Retinol

Details

• Internal ID: 70dbb575-48cb-43c9-abe0-f961a4a04c62
• 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-tetraen-1-ol
• SMILES (Canonical): CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCO)C)C
• SMILES (Isomeric): CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/CO)/C)/C
• InChI: InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
• InChI Key: FPIPGXGPPPQFEQ-OVSJKPMPSA-N
• Popularity: 56,165 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O
• Molecular Weight: 286.50 g/mol
• Exact Mass: 286.229665576 g/mol
• Topological Polar Surface Area (TPSA): 20.20 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.51
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• Vitamin A
• all-trans-Retinol
• 68-26-8
• Vitamin A1
• Alphalin
• Chocola A
• Alphasterol
• Apostavit
• Aquasynth
• Axerophthol
• Epiteliol
• Prepalin
• Testavol
• Veroftal
• Afaxin
• Agiolan
• Agoncal
• Anatola
• Apexol
• Dofsol
• Myvpack
• Vaflol
• Vitpex
• Aoral
• trans-retinol
• Vitamin A alcohol
• Disatabs Tabs
• Oleovitamin A
• Bentavit A
• Dohyfral A
• Alcovit A
• Anatola A
• Vogan-Neu
• all-trans-Retinyl alcohol
• A-Mulsal
• Biosterol
• Ophthalamin
• Plivit A
• Vi-Alpha
• A-Vitan
• All-trans retinol
• Atars
• Avibon
• Avitol
• Axerol
• Vafol
• Vogan
• Retrovitamin A
• Lard Factor
• all-trans-Vitamin A alcohol
• Homagenets Aoral
• Sehkraft A
• Testavol S
• Hi-A-Vita
• Vitamin A1 alcohol
• A-Sol
• all-trans-Vitamin A
• A-Vi-Pel
• ACON
• ATAV
• Super A
• Solu-A
• 11103-57-4
• Nio-A-Let
• Vio-A
• Vi-Dom-A
• Anti-infective vitamin
• Antixerophthalmic vitamin
• Vitavel A
• Del-VI-A
• Wachstumsvitamin
• Vitamine A
• Vitavel-A
• Axerophtholum
• Retinolo
• Retinolum
• Thalasphere
• beta-Retinol
• Vitamin A1, all-trans-
• Vitamin A alcohol, all-trans-
• Vitaminum A
• Hydrovit A
• trans-Vitamin A alcohol
• Retinolo [DCIT]
• Cylasphere
• Vi-alpha; Vi-alpha
• Retinol, all trans-
• Antixerophthalmisches Vitamin
• Rovimix A 500
• all-trans-Vitamin A1
• Retinol [INN:BAN]
• Retinolum [INN-Latin]
• Vitamin A1 alcohol, all trans
• All Trans Retinol
• Ro-a-vit
• tROL
• Vitamin A alcohol (VAN)
• Retinol (Vit A)
• (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
• Aquasol A Parenteral
• CCRIS 5444
• HSDB 815
• C20H30O
• Vitamin-A
• UNII-G2SH0XKK91
• .beta.-Retinol
• (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol
• EINECS 200-683-7
• G2SH0XKK91
• [11,12-3H]-Retinol
• NSC 122759
• NSC-122759
• UNII-81G40H8B0T
• BRN 0403040
• Vitamin A (USP)
• (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol
• DTXSID3023556
• Vitamin A [Natural]
• Vitamin A1 alcohol, all-trans-
• ophthalamin (obsolete)
• Retin-11,12-t2-ol (9CI)
• 2,4,6,8-Nonatetraen-1-ol, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)-
• EINECS 234-328-2
• CHEMBL986
• M.V.C. 9+3
• 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclchexen-1-yl)-2,4,6,8-nonatetraen-1-ol
• DTXCID203556
• trans-Retinol acid (Vitamin A)
• CHEBI:17336
• EC 200-683-7
• all-trans-13,14-Dihydro retinol
• 4-06-00-04133 (Beilstein Handbook Reference)
• VITAMINA
• 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-E)-
• LPK
• Vitamin A (Natural)
• NCGC00017343-07
• Retinol-(cellular-retinol-binding-protein)
• 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonate-traen-1-ol
• 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol
