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Record Information
Version1.0
Created at2021-01-05 21:18:28 UTC
Updated at2021-07-15 17:09:39 UTC
NP-MRD IDNP0011695
Secondary Accession NumbersNone
Natural Product Identification
Common NameLandomycin A
Provided ByNPAtlasNPAtlas Logo
Description Landomycin A is found in Apis cerana, Streptomyces cyanogenus, Streptomyces fradiae, Streptomyces globisporus and Streptomyces sp.. It was first documented in 1990 (PMID: 2358402). Based on a literature review very few articles have been published on (6R)-1,6,11-trihydroxy-8-{[(2S,4R,5S,6R)-4-hydroxy-5-{[(2S,4R,5R,6R)-5-hydroxy-4-{[(2S,5S,6S)-5-{[(2S,4R,5S,6R)-4-hydroxy-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}-6-methyloxan-2-yl]oxy}-3-methyl-5,6,7,12-tetrahydrotetraphene-7,12-dione (PMID: 34132308) (PMID: 34094801) (PMID: 31800236) (PMID: 31021647).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC55H74O22
Average Mass1087.1750 Da
Monoisotopic Mass1086.46717 Da
IUPAC Name(6R)-1,6,11-trihydroxy-8-{[(2S,4R,5S,6R)-4-hydroxy-5-{[(2S,4R,5R,6R)-5-hydroxy-4-{[(2S,5S,6S)-5-{[(2S,4R,5S,6R)-4-hydroxy-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}-6-methyloxan-2-yl]oxy}-3-methyl-5,6,7,12-tetrahydrotetraphene-7,12-dione
Traditional Name(6R)-1,6,11-trihydroxy-8-{[(2S,4R,5S,6R)-4-hydroxy-5-{[(2S,4R,5R,6R)-5-hydroxy-4-{[(2S,5S,6S)-5-{[(2S,4R,5S,6R)-4-hydroxy-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}-6-methyloxan-2-yl]oxy}-3-methyl-5,6-dihydrotetraphene-7,12-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]2[C@@H](C)O[C@H](C[C@H]2O)O[C@H]2CC[C@H](O[C@@H]3C[C@H](O[C@@H]4[C@@H](C)O[C@H](C[C@H]4O)OC4=C5C(=O)C6=C(C(=O)C5=C(O)C=C4)C4=C(O)C=C(C)C=C4C[C@H]6O)O[C@H](C)[C@H]3O)O[C@H]2C)O[C@H](C)[C@H]1O
InChI Identifier
InChI=1S/C55H74O22/c1-21-14-28-16-32(59)47-49(45(28)31(58)15-21)53(65)46-30(57)8-10-36(48(46)52(47)64)73-42-18-34(61)55(27(7)71-42)77-44-20-38(51(63)25(5)69-44)75-40-13-11-35(23(3)67-40)72-41-17-33(60)54(26(6)70-41)76-43-19-37(50(62)24(4)68-43)74-39-12-9-29(56)22(2)66-39/h8,10,14-15,22-27,29,32-35,37-44,50-51,54-63H,9,11-13,16-20H2,1-7H3/t22-,23-,24+,25+,26+,27+,29-,32+,33+,34+,35-,37+,38+,39-,40-,41-,42-,43-,44-,50+,51+,54+,55+/m0/s1
InChI KeyYMSZNAXJMXNNPT-OPAYXXSESA-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
Apis ceranaLOTUS Database
Streptomyces cyanogenusLOTUS Database
Streptomyces fradiaeLOTUS Database
Streptomyces globisporusLOTUS Database
Streptomyces sp.NPAtlas
Species Where Detected
Species NameSourceReference
Streptomyces sp. DSM 5087KNApSAcK Database
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
logP1.93ALOGPS
logP4.61ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.22ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area306.74 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity265.03 m³·mol⁻¹ChemAxon
Polarizability114.55 ųChemAxon
Number of Rings10ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA004350
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8164333
KEGG Compound IDC18822
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9988748
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Henkel T, Rohr J, Beale JM, Schwenen L: Landomycins, new angucycline antibiotics from Streptomyces sp. I. Structural studies on landomycins A-D. J Antibiot (Tokyo). 1990 May;43(5):492-503. doi: 10.7164/antibiotics.43.492. [PubMed:2358402 ]
  2. Mendoza F, Jana GA: The inverting mechanism of the metal ion-independent LanGT2: the first step to understand the glycosylation of natural product antibiotic precursors through QM/MM simulations. Org Biomol Chem. 2021 Jul 7;19(26):5888-5898. doi: 10.1039/d1ob00544h. [PubMed:34132308 ]
  3. Hrab P, Ruckert C, Busche T, Ostash I, Kalinowski J, Fedorenko V, Yushchuk O, Ostash B: Complete genome sequence of Streptomyces cyanogenus S136, producer of anticancer angucycline landomycin A. 3 Biotech. 2021 Jun;11(6):282. doi: 10.1007/s13205-021-02834-4. Epub 2021 May 21. [PubMed:34094801 ]
  4. Mendoza F, Jana GA: Unveiling the Dynamical and Structural Features That Determine the Orientation of the Acceptor Substrate in the Landomycin Glycosyltransferase LanGT2 and Its Variant with C-Glycosylation Activity. J Chem Inf Model. 2020 Feb 24;60(2):933-943. doi: 10.1021/acs.jcim.9b00865. Epub 2019 Dec 19. [PubMed:31800236 ]
  5. Yalamanchili S, Lloyd D, Bennett CS: Synthesis of the Hexasaccharide Fragment of Landomycin A Using a Mild, Reagent-Controlled Approach. Org Lett. 2019 May 17;21(10):3674-3677. doi: 10.1021/acs.orglett.9b01118. Epub 2019 Apr 25. [PubMed:31021647 ]