TETRACYCLINE

Search structure
Synonyms:
Status: Approved (1953)
Entry Type: Small molecule
Molecule Category: Parent
ATC: A01AB13
UNII: F8VB5M810T

Structure
InChI Key OFVLGDICTFRJMM-WESIUVDSSA-N
Smile CN(C)[C@@H]1C(O)=C(C(N)=O)C(=O)[C@@]2(O)C(O)=C3C(=O)c4c(O)cccc4[C@@](C)(O)[C@H]3C[C@@H]12
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/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H24N2O8
Molecular Weight 444.44
AlogP -0.21
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 6.0
Number of Rotational Bond 2.0
Polar Surface Area 181.62
Molecular species ZWITTERION
Aromatic Rings 1.0
Heavy Atoms 32.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) -1.30E+00 - EXP
pKa Dissociation Constant 3.3 - EXP
Henry's Law Constant 4.66E-24 atm-m3/mole EST
Atmospheric OH Rate Constant 2.56E-10 cm3/molecule-sec EST
Melting Point 172.5 dec deg C EXP
Water Solubility 231 mg/L EXP
Vapor Pressure 3.09E-23 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Bacterial 70S ribosome inhibitor FDA PubMed Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Metallo protease Metallo protease MAM clan Metallo protease M10A subfamily
- - - - 100
Enzyme Transferase
- - - - 10
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Purine receptor
- - - - 2
Other cytosolic protein
- 4580 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 22
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 13200 - - 10
Unclassified protein
- 4580 - - 40

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Conjunctivitis, Inclusion 3 D003235 ClinicalTrials
Periodontitis 3 D010518 ClinicalTrials
Helicobacter Infections 3 D016481 ClinicalTrials
Vaginosis, Bacterial 3 D016585 ClinicalTrials
Candidiasis, Vulvovaginal 3 D002181 ClinicalTrials
Burns 2 D002056 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Multiple Sclerosis, Chronic Progressive 1 D020528 ClinicalTrials
Multiple Sclerosis, Relapsing-Remitting 1 D020529 ClinicalTrials
Osteomyelitis 0 D010019 ClinicalTrials
Chalazion 0 D017043 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt
Mixture

Cross References

Resources Reference
CAS NUMBER 60-54-8
ChEBI 77932
ChEMBL CHEMBL1440
DrugBank DB00759
DrugCentral 2611
EPA CompTox DTXSID7023645
FDA SRS F8VB5M810T
Human Metabolome Database HMDB0014897
Guide to Pharmacology 10927
KEGG C06570
PDB TAC
SureChEMBL SCHEMBL3098
ZINC ZINC000084441937
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