IMPPAT Phytochemical information: 
Retinol

Retinol
Summary

SMILES: OC/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\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+
InChIKey: FPIPGXGPPPQFEQ-OVSJKPMPSA-N
DeepSMILES: OC/C=C/C=C/C=C/C=C/C=CC)CCCC6C)C)))))))))\C)))))\C
Scaffold Graph/Node/Bond level: C1=CCCCC1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: CO; C/C=C(C)/C=C/C=C(C)/C=C/C(=C(C)C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Retinoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Apocarotenoids|Diterpenoids
NP Classifier Class: Apocarotenoids (β-)|Cyclophytane diterpenoids
Synonymous chemical names:
retinol, Retinol, vitamin a
External chemical identifiers:
CID:CID_445354; ChEMBL:CHEMBL986; ChEBI:CHEBI:17336; ZINC:ZINC000003831417; FDASRS:G2SH0XKK91; SureChEMBL:SCHEMBL3112; MolPort-001-785-962
Chemical structure download


Retinol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 286.46
Log P RDKit 5.51
Topological polar surface area (Å2) RDKit 20.23
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 1
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1


Retinol
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.660593


Retinol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.97
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


Retinol
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001631ENSG00000165409TSHR7253NPASS
TAR_EXP_001636ENSG00000118271TTR7276ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001836ENSG00000144852NR1I28856ChEMBL
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_001868ENSG00000036672USP29099NPASS
TAR_EXP_001551ENSG00000145335SNCA6622ChEMBL, NPASS
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001190ENSG00000126895AVPR2554ChEMBL
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_001171ENSG00000132170PPARG5468NPASS
TAR_EXP_001170ENSG00000112033PPARD5467NPASS
TAR_EXP_001167ENSG00000244474UGT1A454657ChEMBL, NPASS
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001300ENSG00000160801PTH1R5745NPASS
TAR_EXP_001345ENSG00000131759RARA5914ChEMBL
TAR_EXP_001357ENSG00000138207RBP45950ChEMBL, NPASS
TAR_EXP_001378ENSG00000143365RORC6097NPASS
TAR_EXP_000862ENSG00000166603MC4R4160ChEMBL
TAR_EXP_001461ENSG00000186350RXRA6256NPASS
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_001061ENSG00000113448PDE4D5144ChEMBL
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_001665ENSG00000111424VDR7421NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL
TAR_EXP_000203ENSG00000128271ADORA2A135ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_000144ENSG00000101204CHRNA41137ChEMBL
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000088ENSG00000036530CYP46A110858ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000200ENSG00000163485ADORA1134ChEMBL
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000367ENSG00000112759SLC29A12030ChEMBL
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL, NPASS
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_000759ENSG00000169429CXCL83576ChEMBL, NPASS
TAR_EXP_000752ENSG00000142192APP351BindingDB, ChEMBL, NPASS
TAR_EXP_000735ENSG00000166736HTR3A3359ChEMBL
TAR_EXP_000734ENSG00000147246HTR2C3358ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000330ENSG00000144891AGTR1185ChEMBL
TAR_EXP_000720ENSG00000106211HSPB13315NPASS
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL, NPASS
TAR_EXP_000627ENSG00000102539MLNR2862ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000578ENSG00000121853GHSR2693ChEMBL
TAR_EXP_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_000503ENSG00000161905ALOX15246NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216ChEMBL, NPASS
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000853ENSG00000276155MAPT4137NPASS