Retinyl acetate

Details

• Internal ID: 9b08029d-96c6-438b-bace-490f9392df95
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Retinoids
• IUPAC Name: [(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] acetate
• SMILES (Canonical): CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCOC(=O)C)C)C
• SMILES (Isomeric): CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/COC(=O)C)/C)/C
• InChI: 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-QHLGVNSISA-N
• Popularity: 1,737 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₂
• Molecular Weight: 328.50 g/mol
• Exact Mass: 328.240230259 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 6.30
• Atomic LogP (AlogP): 6.08
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• Vitamin A acetate
• Retinol acetate
• 127-47-9
• Retinol, acetate
• all-trans-Retinyl acetate
• Crystalets
• Myvak
• Myvax
• Vitamin A1 acetate
• all-trans-Retinol acetate
• Vitamin A alcohol acetate
• Davitan A 650
• Vitamin A ester
• all-trans-Vitamin A acetate
• Retinol, acetate, all-trans-
• Myvak (VAN)
• Myvax (VAN)
• O~15~-acetylretinol
• all-trans-Retinylacetate
• Vitamin A acetate (VAN)
• Acetic acid, retinyl ester
• Retinyl acetate, all-trans-
• NSC 122045
• CCRIS 1907
• trans-Retinyl acetate
• [(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] acetate
• RO 1-5275
• Retinol acetate [JAN]
• trans-Vitamin A acetate
• EINECS 204-844-2
• (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate
• UNII-3LE3D9D6OY
• BRN 1915439
• 3LE3D9D6OY
• Vitamin A acetate (tritiated)
• DTXSID6021240
• CHEBI:32095
• 9-cis,13-cis-Retinol15-Acetate
• NSC-122045
• NSC-122760
• Retinol, acetate, labeled with tritium
• NCGC00090756-09
• Retinol Acetate/All-trans-retinyl Acetate
• EC 204-844-2
• VitaminAacetate
• DTXCID701240
• Vitamin A, acetate
• O(15)-acetylretinol
• 9-cis Retinol Acetate
• 64536-04-5
• CAS-127-47-9
• trans-Retinol Acetate
• Retinol, acetate, 13-cis-
• SR-05000001431
• Retinol acetate;Vitamin A acetate
• retinyl-acetate
• WLN: L6UTJ A1 B1U1Y1 & U2U1Y1 & U2OV1 C1 C1
• Retinol, acetato
• Vitamin A acetat
• Vitamine A acetate
• 34356-31-5
• Acetic acid retinyl
• MFCD00019413
• ORISTAR RA
• 9-cis-Retinol acetate;9-cis-Vitamin A acetate
• (13Z)-Retinol acetate
• Spectrum5_001195
• Spectrum5_002001
• Retinol acetate (JP17)
• Retinyl (Retinol) Acetate
• RETINOL ACETATE (SEE RETINOIDPROJECTS 1 AND 3)
• retinol, O~15~-acetyl-
• BSPBio_002833
• SPECTRUM1503051
• RETINYL ACETATE [INCI]
• C22H32O2 (retinol acetate)
• CHEMBL486193
• VITAMIN A ACETATE [MI]
• CHEBI:94695
• HMS501K04
• RETINOL ACETATE [WHO-DD]
• RETINYL ACETATE [USP-RS]
• VITAMIN A ACETATE [VANDF]
• HMS1922A19
• HMS2089G20
• Pharmakon1600-01503051
• AMY13865
• HY-N0679
• Retinyl acetate, analytical standard
• Tox21_113549
• Tox21_201423
• Tox21_302737
• BDBM50442911
• CCG-39564
• LMPR01090012
• LS-712
• NSC122045
• NSC122760
• NSC758220
• s4083
• AKOS015914999
• Tox21_113549_1
• CS-8187
• CS-O-02562
• NSC-758220
• 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate
• IDI1_000522
• NCGC00090756-01
• NCGC00090756-02
• NCGC00090756-03
• NCGC00090756-05
• NCGC00090756-06
• NCGC00090756-07
• NCGC00090756-08
• NCGC00090756-10
• NCGC00090756-11
• NCGC00090756-12
• NCGC00256509-01
• NCGC00258974-01
• VITAMIN A (AS ACETATE) [VANDF]
• AC-19999
• ALL-(E)-RETINOL ACETATE [WHO-IP]
• SBI-0051756.P002
• VITAMIN A ACETATE 1.5 M.I.U./G
• RO-1-5275
• A16783
• D01621
• H12041
• Vitamin A acetate 10 microg/mL in Acetonitrile
• AB00052305-02
• AB00052305_03
• EN300-18533003
• EN300-25359996
• Vitamin A acetate in gelatin, 500,000 I.U./g
• Q7316808
• SR-05000001431-1
• SR-05000001431-3
• W-108382
• BRD-K65331431-001-01-3
• Vitamin A (acetate), meets USP testing specifications
• VITAMIN A (AS ACETATE & BETA CAROTENE) [VANDF]
• Retinol acetate, European Pharmacopoeia (EP) Reference Standard
• Retinyl acetate, synthetic, crystalline solid or supercooled liquid
• Retinyl acetate, United States Pharmacopeia (USP) Reference Standard
• RETINOID PROJECT 3 (RETINOL ACETATE) (SEE RETINOID PROJECT 1, 2, AND 4)
• Retinyl acetate, solid or viscous liquid, BioReagent, synthetic, suitable for cell culture
• Retinyl acetate, synthetic, matrix dispersion, 475,000-650,000 USP units/g
• (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenyl acetate
• 3,7-Dimethyl-9-(2,6,6,-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol acetate, (all trans)-
• InChI=1/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
• Retinyl Acetate (Vitamin A Acetate), Pharmaceutical Secondary Standard; Certified Reference Material

