IMPPAT Phytochemical information: 
Rhodiolin

Rhodiolin
Summary

SMILES: OC[C@H]1Oc2c(O[C@@H]1c1ccc(c(c1)OC)O)cc(c1c2oc(c2ccc(cc2)O)c(c1=O)O)O
InChI: InChI=1S/C25H20O10/c1-32-16-8-12(4-7-14(16)28)22-18(10-26)34-24-17(33-22)9-15(29)19-20(30)21(31)23(35-25(19)24)11-2-5-13(27)6-3-11/h2-9,18,22,26-29,31H,10H2,1H3/t18-,22-/m1/s1
InChIKey: POVCYOFRCMBMKD-XMSQKQJNSA-N
DeepSMILES: OC[C@H]OccO[C@@H]6cccccc6)OC)))O)))))))cccc6occccccc6))O)))))cc6=O))O))))))O
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)oc2c3c(ccc12)OC(c1ccccc1)CO3
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2C1CCC1OC(C3CCCCC3)COC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2C1CCC1CC(C3CCCCC3)CCC12
Functional groups: CO; c=O; cO; cOC; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Flavonolignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans|Flavonoids
NP Classifier Class: Flavonolignans|Flavonols
Synonymous chemical names:
rhodiolin
External chemical identifiers:
CID:CID_14778358; ChEMBL:CHEMBL594871
Chemical structure download


Rhodiolin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 480.43
Log P RDKit 3.16
Topological polar surface area (Å2) RDKit 159.05
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 21
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.16
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 4
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Rhodiolin
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 Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.29


Rhodiolin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.02
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No