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Record Information
Version1.0
Created at2022-09-05 23:30:14 UTC
Updated at2022-09-05 23:30:14 UTC
NP-MRD IDNP0221825
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,2s,3s,7s,9r)-10-phenyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,12-dioxatricyclo[7.3.1.0²,⁷]trideca-5,10-diene-6-carboxylic acid
DescriptionCHEBI:69638 Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. (1r,2s,3s,7s,9r)-10-phenyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,12-dioxatricyclo[7.3.1.0²,⁷]trideca-5,10-diene-6-carboxylic acid is found in Lonicera japonica. It was first documented in 2022 (PMID: 36075691). Based on a literature review a significant number of articles have been published on CHEBI:69638 (PMID: 36075690) (PMID: 36075689) (PMID: 36075688) (PMID: 36075687).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC24H28O10
Average Mass476.4780 Da
Monoisotopic Mass476.16825 Da
IUPAC Name(1R,2S,3S,7S,9R)-10-phenyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,12-dioxatricyclo[7.3.1.0^{2,7}]trideca-5,10-diene-6-carboxylic acid
Traditional Name(1R,2S,3S,7S,9R)-10-phenyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,12-dioxatricyclo[7.3.1.0^{2,7}]trideca-5,10-diene-6-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@H]3C[C@@H]4C[C@@H](OC=C4C4=CC=CC=C4)[C@@H]23)C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C24H28O10/c25-8-17-19(26)20(27)21(28)24(33-17)34-23-18-13(15(10-32-23)22(29)30)6-12-7-16(18)31-9-14(12)11-4-2-1-3-5-11/h1-5,9-10,12-13,16-21,23-28H,6-8H2,(H,29,30)/t12-,13-,16-,17-,18+,19-,20+,21-,23+,24+/m1/s1
InChI KeySCTDPJFVWAWKPB-JBKQMOEBSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lonicera japonicaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • Hexose monosaccharide
  • O-glycosyl compound
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Vinylogous ester
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • 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
logP0.11ChemAxon
pKa (Strongest Acidic)4.34ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.14 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity114.51 m³·mol⁻¹ChemAxon
Polarizability46.5 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28490662
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound57395335
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Abioye AI, Sudfeld CR, Hughes MD, Aboud S, Muhihi A, Ulenga N, Nagu TJ, Wang M, Mugusi F, Fawzi WW: Iron status among HIV-infected adults during the first year of antiretroviral therapy in Tanzania. HIV Med. 2022 Sep 8. doi: 10.1111/hiv.13396. [PubMed:36075691 ]
  2. Authors unspecified: Resources Round-up. Altern Lab Anim. 2022 Sep 8:2611929221121256. doi: 10.1177/02611929221121256. [PubMed:36075690 ]
  3. Kim JU, Khan W, Arowoshola L, Ahmad M: Correspondence. Eur Heart J Qual Care Clin Outcomes. 2022 Aug 26. pii: 6677390. doi: 10.1093/ehjqcco/qcac051. [PubMed:36075689 ]
  4. DaVault L: Field Amputations Facilitated by a Surgical Extraction Team. Am Surg. 2022 Sep 8:31348221114521. doi: 10.1177/00031348221114521. [PubMed:36075688 ]
  5. Szanyi J, Walles JK, Tesfaye F, Gudeta AN, Bjorkman P: Intrauterine HIV exposure is associated with linear growth restriction among Ethiopian children in the first 18 months of life. Trop Med Int Health. 2022 Sep;27(9):823-830. doi: 10.1111/tmi.13805. Epub 2022 Aug 17. [PubMed:36075687 ]
  6. LOTUS database [Link]