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Record Information
Version1.0
Created at2021-01-06 08:37:36 UTC
Updated at2021-07-15 17:42:05 UTC
NP-MRD IDNP0023559
Secondary Accession NumbersNone
Natural Product Identification
Common NameAmphistin
Provided ByNPAtlasNPAtlas Logo
Description2-Amino-4-[(1-carboxy-2-{[1-carboxy-2-(1H-imidazol-5-yl)ethyl]amino}ethyl)amino]butanoic acid belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Amphistin is found in Actinomyces sp. It was first documented in 1997 (PMID: 9402984). Based on a literature review very few articles have been published on 2-amino-4-[(1-carboxy-2-{[1-carboxy-2-(1H-imidazol-5-yl)ethyl]amino}ethyl)amino]butanoic acid.
Structure
Data?1624572117
Synonyms
ValueSource
2-Amino-4-[(1-carboxy-2-{[1-carboxy-2-(1H-imidazol-5-yl)ethyl]amino}ethyl)amino]butanoateGenerator
Chemical FormulaC13H21N5O6
Average Mass343.3400 Da
Monoisotopic Mass343.14918 Da
IUPAC Name(2S)-2-amino-4-{[(1R)-1-carboxy-2-{[(1R)-1-carboxy-2-(1H-imidazol-5-yl)ethyl]amino}ethyl]amino}butanoic acid
Traditional Name(2S)-2-amino-4-{[(1R)-1-carboxy-2-{[(1R)-1-carboxy-2-(3H-imidazol-4-yl)ethyl]amino}ethyl]amino}butanoic acid
CAS Registry NumberNot Available
SMILES
NC(CCNC(CNC(CC1=CN=CN1)C(O)=O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C13H21N5O6/c14-8(11(19)20)1-2-16-10(13(23)24)5-17-9(12(21)22)3-7-4-15-6-18-7/h4,6,8-10,16-17H,1-3,5,14H2,(H,15,18)(H,19,20)(H,21,22)(H,23,24)
InChI KeyITQGHQZINPLSLB-UHFFFAOYSA-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
Actinomyces sp.
Chemical Taxonomy
Description Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Amino fatty acid
  • Aralkylamine
  • Fatty acyl
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP-3ALOGPS
logP-10ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.73ChemAxon
pKa (Strongest Basic)9.94ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area190.66 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity80.03 m³·mol⁻¹ChemAxon
Polarizability33.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8264336
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10088799
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Arai N, Shiomi K, Takamatsu S, Komiyama K, Shinose M, Takahashi Y, Tanaka Y, Iwai Y, Liu JR, Omura S: Amphistin, a new melanogenesis inhibitor, produced by an actinomycete. J Antibiot (Tokyo). 1997 Oct;50(10):808-14. doi: 10.7164/antibiotics.50.808. [PubMed:9402984 ]