IMPPAT Phytochemical information: 
Rutaecarpine
Rutaecarpine
Summary

SMILES: O=c1c2ccccc2nc2-c3c(CCn12)c1c([nH]3)cccc1
InChI: InChI=1S/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2
InChIKey: ACVGWSKVRYFWRP-UHFFFAOYSA-N
DeepSMILES: O=ccccccc6nc-ccCCn%146)))cc[nH]5)cccc6
Scaffold Graph/Node/Bond level: O=c1c2ccccc2nc2n1CCc1c-2[nH]c2ccccc12
Scaffold Graph/Node level: OC1C2CCCCC2NC2C3NC4CCCCC4C3CCN12
Scaffold Graph level: CC1C2CCCCC2CC2C1CCC1C3CCCCC3CC12
Functional groups: c=O; cnc; cn(c)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Pyridoindoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids|Anthranilic acid alkaloids
NP Classifier Class: Carboline alkaloids|Quinazoline alkaloids
Synonymous chemical names:
Rhetine, Rutaecarpine, rhetine, rutaecarpine, Rutaccarpine
External chemical identifiers:
CID:CID_65752; ChEMBL:CHEMBL85139; ChEBI:CHEBI:8922; ZINC:ZINC000000898237; FDASRS:8XZV289PRY; SureChEMBL:SCHEMBL288507; MolPort-003-959-449
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Rutaecarpine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 287.32
Log P RDKit 3.1
Topological polar surface area (Å2) RDKit 50.68
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 3
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 16
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.11
Number of rotatable bonds RDKit 0
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 2
Number of aromatic rings RDKit 4
Total number of rings RDKit 5
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 5
Rutaecarpine
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.540057
Rutaecarpine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.90
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
Rutaecarpine
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_001621ENSG00000141510TP537157NPASS
TAR_EXP_001857ENSG00000104321TRPA18989ChEMBL
TAR_EXP_000752ENSG00000142192APP351ChEMBL, NPASS
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL, NPASS
TAR_EXP_000715ENSG00000044574HSPA53309NPASS
TAR_EXP_000687ENSG00000100644HIF1A3091ChEMBL, NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000505ENSG00000198793MTOR2475NPASS
TAR_EXP_000475ENSG00000120948TARDBP23435NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000401ENSG00000163631ALB213ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576BindingDB, ChEMBL, NPASS
TAR_EXP_000264ENSG00000138061CYP1B11545BindingDB, ChEMBL, NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544BindingDB, ChEMBL, NPASS
TAR_EXP_000262ENSG00000140465CYP1A11543BindingDB, ChEMBL, NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_001900ENSG00000123595RAB9A9367ChEMBL, NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000888ENSG00000100985MMP94318BindingDB, ChEMBL, NPASS
TAR_EXP_001811ENSG00000138735PDE5A8654BindingDB, ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915ChEMBL, NPASS
TAR_EXP_001662ENSG00000131408NR1H27376NPASS
TAR_EXP_001631ENSG00000165409TSHR7253NPASS
TAR_EXP_001607ENSG00000090534THPO7066ChEMBL, NPASS
TAR_EXP_001547ENSG00000275349SMN16606ChEMBL, NPASS
TAR_EXP_000846ENSG00000100299ARSA410NPASS
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_001300ENSG00000160801PTH1R5745NPASS
TAR_EXP_001485ENSG00000197299BLM641NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001150ENSG00000070501POLB5423NPASS
TAR_EXP_001141ENSG00000109099PMP225376NPASS
TAR_EXP_001128ENSG00000067225PKM5315NPASS
TAR_EXP_000983ENSG00000141458NPC14864ChEMBL, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_001299ENSG00000073756PTGS25743BindingDB, ChEMBL, NPASS