IMPPAT Phytochemical information: 
Citroside B
Citroside B
Summary

SMILES: OC[C@H]1O[C@@H](O[C@]2(C)C[C@@H](O)CC(C2=C=CC(=O)C)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C19H30O8/c1-10(21)5-6-13-18(2,3)7-11(22)8-19(13,4)27-17-16(25)15(24)14(23)12(9-20)26-17/h5,11-12,14-17,20,22-25H,7-9H2,1-4H3/t6?,11-,12+,14+,15-,16+,17-,19+/m0/s1
InChIKey: XTODSGVDHGMKSN-SIEIHWOKSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@]C)C[C@@H]O)CCC6=C=CC=O)C)))))C)C)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C=C1CCCCC1OC1CCCCO1
Scaffold Graph/Node level: CC1CCCCC1OC1CCCCO1
Scaffold Graph level: CC1CCCCC1CC1CCCCC1
Functional groups: CO; CO[C@@H](C)OC; CC(=O)C=C=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Apocarotenoids
NP Classifier Class: Megastigmanes
Synonymous chemical names:
citroside b, citroside a
External chemical identifiers:
CID:CID_14312562; ChEMBL:CHEMBL1814429; ChEBI:CHEBI:69850; ZINC:ZINC000031155114
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Citroside B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 386.44
Log P RDKit -0.59
Topological polar surface area (Å2) RDKit 136.68
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.37
Number of sp hybridized carbon atoms RDKit 1
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.83
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Citroside B
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 1
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.32
Citroside B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.81
Number of PAINS structural alerts SwissADME 0
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 Yes