Natural Product (NP) Details

General Information of the NP (ID: NP4522)
Name
Retinol
Synonyms
retinol; Vitamin A; all-trans-Retinol; 68-26-8; Vitamin A1; Alphalin; Axerophthol; Afaxin; Vitamin A alcohol; Oleovitamin A; Chocola A; Alphasterol; Apostavit; Aquasynth; Biosterol; Epiteliol; Ophthalamin; Agiolan; Agoncal; Anatola; Myvpack; Prepalin; Testavol; Veroftal; Aoral; Apexol; Avibon; Avitol; Axerol; Dofsol; Vaflol; Vitpex; Vogan; Disatabs Tabs; Lard Factor; all-trans-Retinyl alcohol; Bentavit A; Dohyfral A; Alcovit A; Anatola A; Vogan-Neu; A-Mulsal; Plivit A; Vi-Alpha; A-Vitan; All-trans retinol; Atars; trans-retinol; Vafol; all-trans-Vitamin A alcohol; Retrovitamin A; Homagenets Aoral; A-Sol; Hi-A-Vita; Sehkraft A; Vitamin A1 alcohol; all-trans-Vitamin A; A-Vi-Pel; ACON; ATAV; Vi-Dom-A; Super A; Anti-infective vitamin; Solu-A; Nio-A-Let; Vio-A; Antixerophthalmic vitamin; Del-VI-A; Vitavel A; Thalasphere; 11103-57-4; trans-Vitamin A alcohol; Vitamin A alcohol, all-trans-; Vitamin A1, all-trans-; Retinol, all trans-; all-trans-Vitamin A1; Vitamin A Oil; Vi-a; UNII-G2SH0XKK91; .beta.-Retinol; beta-Retinol; Vitamin A1 alcohol, all-trans-; (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol; (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol; MFCD00001552; CHEMBL986; G2SH0XKK91; (all-E)-3,7-Dimethyl-9-(2,6,6-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)-, (all-E)-; Axerophtholum; CHEBI:17336; Wachstumsvitamin; Vitaminum A; Vitamine A; Vitavel-A; VITAMINA; NSC-122759; Retinolo [DCIT]; NCGC00017343-07; Cylasphere; Retinolo; Retinolum; Retinol [INN:BAN]; all-trans-Retinol, 95%; DSSTox_CID_3556; Hydrovit A; Retinolum [INN-Latin]; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol; DSSTox_RID_77080; DSSTox_GSID_23556; Ro-a-vit; tROL; Vitamin A alcohol (VAN); Antixerophthalmisches Vitamin; Aquasol A Parenteral; Vi-alpha; Vi-alpha; Rovimix A 500; Vitamin A1 alcohol, all trans; Retinol solution; (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetr aen-1-ol; CAS-68-26-8; SMR000112036; Retinol (Vit A); [11,12-3H]-Retinol; 9-cis,13-cis-Retinol; Vitamin A (USP); CCRIS 5444; HSDB 815; Vitamin A [Natural]; SR-01000763813; Retin-11,12-t2-ol (9CI); EINECS 200-683-7; NSC 122759; BRN 0403040; Tegosphere VitA; .alpha.sterol; .alpha.lin; Retinyl A; trans-Retinol acid (Vitamin A); 1rbp; Vi-.alpha.; EINECS 234-328-2; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclchexen-1-yl)-2,4,6,8-nonatetraen-1-ol; (9Z)-Retinol; PubChem18446; 1gx8; Retinol-(cellular-retinol-binding-protein); Spectrum5_000993; Spectrum5_001997; Retinol, 95%, synthetic; EC 200-683-7; all-trans vitamin A alcohol; SCHEMBL3112; 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, (all-E)-; Alcohol 9,13-dimethyl-7-(1,1,5-trimethyl-6-cyclohexen-5-yl)-7,9,11,13-nonatetraen-15-ol; all-trans-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol; BIDD:PXR0102; 4-06-00-04133 (Beilstein Handbook Reference); MLS001066379; MLS001074751; MLS006010008; Retinol, all-trans- (8CI); SPECTRUM1501203; GTPL4053; Vitamin A; ; ; Retinoid analogues; DTXSID3023556; HMS501I08; Zinc-ethylenebis(dithiocarbamate); all-trans-13,14-Dihydro retinol; HMS1921B04; HMS2092L13; HMS2270C05; Pharmakon1600-01501203; BCP06593; HY-B1342; ZINC3831417; Tox21_110818; Tox21_202441; Tox21_300287; BDBM50092056; CCG-38864; LMPR01090001; NSC122759; NSC758150; s5592; AKOS015902578; DB00162; NSC-758150; SDCCGMLS-0066724.P001; IDI1_000486; Retinol solution, >=95.0% (HPLC); 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; ST057232; SBI-0051690.P002; CS-0013091; C00473; C17276; D06543; 33563-EP2272846A1; 33563-EP2277869A1; 33563-EP2277870A1; 33563-EP2281813A1; 33563-EP2284174A1; 33563-EP2292608A1; 33563-EP2301936A1; 33563-EP2311820A1; 33563-EP2374791A1; AB00052248_05; 103V574; 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; UNII-81G40H8B0T component FPIPGXGPPPQFEQ-OVSJKPMPSA-N; 3,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol; 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, all (E)-; (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; Retinol solution, 100 mug/mL +/- 25% (Refer to COA) (Ethanol with 0.1% (w/v) BHT), ampule of 1 mL, certified reference material
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Species Origin Daucus carota ...     Click to Show/Hide
Daucus carota
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Apiales
Family: Apiaceae
Genus: Daucus
Species: Daucus carota
Disease Light sensitivity impairment [ICD-11: 9D45] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.657
 
