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Record Information
Version2.0
Created at2022-09-03 22:45:48 UTC
Updated at2022-09-03 22:45:48 UTC
NP-MRD IDNP0183795
Secondary Accession NumbersNone
Natural Product Identification
Common Nameerythromycin b
DescriptionErythromycin B, also known as beritromicina, belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. Thus, erythromycin b is considered to be a macrolide lipid molecule. Erythromycin B is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. erythromycin b is found in Saccharopolyspora erythraea. erythromycin b was first documented in 2000 (PMID: 10669574). An erythromycin that consists of erythronolide B having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively (PMID: 20381987) (PMID: 21175699).
Structure
Thumb
Synonyms
ValueSource
12-DeoxyerythromycinChEBI
BeritromicinaChEBI
BerythromycinChEBI
BerythromycineChEBI
BerythromycinumChEBI
Berythromycin, (8S)-isomerMeSH
12-Deoxyerythromycin aMeSH
Chemical FormulaC37H67NO12
Average Mass717.9274 Da
Monoisotopic Mass717.46633 Da
IUPAC Name(3R,4S,5S,6R,7R,9R,11R,12S,13R,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
Traditional Nameerythromycin B
CAS Registry NumberNot Available
SMILES
[H][C@@]1(C)C[C@]([H])(N(C)C)[C@@]([H])(O)[C@]([H])(O[C@]2([H])[C@@]([H])(C)[C@]([H])(O[C@@]3([H])C[C@@](C)(OC)[C@@]([H])(O)[C@]([H])(C)O3)[C@@]([H])(C)C(=O)O[C@]([H])(CC)[C@]([H])(C)[C@]([H])(O)[C@@]([H])(C)C(=O)[C@]([H])(C)C[C@@]2(C)O)O1
InChI Identifier
InChI=1S/C37H67NO12/c1-14-26-20(4)29(40)21(5)28(39)18(2)16-36(9,44)33(50-35-30(41)25(38(11)12)15-19(3)46-35)22(6)31(23(7)34(43)48-26)49-27-17-37(10,45-13)32(42)24(8)47-27/h18-27,29-33,35,40-42,44H,14-17H2,1-13H3/t18-,19-,20+,21+,22+,23-,24+,25+,26-,27+,29+,30-,31+,32+,33-,35+,36-,37-/m1/s1
InChI KeyIDRYSCOQVVUBIJ-PPGFLMPOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Saccharopolyspora erythraeaLOTUS Database
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 Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.72ALOGPS
logP3.49ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)12.61ChemAxon
pKa (Strongest Basic)8.38ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area173.68 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity184.72 m³·mol⁻¹ChemAxon
Polarizability78.17 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06653
BioCyc IDCPD-13805
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9918244
PDB IDNot Available
ChEBI ID28196
Good Scents IDNot Available
References
General References
  1. Mordi MN, Pelta MD, Boote V, Morris GA, Barber J: Acid-catalyzed degradation of clarithromycin and erythromycin B: a comparative study using NMR spectroscopy. J Med Chem. 2000 Feb 10;43(3):467-74. doi: 10.1021/jm9904811. [PubMed:10669574 ]
  2. Van den Bossche L, Lodi A, Schaar J, Shaakov S, Zorzan M, Tranquillini ME, Overballe-Petersen C, Hoogmartens J, Adams E: An interlaboratory study on the suitability of a gradient LC-UV method as a compendial method for the determination of erythromycin and its related substances. J Pharm Biomed Anal. 2010 Sep 21;53(1):109-12. doi: 10.1016/j.jpba.2010.03.012. Epub 2010 Mar 17. [PubMed:20381987 ]
  3. Zhang Q, Wu J, Qian J, Chu J, Zhuang Y, Zhang S, Liu W: Knocking out of tailoring genes eryK and eryG in an industrial erythromycin-producing strain of Saccharopolyspora erythraea leading to overproduction of erythromycin B, C and D at different conversion ratios. Lett Appl Microbiol. 2011 Feb;52(2):129-37. doi: 10.1111/j.1472-765X.2010.02973.x. Epub 2010 Dec 22. [PubMed:21175699 ]
  4. LOTUS database [Link]