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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:12:55 UTC
Update Date2021-09-14 15:44:41 UTC
HMDB IDHMDB0061019
Secondary Accession Numbers
  • HMDB61019
Metabolite Identification
Common Name14-hydroxyclarithromycin
Description14-hydroxyclarithromycin is a metabolite of clarithromycin. Clarithromycin is a macrolide antibiotic used to treat pharyngitis, tonsillitis, acute maxillary sinusitis, acute bacterial exacerbation of chronic bronchitis, pneumonia (especially atypical pneumonias associated with Chlamydia pneumoniae or TWAR), skin and skin structure infections. In addition, it is sometimes used to treat Legionellosis, Helicobacter pylori, and lyme disease. (Wikipedia)
Structure
Data?1563866135
Synonyms
ValueSource
14-Hydroxy-6-O-methylerythromycinHMDB
14-Hydroxy-6-0-methylerthromycin aHMDB
14-Hydroxyclarithromycin, (14R)-isomerHMDB
14-OH-ClarithromycinHMDB
14-Hydroxyclarithromycin, (14S)-isomerHMDB
Chemical FormulaC38H69NO14
Average Molecular Weight763.9528
Monoisotopic Molecular Weight763.471805921
IUPAC Name(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-14-(1-hydroxyethyl)-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
Traditional Name(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-14-(1-hydroxyethyl)-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
CAS Registry NumberNot Available
SMILES
CO[C@]1(C)C[C@H](O[C@H]2[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@@](C)(C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@H](OC(=O)[C@@H]2C)C(C)O)OC)O[C@@H](C)[C@@H]1O
InChI Identifier
InChI=1S/C38H69NO14/c1-18-16-37(9,48-14)32(53-35-28(42)25(39(11)12)15-19(2)49-35)21(4)29(51-26-17-36(8,47-13)31(44)24(7)50-26)22(5)34(45)52-33(23(6)40)38(10,46)30(43)20(3)27(18)41/h18-26,28-33,35,40,42-44,46H,15-17H2,1-14H3/t18-,19-,20+,21+,22-,23?,24+,25+,26+,28-,29+,30-,31+,32-,33-,35+,36-,37-,38+/m1/s1
InChI KeyBLPFDXNVUDZBII-KNPZYKNQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Macrolide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Monosaccharide
  • Tertiary alcohol
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Ketone
  • Cyclic ketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Lactone
  • Acetal
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.49 g/LALOGPS
logP2.44ALOGPS
logP2.09ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)12.43ChemAxon
pKa (Strongest Basic)8.38ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area203.14 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity192.23 m³·mol⁻¹ChemAxon
Polarizability81.95 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+260.05430932474
DeepCCS[M-H]-258.36730932474
DeepCCS[M-2H]-292.39930932474
DeepCCS[M+Na]+266.17730932474
AllCCS[M+H]+265.132859911
AllCCS[M+H-H2O]+264.732859911
AllCCS[M+NH4]+265.432859911
AllCCS[M+Na]+265.432859911
AllCCS[M-H]-262.732859911
AllCCS[M+Na-2H]-268.632859911
AllCCS[M+HCOO]-275.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
14-hydroxyclarithromycinCO[C@]1(C)C[C@H](O[C@H]2[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@@](C)(C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@H](OC(=O)[C@@H]2C)C(C)O)OC)O[C@@H](C)[C@@H]1O3339.3Standard polar33892256
14-hydroxyclarithromycinCO[C@]1(C)C[C@H](O[C@H]2[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@@](C)(C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@H](OC(=O)[C@@H]2C)C(C)O)OC)O[C@@H](C)[C@@H]1O4365.1Standard non polar33892256
14-hydroxyclarithromycinCO[C@]1(C)C[C@H](O[C@H]2[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@@](C)(C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@H](OC(=O)[C@@H]2C)C(C)O)OC)O[C@@H](C)[C@@H]1O4494.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-9200000700-ad2e60c83f8e99d1eef42017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (TBDMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (TBDMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14-hydroxyclarithromycin GC-MS (TBDMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14-hydroxyclarithromycin 10V, Positive-QTOFsplash10-052s-0100294600-1b4f10429831abba55462017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14-hydroxyclarithromycin 20V, Positive-QTOFsplash10-052s-0300892100-588a4888f1d6d44d86922017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14-hydroxyclarithromycin 40V, Positive-QTOFsplash10-052k-9400880000-d339383371f4557521872017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14-hydroxyclarithromycin 10V, Negative-QTOFsplash10-03dr-0500033900-6bc116d632844549ab752017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14-hydroxyclarithromycin 20V, Negative-QTOFsplash10-0a71-0300394500-e1405cd8c1707f750dbb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14-hydroxyclarithromycin 40V, Negative-QTOFsplash10-05fr-8400931100-1acaf1c362f87a513ecb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14-hydroxyclarithromycin 10V, Negative-QTOFsplash10-03di-0000001900-ab6d1b3903c98aea75272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14-hydroxyclarithromycin 20V, Negative-QTOFsplash10-000f-4800033900-d85968b75f17ff6539172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14-hydroxyclarithromycin 40V, Negative-QTOFsplash10-056r-6900022400-92586a816d832f9995262021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14-hydroxyclarithromycin 10V, Positive-QTOFsplash10-03di-0000000900-345a01928330722fdfbc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14-hydroxyclarithromycin 20V, Positive-QTOFsplash10-0abi-1400052900-2c9730d825f51e5be67f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14-hydroxyclarithromycin 40V, Positive-QTOFsplash10-0btd-5900010000-6a9aa6cd465f449583632021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound84020
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available