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Record Information
Version1.0
Created at2020-12-09 00:12:08 UTC
Updated at2021-07-15 16:45:33 UTC
NP-MRD IDNP0003114
Secondary Accession NumbersNone
Natural Product Identification
Common NameGibbestatin C
Provided ByNPAtlasNPAtlas Logo
Description Gibbestatin C is found in Streptomyces sp. C39. It was first documented in 1999 (PMID: 10604763). Based on a literature review very few articles have been published on 2-hydroxyphenyl 2-hydroxy-6-[(1E,3E,5S,7E)-5-[(1S)-1-methoxyethyl]-7-methyl-8-(3-methyloxiran-2-yl)-6-oxoocta-1,3,7-trien-1-yl]benzoate.
Structure
Data?1624573732
Synonyms
ValueSource
2-Hydroxyphenyl 2-hydroxy-6-[(1E,3E,5S,7E)-5-[(1S)-1-methoxyethyl]-7-methyl-8-(3-methyloxiran-2-yl)-6-oxoocta-1,3,7-trien-1-yl]benzoic acidGenerator
Chemical FormulaC28H30O7
Average Mass478.5410 Da
Monoisotopic Mass478.19915 Da
IUPAC Name2-hydroxyphenyl 2-hydroxy-6-[(1E,3E,5S,7E)-5-[(1S)-1-methoxyethyl]-7-methyl-8-[(2S,3S)-3-methyloxiran-2-yl]-6-oxoocta-1,3,7-trien-1-yl]benzoate
Traditional Name2-hydroxyphenyl 2-hydroxy-6-[(1E,3E,5S,7E)-5-[(1S)-1-methoxyethyl]-7-methyl-8-[(2S,3S)-3-methyloxiran-2-yl]-6-oxoocta-1,3,7-trien-1-yl]benzoate
CAS Registry NumberNot Available
SMILES
CO[C@@H](C)[C@H](\C=C\C=C\C1=CC=CC(O)=C1C(=O)OC1=CC=CC=C1O)C(=O)C(\C)=C\C1OC1C
InChI Identifier
InChI=1S/C28H30O7/c1-17(16-25-19(3)34-25)27(31)21(18(2)33-4)12-6-5-10-20-11-9-14-23(30)26(20)28(32)35-24-15-8-7-13-22(24)29/h5-16,18-19,21,25,29-30H,1-4H3/b10-5+,12-6+,17-16+/t18-,19?,21-,25?/m0/s1
InChI KeySWTFYUUPAJQCHB-GVYFAZOZSA-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
Streptomyces sp. C39
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
logP4.75ALOGPS
logP6.96ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)9.52ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.59 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity136.16 m³·mol⁻¹ChemAxon
Polarizability52.72 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA009624
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8847660
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10672308
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Hayashi K, Nozaki H: Isolation and characterization of gibbestatin B, an inhibitor of gibberellin-induced expression of alpha-amylase, and gibbestatin C from streptomycetaes. J Antibiot (Tokyo). 1999 Oct;52(10):917-20. doi: 10.7164/antibiotics.52.917. [PubMed:10604763 ]