SID17389774

ID: ALA1607480

Chembl Id: CHEMBL1607480

Max Phase: Approved

First Approval: 1964

Molecular Formula: C22H25ClN2O9

Molecular Weight: 460.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Oxytetracycline hcl | Oxytetracycline hydrochloride | Oxytetracyclini hydrochloridum

Trade Names(3): Oxy-kesso-tetra | Oxytetracycline hydrochloride | Terramycin

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.Cl

Standard InChI:  InChI=1S/C22H24N2O9.ClH/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);1H/t12-,13-,14+,17+,21-,22+;/m1./s1

Standard InChI Key:  UBDNTYUBJLXUNN-IFLJXUKPSA-N

Molecule Features

Natural Product: No

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

Calculated 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

1. PubChem BioAssay data set, 

2. Unpublished dataset, 

3. PubChem BioAssay data set, 

4. Okanya PW, Mohr KI, Gerth K, Steinmetz H, Huch V, Jansen R, Müller R..  (2012)  Hyaladione, an S-methyl cyclohexadiene-dione from Hyalangium minutum.,  75  (4): [PMID:22497473] [10.1021/np200776v]

5. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

6. PubChem BioAssay data set, 

7. Thongbai B, Surup F, Mohr K, Kuhnert E, Hyde KD, Stadler M..  (2013)  Gymnopalynes A and B, chloropropynyl-isocoumarin antibiotics from cultures of the basidiomycete Gymnopus sp.,  76  (11): [PMID:24175638] [10.1021/np400609f]

8. Jansen R, Sood S, Huch V, Kunze B, Stadler M, Müller R..  (2014)  Pyrronazols, metabolites from the myxobacteria Nannocystis pusilla and N. exedens, are unusual chlorinated pyrone-oxazole-pyrroles.,  77  (2): [PMID:24460410] [10.1021/np400877r]

9. Shea TA, Burburan PJ, Matubia VN, Ramcharan SS, Rosario I, Parkin DW, Stockman BJ..  (2014)  Identification of proton-pump inhibitor drugs that inhibit Trichomonas vaginalis uridine nucleoside ribohydrolase.,  24  (4): [PMID:24468412] [10.1016/j.bmcl.2014.01.014]

10. PubChem BioAssay data set, 

11. PubChem BioAssay data set, 

12. Jansen R, Mohr KI, Bernecker S, Stadler M, Müller R..  (2014)  Indothiazinone, an indolyl thiazolyl ketone from a novel myxobacterium belonging to the Sorangiineae.,  77  (4): [PMID:24697522] [10.1021/np500144t]

13. Jansen R, Sood S, Mohr KI, Kunze B, Irschik H, Stadler M, Müller R..  (2014)  Nannozinones and sorazinones, unprecedented pyrazinones from myxobacteria.,  77  (11): [PMID:25397992] [10.1021/np500632c]

14. Surup F, Thongbai B, Kuhnert E, Sudarman E, Hyde KD, Stadler M..  (2015)  Deconins A-E: Cuparenic and Mevalonic or Propionic Acid Conjugates from the Basidiomycete Deconica sp. 471.,  78  (4): [PMID:25871540] [10.1021/np5010104]

15. British National Formulary (72nd edition), 

16. Unpublished dataset, 

17. Paulsen MH, Ausbacher D, Bayer A, Engqvist M, Hansen T, Haug T, Anderssen T, Andersen JH, Sollid JUE, Strøm MB..  (2019)  Antimicrobial activity of amphipathic α,α-disubstituted β-amino amide derivatives against ESBL - CARBA producing multi-resistant bacteria; effect of halogenation, lipophilicity and cationic character.,  183  [PMID:31536892] [10.1016/j.ejmech.2019.111671]

18. Garcia KYM, Phukhamsakda C, Quimque MTJ, Hyde KD, Stadler M, Stadler M, Macabeo APG..  (2021)  Catechol-Bearing Polyketide Derivatives from Sparticola junci.,  84  (7.0): [PMID:34197704] [10.1021/acs.jnatprod.1c00415]

Source

Source(6):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• British National Formulary