Np mrd loader

Record Information
Version2.0
Created at2022-04-28 10:26:54 UTC
Updated at2022-04-28 10:26:54 UTC
NP-MRD IDNP0066249
Secondary Accession NumbersNone
Natural Product Identification
Common NameMarcfortine C
DescriptionMarcfortine C belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. Marcfortine C is found in Penicillium roqueforti and Penicillium roqueforti strain B26. Marcfortine C was first documented in 2007 (PMID: 18596842). Based on a literature review a small amount of articles have been published on Marcfortine C (PMID: 32525684) (PMID: 24083654).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC27H33N3O3
Average Mass447.5790 Da
Monoisotopic Mass447.25219 Da
IUPAC Name(1'S,3R,8'S,10'S)-7,7,11',11'-tetramethyl-2,7-dihydro-1H-3',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,12'-tetracyclo[6.5.2.0^{1,10}.0^{3,8}]pentadecane]-2,15'-dione
Traditional Name(1'S,3R,8'S,10'S)-7,7,11',11'-tetramethyl-1H-3',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,12'-tetracyclo[6.5.2.0^{1,10}.0^{3,8}]pentadecane]-2,15'-dione
CAS Registry NumberNot Available
SMILES
CC1(C)[C@@H]2C[C@]34CCCCN3C[C@@]2(C[C@@]11C(=O)NC2=C1C=CC1=C2C=CC(C)(C)O1)NC4=O
InChI Identifier
InChI=1S/C27H33N3O3/c1-23(2)11-9-16-18(33-23)8-7-17-20(16)28-22(32)27(17)14-25-15-30-12-6-5-10-26(30,21(31)29-25)13-19(25)24(27,3)4/h7-9,11,19H,5-6,10,12-15H2,1-4H3,(H,28,32)(H,29,31)/t19-,25+,26-,27+/m0/s1
InChI KeyMEDWEEBWLKOHES-DWJNZRAMSA-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
Penicillium roquefortiLOTUS Database
Penicillium roqueforti strain B26Fungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • 2,2-dimethyl-1-benzopyran
  • Azaspirodecane
  • Benzopyran
  • Piperazino-1,2-a-piperidine
  • 1-benzopyran
  • Quinolizidine
  • Indole or derivatives
  • Dihydroindole
  • Alkyl aryl ether
  • Delta-lactam
  • Aralkylamine
  • N-alkylpiperazine
  • Piperidinone
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • Piperidine
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxamide group
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Oxacycle
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • 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
logP3.68ALOGPS
logP3.08ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.02ChemAxon
pKa (Strongest Basic)5.98ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.67 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity128.19 m³·mol⁻¹ChemAxon
Polarizability50.16 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00023602
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24767756
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Trost BM, Mata G: Forging Odd-Membered Rings: Palladium-Catalyzed Asymmetric Cycloadditions of Trimethylenemethane. Acc Chem Res. 2020 Jul 21;53(7):1293-1305. doi: 10.1021/acs.accounts.0c00152. Epub 2020 Jun 11. [PubMed:32525684 ]
  2. Trost BM, Bringley DA, Zhang T, Cramer N: Rapid access to spirocyclic oxindole alkaloids: application of the asymmetric palladium-catalyzed [3 + 2] trimethylenemethane cycloaddition. J Am Chem Soc. 2013 Nov 6;135(44):16720-35. doi: 10.1021/ja409013m. [PubMed:24083654 ]
  3. Greshock TJ, Grubbs AW, Williams RM: Concise, Biomimetic Total Synthesis of d,l-Marcfortine C. Tetrahedron. 2007 Jul 2;63(27):6124-6130. doi: 10.1016/j.tet.2007.03.016. [PubMed:18596842 ]