IMPPAT Phytochemical information: 
Nantenoside A
Nantenoside A
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2)C=O)[C@@H]([C@H]([C@@H]1OC(=O)/C=C/c1ccc(cc1)O)O)O
InChI: InChI=1S/C22H22O9/c23-11-14-3-8-16(9-4-14)29-22-20(28)19(27)21(17(12-24)30-22)31-18(26)10-5-13-1-6-15(25)7-2-13/h1-11,17,19-22,24-25,27-28H,12H2/b10-5+/t17-,19-,20-,21-,22-/m1/s1
InChIKey: UUSUOYGDBHFQCH-MJFMRVSTSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6))C=O)))))))[C@@H][C@H][C@@H]6OC=O)/C=C/cccccc6))O))))))))))O))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCC(Oc2ccccc2)OC1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCC(OC2CCCCC2)OC1
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCC(CC2CCCCC2)CC1
Functional groups: CO; cO[C@@H](C)OC; cC=O; c/C=C/C(=O)OC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acids and derivatives
Synonymous chemical names:
nantenoside a, Nantenoside A
External chemical identifiers:
CID:CID_132599877
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Nantenoside A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 430.41
Log P RDKit 0.65
Topological polar surface area (Å2) RDKit 142.75
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.27
Number of rotatable bonds RDKit 8
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
Nantenoside A
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 Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.28
Nantenoside 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 Low
Log Kp (Skin permeation, cm/s) SwissADME -8.77
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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