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Record Information
Version2.0
Created at2022-09-06 22:35:30 UTC
Updated at2022-09-06 22:35:30 UTC
NP-MRD IDNP0239083
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3s,6r)-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-3-(hydroxymethyl)-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione
Description(3S,6R)-19-{[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-3-(hydroxymethyl)-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]Henicosa-1(13),7(12),8,10,15(20),16,18-heptaene-4,14,21-trione belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. (3s,6r)-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-3-(hydroxymethyl)-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione is found in Streptomyces venezuelae. Based on a literature review very few articles have been published on (3S,6R)-19-{[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-3-(hydroxymethyl)-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]Henicosa-1(13),7(12),8,10,15(20),16,18-heptaene-4,14,21-trione.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC27H25NO10
Average Mass523.4940 Da
Monoisotopic Mass523.14785 Da
IUPAC Name(3S,6R)-19-{[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-3-(hydroxymethyl)-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0^{2,6}.0^{7,12}.0^{15,20}]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione
Traditional Name(3S,6R)-19-{[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-3-(hydroxymethyl)-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0^{2,6}.0^{7,12}.0^{15,20}]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione
CAS Registry NumberNot Available
SMILES
C[C@@H]1O[C@H](C[C@@H](O)[C@H]1O)OC1=C2C(=O)C3=C(C(=O)C2=CC=C1)C1=C(O)C=C(C)C=C1[C@H]1OC(=O)[C@H](CO)N31
InChI Identifier
InChI=1S/C27H25NO10/c1-10-6-13-19(15(30)7-10)21-22(28-14(9-29)27(35)38-26(13)28)25(34)20-12(24(21)33)4-3-5-17(20)37-18-8-16(31)23(32)11(2)36-18/h3-7,11,14,16,18,23,26,29-32H,8-9H2,1-2H3/t11-,14-,16+,18-,23-,26+/m0/s1
InChI KeyYJZPHITXTBWGEN-VXUIHZKTSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces venezuelaeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentPhenanthridines and derivatives
Alternative Parents
Substituents
  • Phenanthridine
  • Alpha-amino acid ester
  • Hexose monosaccharide
  • Naphthoquinone
  • Quinoline quinone
  • Glycosyl compound
  • O-glycosyl compound
  • Alpha-amino acid or derivatives
  • Naphthalene
  • Aryl ketone
  • Quinone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monosaccharide
  • Oxane
  • Oxazolidinone
  • Benzenoid
  • Oxazolidine
  • Vinylogous amide
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Carboxylic acid derivative
  • Enamine
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Acetal
  • Oxacycle
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • 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
logP1.46ChemAxon
pKa (Strongest Acidic)8.18ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area163.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity130.64 m³·mol⁻¹ChemAxon
Polarizability52.41 ųChemAxon
Number of Rings6ChemAxon
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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162868596
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]