IMPPAT Phytochemical information: 
Cucurbitacin I
Cucurbitacin I
Summary

SMILES: OC1=C[C@@H]2C(=CC[C@@H]3[C@@]2(C)C(=O)C[C@]2([C@@]3(C)C[C@H]([C@@H]2[C@](C(=O)/C=C/C(O)(C)C)(O)C)O)C)C(C1=O)(C)C
InChI: InChI=1S/C30H42O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-13,17,19-20,23,31-32,36-37H,10,14-15H2,1-8H3/b12-11+/t17-,19-,20+,23+,27+,28-,29+,30+/m1/s1
InChIKey: NISPVUDLMHQFRQ-MKIKIEMVSA-N
DeepSMILES: OC=C[C@@H]C=CC[C@@H][C@@]6C)C=O)C[C@][C@@]6C)C[C@H][C@@H]5[C@]C=O)/C=C/CO)C)C)))))O)C)))O))))C))))))))CC6=O))C)C
Scaffold Graph/Node/Bond level: O=C1C=CC2C(=CCC3C4CCCC4CC(=O)C23)C1
Scaffold Graph/Node level: OC1CCC2C(CCC3C4CCCC4CC(O)C23)C1
Scaffold Graph level: CC1CCC2C(CCC3C4CCCC4CC(C)C23)C1
Functional groups: CC(=O)C(O)=CC; CC=C(C)C; CC(=O)C; C/C=C/C(C)=O; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Cucurbitacins
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Cucurbitane triterpenoids
Synonymous chemical names:
cucurbitacin i (elatericin b), cucurbitacin i, elatericin b (cucurbitacin i), cucurbitacin I, elatericin b, Cucurbitacin I, Elatericin B
External chemical identifiers:
CID:CID_5281321; ChEMBL:CHEMBL387737; ChEBI:CHEBI:3947; ZINC:ZINC000004097803; FDASRS:SHQ47990PH; SureChEMBL:SCHEMBL2523066; MolPort-023-276-142
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cucurbitacin I
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 514.66
Log P RDKit 3.62
Topological polar surface area (Å2) RDKit 132.13
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Cucurbitacin I
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.332726
Cucurbitacin I
ADME 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 Low
Log Kp (Skin permeation, cm/s) SwissADME -7.54
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 Yes
P-glycoprotein substrate SwissADME Yes
Cucurbitacin I
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000070ENSG00000172757CFL11072ChEMBL
TAR_EXP_000776ENSG00000005844ITGAL3683ChEMBL, NPASS