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Record Information
Version2.0
Created at2020-12-09 06:48:18 UTC
Updated at2021-07-15 17:03:12 UTC
NP-MRD IDNP0009415
Secondary Accession NumbersNone
Natural Product Identification
Common NameAvidinorubicin
Provided ByNPAtlasNPAtlas Logo
Description Avidinorubicin is found in Streptomyces, Streptomyces avidinii and Streptomyces avidinii NR0576. Avidinorubicin was first documented in 1991 (PMID: 2071489). Based on a literature review very few articles have been published on 4-{[(2S,3R,4R,6R)-6-{[(2R,3R,4S,6S)-4-amino-6-{[(2R,3R,4S,6S)-4-amino-6-{[(1S,10S,12R,21S,22R,23S,24R)-23-(dimethylamino)-10-{[(2R,4R,5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8,12,15,22-tetrahydroxy-1,12-dimethyl-6,17-dioxo-20,25-dioxahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴]Pentacosa-2(19),3,5(18),7(16),8,14-hexaen-24-yl]oxy}-2,4-dimethyloxan-3-yl]oxy}-2,4-dimethyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-4-oxobutanoic acid.
Structure
Thumb
Synonyms
ValueSource
4-{[(2S,3R,4R,6R)-6-{[(2R,3R,4S,6S)-4-amino-6-{[(2R,3R,4S,6S)-4-amino-6-{[(1S,10S,12R,21S,22R,23S,24R)-23-(dimethylamino)-10-{[(2R,4R,5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8,12,15,22-tetrahydroxy-1,12-dimethyl-6,17-dioxo-20,25-dioxahexacyclo[19.3.1.0,.0,.0,.0,]pentacosa-2(19),3,5(18),7(16),8,14-hexaen-24-yl]oxy}-2,4-dimethyloxan-3-yl]oxy}-2,4-dimethyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-4-oxobutanoateGenerator
Chemical FormulaC60H86N4O22
Average Mass1215.3540 Da
Monoisotopic Mass1214.57337 Da
IUPAC Name4-{[(2S,3R,4R,6R)-6-{[(2R,3R,4S,6S)-4-amino-6-{[(2R,3R,4S,6S)-4-amino-6-{[(1S,10S,12R,21S,22R,23S,24R)-23-(dimethylamino)-10-{[(2R,4R,5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8,12,15,22-tetrahydroxy-1,12-dimethyl-6,17-dioxo-20,25-dioxahexacyclo[19.3.1.0^{2,19}.0^{5,18}.0^{7,16}.0^{9,14}]pentacosa-2(19),3,5(18),7,9(14),15-hexaen-24-yl]oxy}-2,4-dimethyloxan-3-yl]oxy}-2,4-dimethyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-4-oxobutanoic acid
Traditional Name4-{[(2S,3R,4R,6R)-6-{[(2R,3R,4S,6S)-4-amino-6-{[(2R,3R,4S,6S)-4-amino-6-{[(1S,10S,12R,21S,22R,23S,24R)-23-(dimethylamino)-10-{[(2R,4R,5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-8,12,15,22-tetrahydroxy-1,12-dimethyl-6,17-dioxo-20,25-dioxahexacyclo[19.3.1.0^{2,19}.0^{5,18}.0^{7,16}.0^{9,14}]pentacosa-2(19),3,5(18),7,9(14),15-hexaen-24-yl]oxy}-2,4-dimethyloxan-3-yl]oxy}-2,4-dimethyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-4-oxobutanoic acid
CAS Registry NumberNot Available
SMILES
CO[C@@H]1C[C@@H](O[C@H]2[C@@H](C)O[C@H](C[C@]2(C)N)O[C@H]2[C@@H](C)O[C@H](C[C@]2(C)N)O[C@@H]2[C@H]([C@@H](O)[C@H]3OC4=C(C=CC5=C4C(=O)C4=C(C(O)=C6[C@H](C[C@](C)(O)CC6=C4O)O[C@H]4C[C@H]([C@H](O)[C@@H](C)O4)N(C)C)C5=O)[C@]2(C)O3)N(C)C)O[C@@H](C)[C@H]1OC(=O)CCC(O)=O
InChI Identifier
InChI=1S/C60H86N4O22/c1-24-45(68)31(63(9)10)18-36(76-24)80-33-21-57(5,74)20-29-40(33)48(71)42-43(47(29)70)49(72)41-28(46(42)69)14-15-30-52(41)85-56-50(73)44(64(11)12)55(60(30,8)86-56)84-39-23-59(7,62)54(27(4)79-39)83-38-22-58(6,61)53(26(3)78-38)82-37-19-32(75-13)51(25(2)77-37)81-35(67)17-16-34(65)66/h14-15,24-27,31-33,36-39,44-45,50-51,53-56,68,70-71,73-74H,16-23,61-62H2,1-13H3,(H,65,66)/t24-,25+,26-,27-,31-,32-,33+,36+,37-,38+,39+,44+,45-,50-,51-,53+,54+,55-,56+,57-,58+,59+,60+/m1/s1
InChI KeyXMRHMVSZMLOUMS-WCRFGKPLSA-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
StreptomycesNPAtlas
Streptomyces avidiniiLOTUS Database
Streptomyces avidinii NR0576Bacteria
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
logP0.4ALOGPS
logP0.38ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.64ChemAxon
pKa (Strongest Basic)10.4ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area358.94 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity299.68 m³·mol⁻¹ChemAxon
Polarizability130.99 ųChemAxon
Number of Rings10ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA020663
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78442922
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139588917
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Aoki M, Shirai H, Nakayama N, Itezono Y, Mori M, Satoh T, Ohshima S, Watanabe J, Yokose K, Seto H: Structural studies on avidinorubicin, a novel anthracycline with platelet aggregation inhibitory activity. J Antibiot (Tokyo). 1991 Jun;44(6):635-45. doi: 10.7164/antibiotics.44.635. [PubMed:2071489 ]