IMPPAT Phytochemical information: 
Metasequirin A

Metasequirin A
Summary

SMILES: Oc1ccc(cc1)[C@H]1[C@H](O)CO[C@@H]1[C@H](c1ccc(c(c1)O)O)O
InChI: InChI=1S/C17H18O6/c18-11-4-1-9(2-5-11)15-14(21)8-23-17(15)16(22)10-3-6-12(19)13(20)7-10/h1-7,14-22H,8H2/t14-,15+,16+,17+/m1/s1
InChIKey: IUXYOUYIVWPTJW-QZWWFDLISA-N
DeepSMILES: Occcccc6))[C@H][C@H]O)CO[C@@H]5[C@H]cccccc6)O))O)))))O
Scaffold Graph/Node/Bond level: c1ccc(CC2OCCC2c2ccccc2)cc1
Scaffold Graph/Node level: C1CCC(CC2OCCC2C2CCCCC2)CC1
Scaffold Graph level: C1CCC(CC2CCCC2C2CCCCC2)CC1
Functional groups: cO; CO; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenols
ClassyFire Subclass: Benzenediols
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Neolignans
Synonymous chemical names:
Metasequirin A, metasequirin a
External chemical identifiers:
CID:CID_101324827; ZINC:ZINC000238761203
Chemical structure download


Metasequirin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 318.33
Log P RDKit 1.38
Topological polar surface area (Å2) RDKit 110.38
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 6
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 3
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 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Metasequirin A
Drug-likeness properties
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.54693


Metasequirin A
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 -7.65
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