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Record Information
Version1.0
Created at2020-12-09 00:41:49 UTC
Updated at2021-07-15 16:46:25 UTC
NP-MRD IDNP0003445
Secondary Accession NumbersNone
Natural Product Identification
Common NameUCF-116-A
Provided ByNPAtlasNPAtlas Logo
DescriptionUCF-116A belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. UCF-116-A is found in Streptomyces sp. It was first documented in 2000 (PMID: 10994815). Based on a literature review very few articles have been published on UCF-116A.
Structure
Thumb
Synonyms
ValueSource
N-[1-({[(5R,6Z,8Z,13S,14R,15R,16Z)-3,15-dihydroxy-5-methoxy-14,16-dimethyl-22,24-dioxo-2-azabicyclo[18.3.1]tetracosa-1(23),2,6,8,10,16,20-heptaen-13-yl]oxy}carbonyl)cyclopropyl]cyclohexanecarboximidateGenerator
Chemical FormulaC37H48N2O8
Average Mass648.7970 Da
Monoisotopic Mass648.34107 Da
IUPAC Name(5R,6Z,8Z,10Z,13S,14R,15R,16Z)-15-hydroxy-5-methoxy-14,16-dimethyl-3,22,24-trioxo-2-azabicyclo[18.3.1]tetracosa-1(23),6,8,10,16,20-hexaen-13-yl 1-cyclohexaneamidocyclopropane-1-carboxylate
Traditional Name(5R,6Z,8Z,10Z,13S,14R,15R,16Z)-15-hydroxy-5-methoxy-14,16-dimethyl-3,22,24-trioxo-2-azabicyclo[18.3.1]tetracosa-1(23),6,8,10,16,20-hexaen-13-yl 1-cyclohexaneamidocyclopropane-1-carboxylate
CAS Registry NumberNot Available
SMILES
CO[C@@H]1CC(=O)NC2=CC(=O)C=C(CC\C=C(C)/[C@H](O)[C@@H](C)[C@H](C\C=C/C=C\C=C/1)OC(=O)C1(CC1)NC(=O)C1CCCCC1)C2=O
InChI Identifier
InChI=1S/C37H48N2O8/c1-24-13-12-16-27-21-28(40)22-30(34(27)43)38-32(41)23-29(46-3)17-10-5-4-6-11-18-31(25(2)33(24)42)47-36(45)37(19-20-37)39-35(44)26-14-8-7-9-15-26/h4-6,10-11,13,17,21-22,25-26,29,31,33,42H,7-9,12,14-16,18-20,23H2,1-3H3,(H,38,41)(H,39,44)/b5-4-,11-6-,17-10-,24-13-/t25-,29-,31-,33-/m0/s1
InChI KeyXIINXLCERXPPLH-TYTFVDOPSA-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
Streptomyces sp.NPAtlas
Chemical Taxonomy
Description Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolactams
Sub ClassNot Available
Direct ParentMacrolactams
Alternative Parents
Substituents
  • Macrolactam
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Cyclopropanecarboxylic acid or derivatives
  • Vinylogous amide
  • Carboxamide group
  • Carboxylic acid ester
  • Ketone
  • Lactam
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • 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
logP4.45ALOGPS
logP4.39ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)12.3ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area148.1 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity183.92 m³·mol⁻¹ChemAxon
Polarizability69.77 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA000118
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 Compound101073377
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Hara M, Soga S, Itoh M, Shono K, Eishima J, Mizukami T: UCF116, new inhibitors of farnesyltransferase produced by Streptomyces. J Antibiot (Tokyo). 2000 Jul;53(7):720-3. doi: 10.7164/antibiotics.53.720. [PubMed:10994815 ]