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Record Information
Version2.0
Created at2022-04-27 22:05:07 UTC
Updated at2022-04-27 22:05:07 UTC
NP-MRD IDNP0050750
Secondary Accession NumbersNone
Natural Product Identification
Common NameIresinin I
Description(2S)-2-carboxy-5-{[(2S,3R,4S,5S,6R)-3-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-6-({[(3R)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-4,5-dihydroxyoxan-2-yl]oxy}-1-{2-[(2S)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-2,3-dihydro-1H-1λ⁵-indol-1-ylium-6-olate belongs to the class of organic compounds known as betacyanins and derivatives. These are organic compounds containing a glycoside of indolium-2-carboxylic acid attached, with the nitrogen ring of the indolium ring attached to an ethylpyridine-2,6-dicarboxylic acid derivative. Betacyanins are red nitrogenous pigments found in certain plants, such as beetroots. Iresinin I is found in Iresine herbstii . Based on a literature review very few articles have been published on (2S)-2-carboxy-5-{[(2S,3R,4S,5S,6R)-3-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-6-({[(3R)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-4,5-dihydroxyoxan-2-yl]oxy}-1-{2-[(2S)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-2,3-dihydro-1H-1λ⁵-indol-1-ylium-6-olate.
Structure
Thumb
Synonyms
ValueSource
(2S)-2-Carboxy-5-{[(2S,3R,4S,5S,6R)-3-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-6-({[(3R)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-4,5-dihydroxyoxan-2-yl]oxy}-1-{2-[(2S)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-2,3-dihydro-1H-1-indol-1-ylium-6-olic acidGenerator
Chemical FormulaC36H42N2O23
Average Mass870.7230 Da
Monoisotopic Mass870.21784 Da
IUPAC Name(1E,2S)-5-{[(2S,3R,4S,5S,6R)-3-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-6-({[(3R)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-4,5-dihydroxyoxan-2-yl]oxy}-1-{2-[(2S,4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-6-hydroxy-2,3-dihydro-1H-1lambda5-indol-1-ylium-2-carboxylate
Traditional Name(1E,2S)-5-{[(2S,3R,4S,5S,6R)-3-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-6-({[(3R)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-4,5-dihydroxyoxan-2-yl]oxy}-1-{2-[(2S,4E)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene}-6-hydroxy-2,3-dihydro-1H-1lambda5-indol-1-ylium-2-carboxylate
CAS Registry NumberNot Available
SMILES
C[C@@](O)(CC(O)=O)CC(=O)OC[C@H]1O[C@@H](OC2=C(O)C=C3C(C[C@@H](C([O-])=O)\[N+]3=C/C=C3\C[C@H](NC(=C3)C(O)=O)C(O)=O)=C2)[C@H](O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C36H42N2O23/c1-36(56,9-21(40)41)10-22(42)57-11-20-23(43)25(45)29(61-34-27(47)24(44)26(46)28(60-34)33(54)55)35(59-20)58-19-7-13-6-17(32(52)53)38(16(13)8-18(19)39)3-2-12-4-14(30(48)49)37-15(5-12)31(50)51/h2-4,7-8,15,17,20,23-29,34-35,43-47,56H,5-6,9-11H2,1H3,(H6,39,40,41,48,49,50,51,52,53,54,55)/t15-,17-,20+,23+,24-,25-,26-,27+,28-,29+,34-,35+,36+/m0/s1
InChI KeyGTTSBGCXUNBAOH-ZQHVOMFASA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Iresine herbstiiPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as betacyanins and derivatives. These are organic compounds containing a glycoside of indolium-2-carboxylic acid attached, with the nitrogen ring of the indolium ring attached to an ethylpyridine-2,6-dicarboxylic acid derivative. Betacyanins are red nitrogenous pigments found in certain plants, such as beetroots.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassBetalains
Sub ClassBetacyanins and derivatives
Direct ParentBetacyanins and derivatives
Alternative Parents
Substituents
  • Betacyanin
  • Hexacarboxylic acid or derivatives
  • Saccharolipid
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Indolecarboxylic acid
  • Indolecarboxylic acid derivative
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • L-alpha-amino acid
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Indole or derivatives
  • Beta-hydroxy acid
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • Tetrahydropyridine
  • Fatty acyl
  • Hydropyridine
  • Hydroxy acid
  • Benzenoid
  • Oxane
  • Pyran
  • Tertiary alcohol
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Shiff base
  • Secondary alcohol
  • Amino acid or derivatives
  • Amino acid
  • Secondary aliphatic amine
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Azacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Enamine
  • Secondary amine
  • Carboxylic acid derivative
  • Oxacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic zwitterion
  • Carbonyl group
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP-0.75ALOGPS
logP-6.9ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)1.44ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area409.2 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity212.63 m³·mol⁻¹ChemAxon
Polarizability82.95 ųChemAxon
Number of Rings5ChemAxon
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 IDC00001592
Chemspider ID10128206
KEGG Compound IDC08550
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound441619
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available