IMPPAT Phytochemical information: 
(S)-2-Amino-3-{[(E)-4-hydroxy-3-methylbut-2-enylamino]purin-9-yl}propanoic acid
(S)-2-Amino-3-{[(E)-4-hydroxy-3-methylbut-2-enylamino]purin-9-yl}propanoic acid
Summary

SMILES: OC/C(=C/CNc1ncnc2c1ncn2C[C@H](C(=O)O)N)/C
InChI: InChI=1S/C13H18N6O3/c1-8(5-20)2-3-15-11-10-12(17-6-16-11)19(7-18-10)4-9(14)13(21)22/h2,6-7,9,20H,3-5,14H2,1H3,(H,21,22)(H,15,16,17)/b8-2+/t9-/m1/s1
InChIKey: LJJHXRRUVASJDX-YPNJUMGQSA-N
DeepSMILES: OC/C=C/CNcncncc6ncn5C[C@H]C=O)O))N)))))))))))))))/C
Scaffold Graph/Node/Bond level: c1ncc2nc[nH]c2n1
Scaffold Graph/Node level: C1NCC2NCNC2N1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: CO; C/C=C(/C)C; cNC; cnc; cn(C)c; CC(=O)O; CN
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Imidazopyrimidines
ClassyFire Subclass: Purines and purine derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Purine alkaloids
Synonymous chemical names:
(s)-(e)-lupinic acid
External chemical identifiers:
CID:CID_5461055; ChEBI:CHEBI:30886; ZINC:ZINC000013508622
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(S)-2-Amino-3-{[(E)-4-hydroxy-3-methylbut-2-enylamino]purin-9-yl}propanoic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 306.33
Log P RDKit -0.41
Topological polar surface area (Å2) RDKit 139.18
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 13
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 6
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2
(S)-2-Amino-3-{[(E)-4-hydroxy-3-methylbut-2-enylamino]purin-9-yl}propanoic acid
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 Good
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 0.51
(S)-2-Amino-3-{[(E)-4-hydroxy-3-methylbut-2-enylamino]purin-9-yl}propanoic acid
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 -10.33
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No