IMPPAT Phytochemical information: 
Gentiacaulein

Gentiacaulein
Summary

SMILES: COc1cc(O)c2c(c1)oc1c(c2=O)c(OC)c(cc1)O
InChI: InChI=1S/C15H12O6/c1-19-7-5-9(17)12-11(6-7)21-10-4-3-8(16)15(20-2)13(10)14(12)18/h3-6,16-17H,1-2H3
InChIKey: WYOSCUWDVFHQFY-UHFFFAOYSA-N
DeepSMILES: COcccO)ccc6)occc6=O))cOC))ccc6))O
Scaffold Graph/Node/Bond level: O=c1c2ccccc2oc2ccccc12
Scaffold Graph/Node level: OC1C2CCCCC2OC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CC2CCCCC21
Functional groups: cOC; cO; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Polyketides|Shikimates and Phenylpropanoids
NP Classifier Superclass: Xanthones
NP Classifier Class: Plant xanthones
Synonymous chemical names:
gentiacaulein, Gentiacaulein
External chemical identifiers:
CID:CID_5281634; ChEMBL:CHEMBL467590; ChEBI:CHEBI:5313
Chemical structure download


Gentiacaulein
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 288.26
Log P RDKit 2.37
Topological polar surface area (Å2) RDKit 89.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 6
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 2
Shape complexity RDKit 0.13
Number of rotatable bonds RDKit 2
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


Gentiacaulein
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 0.70366


Gentiacaulein
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -6.11
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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


Gentiacaulein
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_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000843ENSG00000284190MIR21406991ChEMBL
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000475ENSG00000120948TARDBP23435NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000962ENSG00000163399ATP1A1476ChEMBL
TAR_EXP_000963ENSG00000018625ATP1A2477ChEMBL
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_000604ENSG00000112164GLP1R2740NPASS
TAR_EXP_000972ENSG00000143153ATP1B1481ChEMBL
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001621ENSG00000141510TP537157NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_000965ENSG00000105409ATP1A3478ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000971ENSG00000132681ATP1A4480ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_000973ENSG00000129244ATP1B2482ChEMBL
TAR_EXP_000974ENSG00000069849ATP1B3483ChEMBL
TAR_EXP_000981ENSG00000137731FXYD2486ChEMBL, NPASS