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Record Information
Version2.0
Created at2022-09-12 15:06:10 UTC
Updated at2022-09-12 15:06:11 UTC
NP-MRD IDNP0330082
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,5's,6s,6's,7r,8s,9r,11r,13s,14r,15r,22r,25s,27r,29r)-22-ethyl-7,9,13,15-tetrahydroxy-29-(3-hydroxypropyl)-6'-[(2r)-2-hydroxypropyl]-11-methoxy-5',6,8,14-tetramethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-trien-3-one
DescriptionNeomaclafungin A belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (1s,5's,6s,6's,7r,8s,9r,11r,13s,14r,15r,22r,25s,27r,29r)-22-ethyl-7,9,13,15-tetrahydroxy-29-(3-hydroxypropyl)-6'-[(2r)-2-hydroxypropyl]-11-methoxy-5',6,8,14-tetramethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-trien-3-one was first documented in 2017 (PMID: 28695580). Based on a literature review very few articles have been published on Neomaclafungin A.
Structure
Thumb
Synonyms
ValueSource
34-Deoxy-34,36-didesmethylmaclafunginMeSH
Chemical FormulaC44H76O11
Average Mass781.0810 Da
Monoisotopic Mass780.53876 Da
IUPAC Name(1S,5'S,6S,6'S,7R,8S,9R,11R,13S,14R,15R,22R,25S,27R,29R)-22-ethyl-7,9,13,15-tetrahydroxy-29-(3-hydroxypropyl)-6'-[(2R)-2-hydroxypropyl]-11-methoxy-5',6,8,14-tetramethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-trien-3-one
Traditional Name(1S,5'S,6S,6'S,7R,8S,9R,11R,13S,14R,15R,22R,25S,27R,29R)-22-ethyl-7,9,13,15-tetrahydroxy-29-(3-hydroxypropyl)-6'-[(2R)-2-hydroxypropyl]-11-methoxy-5',6,8,14-tetramethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-trien-3-one
CAS Registry NumberNot Available
SMILES
CC[C@@H]1CC[C@@H]2O[C@]3(CC[C@H](C)[C@H](C[C@@H](C)O)O3)C[C@H](OC(=O)C=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](O)C[C@@H](C[C@H](O)[C@H](C)[C@H](O)CCC=CC=C1)OC)[C@@H]2CCCO
InChI Identifier
InChI=1S/C44H76O11/c1-8-33-14-11-9-10-12-16-36(47)31(5)37(48)25-34(52-7)26-38(49)32(6)43(51)29(3)17-20-42(50)53-41-27-44(22-21-28(2)40(55-44)24-30(4)46)54-39(19-18-33)35(41)15-13-23-45/h9-11,14,17,20,28-41,43,45-49,51H,8,12-13,15-16,18-19,21-27H2,1-7H3/t28-,29-,30+,31+,32-,33-,34+,35+,36+,37-,38+,39-,40-,41-,43+,44-/m0/s1
InChI KeyCZYYOXFXSUDWRV-FZRHHGSDSA-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Ketal
  • Oxane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP5.09ChemAxon
pKa (Strongest Acidic)14.12ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area175.37 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity217.57 m³·mol⁻¹ChemAxon
Polarizability88.52 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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139583190
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Zhu S, Wu Y: Synthesis and Configuration of Neomaclafungin A. Chem Asian J. 2017 Sep 5;12(17):2211-2215. doi: 10.1002/asia.201700950. Epub 2017 Aug 11. [PubMed:28695580 ]
  2. LOTUS database [Link]