NP-MRD: Showing NP-Card for amburoside a (NP0260548)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 02:44:49 UTC

Updated at

2022-09-08 02:44:49 UTC

NP-MRD ID

NP0260548

Secondary Accession Numbers

None

Natural Product Identification

Common Name

amburoside a

Description

Amburoside A 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. Amburoside A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. amburoside a is found in Amburana cearensis and Origanum vulgare. amburoside a was first documented in 2008 (PMID: 18404596). Based on a literature review a small amount of articles have been published on amburoside A (PMID: 35528510) (PMID: 33629672) (PMID: 20638258) (PMID: 19053991).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082204442D          

 30 32  0  0  1  0            999 V2000
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
  8 21  1  0  0  0  0
 21 22  2  0  0  0  0
  5 22  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 23 30  1  0  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    3.4132   -1.0007   -0.9963 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2092   -0.8233   -0.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0067   -1.5314    1.1220 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9225   -2.4102    1.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413   -1.6738    1.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5390   -0.2902    1.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3697    0.3863    0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8014   -0.2995    0.6396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9901    0.3736    0.4568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2585   -0.1140    0.1797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6634    0.4759   -1.0230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8758   -0.0402   -1.4694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3447    0.7668   -2.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5629    0.2297   -3.0849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9073   -0.0525   -0.3688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8778   -1.3108    0.2265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4044    0.9342    0.6933 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9556    2.1188    0.0933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1870    0.2829    1.3162 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5928   -0.8546    2.0380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7450   -1.6694    0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4591   -2.3284    0.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3184    0.1112   -0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4690    0.7786   -1.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5085    1.6614   -1.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4172    1.8877   -0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4600    2.7872   -0.7419 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2764    1.2194    0.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2019    1.4604    1.6710 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2320    0.3471    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9829   -3.2260    0.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9248   -2.8897    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4878    0.2287    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3518    1.4623    0.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2374   -1.2127    0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7349   -1.0816   -1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5227    1.8346   -2.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6060    0.6330   -3.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3063    0.8568   -2.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9175    0.2278   -0.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7703   -1.7332    0.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1787    1.1913    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1019    2.4416    0.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7464    0.9979    2.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9481   -1.6058    1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -2.2927    0.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5214   -3.4202    0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7702    0.6247   -2.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6392    2.1962   -2.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5835    3.2820   -1.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0726    0.9559    2.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917   -0.1936    1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
  5 22  1  0
 22 21  2  0
 10 19  1  0
 19 20  1  0
 19 17  1  0
 17 18  1  0
 17 15  1  0
 15 16  1  0
 15 12  1  0
 21  8  1  0
 30 23  1  0
 14 39  1  0
 13 37  1  0
 13 38  1  0
 12 36  1  6
 10 35  1  6
  7 34  1  0
  6 33  1  0
  4 31  1  0
  4 32  1  0
 24 48  1  0
 25 49  1  0
 27 50  1  0
 29 51  1  0
 30 52  1  0
 22 47  1  0
 21 46  1  0
 19 44  1  1
 20 45  1  0
 17 42  1  1
 18 43  1  0
 15 40  1  6
 16 41  1  0
M  END


  Mrv1652309082204442D          

 30 32  0  0  1  0            999 V2000
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
  8 21  1  0  0  0  0
 21 22  2  0  0  0  0
  5 22  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 23 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260548

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C(COC(=O)C3=CC=C(O)C(O)=C3)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O10/c21-8-15-16(24)17(25)18(26)20(30-15)29-12-4-1-10(2-5-12)9-28-19(27)11-3-6-13(22)14(23)7-11/h1-7,15-18,20-26H,8-9H2/t15-,16-,17+,18-,20-/m1/s1

> <INCHI_KEY>
LRFIKYDSTHZRKW-BFMVXSJESA-N

> <FORMULA>
C20H22O10

> <MOLECULAR_WEIGHT>
422.386

> <EXACT_MASS>
422.121296908

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.33349469571961

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.522431839

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.881116318891118

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.557252403329317

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343686494

> <JCHEM_POLAR_SURFACE_AREA>
166.14000000000001

> <JCHEM_REFRACTIVITY>
100.783

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 3,4-dihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22                                                       
CONECT   22   21    5                                                       
CONECT   23    2   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   23                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
4-(O-beta-D-Glucopyranosyl)benzyl protocatechoate	ChEBI
4-(O-b-D-Glucopyranosyl)benzyl protocatechoate	Generator
4-(O-b-D-Glucopyranosyl)benzyl protocatechoic acid	Generator
4-(O-beta-D-Glucopyranosyl)benzyl protocatechoic acid	Generator
4-(O-Β-D-glucopyranosyl)benzyl protocatechoate	Generator
4-(O-Β-D-glucopyranosyl)benzyl protocatechoic acid	Generator

