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Record Information
Version2.0
Created at2022-04-27 21:57:38 UTC
Updated at2022-04-27 21:57:39 UTC
NP-MRD IDNP0050573
Secondary Accession NumbersNone
Natural Product Identification
Common NameZeaxanthin-3-O-beta-D-glucopyranoside
Description(2R,3R,4S,5S,6R)-2-{[(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Zeaxanthin-3-O-beta-D-glucopyranoside is found in Erwinia herbicola and Erwinia uredovora. Based on a literature review very few articles have been published on (2R,3R,4S,5S,6R)-2-{[(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC46H66O7
Average Mass731.0270 Da
Monoisotopic Mass730.48085 Da
IUPAC Name(2R,3R,4S,5S,6R)-2-{[(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name(2R,3R,4S,5S,6R)-2-{[(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
CAS Registry NumberNot Available
SMILES
C\C(\C=C\C=C(/C)\C=C\C1=C(C)C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@H](CC1(C)C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C46H66O7/c1-30(17-13-19-32(3)21-23-38-34(5)25-36(48)27-45(38,7)8)15-11-12-16-31(2)18-14-20-33(4)22-24-39-35(6)26-37(28-46(39,9)10)52-44-43(51)42(50)41(49)40(29-47)53-44/h11-24,36-37,40-44,47-51H,25-29H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,30-15+,31-16+,32-19+,33-20+/t36-,37+,40+,41+,42-,43+,44+/m0/s1
InChI KeyBSWLTLQDCPLUPH-KRJGRXGMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pantoea agglomeransBacteria
Pantoea ananatisBacteria
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative Parents
Substituents
  • Xanthophyll
  • Terpene glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP6.86ALOGPS
logP6.58ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area119.61 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity227.36 m³·mol⁻¹ChemAxon
Polarizability89.8 ųChemAxon
Number of Rings3ChemAxon
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 Compound163068064
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available