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Record Information
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:14:08 UTC
Secondary Accession Numbers
  • HMDB15066
Metabolite Identification
Common NameMethacycline
DescriptionMethacycline is only found in individuals that have used or taken this drug. It is a broad-spectrum semisynthetic antibiotic related to tetracycline but excreted more slowly and maintaining effective blood levels for a more extended period. [PubChem]Methacycline, a tetracycline antibiotic, is a protein synthesis inhibitors, inhibiting the binding of aminoacyl-tRNA to the mRNA-ribosome complex. Methacycline inhibits cell growth by inhibiting translation. It binds to the 16S part of 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. Tetracyclines also have been found to inhibit matrix metalloproteinases. This mechanism does not add to their antibiotic effects, but has led to extensive research on chemically modified tetracyclines or CMTs (like incyclinide) for the treatmet of rosacea, acne, and various types of neoplasms.
Chemical FormulaC22H22N2O8
Average Molecular Weight442.4187
Monoisotopic Molecular Weight442.13761569
IUPAC Name(4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-5,10,12,12a-tetrahydroxy-6-methylidene-1,3,11-trioxo-1,2,3,4,4a,5,5a,6,11,12a-decahydrotetracene-2-carboxamide
Traditional Namemethacycline
CAS Registry Number914-00-1
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Sub ClassNot Available
Direct ParentTetracyclines
Alternative Parents
  • Tetracycline
  • Anthracene carboxylic acid or derivatives
  • 2-naphthalenecarboxamide
  • Tetralin
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1,3-diketone
  • 1,3-dicarbonyl compound
  • Benzenoid
  • Cyclic alcohol
  • Tertiary alcohol
  • Vinylogous acid
  • Tertiary aliphatic amine
  • Amino acid or derivatives
  • Cyclic ketone
  • Tertiary amine
  • Carboxamide group
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Ketone
  • Polyol
  • Carboxylic acid derivative
  • Enol
  • Organic oxide
  • Organic oxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organooxygen compound
  • Amine
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available

Biological location:


Naturally occurring process:


Industrial application:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.73 g/LNot Available
LogP-0.3Not Available
Predicted Properties
Water Solubility0.73 g/LALOGPS
pKa (Strongest Acidic)2.21ChemAxon
pKa (Strongest Basic)6.16ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area178.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity111.57 m³·mol⁻¹ChemAxon
Polarizability42.07 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6w-6493300000-ed2bff4e67abd56cbb4aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0007-1732519000-1959eec7fc4de17f2b8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0000900000-0f0e7c486dfd89e42cdfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0101900000-29aab97c2620fad875d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-114i-4798800000-53616fd55bcea82c4439View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0113900000-53614fcf9e0af28211d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-1329400000-0bcb16e9d2c356437a39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9243000000-895316640742d9e1724aView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00931 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00931 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID26329510
KEGG Compound IDC07654
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetacycline
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Agwuh KN, MacGowan A: Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines. J Antimicrob Chemother. 2006 Aug;58(2):256-65. Epub 2006 Jul 1. [PubMed:16816396 ]
  2. Li J, Chen L, Wang X, Jin H, Ding L, Zhang K, Zhang H: Determination of tetracyclines residues in honey by on-line solid-phase extraction high-performance liquid chromatography. Talanta. 2008 Jun 15;75(5):1245-52. doi: 10.1016/j.talanta.2008.01.027. Epub 2008 Jan 20. [PubMed:18585209 ]