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Record Information
Version2.0
Created at2022-09-10 13:25:14 UTC
Updated at2022-09-10 13:25:15 UTC
NP-MRD IDNP0300815
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r)-1-[(1s,3r,4s,9r,13r,14r)-13-hydroxy-3-[(2r,5s)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-4,14,16,16-tetramethyl-7,11-dioxo-2,6,10,17-tetraoxatricyclo[11.3.1.1¹,⁵]octadecan-9-yl]ethyl acetate
DescriptionManauealide C 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. (1r)-1-[(1s,3r,4s,9r,13r,14r)-13-hydroxy-3-[(2r,5s)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-4,14,16,16-tetramethyl-7,11-dioxo-2,6,10,17-tetraoxatricyclo[11.3.1.1¹,⁵]octadecan-9-yl]ethyl acetate is found in Gracilaria coronopifolia. (1r)-1-[(1s,3r,4s,9r,13r,14r)-13-hydroxy-3-[(2r,5s)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-4,14,16,16-tetramethyl-7,11-dioxo-2,6,10,17-tetraoxatricyclo[11.3.1.1¹,⁵]octadecan-9-yl]ethyl acetate was first documented in 1998 (PMID: 27392593). Based on a literature review very few articles have been published on Manauealide C.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC34H50O11
Average Mass634.7630 Da
Monoisotopic Mass634.33531 Da
IUPAC Name(1R)-1-[(1S,3R,4S,9R,13R,14R)-13-hydroxy-3-[(2R,5S)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-4,14,16,16-tetramethyl-7,11-dioxo-2,6,10,17-tetraoxatricyclo[11.3.1.1^{1,5}]octadecan-9-yl]ethyl acetate
Traditional Name(1R)-1-[(1S,3R,4S,9R,13R,14R)-13-hydroxy-3-[(2R,5S)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-4,14,16,16-tetramethyl-7,11-dioxo-2,6,10,17-tetraoxatricyclo[11.3.1.1^{1,5}]octadecan-9-yl]ethyl acetate
CAS Registry NumberNot Available
SMILES
CO[C@@H](CC[C@@H](C)[C@H]1O[C@@]23CC(OC(=O)C[C@@H](OC(=O)C[C@@](O)(O2)[C@H](C)CC3(C)C)[C@@H](C)OC(C)=O)[C@@H]1C)C1=CC=CC(O)=C1
InChI Identifier
InChI=1S/C34H50O11/c1-19(12-13-26(40-8)24-10-9-11-25(36)14-24)31-21(3)28-17-34(44-31)32(6,7)16-20(2)33(39,45-34)18-30(38)42-27(15-29(37)43-28)22(4)41-23(5)35/h9-11,14,19-22,26-28,31,36,39H,12-13,15-18H2,1-8H3/t19-,20-,21+,22-,26+,27-,28?,31-,33-,34+/m1/s1
InChI KeyTYIVYKUKAGDZDP-IKIQRMHMSA-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
Gracilaria coronopifoliaLOTUS Database
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
  • Tricarboxylic acid or derivatives
  • Benzylether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Ketal
  • Phenol
  • Benzenoid
  • Oxane
  • Monocyclic benzene moiety
  • Lactone
  • Hemiacetal
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP5.71ChemAxon
pKa (Strongest Acidic)9.36ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area147.05 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity161.24 m³·mol⁻¹ChemAxon
Polarizability67.61 ųChemAxon
Number of Rings4ChemAxon
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 IDC00050385
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101982289
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Nagai H, Kan Y, Fujita T, Sakamoto B, Hokama Y: Manauealide C and Anhydrodebromoaplysiatoxin, Toxic Constituents of the Hawaiian Red Alga, Gracilaria coronopifolia. Biosci Biotechnol Biochem. 1998;62(5):1011-3. doi: 10.1271/bbb.62.1011. [PubMed:27392593 ]
  2. LOTUS database [Link]