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Record Information
Version2.0
Created at2020-12-09 03:08:00 UTC
Updated at2021-07-15 16:53:42 UTC
NP-MRD IDNP0006053
Secondary Accession NumbersNone
Natural Product Identification
Common NameCyanopeptolin 954
Provided ByNPAtlasNPAtlas Logo
DescriptionCyanopeptolin 954 belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. Cyanopeptolin 954 is found in Microcystis aeruginosa and Microcystis aeruginosa NIVA Cya 43. Cyanopeptolin 954 was first documented in 2005 (PMID: 16180807). Based on a literature review very few articles have been published on cyanopeptolin 954.
Structure
Thumb
Synonyms
ValueSource
(2S)-N-[(2R,5S,8S,11S,12S,15S,18S,21R)-2-Benzyl-5-[(3-chloro-4-hydroxyphenyl)methyl]-6,13,16,21-tetrahydroxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-8-(propan-2-yl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-[(1-hydroxyethylidene)amino]pentanediimidateGenerator
Chemical FormulaC46H63ClN8O12
Average Mass955.5000 Da
Monoisotopic Mass954.42540 Da
IUPAC Name(2S)-N-[(5S,8S,11S,12S,15S,18S,21R)-2-benzyl-5-[(3-chloro-4-hydroxyphenyl)methyl]-21-hydroxy-4,11-dimethyl-15-(2-methylpropyl)-3,6,9,13,16,22-hexaoxo-8-(propan-2-yl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosan-12-yl]-2-acetamidopentanediamide
Traditional Name(2S)-N-[(5S,8S,11S,12S,15S,18S,21R)-2-benzyl-5-[(3-chloro-4-hydroxyphenyl)methyl]-21-hydroxy-8-isopropyl-4,11-dimethyl-15-(2-methylpropyl)-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosan-12-yl]-2-acetamidopentanediamide
CAS Registry NumberNot Available
SMILES
CC(C)C[C@@H]1NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(C)=O)[C@H](C)OC(=O)[C@@H](NC(=O)[C@H](CC2=CC(Cl)=C(O)C=C2)N(C)C(=O)[C@@H](CC2=CC=CC=C2)N2[C@H](O)CC[C@H](NC1=O)C2=O)C(C)C
InChI Identifier
InChI=1S/C46H63ClN8O12/c1-23(2)19-32-41(61)50-31-15-18-37(59)55(44(31)64)34(21-27-11-9-8-10-12-27)45(65)54(7)33(22-28-13-16-35(57)29(47)20-28)42(62)52-38(24(3)4)46(66)67-25(5)39(43(63)51-32)53-40(60)30(49-26(6)56)14-17-36(48)58/h8-13,16,20,23-25,30-34,37-39,57,59H,14-15,17-19,21-22H2,1-7H3,(H2,48,58)(H,49,56)(H,50,61)(H,51,63)(H,52,62)(H,53,60)/t25-,30-,31-,32-,33-,34+,37+,38-,39-/m0/s1
InChI KeyJECPFNPTJNKMMN-ZMFSYKMZSA-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
Microcystis aeruginosaNPAtlas
Microcystis aeruginosa NIVA Cya 43-
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassDepsipeptides
Direct ParentCyclic depsipeptides
Alternative Parents
Substituents
  • Cyclic depsipeptide
  • Alpha-amino acid ester
  • Macrolactam
  • Alpha-amino acid or derivatives
  • 2-chlorophenol
  • 2-halophenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Piperidinone
  • Halobenzene
  • Delta-lactam
  • Chlorobenzene
  • Benzenoid
  • Piperidine
  • Aryl halide
  • Monocyclic benzene moiety
  • Aryl chloride
  • Tertiary carboxylic acid amide
  • Cyclic carboximidic acid
  • Lactam
  • Lactone
  • Carboxylic acid ester
  • Carboxamide group
  • Alkanolamine
  • Carboximidic acid
  • Carboximidic acid derivative
  • Oxacycle
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen 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
logP2.04ALOGPS
logP0.55ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)7.94ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area295.97 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity241.23 m³·mol⁻¹ChemAxon
Polarizability98.58 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA011230
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00042428
Chemspider ID78440275
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139586215
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. von Elert E, Oberer L, Merkel P, Huhn T, Blom JF: Cyanopeptolin 954, a chlorine-containing chymotrypsin inhibitor of Microcystis aeruginosa NIVA Cya 43. J Nat Prod. 2005 Sep;68(9):1324-7. doi: 10.1021/np050079r. [PubMed:16180807 ]