IMPPAT Phytochemical information: 
Higenamine

Higenamine
Summary

SMILES: Oc1ccc(cc1)CC1NCCc2c1cc(O)c(c2)O
InChI: InChI=1S/C16H17NO3/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14/h1-4,8-9,14,17-20H,5-7H2
InChIKey: WZRCQWQRFZITDX-UHFFFAOYSA-N
DeepSMILES: Occcccc6))CCNCCcc6ccO)cc6)O
Scaffold Graph/Node/Bond level: c1ccc(CC2NCCc3ccccc32)cc1
Scaffold Graph/Node level: C1CCC(CC2NCCC3CCCCC32)CC1
Scaffold Graph level: C1CCC(CC2CCCC3CCCCC32)CC1
Functional groups: cO; CNC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isoquinolines and derivatives
ClassyFire Subclass: Benzylisoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
norcoclaurine, higenamine
External chemical identifiers:
CID:CID_114840; ChEMBL:CHEMBL19344; ChEBI:CHEBI:18418; FDASRS:TBV5O16GAP; SureChEMBL:SCHEMBL636788; MolPort-003-986-980
Chemical structure download


Higenamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 271.32
Log P RDKit 2.23
Topological polar surface area (Å2) RDKit 72.72
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 4
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 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.25
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 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 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Higenamine
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 Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.63


Higenamine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.36
Number of PAINS structural alerts SwissADME 1
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


Higenamine
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000216117HMOX1818
ENSP00000327251NOS2733
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.