IMPPAT Phytochemical information: 
Neobetanin
Neobetanin
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc3C[C@H](N(c3cc2O)/C=C/c2cc(nc(c2)C(=O)O)C(=O)O)C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C24H24N2O13/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/h1-4,6-7,14,17-20,24,27-31H,5,8H2,(H,32,33)(H,34,35)(H,36,37)/b2-1+/t14-,17+,18+,19-,20+,24+/m0/s1
InChIKey: JGRJFJIJVQCUMW-HQSRNOONSA-N
DeepSMILES: OC[C@H]O[C@@H]OcccC[C@H]Nc5cc9O))))/C=C/cccncc6)C=O)O))))C=O)O))))))))C=O)O))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C(=CN1CCc2cc(OC3CCCCO3)ccc21)c1ccncc1
Scaffold Graph/Node level: C1CCC(OC2CCC3C(CCN3CCC3CCNCC3)C2)OC1
Scaffold Graph level: C1CCC(CCC2CCC3CC(CC4CCCCC4)CCC23)CC1
Functional groups: CO; cO[C@@H](C)OC; c/C=C/N(c)C; cO; cnc; cC(=O)O; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Betalain alkaloids
Synonymous chemical names:
neobetanin (14, 15-dehydro betanin), neobetanin
External chemical identifiers:
CID:CID_102401026
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Neobetanin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 548.46
Log P RDKit -1.15
Topological polar surface area (Å2) RDKit 247.64
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 6
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
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
Neobetanin
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 0.193911
Neobetanin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.77
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 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 No