Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2021-01-05 23:15:23 UTC
Updated at2021-07-15 17:16:01 UTC
NP-MRD IDNP0013984
Secondary Accession NumbersNone
Natural Product Identification
Common NameEpothilone A
Provided ByNPAtlasNPAtlas Logo
DescriptionEpothilone a, also known as epo a, belongs to the class of organic compounds known as epothilones and analogues. These are macrolides consisting of a 16-member lactone ring conjugated at the carbon 16 with a 1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl group. Some epothilone analogues containing a lactam ring instead of the lactone ring. Thus, epothilone a is considered to be a macrolide. Epothilone a is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Epothilone A is found in Sorangium cellulosum. It was first documented in 2000 (PMID: 10831849). Based on a literature review a significant number of articles have been published on Epothilone a (PMID: 25855820) (PMID: 11133086) (PMID: 16134928) (PMID: 18271516).
Structure
Thumb
Synonyms
ValueSource
(-)-Epothilone aChEBI
(1S,7S,10R,11S,12S,16R)-7-Hydroxy-11-(S)-hydroxy-8,8,10,12-tetramethyl-3-[(e)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dioneChEBI
Epo aChEBI
Epothilon aMeSH
Chemical FormulaC26H39NO6S
Average Mass493.6560 Da
Monoisotopic Mass493.24981 Da
IUPAC Name(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
Traditional Nameepothilone A
CAS Registry NumberNot Available
SMILES
C[C@H]1CCC[C@H]2O[C@H]2C[C@H](OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@H]1O)C(\C)=C\C1=CSC(C)=N1
InChI Identifier
InChI=1S/C26H39NO6S/c1-14-8-7-9-19-21(32-19)11-20(15(2)10-18-13-34-17(4)27-18)33-23(29)12-22(28)26(5,6)25(31)16(3)24(14)30/h10,13-14,16,19-22,24,28,30H,7-9,11-12H2,1-6H3/b15-10+/t14-,16+,19+,20-,21-,22-,24-/m0/s1
InChI KeyHESCAJZNRMSMJG-KKQRBIROSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Sorangium cellulosumNPAtlas
Chemical Taxonomy
Description Belongs to the class of organic compounds known as epothilones and analogues. These are macrolides consisting of a 16-member lactone ring conjugated at the carbon 16 with a 1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl group. Some epothilone analogues containing a lactam ring instead of the lactone ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassEpothilones and analogues
Direct ParentEpothilones and analogues
Alternative Parents
Substituents
  • Epothilone
  • 2,4-disubstituted 1,3-thiazole
  • Azole
  • Heteroaromatic compound
  • Thiazole
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Secondary alcohol
  • Cyclic ketone
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP3.28ALOGPS
logP3.84ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)2.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area109.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity130.12 m³·mol⁻¹ChemAxon
Polarizability54.07 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA009778
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00045298
Chemspider ID395491
KEGG Compound IDC12153
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound448799
PDB IDNot Available
ChEBI ID31549
Good Scents IDNot Available
References
General References
  1. Authors unspecified: Erratum: Borderud SP, Li Y, Burkhalter JE, Sheffer CE and Ostroff JS. Electronic cigarette use among patients with cancer: Characteristics of electronic cigarette users and their smoking cessation outcomes. Cancer. doi: 10.1002/ cncr.28811. Cancer. 2015 Mar 1;121(5):800. doi: 10.1002/cncr.29118. [PubMed:25855820 ]
  2. Julien B, Shah S, Ziermann R, Goldman R, Katz L, Khosla C: Isolation and characterization of the epothilone biosynthetic gene cluster from Sorangium cellulosum. Gene. 2000 May 16;249(1-2):153-60. doi: 10.1016/s0378-1119(00)00149-9. [PubMed:10831849 ]
  3. Altmann KH, Bold G, Caravatti G, Florsheimer A, Guagnano V, Wartmann M: Synthesis and biological evaluation of highly potent analogues of epothilones B and D. Bioorg Med Chem Lett. 2000 Dec 18;10(24):2765-8. doi: 10.1016/s0960-894x(00)00555-2. [PubMed:11133086 ]
  4. Nicolaou KC: Joys of molecules. 2. Endeavors in chemical biology and medicinal chemistry. J Med Chem. 2005 Sep 8;48(18):5613-38. doi: 10.1021/jm050524f. [PubMed:16134928 ]
  5. Erdelyi M, Pfeiffer B, Hauenstein K, Fohrer J, Gertsch J, Altmann KH, Carlomagno T: Conformational preferences of natural and C3-modified epothilones in aqueous solution. J Med Chem. 2008 Mar 13;51(5):1469-73. doi: 10.1021/jm7013452. Epub 2008 Feb 14. [PubMed:18271516 ]