectrum5_001201
• All-(e)-retinol palmitate
• bmse000501
• Retinol palmitate (JP17)
• CHEMBL1675
• SCHEMBL41649
• MLS001332437
• MLS001332438
• SPECTRUM1503604
• all-trans-retinyl hexadecanoate
• RETINYL PALMITATE [INCI]
• HMS500M11
• RETINYL PALMITATE [VANDF]
• VITAMIN A PALMITATE [MI]
• Vitamin a palmitate (solubilized)
• HMS1922E10
• HMS2093G13
• HMS2268C06
• Pharmakon1600-01503604
• RETINOL PALMITATE [WHO-DD]
• RETINYL PALMITATE [USP-RS]
• AMY13840
• HY-B1384
• VAE 16:0
• VITAMIN A PALMITATE [VANDF]
• Tox21_113452
• Tox21_303008
• CCG-39342
• LMPR01090013
• MFCD00019414
• NSC758478
• s4126
• retinol, O~15~-(1-oxohexadecyl)-
• AKOS015918435
• C36-H60-O2
• CS-O-02552
• LS-2307
• NSC 758478
• Vitamin A palmitate, 1.7 M.I.U./g
• IDI1_000249
• NCGC00095056-01
• NCGC00095056-02
• NCGC00256427-01
• AC-20001
• MS-29721
• VITAMIN A PALMITATE [ORANGE BOOK]
• SBI-0051830.P002
• ALL-(E)-RETINOL PALMITATE [WHO-IP]
• CS-0013116
• C02588
• C76552
• D00164
• AB00052360_04
• A839762
• SR-05000001910
• VITAMIN A PALMITATE (SOLUBILIZED) [VANDF]
• Q7316807
• SR-05000001910-1
• Retinyl palmitate (Vitamin A palmitate; Retinol palmitate)
• Retinyl palmitate, potency: >=1,700,000 USP units per g
• VITAMIN A (AS PALMITATE & BETA CAROTENE) [VANDF]
• Retinyl palmitate, United States Pharmacopeia (USP) Reference Standard
• [3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] hexadecanoate
• 3,7-Dimethyl-9-(2,6,6,-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol palmitate
• (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-en-1-yl)-2,4,6,8-nonateetraen-1-yl-palmitate
• (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenyl palmitate
• 110067-62-4
• 37340-08-2
• hexadecanoic acid [(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl] ester
• Retinyl Palmitate (Vitamin A Palmitate), Pharmaceutical Secondary Standard; Certified Reference Material

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.5802	58.02%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6731	67.31%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7960	79.60%
OATP1B3 inhibitior	+	0.8223	82.23%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.9967	99.67%
P-glycoprotein inhibitior	-	0.8136	81.36%
P-glycoprotein substrate	-	0.7063	70.63%
CYP3A4 substrate	+	0.6856	68.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8852	88.52%
CYP3A4 inhibition	-	0.8487	84.87%
CYP2C9 inhibition	-	0.8807	88.07%
CYP2C19 inhibition	-	0.7576	75.76%
CYP2D6 inhibition	-	0.8891	88.91%
CYP1A2 inhibition	-	0.7442	74.42%
CYP2C8 inhibition	+	0.5569	55.69%
CYP inhibitory promiscuity	-	0.5215	52.15%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7000	70.00%
Carcinogenicity (trinary)	Warning	0.5686	56.86%
Eye corrosion	-	0.9242	92.42%
Eye irritation	-	0.8761	87.61%
Skin irritation	-	0.6435	64.35%
Skin corrosion	-	0.9955	99.55%
Ames mutagenesis	-	0.9708	97.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.8056	80.56%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.8625	86.25%
skin sensitisation	+	0.6833	68.33%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	-	0.5250	52.50%
Mitochondrial toxicity	-	0.9125	91.25%
Nephrotoxicity	+	0.7438	74.38%
Acute Oral Toxicity (c)	IV	0.6306	63.06%
Estrogen receptor binding	-	0.8681	86.81%
Androgen receptor binding	-	0.5357	53.57%
Thyroid receptor binding	+	0.5238	52.38%
Glucocorticoid receptor binding	+	0.6021	60.21%
Aromatase binding	+	0.5787	57.87%
PPAR gamma	+	0.5276	52.76%
Honey bee toxicity	-	0.9059	90.59%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.7718	77.18%
Fish aquatic toxicity	+	0.9971	99.71%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL230	P35354	Cyclooxygenase-2	99.71%	89.63%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.11%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.91%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.78%	86.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	93.63%	91.71%
CHEMBL2061	P19793	Retinoid X receptor alpha	93.43%	91.67%
CHEMBL1870	P28702	Retinoid X receptor beta	92.98%	95.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.47%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.91%	99.17%
CHEMBL2581	P07339	Cathepsin D	91.26%	98.95%
CHEMBL2004	P48443	Retinoid X receptor gamma	90.60%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.77%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.67%	94.45%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	86.91%	92.86%
CHEMBL299	P17252	Protein kinase C alpha	86.39%	98.03%
CHEMBL221	P23219	Cyclooxygenase-1	86.23%	90.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.35%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.48%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	84.38%	94.75%
CHEMBL2996	Q05655	Protein kinase C delta	83.94%	97.79%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.14%	96.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.05%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.49%	99.23%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.68%	98.75%

Plants that contains it

• Fagopyrum esculentum

Cross-Links

• PubChem: 5280531
• NPASS: NPC228978
• ChEMBL: CHEMBL1675