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: C/C=C(C)/C=C/C=C(C)/C=C/C(C)=C(C)C; CO
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, vitamin a
External chemical identifiers:
CID:445354; ChEMBL:CHEMBL986; 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 properties
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 0.6606


Retinol
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.31
Number of PAINS structural alerts SwissADME 1.0
Number of Brenk structural alerts SwissADME 2.0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No


Retinol
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000171214RDH8935
ENSP00000209668ADH1A970
ENSP00000222271COMP795
ENSP00000224356CYP26A1956
ENSP00000224600RBP3849
ENSP00000227667APOC3914
ENSP00000231572RARS956
ENSP00000232217RBP2996
ENSP00000232219RBP1992
ENSP00000233242APOB922
ENSP00000236850APOA1912
ENSP00000237014TTR993
ENSP00000240285RDH10952
ENSP00000243077LRP1900
ENSP00000247001SUGP1759
ENSP00000249389OPN1SW900
ENSP00000249750ALDH1A2952
ENSP00000252486APOE914
ENSP00000252723EPO839
ENSP00000254227NR0B2800
ENSP00000254351SDC1900
ENSP00000257895RDH5914
ENSP00000259938CLPS900
ENSP00000260630CYP1B1726
ENSP00000262340RPE65960
ENSP00000263321TYR800
ENSP00000263816LRP2911
ENSP00000264039GPC1900
ENSP00000265512ADH4962
ENSP00000265723ABCB4800
ENSP00000266560RBP5974
ENSP00000267502RDH12936
ENSP00000268125RLBP1943
ENSP00000277508PAEP805
ENSP00000278353HSD17B12800
ENSP00000283916TMPRSS11D786
ENSP00000285930AKR1B1700
ENSP00000292377GPC2900
ENSP00000294312FGF19786
ENSP00000295453ALPPL2829
ENSP00000295802RETSAT914
ENSP00000295897ALB872
ENSP00000296271RHO929
ENSP00000296412ADH5961
ENSP00000297785ALDH1A1910
ENSP00000299022LIPC909
ENSP00000299529CRABP1855
ENSP00000301645CYP7A1800
ENSP00000303634LRP8900
ENSP00000304858ORMDL3786
ENSP00000306606ADH1B968
ENSP00000307046SDC2900
ENSP00000307607SDR16C5911
ENSP00000311032CASP3737
ENSP00000312652LEP834
ENSP00000313021MAK800
ENSP00000316670DHRS9921
ENSP00000317842CES2909
ENSP00000318631HSD17B6919
ENSP00000322788MMP1817
ENSP00000326219DHRS4910
ENSP00000330442PLB1900
ENSP00000332256ALDH1A3941
ENSP00000332258DGAT1900
ENSP00000334801DHRS4L2900
ENSP00000337224LRAT960
ENSP00000339730THBS4705
ENSP00000344456CTNNB1946
ENSP00000344468SDC3900
ENSP00000346839FN1951
ENSP00000350425APOA4907
ENSP00000352584AKR1B10900
ENSP00000353720CES1908
ENSP00000356969APOA2900
ENSP00000357204CRABP2704
ENSP00000357362THBS3705
ENSP00000358223PNLIP908
ENSP00000358945OPN1MW2900
ENSP00000358967OPN1LW900
ENSP00000359245ABCA4935
ENSP00000359864GPC4900
ENSP00000360519RBP4994
ENSP00000361818SDC4900
ENSP00000363827HSPG2914
ENSP00000363965ALPL830
ENSP00000365397DHRS3950
ENSP00000366246GPC6900
ENSP00000366267GPC5900
ENSP00000367123SLC3A2814
ENSP00000368678AGRN900
ENSP00000368683EDN1786
ENSP00000370430PNPLA4911
ENSP00000370571TH816
ENSP00000370648RDH14800
ENSP00000370750RDH11939
ENSP00000375881ALPP829
ENSP00000377836GPC3900
ENSP00000378359ADH6963
ENSP00000381206RDH16920
ENSP00000386331MYO7A900
ENSP00000387699CREB1725
ENSP00000391121RDH13826
ENSP00000414303BDNF824
ENSP00000420269ADH7974
ENSP00000421172AWAT2900
ENSP00000428864CES5A900
ENSP00000444052CES4A900
ENSP00000447173VDR852
ENSP00000454071LDLR907
ENSP00000456609STRA6973
ENSP00000466795800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.