IMPPAT Phytochemical information: 
Naringetol
Naringetol
Summary

SMILES: Oc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O
InChI: InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1
InChIKey: FTVWIRXFELQLPI-ZDUSSCGKSA-N
DeepSMILES: Occcccc6))[C@@H]CC=O)ccO6)cccc6O)))O
Scaffold Graph/Node/Bond level: O=C1CC(c2ccccc2)Oc2ccccc21
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CCCCC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CCCCC12
Functional groups: cO; cC(=O)C; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavanones
Synonymous chemical names:
naringenin, narigenin, Naringenin
External chemical identifiers:
CID:CID_439246; ChEMBL:CHEMBL9352; ChEBI:CHEBI:17846; ZINC:ZINC000000156701; FDASRS:HN5425SBF2; SureChEMBL:SCHEMBL20570; MolPort-001-796-145
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Naringetol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 272.26
Log P RDKit 2.51
Topological polar surface area (Å2) RDKit 86.99
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.13
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3
Naringetol
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.742114
Naringetol
ADME 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 High
Log Kp (Skin permeation, cm/s) SwissADME -6.17
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 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 Yes
Naringetol
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_000053ENSG00000079337RAPGEF310411NPASS
TAR_EXP_000516ENSG00000151151IPMK253430ChEMBL, NPASS
TAR_EXP_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_000611ENSG00000174876AMY1B277BindingDB
TAR_EXP_000609ENSG00000237763AMY1A276ChEMBL
TAR_EXP_000462ENSG00000122025FLT32322ChEMBL, NPASS
TAR_EXP_000603ENSG00000124767GLO12739ChEMBL, NPASS
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000428ENSG00000165140FBP12203ChEMBL, NPASS
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_001906ENSG00000118777ABCG29429ChEMBL
TAR_EXP_001819ENSG00000159231CBR3874ChEMBL, NPASS
TAR_EXP_001818ENSG00000159228CBR1873BindingDB, ChEMBL, NPASS
TAR_EXP_001811ENSG00000138735PDE5A8654ChEMBL, NPASS
TAR_EXP_001736ENSG00000143933CALM2805ChEMBL
TAR_EXP_001691ENSG00000074410CA12771BindingDB, ChEMBL, NPASS
TAR_EXP_000132ENSG00000137491SLCO2B111309ChEMBL, NPASS
TAR_EXP_000182ENSG00000023839ABCC21244ChEMBL, NPASS
TAR_EXP_000262ENSG00000140465CYP1A11543BindingDB, ChEMBL, NPASS
TAR_EXP_001686ENSG00000167434CA4762BindingDB, ChEMBL, NPASS
TAR_EXP_001684ENSG00000104267CA2760BindingDB, ChEMBL, NPASS
TAR_EXP_001683ENSG00000133742CA1759BindingDB, ChEMBL, NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544BindingDB, ChEMBL, NPASS
TAR_EXP_000264ENSG00000138061CYP1B11545BindingDB, ChEMBL, NPASS
TAR_EXP_001678ENSG00000158125XDH7498BindingDB, ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001659ENSG00000277132UGT2B157366ChEMBL, NPASS
TAR_EXP_001647ENSG00000077498TYR7299ChEMBL, NPASS
TAR_EXP_001636ENSG00000118271TTR7276ChEMBL
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL, NPASS
TAR_EXP_001571ENSG00000109193SULT1E16783ChEMBL
TAR_EXP_000273ENSG00000138109CYP2C91559NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000285ENSG00000137869CYP19A11588BindingDB, ChEMBL, NPASS
TAR_EXP_000322ENSG00000197635DPP41803BindingDB, ChEMBL, NPASS
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_001689ENSG00000168748CA7766BindingDB, ChEMBL, NPASS
TAR_EXP_000881ENSG00000087085ACHE43BindingDB, ChEMBL, NPASS
TAR_EXP_000660ENSG00000082701GSK3B2932BindingDB, ChEMBL, NPASS
TAR_EXP_001148ENSG00000172115CYCS54205ChEMBL, NPASS
TAR_EXP_001152ENSG00000005421PON15444ChEMBL, NPASS
TAR_EXP_001160ENSG00000242515UGT1A1054575ChEMBL, NPASS
TAR_EXP_001161ENSG00000242366UGT1A854576ChEMBL, NPASS
TAR_EXP_001166ENSG00000186951PPARA5465ChEMBL, NPASS
TAR_EXP_001167ENSG00000244474UGT1A454657ChEMBL, NPASS
TAR_EXP_001493ENSG00000129214SHBG6462BindingDB, ChEMBL, NPASS
TAR_EXP_001343ENSG00000114200BCHE590ChEMBL, NPASS
TAR_EXP_001306ENSG00000196396PTPN15770BindingDB, ChEMBL, NPASS
TAR_EXP_001168ENSG00000241635UGT1A154658ChEMBL, NPASS
TAR_EXP_001169ENSG00000288702UGT1A354659ChEMBL, NPASS
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL, NPASS
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL, NPASS
TAR_EXP_001170ENSG00000112033PPARD5467ChEMBL, NPASS
TAR_EXP_001171ENSG00000132170PPARG5468ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001273ENSG00000100804PSMB55693BindingDB, ChEMBL, NPASS
TAR_EXP_001280ENSG00000198074AKR1B1057016ChEMBL
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL, NPASS
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL, NPASS
TAR_EXP_001062ENSG00000068745IP6K251447ChEMBL, NPASS
TAR_EXP_001300ENSG00000160801PTH1R5745NPASS
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL, NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028NPASS
TAR_EXP_000711ENSG00000086696HSD17B23294BindingDB, ChEMBL, NPASS
TAR_EXP_000747ENSG00000138413IDH13417ChEMBL, NPASS
TAR_EXP_000752ENSG00000142192APP351ChEMBL
TAR_EXP_000851ENSG00000189221MAOA4128NPASS
TAR_EXP_000852ENSG00000069535MAOB4129NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000709ENSG00000108786HSD17B13292BindingDB, ChEMBL, NPASS
TAR_EXP_000898ENSG00000103222ABCC14363ChEMBL, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS