IMPPAT Phytochemical information: 
Crotonoside

Crotonoside
Summary

SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(=O)[nH]c2N
InChI: InChI=1S/C10H13N5O5/c11-7-4-8(14-10(19)13-7)15(2-12-4)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1
InChIKey: MIKUYHXYGGJMLM-UUOKFMHZSA-N
DeepSMILES: OC[C@H]O[C@H][C@@H][C@@H]5O))O))ncncc5nc=O)[nH]c6N
Scaffold Graph/Node/Bond level: O=c1nc2c(c[nH]1)ncn2C1CCCO1
Scaffold Graph/Node level: OC1NCC2NCN(C3CCCO3)C2N1
Scaffold Graph level: CC1CCC2CCC(C3CCCC3)C2C1
Functional groups: CO; COC; cn(C)c; cnc; c=O; c[nH]c; cN
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Nucleosides, nucleotides, and analogues
ClassyFire Class: Purine nucleosides
NP Classifier Biosynthetic pathway: Carbohydrates
NP Classifier Superclass: Nucleosides
NP Classifier Class: Purine nucleos(t)ides
Synonymous chemical names:
crotonoside, isoguanoriboside
External chemical identifiers:
CID:CID_65085; ChEMBL:CHEMBL1688963; ChEBI:CHEBI:3927; ZINC:ZINC000004082270; FDASRS:6V7FTE1Z1V; SureChEMBL:SCHEMBL2773634; MolPort-046-795-915
Chemical structure download


Crotonoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 283.24
Log P RDKit -2.69
Topological polar surface area (Å2) RDKit 159.51
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 5
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 2
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


Crotonoside
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 Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.4


Crotonoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.14
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No