(4S,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-N-(hydroxymethyl)-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

• ChemBase ID: 336
• Molecular Formular: C23H25ClN2O9
• Molecular Mass: 508.9056
• Monoisotopic Mass: 508.12485807
• SMILES: c1cc(c2c(c1Cl)[C@@]([C@@H]1C(=C([C@]3([C@@H](C1)[C@@H](C(=C(C3=O)C(=O)NCO)O)N(C)C)O)O)C2=O)(C)O)O
• Canonical SMILES: OCNC(=O)C1=C(O)[C@@H](N(C)C)[C@H]2[C@](C1=O)(O)C(=C1[C@H](C2)[C@](C)(O)c2c(C1=O)c(O)ccc2Cl)O
• InChI: InChI=1S/C23H25ClN2O9/c1-22(34)8-6-9-16(26(2)3)18(30)14(21(33)25-7-27)20(32)23(9,35)19(31)12(8)17(29)13-11(28)5-4-10(24)15(13)22/h4-5,8-9,16,27-28,30-31,34-35H,6-7H2,1-3H3,(H,25,33)/t8-,9-,16-,22-,23-/m0/s1
• InChIKey: GJGDLRSSCNAKGL-KMVLDZISSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-N-(hydroxymethyl)-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• IUPAC Traditional name: clomocyclina
• Synonyms: Clomociclina [INN-Spanish]; Clomocyclinum [INN-Latin]; Chlormethylenecycline; Clomocycline

Database IDs

• CAS Number: 1181-54-0
• PubChem SID: 160963799; 46505301
• PubChem CID: 54680675; 5464321

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.012655632
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -4.395534
• LogD (pH = 7.4): -6.200771
• Log P: -3.2647724
• Molar Refractivity: 124.9916 cm^3
• Polarizability: 47.64877 Å^3
• Polar Surface Area: 187.86 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.45
• LOG S: -2.46
• Solubility (Water): 1.77e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 0.2

DETAILS

DrugBank - DB00453

• Drug Groups: approved
• Description: Clomocycline is a tetracycline antibiotic.
• Indication: For the treatment and management of Brucellosis, mycoplasma infection, acne vulgaris, chlamydial infection;Chronic bronchitis
• Pharmacology: Clomocycline is a tetracycline antibiotic that is commonly prescribed by medical doctors for infections and to treat acne. It may also be used to treat urinary tract infections, gum disease, and other bacterial infections such as gonorrhea and chlamydia. Clomocycline is also used commonly as a prophylactic treatment for infection by Bacillus anthracis (anthrax). It is also effective against Yersinia pestis and malaria and is also prescribed for the treatment of Lyme disease. Clomocycline inhibits cell growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. The binding is reversible in nature. Cells become resistant to Clomocycline by at least two mechanisms: efflux and ribosomal protection. In efflux, a resistance gene encodes a membrane protein that actively pumps Clomocycline out of the cell. This is the mechanism of action of the tetracycline resistance gene on the artificial plasmid pBR322. In ribosomal protection, a resistance gene encodes a protein which binds to the ribosome and prevents Clomocycline from acting on the ribosome.
• Affected Organisms: Enteric bacteria and other eubacteria
• External Links: Wikipedia