Minocycline (CHEM018111)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:00:12 UTC
Update Date2016-11-09 01:15:44 UTC
Accession NumberCHEM018111
Identification
Common NameMinocycline
ClassSmall Molecule
DescriptionMinocycline was first described in the literacture in 1966. It is a second generation tetracycline antibiotic that is active against gram-negative and gram-positive bacteria. Like other semisynthetic tetracyclines, minocycline has modifications to carbons 7-9 on the D ring to generate higher efficacy than previous tetracyclines. Minocycline was granted FDA approval on 30 June 1971.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(4S,4AS,5ar,12as)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamideChEBI
7-Dimethylamino-6-demethyl-6-deoxytetracyclineChEBI
MinociclinaChEBI
MinociclinumChEBI
MinomycinChEBI
MINOKegg
Chemical FormulaC23H27N3O7
Average Molecular Mass457.476 g/mol
Monoisotopic Mass457.185 g/mol
CAS Registry Number10118-90-8
IUPAC Name(4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
Traditional Nameminocycline
SMILES[H][C@@]12CC3=C(C(O)=CC=C3N(C)C)C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])C2
InChI IdentifierInChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27,29-30,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17-,23-/m0/s1
InChI KeyDYKFCLLONBREIL-KVUCHLLUSA-N
Chemical Taxonomy
Description 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
ClassTetracyclines
Sub ClassNot Available
Direct ParentTetracyclines
Alternative Parents
Substituents
  • Tetracycline
  • Naphthacene
  • Tetracene
  • Anthracene carboxylic acid or derivatives
  • Tetralin
  • Tertiary aliphatic/aromatic amine
  • Aryl ketone
  • Dialkylarylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexenone
  • Aralkylamine
  • Benzenoid
  • Vinylogous acid
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Amino acid or derivatives
  • Tertiary amine
  • Carboxamide group
  • Primary carboxylic acid amide
  • Ketone
  • Polyol
  • Carboxylic acid derivative
  • Enol
  • Amine
  • Alcohol
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.07 g/LALOGPS
logP-0.03ALOGPS
logP-3.3ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)-2.3ChemAxon
pKa (Strongest Basic)8.25ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area164.63 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity122.54 m³·mol⁻¹ChemAxon
Polarizability45.9 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-5198300000-09d1a0f95ca289894a54Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ab9-4101926000-ecf9ee87bcf7587066caSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Minocycline,2TMS,#6" TMS) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0001900000-6e678a7f126753a02d03Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00dr-0139100000-ff75a26ae387147257dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0293000000-c2ff616578522f961ba6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0390000000-d52131f98ad1d88e178cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0fki-1690000000-e5a98a7122d0379c17ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00dr-1980000000-8e1add1bcba675eab919Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-2940000000-5fb719a03faa19bc3eceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-6920000000-fb4c9cde9587edd4015eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-9300000000-6299955440e9be195128Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0000900000-6f7513e3aaa9e86725ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0011900000-ed3a433871dc9cea2d9fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dr-0559300000-4e1a4ba6692c21980caeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dr-0696000000-f57972687a1b0ffe9411Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1491000000-1847e0c78206ea2f84c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4l-0000900000-ae91ec031bca8b95216eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0001900000-0bc6e4a0b16f4acd3d1dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uei-1149100000-2ea03125f37fabe56999Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001r-1192000000-476045d8accb26d18bb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-015i-1390000000-f6a75360809f9018052aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0000900000-24f0aa03e70485995bfeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-0011900000-d0312060b105b95120e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi1-1349400000-c2d44f2b203b8c8a0d99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-d44b457b4826431b60bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0006900000-d21619964135e5793a97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-8049000000-c546414319e04333465dSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01017
HMDB IDHMDB0015152
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00018686
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDMIY
Wikipedia LinkMinocycline
Chemspider ID16735907
ChEBI ID50694
PubChem Compound IDNot Available
Kegg Compound IDC07225
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Gough A, Chapman S, Wagstaff K, Emery P, Elias E: Minocycline induced autoimmune hepatitis and systemic lupus erythematosus-like syndrome. BMJ. 1996 Jan 20;312(7024):169-72.
2. Chen M, Ona VO, Li M, Ferrante RJ, Fink KB, Zhu S, Bian J, Guo L, Farrell LA, Hersch SM, Hobbs W, Vonsattel JP, Cha JH, Friedlander RM: Minocycline inhibits caspase-1 and caspase-3 expression and delays mortality in a transgenic mouse model of Huntington disease. Nat Med. 2000 Jul;6(7):797-801.
3. Tikka TM, Koistinaho JE: Minocycline provides neuroprotection against N-methyl-D-aspartate neurotoxicity by inhibiting microglia. J Immunol. 2001 Jun 15;166(12):7527-33.
4. Song Y, Wei EQ, Zhang WP, Zhang L, Liu JR, Chen Z: Minocycline protects PC12 cells from ischemic-like injury and inhibits 5-lipoxygenase activation. Neuroreport. 2004 Oct 5;15(14):2181-4.
5. Nirmalananthan N, Greensmith L: Amyotrophic lateral sclerosis: recent advances and future therapies. Curr Opin Neurol. 2005 Dec;18(6):712-9.
6. Wikipedia: http://en.wikipedia.org/wiki/Minocycline
7. MEDSAFE: http://www.medsafe.govt.nz/profs/Datasheet/m/Minotabtab.pdf
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=28709717
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=31630007
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=31719236
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=31733348