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Record Information
Version2.0
Created at2022-09-12 14:13:54 UTC
Updated at2022-09-12 14:13:55 UTC
NP-MRD IDNP0329650
Secondary Accession NumbersNone
Natural Product Identification
Common Name(7s,10s,17s)-3,7,10,28-tetrahydroxy-14-methoxy-24,25-dimethyl-12,18,20-trioxa-25-azaheptacyclo[15.11.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²¹,²⁹.0²²,²⁷]nonacosa-1(29),2(15),3,6(11),13,21,23,27-octaene-5,26-dione
DescriptionSimaomicin 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. (7s,10s,17s)-3,7,10,28-tetrahydroxy-14-methoxy-24,25-dimethyl-12,18,20-trioxa-25-azaheptacyclo[15.11.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²¹,²⁹.0²²,²⁷]nonacosa-1(29),2(15),3,6(11),13,21,23,27-octaene-5,26-dione is found in Actinomadura madurae. (7s,10s,17s)-3,7,10,28-tetrahydroxy-14-methoxy-24,25-dimethyl-12,18,20-trioxa-25-azaheptacyclo[15.11.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²¹,²⁹.0²²,²⁷]nonacosa-1(29),2(15),3,6(11),13,21,23,27-octaene-5,26-dione was first documented in 2004 (PMID: 15081413). Based on a literature review a small amount of articles have been published on Simaomicin (PMID: 17446697) (PMID: 24038677) (PMID: 19077005) (PMID: 18503207).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC28H25NO10
Average Mass535.5050 Da
Monoisotopic Mass535.14785 Da
IUPAC Name(7S,10S,17S)-3,7,10,28-tetrahydroxy-14-methoxy-24,25-dimethyl-12,18,20-trioxa-25-azaheptacyclo[15.11.1.0^{2,15}.0^{4,13}.0^{6,11}.0^{21,29}.0^{22,27}]nonacosa-1(29),2(15),3,6(11),13,21,23,27-octaene-5,26-dione
Traditional Name(7S,10S,17S)-3,7,10,28-tetrahydroxy-14-methoxy-24,25-dimethyl-12,18,20-trioxa-25-azaheptacyclo[15.11.1.0^{2,15}.0^{4,13}.0^{6,11}.0^{21,29}.0^{22,27}]nonacosa-1(29),2(15),3,6(11),13,21,23,27-octaene-5,26-dione
CAS Registry NumberNot Available
SMILES
COC1=C2OC3=C([C@@H](O)CC[C@@H]3O)C(=O)C2=C(O)C2=C1C[C@@H]1OCOC3=C4C=C(C)N(C)C(=O)C4=C(O)C2=C13
InChI Identifier
InChI=1S/C28H25NO10/c1-9-6-10-16(28(35)29(9)2)22(33)19-15-11(7-14-18(19)24(10)38-8-37-14)25(36-3)27-20(21(15)32)23(34)17-12(30)4-5-13(31)26(17)39-27/h6,12-14,30-33H,4-5,7-8H2,1-3H3/t12-,13-,14-/m0/s1
InChI KeyDQPBSXMRMTWOAQ-IHRRRGAJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Actinomadura maduraeLOTUS Database
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
  • Naphthopyranone
  • Phenanthrene
  • Naphthopyran
  • Isoquinolone
  • 1-naphthol
  • Chromone
  • Naphthalene
  • Isoquinoline
  • Anisole
  • Methylpyridine
  • Alkyl aryl ether
  • Pyranone
  • Pyridinone
  • Pyran
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous acid
  • Lactam
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Acetal
  • Ether
  • Polyol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen 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
logP2.18ChemAxon
pKa (Strongest Acidic)7.25ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area155.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity139.17 m³·mol⁻¹ChemAxon
Polarizability55.2 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
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 IDC00017026
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13881180
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ui H, Ishiyama A, Sekiguchi H, Namatame M, Nishihara A, Takahashi Y, Shiomi K, Otoguro K, Omura S: Selective and potent in vitro antimalarial activities found in four microbial metabolites. J Antibiot (Tokyo). 2007 Mar;60(3):220-2. doi: 10.1038/ja.2007.27. [PubMed:17446697 ]
  2. Wang Y, Wang C, Butler JR, Ready JM: Dehydrogenative coupling to enable the enantioselective total synthesis of (-)-simaomicin alpha. Angew Chem Int Ed Engl. 2013 Oct 4;52(41):10796-9. doi: 10.1002/anie.201304812. Epub 2013 Aug 22. [PubMed:24038677 ]
  3. Koizumi Y, Tomoda H, Kumagai A, Zhou XP, Koyota S, Sugiyama T: Simaomicin alpha, a polycyclic xanthone, induces G(1) arrest with suppression of retinoblastoma protein phosphorylation. Cancer Sci. 2009 Feb;100(2):322-6. doi: 10.1111/j.1349-7006.2008.01033.x. [PubMed:19077005 ]
  4. Ishiyama A, Otoguro K, Namatame M, Nishihara A, Furusawa T, Takahashi Y, Masuma R, Shiomi K, Omura S: Simaomicin alpha: effects on the cell cycle of synchronized, cultured Plasmodium falciparum. J Antibiot (Tokyo). 2008 Apr;61(4):254-7. doi: 10.1038/ja.2008.38. [PubMed:18503207 ]
  5. Arai M, Sato H, Kobayashi H, Suganuma M, Kawabe T, Tomoda H, Omura S: Selective inhibition of bleomycin-induced G2 cell cycle checkpoint by simaomicin alpha. Biochem Biophys Res Commun. 2004 May 7;317(3):817-22. doi: 10.1016/j.bbrc.2004.03.117. [PubMed:15081413 ]
  6. LOTUS database [Link]