IMPPAT Phytochemical information: 
Castalagin
Castalagin
Summary

SMILES: O=C1O[C@@H]2COC(=O)c3cc(O)c(c(c3-c3c(C(=O)O[C@H]2[C@@H]2OC(=O)c4c(-c5c1cc(O)c(c5O)O)c(O)c(O)c(c4-c1c4C(=O)O[C@H]2[C@H](O)c4c(c(c1O)O)O)O)cc(O)c(c3O)O)O)O
InChI: InChI=1S/C41H26O26/c42-8-1-5-12(24(48)21(8)45)13-6(2-9(43)22(46)25(13)49)39(60)65-34-11(4-63-37(5)58)64-38(59)7-3-10(44)23(47)26(50)14(7)15-18-16(28(52)32(56)27(15)51)17-19-20(30(54)33(57)29(17)53)31(55)35(66-41(19)62)36(34)67-40(18)61/h1-3,11,31,34-36,42-57H,4H2/t11-,31-,34-,35+,36+/m1/s1
InChIKey: UDYKDZHZAKSYCO-JLQXGYSZSA-N
DeepSMILES: O=CO[C@@H]COC=O)cccO)ccc6-ccC=O)O[C@H]%15[C@@H]OC=O)cc-cc%24ccO)cc6O))O))))))cO)cO)cc6-ccC=O)O[C@H]%14[C@H]O)c6ccc%10O))O))O))))))))))O))))))))))))ccO)cc6O))O)))))))O))O
Scaffold Graph/Node/Bond level: O=C1OCC2OC(=O)c3ccccc3-c3cccc4c3C(=O)OC(C3Cc5cccc-4c5C(=O)O3)C2OC(=O)c2ccccc2-c2ccccc21
Scaffold Graph/Node level: OC1OCC2OC(O)C3CCCCC3C3CCCC4C5CCCC6CC(OC(O)C65)C(OC(O)C34)C2OC(O)C2CCCCC2C2CCCCC12
Scaffold Graph level: CC1CCC2CC(C)C3CCCCC3C3CCCC4C5CCCC6CC(CC(C)C65)C(CC(C)C34)C2CC(C)C2CCCCC2C2CCCCC12
Functional groups: CO; cC(=O)OC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Tannins
ClassyFire Subclass: Hydrolyzable tannins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenolic acids (C6-C1)
NP Classifier Class: Gallotannins
Synonymous chemical names:
castalagin, vescalagin
External chemical identifiers:
CID:12302513; ChEMBL:CHEMBL504485; ZINC:ZINC000169291440; FDASRS:CE78QAZ4U2
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Castalagin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit
Castalagin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.0591
Castalagin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -11.33
Number of PAINS structural alerts SwissADME 1.0
Number of Brenk structural alerts SwissADME 2.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes