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Record Information
Version2.0
Created at2022-04-28 09:59:36 UTC
Updated at2022-04-28 09:59:36 UTC
NP-MRD IDNP0065799
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3S,3'R,4'S,5'R,6R,6'R)-5,18-Didehydro-4',5'-epoxy-5,5',6,6',7,7',8,8'-octahydro-3,3',6-trihydroxy-8-oxo-beta,beta-carotene
DescriptionDihydroprasinoxanthin epoxide 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. Thus, dihydroprasinoxanthin epoxide is considered to be an isoprenoid. (3S,3'R,4'S,5'R,6R,6'R)-5,18-Didehydro-4',5'-epoxy-5,5',6,6',7,7',8,8'-octahydro-3,3',6-trihydroxy-8-oxo-beta,beta-carotene is found in Prasinococcus capsulatus. Based on a literature review very few articles have been published on Dihydroprasinoxanthin epoxide.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC40H58O5
Average Mass618.8990 Da
Monoisotopic Mass618.42842 Da
IUPAC Name(3E,5E,7E,9E,11E,13E,15E)-1-[(1R,4S)-1,4-dihydroxy-2,2-dimethyl-6-methylidenecyclohexyl]-18-[(1R,2R,5R,6S)-5-hydroxy-1,3,3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaen-2-one
Traditional Name(3E,5E,7E,9E,11E,13E,15E)-1-[(1R,4S)-1,4-dihydroxy-2,2-dimethyl-6-methylidenecyclohexyl]-18-[(1R,2R,5R,6S)-5-hydroxy-1,3,3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaen-2-one
CAS Registry NumberNot Available
SMILES
C\C(CC[C@H]1[C@@]2(C)O[C@H]2[C@H](O)CC1(C)C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)C(=O)C[C@]1(O)C(=C)C[C@@H](O)CC1(C)C
InChI Identifier
InChI=1S/C40H58O5/c1-27(17-13-18-29(3)21-22-35-37(6,7)25-34(43)36-39(35,10)45-36)15-11-12-16-28(2)19-14-20-30(4)33(42)26-40(44)31(5)23-32(41)24-38(40,8)9/h11-20,32,34-36,41,43-44H,5,21-26H2,1-4,6-10H3/b12-11+,17-13+,19-14+,27-15+,28-16+,29-18+,30-20+/t32-,34-,35-,36+,39-,40+/m1/s1
InChI KeyTZIQGXRIFCNVHM-OWAUYRPESA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Prasinococcus capsulatusViridiplantae
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
  • Oxepane
  • B'-hydroxy-alpha,beta-unsaturated-ketone
  • Beta-hydroxy ketone
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Acryloyl-group
  • Cyclic alcohol
  • Alpha,beta-unsaturated ketone
  • Enone
  • Tertiary alcohol
  • Secondary alcohol
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Dialkyl ether
  • Oxirane
  • Ether
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen 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
logP7.06ALOGPS
logP7.19ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)13.51ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.29 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity192.47 m³·mol⁻¹ChemAxon
Polarizability75.22 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 IDC00023036
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162912094
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available