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Record Information
Version1.0
Created at2020-12-09 00:31:45 UTC
Updated at2021-07-15 16:45:45 UTC
NP-MRD IDNP0003194
Secondary Accession NumbersNone
Natural Product Identification
Common NameAdxanthromycin A
Provided ByNPAtlasNPAtlas Logo
Description(10S)-10-{[(9S)-3-carboxy-5-hydroxy-4,6,9-trimethyl-10-oxo-2-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracen-9-yl]peroxy}-3,8-dihydroxy-1,7,10-trimethyl-9-oxo-9,10-dihydroanthracene-2-carboxylic acid belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. Adxanthromycin A is found in Streptomyces. It was first documented in 2000 (PMID: 10724002). Based on a literature review very few articles have been published on (10S)-10-{[(9S)-3-carboxy-5-hydroxy-4,6,9-trimethyl-10-oxo-2-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracen-9-yl]peroxy}-3,8-dihydroxy-1,7,10-trimethyl-9-oxo-9,10-dihydroanthracene-2-carboxylic acid.
Structure
Thumb
Synonyms
ValueSource
(10S)-10-{[(9S)-3-carboxy-5-hydroxy-4,6,9-trimethyl-10-oxo-2-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracen-9-yl]peroxy}-3,8-dihydroxy-1,7,10-trimethyl-9-oxo-9,10-dihydroanthracene-2-carboxylateGenerator
Chemical FormulaNot Available
Average MassNot Available
Monoisotopic MassNot Available
IUPAC Name(10S)-10-{[(9S)-3-carboxy-5-hydroxy-4,6,9-trimethyl-10-oxo-2-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracen-9-yl]peroxy}-3,8-dihydroxy-1,7,10-trimethyl-9-oxo-9,10-dihydroanthracene-2-carboxylic acid
Traditional Name(10S)-10-{[(9S)-3-carboxy-5-hydroxy-4,6,9-trimethyl-10-oxo-2-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-9-yl]peroxy}-3,8-dihydroxy-1,7,10-trimethyl-9-oxoanthracene-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC1=CC=C2C(=C1O)C(=O)C1=C(C)C(C(O)=O)=C(O[C@@H]3O[C@@H](CO)[C@@H](O)[C@@H](O)[C@@H]3O)C=C1[C@]2(C)OO[C@@]1(C)C2=CC(O)=C(C(O)=O)C(C)=C2C(=O)C2=C1C=CC(C)=C2O
InChI Identifier
InChI=1S/C42H40O17/c1-14-7-9-18-29(31(14)45)34(48)25-16(3)27(38(52)53)22(44)11-20(25)41(18,5)58-59-42(6)19-10-8-15(2)32(46)30(19)35(49)26-17(4)28(39(54)55)23(12-21(26)42)56-40-37(51)36(50)33(47)24(13-43)57-40/h7-12,24,33,36-37,40,43-47,50-51H,13H2,1-6H3,(H,52,53)(H,54,55)/t24-,33+,36+,37-,40+,41+,42+/m0/s1
InChI KeyJQXRWMLDLWYXKW-FDOZYKMJSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Streptomyces
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthracenecarboxylic acids and derivatives
Direct ParentAnthracenecarboxylic acids
Alternative Parents
Substituents
  • Anthracene carboxylic acid
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Phenolic glycoside
  • 2-naphthalenecarboxylic acid
  • 2-naphthalenecarboxylic acid or derivatives
  • Alkyl glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acyl
  • Oxane
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Vinylogous acid
  • Secondary alcohol
  • Dialkyl peroxide
  • Ketone
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Primary alcohol
  • Aldehyde
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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
logP2.93ALOGPS
logP6.42ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)2.45ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area287.27 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity205.34 m³·mol⁻¹ChemAxon
Polarizability82.94 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA009433
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8899453
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10724120
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Nakano T, Koiwa T, Takahashi S, Nakagawa A: Adxanthromycins A and B, new inhibitors of ICAM-1/LFA-1 mediated cell adhesion molecule from Streptomyces sp. NA-148. I. Taxonomy, production, isolation and biological activities. J Antibiot (Tokyo). 2000 Jan;53(1):12-8. doi: 10.7164/antibiotics.53.12. [PubMed:10724002 ]