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Record Information
Version1.0
Created at2020-12-09 00:13:02 UTC
Updated at2021-07-15 16:45:36 UTC
NP-MRD IDNP0003135
Secondary Accession NumbersNone
Natural Product Identification
Common NameAgrochelin
Provided ByNPAtlasNPAtlas Logo
DescriptionAgrochelin 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. Agrochelin is found in Agrobacterium. It was first documented in 1999 (PMID: 10656570). Based on a literature review very few articles have been published on agrochelin (PMID: 31293678).
Structure
Data?1624573738
SynonymsNot Available
Chemical FormulaC23H34N2O4S2
Average Mass466.6600 Da
Monoisotopic Mass466.19600 Da
IUPAC Name(3S)-3-hydroxy-3-[(2S,4R)-2-[(4R)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2,2-dimethylpropanoic acid
Traditional Name(3S)-3-hydroxy-3-[(2S,4R)-2-[(4R)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2,2-dimethylpropanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCC1=C(C2=N[C@H](CS2)[C@@H]2SC[C@@H]([C@@H](O)C(C)(C)C(O)=O)N2C)C(O)=CC=C1
InChI Identifier
InChI=1S/C23H34N2O4S2/c1-5-6-7-9-14-10-8-11-17(26)18(14)20-24-15(12-30-20)21-25(4)16(13-31-21)19(27)23(2,3)22(28)29/h8,10-11,15-16,19,21,26-27H,5-7,9,12-13H2,1-4H3,(H,28,29)/t15-,16+,19-,21+/m1/s1
InChI KeyQZBCDLLHQSDFIG-ZEVBXJOLSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Agrobacterium
Species Where Detected
Species NameSourceReference
Agrobacterium sp.KNApSAcK Database
Chemical Taxonomy
ClassificationNot classified
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
logP3.51ALOGPS
logP3.44ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)6.46ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area93.36 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity128.31 m³·mol⁻¹ChemAxon
Polarizability51.8 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA017357
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00015420
Chemspider ID24603368
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID65375
Good Scents IDNot Available
References
General References
  1. Acebal C, Canedo LM, Puentes JL, Baz JP, Romero F, de la Calle F, Gravalos MD, Rodriguez P: Agrochelin, a new cytotoxic antibiotic from a marine Agrobacterium. Taxonomy, fermentation, isolation, physico-chemical properties and biological activity. J Antibiot (Tokyo). 1999 Nov;52(11):983-7. doi: 10.7164/antibiotics.52.983. [PubMed:10656570 ]
  2. Diettrich J, Kage H, Nett M: Genomics-inspired discovery of massiliachelin, an agrochelin epimer from Massilia sp. NR 4-1. Beilstein J Org Chem. 2019 Jun 13;15:1298-1303. doi: 10.3762/bjoc.15.128. eCollection 2019. [PubMed:31293678 ]