IMPPAT Phytochemical information: 
Lonchocarpenin

Lonchocarpenin
Summary

SMILES: COc1c2C=CC(Oc2c(c2c1c(O)c(c1ccc(cc1)OC)c(=O)o2)CC=C(C)C)(C)C
InChI: InChI=1S/C27H28O6/c1-15(2)7-12-18-23-19(13-14-27(3,4)33-23)24(31-6)21-22(28)20(26(29)32-25(18)21)16-8-10-17(30-5)11-9-16/h7-11,13-14,28H,12H2,1-6H3
InChIKey: CCYKXDPVYWRNMH-UHFFFAOYSA-N
DeepSMILES: COccC=CCOc6ccc%10cO)ccccccc6))OC))))))c=O)o6))))))CC=CC)C)))))))C)C
Scaffold Graph/Node/Bond level: O=c1oc2cc3c(cc2cc1-c1ccccc1)C=CCO3
Scaffold Graph/Node level: OC1OC2CC3OCCCC3CC2CC1C1CCCCC1
Scaffold Graph level: CC1CC2CC3CCCCC3CC2CC1C1CCCCC1
Functional groups: cOC; cC=CC; cO; c=O; coc; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Hydroxyisoflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Pyranocoumarins
Synonymous chemical names:
lonchocarpenin
External chemical identifiers:
CID:CID_54699185; ChEBI:CHEBI:6521; ZINC:ZINC000001531864
Chemical structure download


Lonchocarpenin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 448.52
Log P RDKit 5.88
Topological polar surface area (Å2) RDKit 78.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 33
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 19
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.3
Number of rotatable bonds RDKit 5
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 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4


Lonchocarpenin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
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 0.388159


Lonchocarpenin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.99
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No