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9965	99.65%
Caco-2	+	0.8481	84.81%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6550	65.50%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	-	0.4738	47.38%
OATP1B3 inhibitior	-	0.5699	56.99%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.9686	96.86%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8885	88.85%
CYP3A4 substrate	+	0.6567	65.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8852	88.52%
CYP3A4 inhibition	-	0.9420	94.20%
CYP2C9 inhibition	-	0.8729	87.29%
CYP2C19 inhibition	-	0.7811	78.11%
CYP2D6 inhibition	-	0.9110	91.10%
CYP1A2 inhibition	-	0.7514	75.14%
CYP2C8 inhibition	-	0.6660	66.60%
CYP inhibitory promiscuity	-	0.6383	63.83%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6528	65.28%
Carcinogenicity (trinary)	Warning	0.5486	54.86%
Eye corrosion	-	0.9400	94.00%
Eye irritation	-	0.9209	92.09%
Skin irritation	+	0.6758	67.58%
Skin corrosion	-	0.9885	98.85%
Ames mutagenesis	-	0.7923	79.23%
Human Ether-a-go-go-Related Gene inhibition	+	0.8310	83.10%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.8148	81.48%
skin sensitisation	+	0.8040	80.40%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	-	0.8000	80.00%
Nephrotoxicity	+	0.8555	85.55%
Acute Oral Toxicity (c)	III	0.6553	65.53%
Estrogen receptor binding	+	0.6414	64.14%
Androgen receptor binding	-	0.5496	54.96%
Thyroid receptor binding	+	0.7066	70.66%
Glucocorticoid receptor binding	-	0.5282	52.82%
Aromatase binding	+	0.8466	84.66%
PPAR gamma	+	0.5640	56.40%
Honey bee toxicity	-	0.8862	88.62%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6555	65.55%
Fish aquatic toxicity	+	0.9946	99.46%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	6309.6 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	14125.4 nM; 22387.2 nM; 18869.9 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	12589.3 nM; 8912.5 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1697668	Q9Y6L6	Solute carrier organic anion transporter family member 1B1	2238.72 nM	IC50	PMID: 23571415
CHEMBL1743121	Q9NPD5	Solute carrier organic anion transporter family member 1B3	5011.87 nM	IC50	PMID: 23571415
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	3548.1 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.35%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	94.18%	89.63%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.00%	91.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.94%	95.50%
CHEMBL2061	P19793	Retinoid X receptor alpha	92.86%	91.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.32%	86.33%
CHEMBL1870	P28702	Retinoid X receptor beta	91.00%	95.00%
CHEMBL1937	Q92769	Histone deacetylase 2	88.81%	94.75%
CHEMBL2004	P48443	Retinoid X receptor gamma	88.37%	100.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.15%	91.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.19%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.86%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.08%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.48%	96.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.45%	98.75%

Plants that contains it

• Nelumbo nucifera

Cross-Links

• PubChem: 638034
• NPASS: NPC226066
• ChEMBL: CHEMBL486193