Np mrd loader

Record Information
Version2.0
Created at2022-09-12 15:25:13 UTC
Updated at2022-09-12 15:25:14 UTC
NP-MRD IDNP0330252
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s,3r,4r,6s)-6-{[(2r,3s,6s)-6-{[(1s,4as,12ar)-3-acetyl-4,4a,6,12a-tetrahydroxy-9-methoxy-11-methyl-2,5,7,10-tetraoxo-1,12-dihydrotetracen-1-yl]oxy}-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl (2z,4r)-2,4-dimethylhept-2-enoate
DescriptionDutomycin belongs to the class of organic compounds known as anthraquinone glycosides. These are organic compounds containing an anthraquinone moiety glycosidically bound to a carbohydrate moiety. (2s,3r,4r,6s)-6-{[(2r,3s,6s)-6-{[(1s,4as,12ar)-3-acetyl-4,4a,6,12a-tetrahydroxy-9-methoxy-11-methyl-2,5,7,10-tetraoxo-1,12-dihydrotetracen-1-yl]oxy}-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl (2z,4r)-2,4-dimethylhept-2-enoate was first documented in 2016 (PMID: 27195476). Based on a literature review a small amount of articles have been published on Dutomycin (PMID: 35630823) (PMID: 34824375) (PMID: 33517652).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC44H54O17
Average Mass854.8990 Da
Monoisotopic Mass854.33610 Da
IUPAC Name(2S,3R,4R,6S)-6-{[(2R,3S,6S)-6-{[(1S,4aS,12aR)-3-acetyl-4,4a,6,12a-tetrahydroxy-9-methoxy-11-methyl-2,5,7,10-tetraoxo-1,2,4a,5,7,10,12,12a-octahydrotetracen-1-yl]oxy}-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl (2Z,4R)-2,4-dimethylhept-2-enoate
Traditional Name(2S,3R,4R,6S)-6-{[(2R,3S,6S)-6-{[(1S,4aS,12aR)-3-acetyl-4,4a,6,12a-tetrahydroxy-9-methoxy-11-methyl-2,5,7,10-tetraoxo-1,12-dihydrotetracen-1-yl]oxy}-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl (2Z,4R)-2,4-dimethylhept-2-enoate
CAS Registry NumberNot Available
SMILES
CCC[C@@H](C)\C=C(\C)C(=O)O[C@@H]1[C@H](C)O[C@H](C[C@@]1(C)O)O[C@H]1CC[C@H](O[C@@H]2C(=O)C(C(C)=O)=C(O)[C@@]3(O)C(=O)C4=C(O)C5=C(C(C)=C4C[C@@]23O)C(=O)C(OC)=CC5=O)O[C@@H]1C
InChI Identifier
InChI=1S/C44H54O17/c1-10-11-18(2)14-19(3)41(52)61-39-23(7)58-29(17-42(39,8)53)59-26-12-13-28(57-22(26)6)60-40-36(49)31(21(5)45)37(50)44(55)38(51)32-24(16-43(40,44)54)20(4)30-33(35(32)48)25(46)15-27(56-9)34(30)47/h14-15,18,22-23,26,28-29,39-40,48,50,53-55H,10-13,16-17H2,1-9H3/b19-14-/t18-,22-,23+,26+,28+,29+,39-,40-,42-,43-,44-/m1/s1
InChI KeyZYPYHMZLLIDAAL-WNMWLNICSA-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anthraquinone glycosides. These are organic compounds containing an anthraquinone moiety glycosidically bound to a carbohydrate moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthraquinones
Direct ParentAnthraquinone glycosides
Alternative Parents
Substituents
  • Anthraquinone glycoside
  • O-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • Naphthalene
  • Tetralin
  • Quinone
  • Aryl alkyl ketone
  • Aryl ketone
  • Cyclohexenone
  • Fatty acid ester
  • Fatty acyl
  • Oxane
  • Vinylogous acid
  • Tertiary alcohol
  • Vinylogous ester
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Acetal
  • Carboxylic acid derivative
  • Enol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Aldehyde
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • 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
logP5.09ChemAxon
pKa (Strongest Acidic)0.25ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area258.95 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity216.67 m³·mol⁻¹ChemAxon
Polarizability88.73 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4952623
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6449963
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Xu R, Hu D, Lin J, Tang J, Zhan R, Liu G, Sun L: The Critical Role of 12-Methyl Group of Anthracycline Dutomycin to Its Antiproliferative Activity. Molecules. 2022 May 23;27(10). pii: molecules27103348. doi: 10.3390/molecules27103348. [PubMed:35630823 ]
  2. Ibusuki Y, Kimata S, Hayakawa Y: 13-Deoxo-13-iminodutomycin, a new neuroprotective compound from Streptomyces sp. RAP78. J Antibiot (Tokyo). 2022 Jan;75(1):40-43. doi: 10.1038/s41429-021-00488-1. Epub 2021 Nov 26. [PubMed:34824375 ]
  3. Jang M, Hara S, Kim GH, Kim SM, Son S, Kwon M, Ryoo IJ, Seo H, Kim MJ, Kim ND, Soung NK, Kwon YT, Kim BY, Osada H, Jang JH, Ko SK, Ahn JS: Dutomycin Induces Autophagy and Apoptosis by Targeting the Serine Protease Inhibitor SERPINB6. ACS Chem Biol. 2021 Feb 19;16(2):360-370. doi: 10.1021/acschembio.0c00889. Epub 2021 Jan 31. [PubMed:33517652 ]
  4. Sun L, Wang S, Zhang S, Shao L, Zhang Q, Skidmore C, Chang CW, Yu D, Zhan J: Characterization of Three Tailoring Enzymes in Dutomycin Biosynthesis and Generation of a Potent Antibacterial Analogue. ACS Chem Biol. 2016 Jul 15;11(7):1992-2001. doi: 10.1021/acschembio.6b00245. Epub 2016 May 19. [PubMed:27195476 ]
  5. LOTUS database [Link]