NP-MRD: Showing NP-Card for trans-Melilotoside (NP0044154)

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Record Information

Version

1.0

Created at

2021-11-12 23:53:09 UTC

Updated at

2021-11-26 17:46:02 UTC

NP-MRD ID

NP0044154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trans-Melilotoside

Description

Trans-beta-D-glucosyl-2-hydroxycinnamic acid, also known as (2E)-3-[2-(b-D-glucopyranosyloxy)phenyl]acrylate or beta-D-glucosyl-2-coumarate, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. trans-Melilotoside is found in Achlys triphylla, Detarium microcarpum, Mikania laevigata, Orchis militaris, Prunus padus and Serpocaulon triseriale. It was first documented in 2020 (PMID: 32208550). Trans-beta-D-glucosyl-2-hydroxycinnamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 32208549) (PMID: 32208530) (PMID: 32208521) (PMID: 32208519).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
    3.3063   -3.1348   -1.3516 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3115   -2.4477   -1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5862   -2.9270   -1.3264 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1332   -1.0818   -0.5694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9590   -0.5757   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7661    0.7663    0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7842    1.6301    0.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146    2.9066    1.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334    3.3470    1.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1925    2.4895    0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4553    1.2318    0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4378    0.3768    0.0915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9338    0.5631    0.1980 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4634   -0.5276    0.8643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8277   -0.4893    1.0276 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2657   -1.8620    1.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622   -2.2008    2.7094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5980   -0.1816   -0.2207 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9081    0.1517    0.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9549    0.8974   -1.0605 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6197    1.0339   -2.2489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5005    0.4817   -1.2295 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8142    1.2939   -2.0948 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0785   -2.8074   -2.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0252   -0.5108   -0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0826   -1.2048   -0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8071    1.3168    0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3441    3.5500    1.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0362    4.3288    1.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1643    2.8337    1.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752    1.5249    0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1431    0.2343    1.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9628   -2.5875    0.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3788   -1.9205    1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8659   -1.5366    3.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6381   -1.0943   -0.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4935   -0.6294    0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9420    1.8175   -0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9691    1.4404   -2.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5120   -0.5861   -1.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4892    0.7267   -2.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
  2  1  2  0
  2  3  1  0
 11 12  1  0
 12 13  1  0
 13 22  1  0
 22 20  1  0
 20 18  1  0
 18 15  1  0
 15 14  1  0
 15 16  1  0
 16 17  1  0
 18 19  1  0
 20 21  1  0
 22 23  1  0
  7  8  1  0
 14 13  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
  7 27  1  0
  5 26  1  0
  4 25  1  0
  3 24  1  0
 13 31  1  1
 22 40  1  6
 20 38  1  1
 18 36  1  6
 15 32  1  1
 16 33  1  0
 16 34  1  0
 17 35  1  0
 19 37  1  0
 21 39  1  0
 23 41  1  0
M  END


  Mrv1652311132100532D          

 23 24  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  1  0  0  0
 19 20  1  0  0  0  0
 16 21  1  6  0  0  0
 15 22  1  1  0  0  0
 14 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044154

> <DATABASE_NAME>
NP-MRD

> <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_IDENTIFIER>
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

> <INCHI_KEY>
GVRIYIMNJGULCZ-ZMKUSUEASA-N

> <FORMULA>
C15H18O8

> <MOLECULAR_WEIGHT>
326.301

> <EXACT_MASS>
326.10016754

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.39118809412247

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
-0.70

> <JCHEM_LOGP>
-0.43554715499999985

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.20011328362007

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7027156712501847

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923461838152

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
77.18520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-D-glucosyl-2-coumarate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    4   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   16                                                            
CONECT   22   15                                                            
CONECT   23   14                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
(2E)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]acrylic acid	ChEBI
beta-D-Glucosyl-2-coumarate	ChEBI
trans-beta-D-Glucosyl-2-hydroxycinnamate	ChEBI
(2E)-3-[2-(b-D-Glucopyranosyloxy)phenyl]acrylate	Generator
(2E)-3-[2-(b-D-Glucopyranosyloxy)phenyl]acrylic acid	Generator
(2E)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]acrylate	Generator
(2E)-3-[2-(Β-D-glucopyranosyloxy)phenyl]acrylate	Generator
(2E)-3-[2-(Β-D-glucopyranosyloxy)phenyl]acrylic acid	Generator
b-D-Glucosyl-2-coumarate	Generator
b-D-Glucosyl-2-coumaric acid	Generator
beta-D-Glucosyl-2-coumaric acid	Generator
β-D-Glucosyl-2-coumarate	Generator
β-D-Glucosyl-2-coumaric acid	Generator
trans-b-D-Glucosyl-2-hydroxycinnamate	Generator
trans-b-D-Glucosyl-2-hydroxycinnamic acid	Generator
trans-β-D-Glucosyl-2-hydroxycinnamate	Generator
trans-β-D-Glucosyl-2-hydroxycinnamic acid	Generator
(2E)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	HMDB
(2E)-3-[2-(β-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	HMDB
2'-(beta-D-Glucopyranosyloxy)cinnamic acid	HMDB
2'-(β-D-Glucopyranosyloxy)cinnamic acid	HMDB
2’-(β-D-Glucopyranosyloxy)cinnamic acid	HMDB
3-[2-(beta-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	HMDB
3-[2-(β-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	HMDB
Coumarin glucoside	HMDB
Melilotoside	HMDB
o-(Glucosyloxy)cinnamic acid	HMDB
o-Coumaroyl beta-D-glucopyranoside	HMDB
o-Coumaroyl β-D-glucopyranoside	HMDB
trans-Melilotoside	HMDB
trans-o-Coumarate 2-glucoside	HMDB
trans-beta-D-Glucosyl-2-hydroxycinnamic acid	HMDB
trans-o-Coumaric acid 2-glucoside	HMDB
trans-o-Hydroxycinnamic acid glucoside	HMDB
Coumarinate glucoside	HMDB
Coumarinic acid glucoside	HMDB
trans-Coumarinic acid-beta-D-glucoside	HMDB
trans-Coumarinic acid-β-D-glucoside	HMDB

