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992-21-2 molecular structure
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(2S)-6-[({[(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracen-2-yl]formamido}methyl)amino]-2-aminohexanoic acid

ChemBase ID: 141
Molecular Formular: C29H38N4O10
Molecular Mass: 602.63282
Monoisotopic Mass: 602.25879344
SMILES and InChIs

SMILES:
c1cc(c2c(c1)[C@@]([C@@H]1C(=C([C@]3([C@@H](C1)[C@@H](C(=C(C3=O)C(=O)NCNCCCC[C@H](N)C(=O)O)O)N(C)C)O)O)C2=O)(C)O)O
Canonical SMILES:
N[C@H](C(=O)O)CCCCNCNC(=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)ccc2)O
InChI:
InChI=1S/C29H38N4O10/c1-28(42)13-7-6-9-17(34)18(13)22(35)19-14(28)11-15-21(33(2)3)23(36)20(25(38)29(15,43)24(19)37)26(39)32-12-31-10-5-4-8-16(30)27(40)41/h6-7,9,14-16,21,31,34,36-37,42-43H,4-5,8,10-12,30H2,1-3H3,(H,32,39)(H,40,41)/t14-,15-,16-,21-,28+,29-/m0/s1
InChIKey:
AHEVKYYGXVEWNO-UEPZRUIBSA-N

Cite this record

CBID:141 http://www.chembase.cn/molecule-141.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-6-[({[(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracen-2-yl]formamido}methyl)amino]-2-aminohexanoic acid
IUPAC Traditional name
limeciclina
Brand Name
Aureomycin
Acronize
Acronize PD
Aureocarmyl
Aureociclin
Aureociclina
Aureocina
Aureocycline
Aureomicina
Aureomycin monohydrochloride
Aureomycin A-377
Aureomykoin
Aurofac
Aurofac 10
Auxeomycin
B-Aureo
Biomitsin
Biomitsin hydrochloride
Biomycin A
Biomycin hydrochloride
Biovetin
Centraureo
Chrusomykine
Chrysomykine
Clorocipan
Duomycin
Flamycin
Isphamycin
Orospray
Psittacin hydrochloride
Tetra 5
Tetralysal
Tetrlysal 300
Tocopherex
Aureomycin hydrochloride
Synonyms
Chlorotetracycline
Chlortetracyclinium chloride
Chlortetracycline hydrochloride
Chlortetracycline
Chlortetracyclin
Chlorotetracycline hydrochloride
CLTC
7-Chlorotetracycline
Lymecycline
CAS Number
992-21-2
PubChem SID
46505518
160963604
PubChem CID
24757945
54707177

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 0.4019689  H Acceptors 13 
H Donor LogD (pH = 5.5) -8.334031 
LogD (pH = 7.4) -8.35059  Log P -8.298649 
Molar Refractivity 154.5096 cm3 Polarizability 59.682735 Å3
Polar Surface Area 242.98 Å2 Rotatable Bonds 10 
Lipinski's Rule of Five false 
Log P -0.27  LOG S -2.66 
Solubility (Water) 1.31e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Soluble (at all physiological pH values) expand Show data source
Hydrophobicity(logP)
0.3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00256 external link
Item Information
Drug Groups approved
Description A tetracycline with a 7-chloro substitution. [PubChem]
Indication For the treatment of 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. Lymecycline 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.
Pharmacology Lymecycline is a tetracycline broad-spectrum antibiotic. It is approximately 5000 times more soluble than tetracycline base and is unique amongst tetracyclines in that it is absorbed by the "active transport" process across the intestinal wall, making use of the same fast and efficient mechanism by which carbohydrates are absorbed. It inhibits cell growth by inhibiting translation.
Toxicity Adverse effects include nausea, vomiting, diarrhoea, glossitis, enterocolitis, dysphagia, dermatitis, hypersensitivity reactions, proctitis, and vaginitis.
Affected Organisms
Enteric bacteria and other eubacteria
Absorption Absorption is fast and efficient. Bioavailability is 100% following oral administration.
References
[Link]
Meynadier J, Alirezai M: Systemic antibiotics for acne. Dermatology. 1998;196(1):135-9. [Pubmed]
External Links
Wikipedia

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Meynadier J, Alirezai M: Systemic antibiotics for acne. Dermatology. 1998;196(1):135-9. Pubmed
  • •  Link
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PATENTS

PATENTS

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INTERNET

INTERNET

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