Chemical Formula

C₂₀H₂₂O₁₀

Average Mass

422.3860 Da

Monoisotopic Mass

422.12130 Da

IUPAC Name

(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 3,4-dihydroxybenzoate

Traditional Name

(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 3,4-dihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=C(COC(=O)C3=CC=C(O)C(O)=C3)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C20H22O10/c21-8-15-16(24)17(25)18(26)20(30-15)29-12-4-1-10(2-5-12)9-28-19(27)11-3-6-13(22)14(23)7-11/h1-7,15-18,20-26H,8-9H2/t15-,16-,17+,18-,20-/m1/s1

InChI Key

LRFIKYDSTHZRKW-BFMVXSJESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amburana cearensis	LOTUS Database	35616633
Origanum vulgare	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
Hexose monosaccharide
O-glycosyl compound
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Benzyloxycarbonyl
Benzoate ester
Benzoic acid or derivatives
Phenol ether
Phenoxy compound
Catechol
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Primary alcohol
Organic oxide
Hydrocarbon derivative
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:65402 )
catechols (CHEBI:65402 )
benzoate ester (CHEBI:65402 )

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	0.52	ChemAxon
pKa (Strongest Acidic)	8.56	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	100.78 m³·mol⁻¹	ChemAxon
Polarizability	41.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8585414

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10409977

PDB ID

Not Available

ChEBI ID

65402

Good Scents ID

Not Available

References

General References

de Araujo AB, Azul FVCS, Silva FRM, de Almeida TS, Oliveira JVN, Pimenta ATA, Bezerra AME, Machado NJ, Leal LKAM: Antineuroinflammatory Effect of Amburana cearensis and Its Molecules Coumarin and Amburoside A by Inhibiting the MAPK Signaling Pathway in LPS-Activated BV-2 Microglial Cells. Oxid Med Cell Longev. 2022 Apr 28;2022:6304087. doi: 10.1155/2022/6304087. eCollection 2022. [PubMed:35528510 ]
Yu H, Zhang P, Liu H, Sun X, Liang J, Sun L, Chen Y: Hypoglycemic activity of Origanum vulgare L. and its main chemical constituents identified with HPLC-ESI-QTOF-MS. Food Funct. 2021 Mar 21;12(6):2580-2590. doi: 10.1039/d0fo03166f. Epub 2021 Feb 25. [PubMed:33629672 ]
Leal LK, Pierdona TM, Goes JG, Fonseca KS, Canuto KM, Silveira ER, Bezerra AM, Viana GS: A comparative chemical and pharmacological study of standardized extracts and vanillic acid from wild and cultivated Amburana cearensis A.C. Smith. Phytomedicine. 2011 Jan 15;18(2-3):230-3. doi: 10.1016/j.phymed.2010.05.012. Epub 2010 Jul 16. [PubMed:20638258 ]
Leal LK, Canuto KM, da Silva Costa KC, Nobre-Junior HV, Vasconcelos SM, Silveira ER, Ferreira MV, Fontenele JB, Andrade GM, de Barros Viana GS: Effects of amburoside A and isokaempferide, polyphenols from Amburana cearensis, on rodent inflammatory processes and myeloperoxidase activity in human neutrophils. Basic Clin Pharmacol Toxicol. 2009 Mar;104(3):198-205. doi: 10.1111/j.1742-7843.2008.00329.x. Epub 2008 Nov 14. [PubMed:19053991 ]
Leal LK, Fonseca FN, Pereira FA, Canuto KM, Felipe CF, Fontenele JB, Pitombeira MV, Silveira ER, Viana GS: Protective effects of amburoside A, a phenol glucoside from Amburana cearensis, against CCl4-induced hepatotoxicity in rats. Planta Med. 2008 Apr;74(5):497-502. doi: 10.1055/s-2008-1074501. Epub 2008 Apr 10. [PubMed:18404596 ]
LOTUS database [Link]

Showing NP-Card for amburoside a (NP0260548)

MOL for NP0260548 (amburoside a)

3D MOL for NP0260548 (amburoside a)

3D SDF for NP0260548 (amburoside a)

3D-SDF for NP0260548 (amburoside a)

PDB for NP0260548 (amburoside a)

3D PDB for NP0260548 (amburoside a)

SMILES for NP0260548 (amburoside a)

INCHI for NP0260548 (amburoside a)

Structure for NP0260548 (amburoside a)

3D Structure for NP0260548 (amburoside a)