Chemical Formula

C₁₅H₁₈O₈

Average Mass

326.3010 Da

Monoisotopic Mass

326.10017 Da

IUPAC Name

(2E)-3-(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

Traditional Name

β-D-glucosyl-2-coumarate

CAS Registry Number

Not Available

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 Identifier

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

InChI Key

GVRIYIMNJGULCZ-ZMKUSUEASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achlys triphylla	LOTUS Database	35616633
Detarium microcarpum	LOTUS Database	35616633
Mikania laevigata	LOTUS Database	35616633
Orchis militaris	LOTUS Database	35616633
Prunus padus	LOTUS Database	35616633
Serpocaulon triseriale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid
Coumaric acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Styrene
Phenol ether
Phenoxy compound
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Secondary alcohol
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Primary alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

glucosyl hydroxycinnamic acid (CHEBI:17531 )
Monolignols (C05158 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.7	ALOGPS
logP	-0.44	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.7	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.19 m³·mol⁻¹	ChemAxon
Polarizability	31.39 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033581

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011656

KNApSAcK ID

Not Available

Chemspider ID

4444329

KEGG Compound ID

C05158

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280759

PDB ID

Not Available

ChEBI ID

17531

Good Scents ID

Not Available

References

General References

Fage CD, Lathouwers T, Vanmeert M, Gao LJ, Vrancken K, Lammens EM, Weir ANM, Degroote R, Cuppens H, Kosol S, Simpson TJ, Crump MP, Willis CL, Herdewijn P, Lescrinier E, Lavigne R, Anne J, Masschelein J: The Kalimantacin Polyketide Antibiotics Inhibit Fatty Acid Biosynthesis in Staphylococcus aureus by Targeting the Enoyl-Acyl Carrier Protein Binding Site of FabI. Angew Chem Int Ed Engl. 2020 Jun 22;59(26):10549-10556. doi: 10.1002/anie.201915407. Epub 2020 Apr 14. [PubMed:32208550 ]
Kolpashchikov DM, Spelkov AA: Binary (Split) Light-up Aptameric Sensors. Angew Chem Int Ed Engl. 2021 Mar 1;60(10):4988-4999. doi: 10.1002/anie.201914919. Epub 2020 Oct 8. [PubMed:32208549 ]
Romita P, Foti C, Barlusconi C, Mercurio S, Hansel K, Stingeni L: Allergic contact dermatitis to 3-O-ethyl-L-ascorbic acid: An underrated allergen in cosmetics? Contact Dermatitis. 2020 Jul;83(1):63-64. doi: 10.1111/cod.13528. Epub 2020 Apr 7. [PubMed:32208530 ]
Huai J, Jing Y, Lin R: Functional analysis of ZmCOP1 and ZmHY5 reveals conserved light signaling mechanism in maize and Arabidopsis. Physiol Plant. 2020 Jul;169(3):369-379. doi: 10.1111/ppl.13099. Epub 2020 Apr 5. [PubMed:32208521 ]
Berni R, Mandlik R, Hausman JF, Guerriero G: Silicon-induced mitigatory effects in salt-stressed hemp leaves. Physiol Plant. 2021 Apr;171(4):476-482. doi: 10.1111/ppl.13097. Epub 2020 Mar 31. [PubMed:32208519 ]
Livia Macedo Dutra et al. (2020). 1H HR-MAS NMR and chemometric methods for discrimination and classification of Baccharis (Asteraceae): A proposal for quality control of Baccharis trimera. Journal of Pharmaceutical and Biomedical Analysis, Volume 184, 30 May 2020, 113200. DOI: 10.1016/j.jpba.2020.113200. Journal of Pharmaceutical and Biomedical Analysis.

Showing NP-Card for trans-Melilotoside (NP0044154)

MOL for NP0044154 (trans-Melilotoside)

3D MOL for NP0044154 (trans-Melilotoside)

3D SDF for NP0044154 (trans-Melilotoside)

3D-SDF for NP0044154 (trans-Melilotoside)

PDB for NP0044154 (trans-Melilotoside)

3D PDB for NP0044154 (trans-Melilotoside)

SMILES for NP0044154 (trans-Melilotoside)

INCHI for NP0044154 (trans-Melilotoside)

Structure for NP0044154 (trans-Melilotoside)

3D Structure for NP0044154 (trans-Melilotoside)