IMPPAT Phytochemical information: 
Isoschimawalin A
Isoschimawalin A
Summary

SMILES: O=CC(C(C1C(O)COC(=O)c2c(-c3c(OC1=O)cc(Oc1c(cc(c(c1O)O)O)C(=O)O)c(c3O)O)c(O)c(c(c2)O)O)OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1Oc1cc2c(=O)oc3c4c2c(c1O)oc(=O)c4cc(c3O)O)O)O
InChI: InChI=1S/C55H34O35/c56-9-27(87-54(81)16-6-21(61)36(67)43(74)45(16)84-25-7-14-30-29-13(52(79)90-48(30)39(25)70)4-22(62)37(68)47(29)89-53(14)80)46(88-50(77)11-1-17(57)33(64)18(58)2-11)31-23(63)10-83-51(78)12-3-19(59)34(65)40(71)28(12)32-24(86-55(31)82)8-26(38(69)41(32)72)85-44-15(49(75)76)5-20(60)35(66)42(44)73/h1-9,23,27,31,46,57-74H,10H2,(H,75,76)
InChIKey: QHUFBIOFLFOWEC-UHFFFAOYSA-N
DeepSMILES: O=CCCCCO)COC=O)cc-ccOC%11=O)))ccOcccccc6O))O))O)))C=O)O)))))cc6O))O))))))cO)ccc6)O))O))))))))))OC=O)cccO)ccc6)O))O))))))))OC=O)cccO)ccc6Occcc=O)occc6cc%10O))oc=O)c6ccc%10O))O)))))))))))))))))O))O
Scaffold Graph/Node/Bond level: O=C(OC(COC(=O)c1ccccc1Oc1cc2oc(=O)c3cccc4oc(=O)c(c1)c2c43)C1CCOC(=O)c2ccccc2-c2ccc(Oc3ccccc3)cc2OC1=O)c1ccccc1
Scaffold Graph/Node level: OC(OC(COC(O)C1CCCCC1OC1CC2OC(O)C3CCCC4OC(O)C(C1)C2C43)C1CCOC(O)C2CCCCC2C2CCC(OC3CCCCC3)CC2OC1O)C1CCCCC1
Scaffold Graph level: CC(CC(CCC(C)C1CCCCC1CC1CC2CC(C)C3CCCC4CC(C)C(C1)C2C43)C1CCCC(C)C2CCCCC2C2CCC(CC3CCCCC3)CC2CC1C)C1CCCCC1
Functional groups: CC=O; CO; c=O; cC(=O)O; cC(=O)OC; cO; cOC(C)=O; cOc; coc
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:
isoschimawalin a
External chemical identifiers:
CID:16130370
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Isoschimawalin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 1254.84
Log P RDKit 3.14
Topological polar surface area (Å2) RDKit 602.59
Number of hydrogen bond acceptors RDKit 34
Number of hydrogen bond donors RDKit 19
Number of carbon atoms RDKit 55
Number of heavy atoms RDKit 90
Number of heteroatoms RDKit 35
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 50
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.09
Number of rotatable bonds RDKit 14
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 7
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 9
Total number of rings RDKit 10
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 10
Isoschimawalin A
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 Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.0159
Isoschimawalin A
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -12.43
Number of PAINS structural alerts SwissADME 1.0
Number of Brenk structural alerts SwissADME 6.0
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