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Record Information
Version1.0
Created at2021-01-05 20:44:37 UTC
Updated at2021-07-15 17:07:32 UTC
NP-MRD IDNP0010949
Secondary Accession NumbersNone
Natural Product Identification
Common NameKapurimycin A1
Provided ByNPAtlasNPAtlas Logo
DescriptionKapurimycin A1 belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Kapurimycin A1 is found in Streptomyces sp. It was first documented in 1990 (PMID: 2276971). Based on a literature review very few articles have been published on Kapurimycin A1.
Structure
Thumb
Synonyms
ValueSource
2-[8-(Acetyloxy)-12-hydroxy-2-(2-methyl-3-propyloxiran-2-yl)-4,11-dioxo-8,9,10,11-tetrahydro-4H-1-oxatetraphen-5-yl]acetateGenerator
Chemical FormulaC27H26O9
Average Mass494.4960 Da
Monoisotopic Mass494.15768 Da
IUPAC Name2-[(8R)-8-(acetyloxy)-12-hydroxy-2-[(2R,3S)-2-methyl-3-propyloxiran-2-yl]-4,11-dioxo-8,9,10,11-tetrahydro-4H-1-oxatetraphen-5-yl]acetic acid
Traditional Name[(8R)-8-(acetyloxy)-12-hydroxy-2-[(2R,3S)-2-methyl-3-propyloxiran-2-yl]-4,11-dioxo-9,10-dihydro-8H-1-oxatetraphen-5-yl]acetic acid
CAS Registry NumberNot Available
SMILES
CCCC1OC1(C)C1=CC(=O)C2=C(O1)C1=C(O)C3=C(C=C1C=C2CC(O)=O)C(CCC3=O)OC(C)=O
InChI Identifier
InChI=1S/C27H26O9/c1-4-5-19-27(3,36-19)20-11-17(30)22-14(10-21(31)32)8-13-9-15-18(34-12(2)28)7-6-16(29)24(15)25(33)23(13)26(22)35-20/h8-9,11,18-19,33H,4-7,10H2,1-3H3,(H,31,32)
InChI KeyUILRBVIPTXHVIG-UHFFFAOYSA-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 naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNaphthopyranones
Direct ParentNaphthopyranones
Alternative Parents
Substituents
  • Naphthopyranone
  • 1-naphthol
  • Chromone
  • Naphthalene
  • Benzopyran
  • Tetralin
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Dicarboxylic acid or derivatives
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Oxacycle
  • Oxirane
  • Ether
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen 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
logP3.36ALOGPS
logP3.51ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)3.48ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area139.73 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity127.96 m³·mol⁻¹ChemAxon
Polarizability51.63 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA001441
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID116227
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131511
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yoshida M, Hara M, Saitoh Y, Sano H: The kapurimycins, new antitumor antibiotics produced by Streptomyces. Physico-chemical properties and structure determination. J Antibiot (Tokyo). 1990 Dec;43(12):1519-23. doi: 10.7164/antibiotics.43.1519. [PubMed:2276971 ]