IMPPAT Phytochemical information: 
Centaureidin

Centaureidin
Summary

SMILES: COc1ccc(cc1O)c1oc2cc(O)c(c(c2c(=O)c1OC)O)OC
InChI: InChI=1S/C18H16O8/c1-23-11-5-4-8(6-9(11)19)16-18(25-3)15(22)13-12(26-16)7-10(20)17(24-2)14(13)21/h4-7,19-21H,1-3H3
InChIKey: BZXULYMZYPRZOG-UHFFFAOYSA-N
DeepSMILES: COcccccc6O)))cocccO)ccc6c=O)c%10OC)))))O))OC
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)oc2ccccc12
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CCCCC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CCCCC12
Functional groups: cOC; cO; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: O-methylated flavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavonols
Synonymous chemical names:
centaureidin
External chemical identifiers:
CID:CID_5315773; ChEMBL:CHEMBL77552; ChEBI:CHEBI:69356; ZINC:ZINC000003871987; FDASRS:548R7290J9; SureChEMBL:SCHEMBL9953; MolPort-023-274-268
Chemical structure download


Centaureidin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 360.32
Log P RDKit 2.6
Topological polar surface area (Å2) RDKit 118.59
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 8
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 15
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.17
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
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


Centaureidin
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 0.649594


Centaureidin
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.52
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No


Centaureidin
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_001704ENSG00000167552TUBA1A7846ChEMBL
TAR_EXP_000604ENSG00000112164GLP1R2740NPASS
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_001637ENSG00000127824TUBA4A7277ChEMBL
TAR_EXP_001638ENSG00000198033TUBA3C7278ChEMBL
TAR_EXP_001640ENSG00000137267TUBB2A7280ChEMBL
TAR_EXP_000845ENSG00000166949SMAD34088NPASS
TAR_EXP_001738ENSG00000101162TUBB181027ChEMBL
TAR_EXP_001776ENSG00000176014TUBB684617ChEMBL, NPASS
TAR_EXP_001782ENSG00000167553TUBA1C84790ChEMBL
TAR_EXP_000749ENSG00000137285TUBB2B347733ChEMBL
TAR_EXP_000748ENSG00000261456TUBB8347688ChEMBL
TAR_EXP_001151ENSG00000170734POLH5429NPASS
TAR_EXP_000747ENSG00000138413IDH13417ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000511ENSG00000136931NR5A12516BindingDB
TAR_EXP_000048ENSG00000123416TUBA1B10376ChEMBL
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000050ENSG00000104833TUBB4A10382ChEMBL
TAR_EXP_000051ENSG00000188229TUBB4B10383ChEMBL
TAR_EXP_000049ENSG00000258947TUBB310381ChEMBL
TAR_EXP_000336ENSG00000169297NR0B1190BindingDB, NPASS
TAR_EXP_000368ENSG00000235067TUBB203068ChEMBL
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_000126ENSG00000292120TUBA3E112714ChEMBL