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Record Information
Version2.0
Created at2022-09-12 14:27:54 UTC
Updated at2022-09-12 14:27:54 UTC
NP-MRD IDNP0329763
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-hydroxy-2-[2-hydroxy-6-methyl-5-(2-methylpropyl)oxan-2-yl]-n-[5,7,21-trihydroxy-17-isopropyl-6-(methoxymethyl)-20-methyl-2,8,15,19,22-pentaoxo-18-oxa-1,4,7,13,14,21,27-heptaazatricyclo[21.4.0.0⁹,¹⁴]heptacos-4-en-16-yl]propanimidic acid
DescriptionAURANTIMYCIN A belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. AURANTIMYCIN A is a strong basic compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC38H64N8O14
Average Mass856.9720 Da
Monoisotopic Mass856.45420 Da
IUPAC NameN-[7,21-dihydroxy-6-(methoxymethyl)-20-methyl-2,5,8,15,19,22-hexaoxo-17-(propan-2-yl)-18-oxa-1,4,7,13,14,21,27-heptaazatricyclo[21.4.0.0⁹,¹⁴]heptacosan-16-yl]-2-hydroxy-2-[2-hydroxy-6-methyl-5-(2-methylpropyl)oxan-2-yl]propanamide
Traditional NameN-[7,21-dihydroxy-17-isopropyl-6-(methoxymethyl)-20-methyl-2,5,8,15,19,22-hexaoxo-18-oxa-1,4,7,13,14,21,27-heptaazatricyclo[21.4.0.0⁹,¹⁴]heptacosan-16-yl]-2-hydroxy-2-[2-hydroxy-6-methyl-5-(2-methylpropyl)oxan-2-yl]propanamide
CAS Registry NumberNot Available
SMILES
COCC1N(O)C(=O)C2CCCNN2C(=O)C(NC(=O)C(C)(O)C2(O)CCC(CC(C)C)C(C)O2)C(OC(=O)C(C)N(O)C(=O)C2CCCNN2C(=O)CNC1=O)C(C)C
InChI Identifier
InChI=1S/C38H64N8O14/c1-20(2)17-24-13-14-38(55,60-23(24)6)37(7,54)36(53)42-29-30(21(3)4)59-35(52)22(5)45(56)32(49)25-11-9-15-40-43(25)28(47)18-39-31(48)27(19-58-8)46(57)33(50)26-12-10-16-41-44(26)34(29)51/h20-27,29-30,40-41,54-57H,9-19H2,1-8H3,(H,39,48)(H,42,53)
InChI KeyJSVPJXYQXDNLRD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassDepsipeptides
Direct ParentCyclic depsipeptides
Alternative Parents
Substituents
  • Cyclic depsipeptide
  • Macrolide lactam
  • Alpha-amino acid ester
  • Macrolactam
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 1,2-diazinane
  • Oxane
  • Cyclic carboximidic acid
  • Tertiary alcohol
  • Carboxylic acid ester
  • Carboxylic acid hydrazide
  • Hemiacetal
  • Hydroxamic acid
  • Lactone
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Polyol
  • Organoheterocyclic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP0.06ALOGPS
logP-1.3ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.28ChemAxon
pKa (Strongest Basic)4.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area289.18 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity229.67 m³·mol⁻¹ChemAxon
Polarizability86.3 ųChemAxon
Number of Rings4ChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73792076
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]