IMPPAT Phytochemical information: 
Bisdemethoxycurcumin
Bisdemethoxycurcumin
Summary

SMILES: O=C(CC(=O)/C=C/c1ccc(cc1)O)/C=C/c1ccc(cc1)O
InChI: InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+
InChIKey: PREBVFJICNPEKM-YDWXAUTNSA-N
DeepSMILES: O=CCC=O)/C=C/cccccc6))O)))))))))/C=C/cccccc6))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)CC(=O)C=Cc1ccccc1
Scaffold Graph/Node level: OC(CCC1CCCCC1)CC(O)CCC1CCCCC1
Scaffold Graph level: CC(CCC1CCCCC1)CC(C)CCC1CCCCC1
Functional groups: c/C=C/C(C)=O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Diarylheptanoids
ClassyFire Subclass: Linear diarylheptanoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Diarylheptanoids
NP Classifier Class: Linear diarylheptanoids
Synonymous chemical names:
bis-desmethoxycurcumin, bidesmethoxycurcumin, curcumin iii, didemethoxycurcumin, Curcumin III, di-p-coumaroylmethane, bisdemethoxycurcumin
External chemical identifiers:
CID:CID_5315472; ChEMBL:CHEMBL105350; ChEBI:CHEBI:71045; ZINC:ZINC000001651126; FDASRS:2EFO1BP34R; SureChEMBL:SCHEMBL428638; MolPort-006-069-216
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Bisdemethoxycurcumin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 308.33
Log P RDKit 3.35
Topological polar surface area (Å2) RDKit 74.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 4
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 18
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.05
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 2
Number of aromatic heterocycles RDKit 0
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
Bisdemethoxycurcumin
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 0.63368
Bisdemethoxycurcumin
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.87
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Bisdemethoxycurcumin
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_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000319ENSG00000130816DNMT11786ChEMBL
TAR_EXP_000603ENSG00000124767GLO12739ChEMBL, NPASS
TAR_EXP_000752ENSG00000142192APP351ChEMBL, NPASS
TAR_EXP_000844ENSG00000175387SMAD24087ChEMBL
TAR_EXP_000845ENSG00000166949SMAD34088ChEMBL
TAR_EXP_000852ENSG00000069535MAOB4129ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL
TAR_EXP_001280ENSG00000198074AKR1B1057016ChEMBL, NPASS
TAR_EXP_001299ENSG00000073756PTGS25743BindingDB, ChEMBL, NPASS
TAR_EXP_001742ENSG00000070808CAMK2A815BindingDB, ChEMBL, NPASS