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Record Information
Version2.0
Created at2021-06-19 21:57:40 UTC
Updated at2021-06-29 23:58:47 UTC
NP-MRD IDNP0030666
Secondary Accession NumbersNone
Natural Product Identification
Common Nametrilobatin D
Provided ByJEOL DatabaseJEOL Logo
DescriptionTrilobatin D belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. trilobatin D is found in Bazzania trilobata. trilobatin D was first documented in 2003 (PMID: 12620330). Based on a literature review a small amount of articles have been published on Trilobatin D (PMID: 31540429).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H24O13
Average Mass532.4540 Da
Monoisotopic Mass532.12169 Da
IUPAC Name(1R,2S)-3-({[(2S,3R,4S,5S)-2-(carboxymethyl)-4,5-dihydroxyoxan-3-yl]oxy}carbonyl)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid
Traditional Name(1R,2S)-3-({[(2S,3R,4S,5S)-2-(carboxymethyl)-4,5-dihydroxyoxan-3-yl]oxy}carbonyl)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H]OC(=O)C([H])([H])[C@]1([H])OC([H])([H])[C@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])OC(=O)C1=C([H])C2=C([H])C(O[H])=C(O[H])C([H])=C2[C@@]([H])(C2=C([H])C(O[H])=C(O[H])C([H])=C2[H])[C@]1([H])C(=O)O[H]
InChI Identifier
InChI=1S/C25H24O13/c26-13-2-1-9(4-14(13)27)20-11-6-16(29)15(28)5-10(11)3-12(21(20)24(34)35)25(36)38-23-18(7-19(31)32)37-8-17(30)22(23)33/h1-6,17-18,20-23,26-30,33H,7-8H2,(H,31,32)(H,34,35)/t17-,18-,20+,21+,22-,23-/m0/s1
InChI KeyBQZDJLGHFNHARS-FMIOCKMGSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Bazzania trilobataJEOL database
    • Scher, J. M., et al., Phytochemistry 62, 769 (2003)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassAryltetralin lignans
Sub ClassNot Available
Direct ParentAryltetralin lignans
Alternative Parents
Substituents
  • 1-aryltetralin lignan
  • 2-naphthalenecarboxylic acid
  • 2-naphthalenecarboxylic acid or derivatives
  • 2-naphthol
  • Naphthalene
  • Tricarboxylic acid or derivatives
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • 1,2-diol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • 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
logP1.73ALOGPS
logP0.75ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.23ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area231.51 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity125.36 m³·mol⁻¹ChemAxon
Polarizability50.38 ųChemAxon
Number of Rings4ChemAxon
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 ID552875
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound637238
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wang L, Liu M, Yin F, Wang Y, Li X, Wu Y, Ye C, Liu J: Trilobatin, a Novel SGLT1/2 Inhibitor, Selectively Induces the Proliferation of Human Hepatoblastoma Cells. Molecules. 2019 Sep 18;24(18). pii: molecules24183390. doi: 10.3390/molecules24183390. [PubMed:31540429 ]
  2. Scher JM, Zapp J, Becker H: Lignan derivatives from the liverwort Bazzania trilobata. Phytochemistry. 2003 Mar;62(5):769-77. doi: 10.1016/s0031-9422(02)00626-x. [PubMed:12620330 ]
  3. Scher, J. M., et al. (2003). Scher, J. M., et al., Phytochemistry 62, 769 (2003). Phytochem..