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Record Information
Version1.0
Created at2020-12-09 02:58:13 UTC
Updated at2021-07-15 16:53:04 UTC
NP-MRD IDNP0005819
Secondary Accession NumbersNone
Natural Product Identification
Common NameSaquayamycin Z
Provided ByNPAtlasNPAtlas Logo
DescriptionSaquayamycin Z belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Saquayamycin Z is found in Micromonospora. It was first documented in 2005 (PMID: 15835721). Based on a literature review very few articles have been published on Saquayamycin Z.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC72H102O29
Average Mass1431.5790 Da
Monoisotopic Mass1430.65068 Da
IUPAC Name(7aR,9R,11aS)-4,7a,11a-trihydroxy-9-{[(2S,5S,6S)-5-{[(2S,4R,5R,6R)-5-hydroxy-4-{[(2S,5S,6S)-5-{[(2S,4R,5R,6R)-5-hydroxy-4-{[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-3-[(2R,4R,5S,6R)-4-hydroxy-5-{[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-{[(2S,5S,6S)-6-methyl-5-{[(2R,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl]oxy}oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]-9-methyl-8,9,10,11,11a,12-hexahydro-7aH-5-oxatetraphene-11,12-dione
Traditional Name(7aR,9R,11aS)-4,7a,11a-trihydroxy-9-{[(2S,5S,6S)-5-{[(2S,4R,5R,6R)-5-hydroxy-4-{[(2S,5S,6S)-5-{[(2S,4R,5R,6R)-5-hydroxy-4-{[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-3-[(2R,4R,5S,6R)-4-hydroxy-5-{[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-{[(2S,5S,6S)-6-methyl-5-{[(2R,6S)-6-methyl-5-oxo-2,6-dihydropyran-2-yl]oxy}oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]-9-methyl-8,10-dihydro-5-oxatetraphene-11,12-dione
CAS Registry NumberNot Available
SMILES
C[C@@H]1O[C@H](CC[C@@H]1O)O[C@@H]1C[C@H](O[C@H]2CC[C@H](O[C@@H]3C[C@H](O[C@H]4CC[C@H](O[C@@]5(C)CC(=O)[C@]6(O)C7=C(OC8=C(C=CC([C@H]9C[C@@H](O)[C@H](O[C@H]%10C[C@H](O)C(O[C@H]%11CC[C@H](O[C@@H]%12O[C@@H](C)C(=O)C=C%12)[C@H](C)O%11)[C@H](C)O%10)[C@@H](C)O9)=C8O)C7=O)C=C[C@]6(O)C5)O[C@H]4C)O[C@H](C)[C@H]3O)O[C@H]2C)O[C@H](C)[C@H]1O
InChI Identifier
InChI=1S/C72H102O29/c1-31-42(73)13-18-54(85-31)93-46-16-21-57(88-33(46)3)99-68-39(9)92-59(26-45(68)76)100-67-38(8)84-50(25-44(67)75)40-11-12-41-65(80)62-49(98-69(41)66(40)81)23-24-71(82)30-70(10,29-53(77)72(62,71)83)101-58-22-17-48(35(5)89-58)95-61-28-52(64(79)37(7)91-61)97-56-20-15-47(34(4)87-56)94-60-27-51(63(78)36(6)90-60)96-55-19-14-43(74)32(2)86-55/h11-13,18,23-24,31-39,43-48,50-52,54-61,63-64,67-68,74-76,78-79,81-83H,14-17,19-22,25-30H2,1-10H3/t31-,32-,33-,34-,35-,36+,37+,38+,39-,43-,44+,45-,46-,47-,48-,50+,51+,52+,54-,55-,56-,57-,58-,59-,60-,61-,63+,64+,67+,68?,70-,71-,72-/m0/s1
InChI KeyHXKIEUQACANSNK-SBCHTQRNSA-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
MicromonosporaNPAtlas
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentXanthones
Alternative Parents
Substituents
  • Xanthone
  • Naphthopyran
  • Chromone
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Naphthalene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Dihydropyranone
  • Pyranone
  • Pyran
  • Oxane
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Cyclic ketone
  • Ketone
  • Polyol
  • Oxacycle
  • Acetal
  • Ether
  • Dialkyl ether
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • 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
logP1.98ALOGPS
logP4.45ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)8.68ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count29ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area379.19 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity348.94 m³·mol⁻¹ChemAxon
Polarizability153.18 ųChemAxon
Number of Rings13ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA002196
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78436504
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139583709
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Antal N, Fiedler HP, Stackebrandt E, Beil W, Stroch K, Zeeck A: Retymicin, galtamycin B, saquayamycin Z and ribofuranosyllumichrome, novel secondary metabolites from Micromonospora sp. Tu 6368. I. Taxonomy, fermentation, isolation and biological activities. J Antibiot (Tokyo). 2005 Feb;58(2):95-102. doi: 10.1038/ja.2005.12. [PubMed:15835721 ]