IMPPAT Phytochemical information: 
Auraptene
Auraptene
Summary

SMILES: C/C(=C\COc1ccc2c(c1)oc(=O)cc2)/CCC=C(C)C
InChI: InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+
InChIKey: RSDDHGSKLOSQFK-RVDMUPIBSA-N
DeepSMILES: C/C=C\COcccccc6)oc=O)cc6))))))))))))/CCC=CC)C
Scaffold Graph/Node/Bond level: O=c1ccc2ccccc2o1
Scaffold Graph/Node level: OC1CCC2CCCCC2O1
Scaffold Graph level: CC1CCC2CCCCC2C1
Functional groups: C/C=C(\C)C; cOC; coc; c=O; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
aurapten, 7-geranyloxycoumarin, 7-geranyloxy coumarin, auraptene, aurapten (7-geranyloxycoumarin)
External chemical identifiers:
CID:CID_1550607; ChEMBL:CHEMBL307341; ChEBI:CHEBI:134355; ZINC:ZINC000001658901; FDASRS:F79I1ZEL2E; SureChEMBL:SCHEMBL2535029; MolPort-001-740-270
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Auraptene
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 298.38
Log P RDKit 4.86
Topological polar surface area (Å2) RDKit 39.44
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 3
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 13
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2
Auraptene
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 Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.564227
Auraptene
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.50
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Auraptene
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_001034ENSG00000137806NDUFAF151103ChEMBL, NPASS
TAR_EXP_000946ENSG00000023228NDUFS14719ChEMBL, NPASS
TAR_EXP_000947ENSG00000149311ATM472NPASS
TAR_EXP_000948ENSG00000158864NDUFS24720ChEMBL, NPASS
TAR_EXP_000949ENSG00000213619NDUFS34722ChEMBL, NPASS
TAR_EXP_000950ENSG00000167792NDUFV14723ChEMBL, NPASS
TAR_EXP_000951ENSG00000164258NDUFS44724ChEMBL, NPASS
TAR_EXP_000952ENSG00000168653NDUFS54725ChEMBL, NPASS
TAR_EXP_000945ENSG00000151366NDUFC24718ChEMBL, NPASS
TAR_EXP_000953ENSG00000145494NDUFS64726ChEMBL, NPASS
TAR_EXP_000955ENSG00000178127NDUFV24729ChEMBL, NPASS
TAR_EXP_000956ENSG00000160194NDUFV34731ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001032ENSG00000186010NDUFA1351079ChEMBL, NPASS
TAR_EXP_000914ENSG00000168412MTNR1A4543BindingDB, ChEMBL, NPASS
TAR_EXP_001151ENSG00000170734POLH5429NPASS
TAR_EXP_001159ENSG00000147123NDUFB1154539ChEMBL, NPASS
TAR_EXP_001171ENSG00000132170PPARG5468BindingDB, ChEMBL
TAR_EXP_000954ENSG00000110717NDUFS84728ChEMBL, NPASS
TAR_EXP_000944ENSG00000109390NDUFC14717ChEMBL, NPASS
TAR_EXP_000943ENSG00000291930NDUFB104716ChEMBL, NPASS
TAR_EXP_000942ENSG00000147684NDUFB94715ChEMBL, NPASS
TAR_EXP_000935ENSG00000090266NDUFB24708ChEMBL, NPASS
TAR_EXP_000934ENSG00000183648NDUFB14707ChEMBL, NPASS
TAR_EXP_000933ENSG00000004779NDUFAB14706ChEMBL, NPASS
TAR_EXP_000932ENSG00000130414NDUFA104705ChEMBL, NPASS
TAR_EXP_000931ENSG00000139180NDUFA94704ChEMBL, NPASS
TAR_EXP_000930ENSG00000119421NDUFA84702ChEMBL, NPASS
TAR_EXP_000929ENSG00000267855NDUFA74701ChEMBL, NPASS
TAR_EXP_000928ENSG00000281013NDUFA64700ChEMBL, NPASS
TAR_EXP_000926ENSG00000128609NDUFA54698ChEMBL, NPASS
TAR_EXP_000925ENSG00000189043COXFA44697ChEMBL, NPASS
TAR_EXP_000924ENSG00000170906NDUFA34696ChEMBL, NPASS
TAR_EXP_000923ENSG00000131495NDUFA24695ChEMBL, NPASS
TAR_EXP_000922ENSG00000125356NDUFA14694ChEMBL, NPASS
TAR_EXP_000938ENSG00000136521NDUFB54711ChEMBL, NPASS
TAR_EXP_000939ENSG00000165264NDUFB64712ChEMBL, NPASS
TAR_EXP_000940ENSG00000099795NDUFB74713ChEMBL, NPASS
TAR_EXP_000941ENSG00000166136NDUFB84714ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_001232ENSG00000184752NDUFA1255967ChEMBL, NPASS
TAR_EXP_001268ENSG00000185633COXFA4L256901ChEMBL, NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000674ENSG00000123636BAZ2B29994NPASS
TAR_EXP_000644ENSG00000123545NDUFAF429078ChEMBL, NPASS
TAR_EXP_000604ENSG00000112164GLP1R2740NPASS
TAR_EXP_000593ENSG00000102393GLA2717NPASS
TAR_EXP_000567ENSG00000177628GBA12629NPASS
TAR_EXP_000559ENSG00000185513L3MBTL126013NPASS
TAR_EXP_000549ENSG00000178057NDUFAF325915ChEMBL, NPASS
TAR_EXP_000503ENSG00000161905ALOX15246BindingDB, ChEMBL, NPASS
TAR_EXP_000491ENSG00000186318BACE123621BindingDB, NPASS
TAR_EXP_000475ENSG00000120948TARDBP23435NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_000186ENSG00000174886NDUFA11126328ChEMBL, NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000794ENSG00000115286NDUFS7374291ChEMBL, NPASS
TAR_EXP_000936ENSG00000119013NDUFB34709ChEMBL, NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_001300ENSG00000160801PTH1R5745NPASS
TAR_EXP_001549ENSG00000166311SMPD16609NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001810ENSG00000067955CBFB865NPASS
TAR_EXP_001857ENSG00000104321TRPA18989ChEMBL
TAR_EXP_001883ENSG00000164182NDUFAF291942ChEMBL, NPASS
TAR_EXP_001923ENSG00000066135KDM4A9682NPASS
TAR_EXP_001942ENSG00000012504NR1H49971ChEMBL, NPASS
TAR_EXP_000937ENSG00000065518NDUFB44710ChEMBL, NPASS
TAR_EXP_000913ENSG00000198695MT-ND64541ChEMBL, NPASS
TAR_EXP_000912ENSG00000198786MT-ND54540ChEMBL, NPASS
TAR_EXP_000911ENSG00000212907MT-ND4L4539ChEMBL, NPASS
TAR_EXP_000910ENSG00000198886MT-ND44538ChEMBL, NPASS
TAR_EXP_000909ENSG00000198840MT-ND34537ChEMBL, NPASS
TAR_EXP_000908ENSG00000198763MT-ND24536ChEMBL, NPASS
TAR_EXP_000907ENSG00000198888MT-ND14535ChEMBL, NPASS
TAR_EXP_000845ENSG00000166949SMAD34088NPASS