IMPPAT Phytochemical information: 
Isobetanin
Isobetanin
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc3C[C@H](/[N+](=CC=C4/C[C@@H](NC(=C4)C(=O)O)C(=O)O)/c3cc2O)C(=O)[O-])[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C24H26N2O13/c27-8-17-18(29)19(30)20(31)24(39-17)38-16-6-10-5-14(23(36)37)26(13(10)7-15(16)28)2-1-9-3-11(21(32)33)25-12(4-9)22(34)35/h1-3,6-7,12,14,17-20,24,27,29-31H,4-5,8H2,(H4,28,32,33,34,35,36,37)/t12-,14+,17-,18-,19+,20-,24-/m1/s1
InChIKey: DHHFDKNIEVKVKS-RYGANQNKSA-N
DeepSMILES: OC[C@H]O[C@@H]OcccC[C@H]/[N+]=CC=C/C[C@@H]NC=C/6)C=O)O))))C=O)O)))))))/c5cc9O)))))C=O)[O-]))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=CC(=CC=[N+]2CCc3cc(OC4CCCCO4)ccc32)CCN1
Scaffold Graph/Node level: C1CCC(OC2CCC3C(CCN3CCC3CCNCC3)C2)OC1
Scaffold Graph level: C1CCC(CCC2CCC3CC(CC4CCCCC4)CCC23)CC1
Functional groups: CC(=O)O; CC(=O)[O-]; CO; c/[N+](C)=C/C=C1/C=C(C(=O)O)NCC1; cO; cO[C@@H](C)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Betalains
ClassyFire Subclass: Betacyanins and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Betalain alkaloids
Synonymous chemical names:
isobetanin
External chemical identifiers:
CID:6325438; ChEBI:5985
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Isobetanin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 550.47
Log P RDKit -3.7
Topological polar surface area (Å2) RDKit 249.38
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 15
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Isobetanin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.1523
Isobetanin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.26
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes