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Record Information
Version2.0
Created at2020-12-09 01:25:06 UTC
Updated at2021-07-15 16:47:35 UTC
NP-MRD IDNP0003863
Secondary Accession NumbersNone
Natural Product Identification
Common Name4'-oxomacrophorin D
Provided ByNPAtlasNPAtlas Logo
Description 4'-oxomacrophorin D is found in Penicillium and Penicillium gladioli. 4'-oxomacrophorin D was first documented in 2001 (PMID: 11575965). Based on a literature review very few articles have been published on 5-{[(1S,6R)-6-{[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]methyl}-2,5-dioxo-7-oxabicyclo[4.1.0]Hept-3-en-3-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid.
Structure
Data?1624573921
Synonyms
ValueSource
5-{[(1S,6R)-6-{[(1S,4as,8as)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]methyl}-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoateGenerator
Chemical FormulaC28H38O8
Average Mass502.6040 Da
Monoisotopic Mass502.25667 Da
IUPAC Name(3S)-5-{[(1S,6R)-6-{[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]methyl}-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid
Traditional Name(3S)-5-{[(1S,6R)-6-{[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]methyl}-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid
CAS Registry NumberNot Available
SMILES
CC(O)(CC(O)=O)CC(=O)OCC1=CC(=O)[C@]2(C[C@H]3C(=C)CC[C@H]4C(C)(C)CCC[C@]34C)O[C@@H]2C1=O
InChI Identifier
InChI=1S/C28H38O8/c1-16-7-8-19-25(2,3)9-6-10-27(19,5)18(16)12-28-20(29)11-17(23(33)24(28)36-28)15-35-22(32)14-26(4,34)13-21(30)31/h11,18-19,24,34H,1,6-10,12-15H2,2-5H3,(H,30,31)/t18-,19-,24+,26?,27+,28-/m0/s1
InChI KeyTZHODXJMZGQSQM-DMDFLFCXSA-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
PenicilliumNPAtlas
Penicillium gladioliLOTUS Database
Chemical Taxonomy
ClassificationNot classified
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
logP3.81ALOGPS
logP3.81ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area130.5 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity130.61 m³·mol⁻¹ChemAxon
Polarizability53.53 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA002415
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78436143
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139583768
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Fujimoto H, Nakamura E, Kim YP, Okuyama E, Ishibashi M, Sassa T: Immunomodulatory constituents from an Ascomycete, Eupenicillium crustaceum, and revised absolute structure of macrophorin D. J Nat Prod. 2001 Sep;64(9):1234-7. doi: 10.1021/np010152n. [PubMed:11575965 ]