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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H18O8
Molecular Weight 326.2986
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MELILOTOSIDE

SMILES

OC[C@H]1O[C@@H](OC2=CC=CC=C2\C=C\C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=GVRIYIMNJGULCZ-ZMKUSUEASA-N
InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-2-1-3-8(9)5-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-5+/t10-,12-,13+,14-,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula C15H18O8
Molecular Weight 326.2986
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 1
Optical Activity UNSPECIFIED

Meliltoside is a 2-glucosyloxycinnamic acid found in Dendrobium medicinal plants, Ajuga laxmannii, Ajuga chamaecistus ssp. tomentella, and Teloxys graveolens. It demonstrated moderate antiprotozoal and anti-cancer activity in vitro.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antiprotozoal activity of the constituents of Teloxys graveolens.
2003 Aug
High-performance liquid chromatography-diode array detection/electrospray ionization mass spectrometry for the simultaneous analysis of cis-, trans- and dihydro-2-glucosyloxycinnamic acid derivatives from Dendrobium medicinal plants.
2007
Bio-guided isolation of antioxidants from the stems of Dendrobium aurantiacum var. denneanum.
2007 Jul
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In an assay for Plasmodium falciparum, parasite cultures of P. falciparum were incubated in RPMI 1640 medium with 5% Albumax (without hypoxanthine). A series of meliltoside dilutions were applied in microtitre plates and incubated for 48 h at 37 C in a reduced oxygen atmosphere. In another assay, Trypanosoma brucei rhodesiense STIB 900 strain (10(4) blood stream forms of T. b. rhodesiense STIB 900 in 50 uL) was incubated at 37 C under a 5% CO2 atmosphere for 72 h in a medium (50 uM) supplemented with 25 mM HEPES, 1 g/L additional glucose, 1% MEM nonessential amino acids (100x), 0.2 mM 2-mercaptoethanol, 1 mM Na-pyruvate and 15% heat inactivated horse serum with addition of serial drug dilutions of seven 3-fold dilution steps covering a range from 90 to 0.123 ug/mL. Finally, in an assay for Trypanosoma cruzi, L-6 cells were seeded in 96-well microtitre plates in 100 mL RPMI 1640 medium with 10% FBS and 2 mM L-glutamine for 24 h. After that, the medium was removed and replaced by 100 uL per well containing 5000 trypomastigote forms of T. cruzi Tulahuen strain C2C4 containing the b-galactosidase (Lac Z) gene. The medium was removed from the wells after 48 h, and replaced by 100 uL fresh medium with or without a serial drug dilution of seven 3-fold dilution steps covering a range from 90 to 0.123 ug/mL and incubated for another 96 h. The compound demonstrated antiprotozoal activity with IC50 values of 58.9, 58.0 and 48.7 ug/ml against T. b. rhodesiense, T. cruzi and P. falciparum, respectively.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:01:22 GMT 2023
Edited
by admin
on Sat Dec 16 10:01:22 GMT 2023
Record UNII
M87W7715UB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MELILOTOSIDE
MI  
Common Name English
TRANS-MELILOTOSIDE
Common Name English
MELILOTOSIDE [MI]
Common Name English
2-PROPENOIC ACID, 3-(2-(.BETA.-D-GLUCOPYRANOSYLOXY)PHENYL)-, (2E)-
Systematic Name English
TRANS-O-HYDROXYCINNAMIC ACID GLUCOSIDE
Common Name English
2-PROPENOIC ACID, 3-(2-(.BETA.-D-GLUCOPYRANOSYLOXY)PHENYL)-, (E)-
Systematic Name English
Code System Code Type Description
PUBCHEM
5280759
Created by admin on Sat Dec 16 10:01:22 GMT 2023 , Edited by admin on Sat Dec 16 10:01:22 GMT 2023
PRIMARY
CAS
618-67-7
Created by admin on Sat Dec 16 10:01:22 GMT 2023 , Edited by admin on Sat Dec 16 10:01:22 GMT 2023
PRIMARY
FDA UNII
M87W7715UB
Created by admin on Sat Dec 16 10:01:22 GMT 2023 , Edited by admin on Sat Dec 16 10:01:22 GMT 2023
PRIMARY
MERCK INDEX
m304
Created by admin on Sat Dec 16 10:01:22 GMT 2023 , Edited by admin on Sat Dec 16 10:01:22 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID101024266
Created by admin on Sat Dec 16 10:01:22 GMT 2023 , Edited by admin on Sat Dec 16 10:01:22 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS