IMPPAT Phytochemical information: 
Grahamine
Grahamine
Summary

SMILES: CCC(C(=O)OC1(C)C(C)C(=O)OC2CCN3C2C(=CC3)COC(=O)C1(C)O)C
InChI: InChI=1S/C21H31NO7/c1-6-12(2)17(23)29-21(5)13(3)18(24)28-15-8-10-22-9-7-14(16(15)22)11-27-19(25)20(21,4)26/h7,12-13,15-16,26H,6,8-11H2,1-5H3
InChIKey: BGODDTSFBHJRGK-UHFFFAOYSA-N
DeepSMILES: CCCC=O)OCC)CC)C=O)OCCCNC5C=CC5))COC=O)C%14C)O)))))))))))))))))C
Scaffold Graph/Node/Bond level: O=C1CCCC(=O)OC2CCN3CC=C(CO1)C23
Scaffold Graph/Node level: OC1CCCC(O)OC2CCN3CCC(CO1)C23
Scaffold Graph level: CC1CCCC(C)CC2CCC3CCC(CC1)C32
Functional groups: COC(C)=O; COC(=O)C; CN(C)C; CC=C(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Tricarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Pyrrolizidine alkaloids
Synonymous chemical names:
grahamine, Grahamine
External chemical identifiers:
CID:CID_91753270
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Grahamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 409.48
Log P RDKit 1.2
Topological polar surface area (Å2) RDKit 102.37
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.76
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Grahamine
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 Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.42
Grahamine
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 High
Log Kp (Skin permeation, cm/s) SwissADME -7.92
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