IMPPAT Phytochemical information: 
Trachelogenin

Trachelogenin
Summary

SMILES: COc1cc(ccc1OC)C[C@H]1COC(=O)[C@]1(O)Cc1ccc(c(c1)OC)O
InChI: InChI=1S/C21H24O7/c1-25-17-7-5-13(9-19(17)27-3)8-15-12-28-20(23)21(15,24)11-14-4-6-16(22)18(10-14)26-2/h4-7,9-10,15,22,24H,8,11-12H2,1-3H3/t15-,21-/m0/s1
InChIKey: YFVZKLQNMNKWSB-BTYIYWSLSA-N
DeepSMILES: COcccccc6OC)))))C[C@H]COC=O)[C@]5O)Ccccccc6)OC)))O
Scaffold Graph/Node/Bond level: O=C1OCC(Cc2ccccc2)C1Cc1ccccc1
Scaffold Graph/Node level: OC1OCC(CC2CCCCC2)C1CC1CCCCC1
Scaffold Graph level: CC1CCC(CC2CCCCC2)C1CC1CCCCC1
Functional groups: cOC; COC(=O)C; CO; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Furanoid lignans
ClassyFire Subclass: Tetrahydrofuran lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Dibenzylbutyrolactone lignans
Synonymous chemical names:
Trachelogenin, trachelogenin
External chemical identifiers:
CID:CID_452855; ChEMBL:CHEMBL491178; ChEBI:CHEBI:9647; ZINC:ZINC000003589244; FDASRS:379VHZ3K1I; SureChEMBL:SCHEMBL3980011; MolPort-039-339-163
Chemical structure download


Trachelogenin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 388.42
Log P RDKit 2.11
Topological polar surface area (Å2) RDKit 94.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 7
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


Trachelogenin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.7


Trachelogenin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.67
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes