IMPPAT Phytochemical information: 
Tetracycline

Tetracycline
Summary

SMILES: CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1C[C@H]1C(=C(O)c3c([C@@]1(C)O)cccc3O)C2=O)O)O)C(=O)N)C
InChI: InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25-26,29,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
InChIKey: NWXMGUDVXFXRIG-WESIUVDSSA-N
DeepSMILES: CN[C@@H]C=O)C=C[C@@][C@H]6C[C@H]C=CO)cc[C@@]6C)O))cccc6O))))))))C6=O))))))O))O))C=O)N)))))C
Scaffold Graph/Node/Bond level: O=C1C=CC2C(=O)C3=Cc4ccccc4CC3CC2C1
Scaffold Graph/Node level: OC1CCC2C(C1)CC1CC3CCCCC3CC1C2O
Scaffold Graph level: CC1CCC2C(C1)CC1CC3CCCCC3CC1C2C
Functional groups: CN(C)C; CC(=O)C(C(N)=O)=C(O)C; cC(O)=C(C)C(=O)C; CO; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Tetracyclines
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Polycyclic aromatic polyketides
NP Classifier Class: Tetracyclines
Synonymous chemical names:
tetracycline
External chemical identifiers:
CID:CID_54675776; ZINC:ZINC000100303069; SureChEMBL:SCHEMBL21271987
Chemical structure download


Tetracycline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 444.44
Log P RDKit -0.37
Topological polar surface area (Å2) RDKit 181.62
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.41
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
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 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Tetracycline
Drug-likeness properties
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 0
Ghose filter RDKit Passed
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 0.331519


Tetracycline
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 -8.83
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 Yes