• 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-E)-Isomer
• Alcohol 9,13-dimethyl-7-(1,1,5-trimethyl-6-cyclohexen-5-yl)-7,9,11,13-nonatetraen-15-ol
• Vi-a
• ALL-TRANS RETINOL (SEE ALSO RETINOID PROJECT 1)
• Homagenets aorl
• Vogan-nu
• Vitamin A cryst
• Zinosan N
• CAS-68-26-8
• all-trans-Retinol;(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
• SMR000112036
• Vitamin A (Feed)
• 9-cis,13-cis-Retinol
• SR-01000763813
• MFCD00001552
• CHEBI:50211
• Tricyclics
• lard-factor
• Tegosphere VitA
• vitamins A
• .alpha.sterol
• b-Retinol
• Retinol-
• .alpha.lin
• Retinyl A
• 1rbp
• vitamin A vitamer
• Vitamin-A alcohol
• Vitamin-A1
• vitamin A vitamers
• Vi-.alpha.
• (9Z)-Retinol
• LUTAVIT A
• MICROVIT A
• VIATMIN A
• 1gx8
• RETINOL [HSDB]
• RETINOL [INCI]
• RETINOL [INN]
• retinolum densatum oleosum
• Spectrum5_000993
• Spectrum5_001997
• VITAMIN A [MI]
• RETINOL [WHO-DD]
• D0AO6P
• D0S7WX
• Retinol, 95%, synthetic
• all-trans vitamin A alcohol
• SCHEMBL3112
• VITAMIN A (MART.)
• all-trans-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol
• Retinol, all-trans-(8CI)
• VITAMIN A CONCENTRATE
• BIDD:PXR0102
• MLS001066379
• MLS001074751
• MLS006010008
• Retinol, all-trans- (8CI)
• SPECTRUM1501203
• (ALL-E)-
• GTPL4053
• HMS501I08
• A11CA01
• D10AD02
• R01AX02
• S01XA02
• VITAMIN A (EP MONOGRAPH)
• 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
• VITAMIN A (USP MONOGRAPH)
• 81G40H8B0T
• DTXSID301014459
• HMS1921B04
• HMS2092L13
• HMS2270C05
• Pharmakon1600-01501203
• VITAMIN A, UNSPECIFIED FORM
• BCP06593
• HY-B1342
• Tox21_110818
• Tox21_202441
• Tox21_300287
• BDBM50092056
• CCG-38864
• LMPR01090001
• NSC122759
• NSC758150
• s5592
• 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-nona-2,4,6,8-tetraen-1-ol
• AKOS015902578
• DB00162
• LS-1578
• NSC-758150
• SDCCGMLS-0066724.P001
• (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetr aen-1-ol
• IDI1_000486
• SMP2_000102
• NCGC00017343-02
• NCGC00017343-03
• NCGC00017343-04
• NCGC00017343-05
• NCGC00017343-06
• NCGC00017343-08
• NCGC00017343-09
• NCGC00017343-11
• NCGC00091784-01
• NCGC00091784-02
• NCGC00091784-03
• NCGC00091784-04
• NCGC00091784-05
• NCGC00091784-06
• NCGC00254024-01
• NCGC00259990-01
• AC-11701
• BS-17906
• SBI-0051690.P002
• CS-0013091
• C00473
• C17276
• D06543
• AB00052248_05
• EN300-6733268
• A836068
• Q424976
• Retinol, >=95.0% (HPLC), ~2700 U/mg
• Retinol, synthetic, >=95% (HPLC), crystalline
• J-014834
• J-017515
• Q-201926
• SR-01000763813-2
• SR-01000763813-4
• W-104683
• BRD-K22429181-001-06-8
• BRD-K64634304-001-01-5
• WLN: L6UTJ A1 B1U1Y1&U2U1Y1&U2Q C1 C1
• Retinol, BioXtra, >=97.5% (HPLC), ~3100 U/mg
• Z2315574891
• 3,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol
• 2,4,6,8-NONATETRAEN-1-OL, 3,7-DIMETHYL-9-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-
• 2,6,8-Nonatetraen-1-ol, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)-
• 3,7-Dimethyl-9-(2,6, 6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol
• 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, all (E)-
• 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraen-1-ol
• (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-1-nona-2,4,6,8-tetraenol
• (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraen-1-ol
• (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraen-1-ol
