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: CC(=O)C(C(N)=O)=C(C)O; CN(C)C; CO; cC(O)=C(C)C(C)=O; 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: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 0.3315


Tetracycline
ADMET 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 0.0
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