IMPPAT Phytochemical information: 
Metasequirin B
Metasequirin B
Summary

SMILES: O[C@@H]1[C@H]2OC[C@H]([C@@H]2c2c(-c3c1cc(O)c(c3)O)cc(c(c2)O)O)O
InChI: InChI=1S/C17H16O7/c18-10-1-6-7-2-11(19)13(21)4-9(7)16(23)17-15(14(22)5-24-17)8(6)3-12(10)20/h1-4,14-23H,5H2/t14-,15+,16+,17+/m1/s1
InChIKey: VOTPLSCESBOZLX-QZWWFDLISA-N
DeepSMILES: O[C@@H][C@H]OC[C@H][C@@H]5cc-cc%10ccO)cc6)O))))))cccc6)O))O))))))O
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CC1OCCC1c1ccccc1-2
Scaffold Graph/Node level: C1CCC2C(C1)CC1OCCC1C1CCCCC21
Scaffold Graph level: C1CCC2C(C1)CC1CCCC1C1CCCCC21
Functional groups: CO; COC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
Synonymous chemical names:
Metasequirin B, metasequirin b
External chemical identifiers:
CID:CID_101593088
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Metasequirin B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 332.31
Log P RDKit 1.07
Topological polar surface area (Å2) RDKit 130.61
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Metasequirin B
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 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.397808
Metasequirin B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.20
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No