• (2Z,4Z,6Z,8Z)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetren-1-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	+	0.9538	95.38%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Lysosomes	0.8110	81.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.7738	77.38%
OATP1B3 inhibitior	-	0.5699	56.99%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9064	90.64%
P-glycoprotein inhibitior	-	0.7702	77.02%
P-glycoprotein substrate	-	0.8829	88.29%
CYP3A4 substrate	+	0.6094	60.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7906	79.06%
CYP3A4 inhibition	-	0.8420	84.20%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.7416	74.16%
CYP inhibitory promiscuity	-	0.7388	73.88%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7128	71.28%
Carcinogenicity (trinary)	Non-required	0.6196	61.96%
Eye corrosion	-	0.8866	88.66%
Eye irritation	-	0.9541	95.41%
Skin irritation	+	0.6201	62.01%
Skin corrosion	-	0.9478	94.78%
Ames mutagenesis	+	0.7985	79.85%
Human Ether-a-go-go-Related Gene inhibition	+	0.8542	85.42%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.9159	91.59%
skin sensitisation	+	0.8365	83.65%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.7684	76.84%
Acute Oral Toxicity (c)	III	0.8739	87.39%
Estrogen receptor binding	+	0.6814	68.14%
Androgen receptor binding	-	0.5870	58.70%
Thyroid receptor binding	+	0.7825	78.25%
Glucocorticoid receptor binding	-	0.5577	55.77%
Aromatase binding	+	0.8115	81.15%
PPAR gamma	+	0.7953	79.53%
Honey bee toxicity	-	0.9303	93.03%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9625	96.25%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	25118.9 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	12589.3 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	31.6 nM; 31.6 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1293224	P10636	Microtubule-associated protein tau	25118.9 nM; 22387.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	10000 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.83%	91.11%
CHEMBL2061	P19793	Retinoid X receptor alpha	94.13%	91.67%
CHEMBL1937	Q92769	Histone deacetylase 2	93.56%	94.75%
CHEMBL1870	P28702	Retinoid X receptor beta	92.97%	95.00%
CHEMBL2004	P48443	Retinoid X receptor gamma	92.61%	100.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	90.84%	91.71%
CHEMBL230	P35354	Cyclooxygenase-2	90.63%	89.63%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.01%	95.50%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.96%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.88%	86.33%
CHEMBL1977	P11473	Vitamin D receptor	87.09%	99.43%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.62%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.08%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.93%	100.00%

Plants that contains it

• Angelica sinensis
• Anodendron affine
• Artemisia capillaris
• Cedrela salvadorensis
• Cornus officinalis
• Datura metel
• Galium latoramosum
• Garcinia gummi-gutta
• Hansenia weberbaueriana
• Hertia cheirifolia
• Hippophae rhamnoides
• Licaria chrysophylla
• Ormosia hosiei
• Ornithoglossum viride
• Papaver somniferum
• Petasites radiatus
• Podophyllum hexandrum
• Schizanthus tricolor
• Sphaeranthus confertifolius
• Taraxacum officinale
• Vigna radiata
• Vitex trifolia

Cross-Links

• PubChem: 445354
• NPASS: NPC55412
• ChEMBL: CHEMBL986
• LOTUS: LTS0234636
• wikiData: Q424976