Tocoretinate

Details

• Internal ID: 39402dbf-5f38-41f1-a15a-2881230b97aa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Quinone and hydroquinone lipids > Vitamin E compounds
• IUPAC Name: [(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl] (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate
• SMILES (Canonical): CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)OC2=C(C3=C(C(=C2C)C)OC(CC3)(C)CCCC(C)CCCC(C)CCCC(C)C)C)C)C
• SMILES (Isomeric): CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)OC2=C(C3=C(C(=C2C)C)O[C@](CC3)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C)/C)/C
• InChI: InChI=1S/C49H76O3/c1-34(2)19-14-20-35(3)21-15-22-36(4)25-17-31-49(13)32-29-43-42(10)46(40(8)41(9)47(43)52-49)51-45(50)33-38(6)24-16-23-37(5)27-28-44-39(7)26-18-30-48(44,11)12/h16,23-24,27-28,33-36H,14-15,17-22,25-26,29-32H2,1-13H3/b24-16+,28-27+,37-23+,38-33+/t35-,36-,49-/m1/s1
• InChI Key: RIQIJXOWVAHQES-UNAKLNRMSA-N
• Popularity: 304 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₇₆O₃
• Molecular Weight: 713.10 g/mol
• Exact Mass: 712.57944628 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 16.90
• Atomic LogP (AlogP): 14.57
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 18

Synonyms

• tretinoin tocoferil
• 40516-48-1
• Tocopheryl retinoate
• Tretinoin tocoferil [INN]
• Toco-retinoate
• UNII-CTD060B1SS
• 40516-49-2
• CTD060B1SS
• alpha-Tocopheryl retinoate
• Tretinoin tocoferil (JAN)
• UNII-0WN694NBMM
• dl-alpha-TocopherylRetinoate
• d-alpha-Tocopheryl Retinoate
• 0WN694NBMM
• NCGC00181354-01
• [(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl] (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate
• DTXSID6046923
• CHEBI:32240
• L300
• olcenon
• TRETINOIN TOCOFERIL [JAN]
• C49-H76-O3
• (+-)-(2R*)-2,5,7,8-Tetramethyl-2-((4R*,8R*)-4,8,12-trimethyltridecyl)-6-chromanyl retinoate
• AC1NQZMB
• Tocorretinate
• dl-alpha-Tocopheryl Retinoate
• (+-)-(2R*)-2,5,7,8-tetramethyl-2-[(4R*,8R*)-4,8,12-trimethyltridecyl]-6-chromanyl retinoate
• L-300
• N-021
• TOCORETINATE [MI]
• TOCORETINATE [JAN]
• SCHEMBL668391
• CHEMBL262520
• DTXCID4026923
• TOCOPHERYL RETINOATE [INCI]
• C49H76O3
• Retinoic acid, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-yl ester, (2R-(2R*(4R*,8R*)))-
• .ALPHA.-TOCOPHERYL RETINOATE
• Tox21_112812
• AC-790
• TRETINOIN TOCOFERIL [WHO-DD]
• AKOS015961939
• D-.ALPHA.-TOCOPHEROL RETINOATE
• D-.ALPHA.-TOCOPHERYL RETINOATE
• [(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]chroman-6-yl] (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate
• N021
• CAS-40516-48-1
• D01516
• RETINOIC ACID .ALPHA.-TOCOPHERYL ESTER [MI]
• Q27114835
• (+/-)-(2R*)-2,5,7,8-TETRAMETHYL-2-((4R*,8R*)-4,8,12-TRIMETHYLTRIDECYL)-6-CHROMANYL RETINOATE
• (2E,4E,6E,8E)-((R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl) 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate
• (2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol retinoate
• RETINOIC ACID, (2R)-3,4-DIHYDRO-2,5,7,8-TETRAMETHYL-2-((4R,8R)-4,8,12-TRIMETHYLTRIDECYL)-2H-1-BENZOPYRAN-6-YL ESTER
• RETINOIC ACID, (2R)-3,4-DIHYDRO-2,5,7,8-TETRAMETHYL-2-((4R,8R)-4,8,12-TRIMETHYLTRIDECYL)-2H-1-BENZOPYRAN-6-YL ESTER, (+/-)-
• RETINOIC ACID, 3,4-DIHYDRO-2,5,7,8-TETRAMETHYL-2-(4,8,12-TRIMETHYLTRIDECYL)-2H-1-BENZOPYRAN-6-YL ESTER, (2R*(4R*,8R*))-(+/-)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9963	99.63%
Caco-2	-	0.7982	79.82%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7916	79.16%
OATP2B1 inhibitior	+	0.5691	56.91%
OATP1B1 inhibitior	+	0.7381	73.81%
OATP1B3 inhibitior	+	0.8855	88.55%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9973	99.73%
P-glycoprotein inhibitior	+	0.8130	81.30%
P-glycoprotein substrate	+	0.5981	59.81%
CYP3A4 substrate	+	0.7298	72.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8811	88.11%
CYP3A4 inhibition	-	0.6498	64.98%
CYP2C9 inhibition	-	0.6241	62.41%
CYP2C19 inhibition	+	0.8074	80.74%
CYP2D6 inhibition	-	0.8495	84.95%
CYP1A2 inhibition	+	0.5058	50.58%
CYP2C8 inhibition	+	0.6675	66.75%
CYP inhibitory promiscuity	+	0.5754	57.54%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6845	68.45%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9045	90.45%
Skin irritation	-	0.7248	72.48%
Skin corrosion	-	0.9719	97.19%
Ames mutagenesis	-	0.8045	80.45%
Human Ether-a-go-go-Related Gene inhibition	+	0.9070	90.70%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.6077	60.77%
skin sensitisation	-	0.6645	66.45%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.4626	46.26%
Acute Oral Toxicity (c)	IV	0.5581	55.81%
Estrogen receptor binding	+	0.8905	89.05%
Androgen receptor binding	+	0.8303	83.03%
Thyroid receptor binding	+	0.8461	84.61%
Glucocorticoid receptor binding	+	0.8110	81.10%
Aromatase binding	+	0.8685	86.85%
PPAR gamma	+	0.6746	67.46%
Honey bee toxicity	-	0.7402	74.02%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6445	64.45%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.01%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.13%	94.45%
CHEMBL2061	P19793	Retinoid X receptor alpha	95.81%	91.67%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	94.94%	98.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	93.97%	95.50%
CHEMBL1870	P28702	Retinoid X receptor beta	92.72%	95.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.06%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.56%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.54%	96.09%
CHEMBL2004	P48443	Retinoid X receptor gamma	91.34%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	90.72%	94.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.64%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.81%	95.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.62%	96.47%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.85%	89.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.61%	93.56%
CHEMBL3902	P09211	Glutathione S-transferase Pi	85.90%	93.81%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.87%	91.71%
CHEMBL3401	O75469	Pregnane X receptor	85.76%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.95%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.93%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.43%	96.77%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.34%	89.50%
CHEMBL2039	P27338	Monoamine oxidase B	82.22%	92.51%
CHEMBL230	P35354	Cyclooxygenase-2	82.19%	89.63%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.96%	89.05%
CHEMBL236	P41143	Delta opioid receptor	80.45%	99.35%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.04%	90.08%

Plants that contains it

• Sesamum indicum

Cross-Links

• PubChem: 5282180
• NPASS: NPC156298