IMPPAT Phytochemical information: 
Isogomphrenin I
Isogomphrenin I
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc3c(cc2O)C[C@@H](N3/C=C/C2=CC(=N[C@@H](C2)C(=O)O)C(=O)O)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)38-16-7-13-10(6-15(16)28)5-14(23(36)37)26(13)2-1-9-3-11(21(32)33)25-12(4-9)22(34)35/h1-3,6-7,12,14,17-20,24,27-31H,4-5,8H2,(H,32,33)(H,34,35)(H,36,37)/b2-1+/t12-,14+,17+,18+,19-,20+,24+/m0/s1
InChIKey: IKCBLEDGTPAJDE-VRFZYHLASA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6O)))C[C@@H]N5/C=C/C=CC=N[C@@H]C6)C=O)O))))C=O)O))))))))C=O)O)))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C(=CN1CCc2ccc(OC3CCCCO3)cc21)C1=CC=NCC1
Scaffold Graph/Node level: C1CCC(OC2CCC3CCN(CCC4CCNCC4)C3C2)OC1
Scaffold Graph level: C1CCC(CCC2CCC3CCC(CC4CCCCC4)CC23)CC1
Functional groups: CO; cO[C@@H](C)OC; cO; cN(/C=C/C1=CC(C(=O)O)=NCC1)C; 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:
isogomphrenin i
External chemical identifiers:
CID:CID_101105495
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Isogomphrenin I
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 550.47
Log P RDKit -1.79
Topological polar surface area (Å2) RDKit 247.11
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 8
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
Isogomphrenin I
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 0.1781
Isogomphrenin I
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 -10.55
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