IMPPAT Phytochemical information: 
Sanguinine

Sanguinine
Summary

SMILES: O[C@H]1C=C[C@@]23[C@H](C1)Oc1c3c(ccc1O)CN(CC2)C
InChI: InChI=1S/C16H19NO3/c1-17-7-6-16-5-4-11(18)8-13(16)20-15-12(19)3-2-10(9-17)14(15)16/h2-5,11,13,18-19H,6-9H2,1H3/t11-,13-,16-/m0/s1
InChIKey: OYSGWKOGUVOGFQ-RBOXIYTFSA-N
DeepSMILES: O[C@H]C=C[C@][C@H]C6)Occ5cccc6O))))CNCC%10))C
Scaffold Graph/Node/Bond level: C1=CC23CCNCc4cccc(c42)OC3CC1
Scaffold Graph/Node level: C1CC2CNCCC34CCCCC3OC(C1)C24
Scaffold Graph level: C1CCC23CCCCC2CC2CCCC(C1)C23
Functional groups: CO; CC=CC; cOC; cO; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Amaryllidaceae alkaloids
ClassyFire Subclass: Galanthamine-type amaryllidaceae alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Amarylidaceae alkaloids
Synonymous chemical names:
sanguinine
External chemical identifiers:
CID:CID_443722; ChEMBL:CHEMBL1524; ChEBI:CHEBI:32117; ZINC:ZINC000004102420; FDASRS:L7ZOW3CZ7W; SureChEMBL:SCHEMBL19766125
Chemical structure download


Sanguinine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 273.33
Log P RDKit 1.55
Topological polar surface area (Å2) RDKit 52.93
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
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 4


Sanguinine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.704207


Sanguinine
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.90
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes