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Record Information
Version1.0
Created at2022-09-06 01:26:48 UTC
Updated at2022-09-06 01:26:48 UTC
NP-MRD IDNP0223372
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r)-n-[(3r)-2-hydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-(n-methyloctanamido)-3-phenylpropanimidic acid
DescriptionCiliatamide B belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Ciliatamide B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 2008 (PMID: 18257536). Based on a literature review very few articles have been published on ciliatamide B (PMID: 18788742).
Structure
Thumb
Synonyms
ValueSource
(R,R)-Ciliatamide bChEBI
N-Methyl-N-[(2R)-1-oxo-1-[[(3R)-2-oxoazepan-3-yl]amino]-3-phenylpropan-2-yl]octanamideChEBI
Chemical FormulaC24H37N3O3
Average Mass415.5780 Da
Monoisotopic Mass415.28349 Da
IUPAC Name(2R)-N-[(6R)-7-hydroxy-3,4,5,6-tetrahydro-2H-azepin-6-yl]-2-(N-methyloctanamido)-3-phenylpropanimidic acid
Traditional Name(2R)-N-[(3R)-2-hydroxy-4,5,6,7-tetrahydro-3H-azepin-3-yl]-2-(N-methyloctanamido)-3-phenylpropanimidic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCC(=O)N(C)[C@H](CC1=CC=CC=C1)C(O)=N[C@@H]1CCCCN=C1O
InChI Identifier
InChI=1S/C24H37N3O3/c1-3-4-5-6-10-16-22(28)27(2)21(18-19-13-8-7-9-14-19)24(30)26-20-15-11-12-17-25-23(20)29/h7-9,13-14,20-21H,3-6,10-12,15-18H2,1-2H3,(H,25,29)(H,26,30)/t20-,21-/m1/s1
InChI KeyFNPKNWJUFWGJJV-NHCUHLMSSA-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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Phenylalanine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Caprolactam
  • Azepane
  • N-acyl-amine
  • Monocyclic benzene moiety
  • Fatty amide
  • Benzenoid
  • Fatty acyl
  • Tertiary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
logP2.39ChemAxon
pKa (Strongest Acidic)-4.3ChemAxon
pKa (Strongest Basic)12.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.49 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity119.54 m³·mol⁻¹ChemAxon
Polarizability47.84 ųChemAxon
Number of Rings2ChemAxon
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 IDC00038763
Chemspider ID28532948
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25112530
PDB IDNot Available
ChEBI ID65631
Good Scents IDNot Available
References
General References
  1. Lewis JA, Daniels RN, Lindsley CW: Total synthesis of Ciliatamides A-C: stereochemical revision and the natural product-guided synthesis of unnatural analogs. Org Lett. 2008 Oct 16;10(20):4545-8. doi: 10.1021/ol801842v. Epub 2008 Sep 13. [PubMed:18788742 ]
  2. Nakao Y, Kawatsu S, Okamoto C, Okamoto M, Matsumoto Y, Matsunaga S, van Soest RW, Fusetani N: Ciliatamides A-C, bioactive lipopeptides from the deep-sea sponge Aaptos ciliata. J Nat Prod. 2008 Mar;71(3):469-72. doi: 10.1021/np8000317. Epub 2008 Feb 8. [PubMed:18257536 ]
  3. LOTUS database [Link]