ID: ALA1517

Max Phase: Approved

First Approval: 1964

Molecular Formula: C22H24N2O9

Molecular Weight: 460.44

Molecule Type: Small molecule

Representations

Synonyms (13): 5-hydroxytetracycline dihydrate | Nitox | Oxitetracycline | Oxytetracycline | Oxytetracycline (anhydrous) | Oxytetracycline anhydrous | Oxytetracycline dehydrate | Oxytetracycline dihydrate | Oxytetracyclinum dihydras | Terrafungine | Terramycine | NSC-757262 | NSC-9169
Synonyms from Alternative Forms(13):

Trade Names(12): Berkmycen | Chemocycline | Galenomycin | Hi-Tet | Imperacin | Microtet | OXTC | Oxymycin | Oxytetramix-250 | Terramycin | Tetraplex | Unimycin

Canonical SMILES:  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]3[C@H](O)[C@@H]12

Standard InChI:  InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1

Standard InChI Key:  IWVCMVBTMGNXQD-PXOLEDIWSA-N

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 460.44

Molecular Weight (Monoisotopic): 460.1482

AlogP: -1.24

#Rotatable Bonds: 2

Polar Surface Area: 201.85

Molecular Species: ACID

HBA: 10

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.84

CX Basic pKa: 7.38

CX LogP: -4.50

CX LogD: -4.82

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.26

Np Likeness Score: 1.83

References

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18. Singh N, Rai V, Tripathi CKM.  (2012)  Production and optimization of oxytetracycline by a new isolate Streptomyces rimosus using response surface methodology,  21  (10): [10.1007/s00044-011-9845-4]

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33. Unpublished dataset, 

34. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

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42. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

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Source

Source(12):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• TP-search Transporter Database
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6