MDCK Permeability
 -4.846
 
PAMPA
 - -
 
HIA
 - - -
 
Distribution
VDss
 0.43
 
PPB
 91%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 +++
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 +++
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 +++
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 +++
CYP3A4 inhibitor
 +++
CYP3A4 substrate
 +++
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 - -
CYP2C8 inhibitor
 ++
HLM Stability
 +++
 
Excretion
CLplasma
 8.613
 
T1/2
 0.262
Toxicity
DILI
 +
 
Rat Oral Acute Toxicity
 - -
 
FDAMDD
 +
 
Respiratory
 ++
 
Human Hepatotoxicity
 ++
 
Ototoxicity
 +
 
Drug-induced Nephrotoxicity
 +
 
Drug-induced Neurotoxicity
 -
 
Hematotoxicity
 +
 
Genotoxicity
 - -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C20H30O
PubChem CID
445354
Canonical SMILES
CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCO)C)C
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+
InChIKey
FPIPGXGPPPQFEQ-OVSJKPMPSA-N
CAS Number
CAS 11103-57-4
ChEBI ID
CHEBI:17336
Herb ID
HBIN042130
SymMap ID
SMIT17437
TTD Drug ID
D0S7WX
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Monodesbutyl benflumetol      Malaria     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Plasmodium falciparum Microorganism model Plasmodium falciparum
                    In-vivo Model Clinical Trial
                    Experimental
                    Result(s)		 Monodesbutyl-benflumetol and retinol combination showed synergistic interaction in Plasmodium falciparum.
          Oxacillin + Ampicillin     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Staphylococcus aureus strains Microorganism model Staphylococcus aureus
Staphylococcus aureus ATCC 33591 Microorganism model Staphylococcus aureus
Staphylococcus aureus ATCC 25923 Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 Rhein in combination with AM or OX could lead to the development of new combinations of antibiotics against MRSA infection.
Target and Pathway
Target(s) Retinoic acid receptor RXR-gamma (RXRG)  Molecule Info  [4]
Trypanosoma Trypanothione reductase (Trypano TPR)  Molecule Info  [5]
KEGG Pathway PPAR signaling pathway Click to Show/Hide
2 Thyroid hormone signaling pathway
3 Adipocytokine signaling pathway
4 Pathways in cancer
5 Transcriptional misregulation in cancer
6 Thyroid cancer
7 Small cell lung cancer
8 Non-small cell lung cancer
Pathway Interaction Database Regulation of Androgen receptor activity Click to Show/Hide
2 RXR and RAR heterodimerization with other nuclear receptor
3 Retinoic acid receptors-mediated signaling
4 a6b1 and a6b4 Integrin signaling
Reactome Nuclear Receptor transcription pathway Click to Show/Hide
WikiPathways Vitamin A and Carotenoid Metabolism Click to Show/Hide
2 Adipogenesis
3 Nuclear Receptors
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4053).
Reference 2 Synergistic interaction between monodesbutyl-benflumetol and retinol in Plasmodium falciparum. Wien Klin Wochenschr. 2007;119(19-20 Suppl 3):53-9.
Reference 3 Synergistic effect of rhein in combination with ampicillin or oxacillin against methicillin-resistant Staphylococcus aureus. Exp Ther Med. 2012 Apr;3(4):608-612.
Reference 4 Vitamins and cofactors: highlights of ESBOC 2009. Nat Chem Biol. 2009 Aug;5(8):530-3.
Reference 5 Opportunities and challenges in antiparasitic drug discovery. Nat Rev Drug Discov. 2005 Sep;4(9):727-40.
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