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Record Information
Version1.0
Created at2021-01-05 22:49:51 UTC
Updated at2021-07-15 17:14:36 UTC
NP-MRD IDNP0013482
Secondary Accession NumbersNone
Natural Product Identification
Common NameChlorocatechelin A
Provided ByNPAtlasNPAtlas Logo
DescriptionChlorocatechelin A 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. Chlorocatechelin A is found in Streptomyces sp. It was first documented in 2014 (PMID: 25408968). Based on a literature review very few articles have been published on Chlorocatechelin A (PMID: 26018853).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC26H30Cl2N6O11
Average Mass673.4600 Da
Monoisotopic Mass672.13496 Da
IUPAC Name(2R)-2-[(2R)-5-[(E)-{amino[(4-chloro-2,3-dihydroxyphenyl)formamido]methylidene}amino]-2-[(4-chloro-2,3-dihydroxyphenyl)formamido]pentanamido]-5-(N-hydroxyformamido)pentanoic acid
Traditional Name(2R)-2-[(2R)-5-[(E)-{amino[(4-chloro-2,3-dihydroxyphenyl)formamido]methylidene}amino]-2-[(4-chloro-2,3-dihydroxyphenyl)formamido]pentanamido]-5-(N-hydroxyformamido)pentanoic acid
CAS Registry NumberNot Available
SMILES
NC(NC(=O)C1=C(O)C(O)=C(Cl)C=C1)=NCCC[C@@H](NC(=O)C1=C(O)C(O)=C(Cl)C=C1)C(=O)N[C@H](CCCN(O)C=O)C(O)=O
InChI Identifier
InChI=1S/C26H30Cl2N6O11/c27-14-7-5-12(18(36)20(14)38)22(40)31-16(24(42)32-17(25(43)44)4-2-10-34(45)11-35)3-1-9-30-26(29)33-23(41)13-6-8-15(28)21(39)19(13)37/h5-8,11,16-17,36-39,45H,1-4,9-10H2,(H,31,40)(H,32,42)(H,43,44)(H3,29,30,33,41)/t16-,17-/m1/s1
InChI KeyRNSXINHQKGRUDO-IAGOWNOFSA-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 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
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Hippuric acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Salicylamide
  • Salicylic acid or derivatives
  • 4-halobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • 3-chlorocatechol
  • Benzamide
  • Benzoic acid or derivatives
  • Chlorocatechol
  • Benzoyl
  • 2-chlorophenol
  • 3-halophenol
  • 2-halophenol
  • Catechol
  • 3-chlorophenol
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Halobenzene
  • Chlorobenzene
  • Aryl chloride
  • Aryl halide
  • Fatty acyl
  • Monocyclic benzene moiety
  • Benzenoid
  • Fatty amide
  • N-acyl-amine
  • Vinylogous acid
  • Secondary carboxylic acid amide
  • Guanidine
  • Hydroxamic acid
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP1.95ALOGPS
logP0.21ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)2.92ChemAxon
pKa (Strongest Basic)7.27ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area284.44 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity158.12 m³·mol⁻¹ChemAxon
Polarizability64.97 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA006296
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78437000
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101894342
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kishimoto S, Nishimura S, Hattori A, Tsujimoto M, Hatano M, Igarashi M, Kakeya H: Chlorocatechelins A and B from Streptomyces sp.: new siderophores containing chlorinated catecholate groups and an acylguanidine structure. Org Lett. 2014 Dec 5;16(23):6108-11. doi: 10.1021/ol502964s. Epub 2014 Nov 19. [PubMed:25408968 ]
  2. Kishimoto S, Nishimura S, Hatano M, Igarashi M, Kakeya H: Total Synthesis and Antimicrobial Activity of Chlorocatechelin A. J Org Chem. 2015 Jun 19;80(12):6076-82. doi: 10.1021/acs.joc.5b00532. Epub 2015 Jun 5. [PubMed:26018853 ]