NP-MRD: Showing NP-Card for methyl 4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate (NP0203671)

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Record Information

Version

2.0

Created at

2022-09-04 23:11:22 UTC

Updated at

2022-09-04 23:11:23 UTC

NP-MRD ID

NP0203671

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate

Description

1-Hydroxy-4-[D-apio-beta-D-furanosyloxy]-3-prenyl-2-naphthoic acid methyl ester 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. methyl 4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate is found in Rubia oncotricha. Based on a literature review very few articles have been published on 1-Hydroxy-4-[D-apio-beta-D-furanosyloxy]-3-prenyl-2-naphthoic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052201112D          

 30 32  0  0  1  0            999 V2000
   -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 O   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
    0.0000   -2.4750    0.0000 O   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
    0.7145   -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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0392    0.9019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912    1.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787    2.2295    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9324    2.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0762    3.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4758    3.6272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6282    2.0580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2413    2.6100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   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 C   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
    2.1434   -1.2375    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
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  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  1  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  1  0  0  0
 12 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  2  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
   -6.1393   -0.8874    1.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040   -1.3316    1.0101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7724   -0.4415    0.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1789    0.7278    0.4627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530   -0.9637    0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3739   -0.1861    0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6231    1.2623   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1723    1.4364   -1.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315    2.2418   -2.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2556    2.3547   -3.8404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4322    3.0623   -2.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1084   -0.7257   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9366    0.0447   -0.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8196    0.8166    0.3607 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9859    2.0945   -0.1107 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2066    2.5856    0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9565    1.5278    0.9641 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8266    1.7300    2.3246 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4106    1.4439    0.5763 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9918    0.3735    1.2528 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1887    0.2903    0.5626 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2931   -0.5792    1.6532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0606   -2.0734    0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2798   -2.6913    0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4299   -4.0500    0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692   -4.8426    0.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8531   -4.2427    0.7846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0156   -2.8808    0.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2508   -2.3413    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3551   -3.0840    1.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4526   -0.3627    0.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7933   -1.7623    1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1971   -0.1573    2.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6193    1.7957   -0.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2304    1.6995    0.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464    0.8569   -1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253    1.4933   -4.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3684    2.3130   -3.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9859    3.3182   -4.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441    2.3922   -2.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3387    3.8788   -2.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3960    3.5376   -1.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3573    0.8759    1.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0878    3.5163    0.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230    2.8389   -0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1190    1.2012    2.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5603    1.3977   -0.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9002    2.3712    0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8326    0.3942    2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6763   -0.1424   -0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3898   -0.5777    2.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680   -2.1673   -0.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3943   -4.5304    0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4680   -5.9121    0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6774   -4.8956    1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4261   -4.0438    1.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 12 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29  5  1  0
 21 14  1  0
 28 23  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
 10 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 11 42  1  0
 14 43  1  1
 16 44  1  0
 16 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  6
 22 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 30 56  1  0
M  END


  Mrv1652309052201112D          

 30 32  0  0  1  0            999 V2000
   -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 O   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
    0.0000   -2.4750    0.0000 O   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
    0.7145   -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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0392    0.9019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912    1.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787    2.2295    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9324    2.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0762    3.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4758    3.6272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6282    2.0580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2413    2.6100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   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 C   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
    2.1434   -1.2375    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
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  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  1  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  1  0  0  0
 12 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  2  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203671

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C(CC=C(C)C)C(O[C@@H]2OC[C@](O)(CO)[C@H]2O)=C2C=CC=CC2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O8/c1-12(2)8-9-15-16(20(26)28-3)17(24)13-6-4-5-7-14(13)18(15)30-21-19(25)22(27,10-23)11-29-21/h4-8,19,21,23-25,27H,9-11H2,1-3H3/t19-,21-,22+/m0/s1

> <INCHI_KEY>
XHEQMBRUWDPYAQ-ILWGZMRPSA-N

> <FORMULA>
C22H26O8

> <MOLECULAR_WEIGHT>
418.442

> <EXACT_MASS>
418.162767797

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.400019250763684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate

> <JCHEM_LOGP>
2.963904384999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.861001758604345

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.620724422381494

> <JCHEM_PKA_STRONGEST_BASIC>
-3.142388163814287

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
109.1394

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.073   1.684   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.104   2.828   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.334   4.162   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.741   4.788   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.142   5.626   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.888   6.771   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.173   3.842   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.317   4.872   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   29                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   21                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   17   14   22                                                  
CONECT   22   21                                                            
CONECT   23   12   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23   29                                                  
CONECT   29   28    5   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
1-Hydroxy-4-[D-apio-b-D-furanosyloxy]-3-prenyl-2-naphthoate methyl ester	Generator
1-Hydroxy-4-[D-apio-b-D-furanosyloxy]-3-prenyl-2-naphthoic acid methyl ester	Generator
1-Hydroxy-4-[D-apio-beta-D-furanosyloxy]-3-prenyl-2-naphthoate methyl ester	Generator
1-Hydroxy-4-[D-apio-β-D-furanosyloxy]-3-prenyl-2-naphthoate methyl ester	Generator
1-Hydroxy-4-[D-apio-β-D-furanosyloxy]-3-prenyl-2-naphthoic acid methyl ester	Generator

Chemical Formula

C₂₂H₂₆O₈

Average Mass

418.4420 Da

Monoisotopic Mass

418.16277 Da

IUPAC Name

methyl 4-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate

Traditional Name

methyl 4-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C(CC=C(C)C)C(O[C@@H]2OC[C@](O)(CO)[C@H]2O)=C2C=CC=CC2=C1O

InChI Identifier

InChI=1S/C22H26O8/c1-12(2)8-9-15-16(20(26)28-3)17(24)13-6-4-5-7-14(13)18(15)30-21-19(25)22(27,10-23)11-29-21/h4-8,19,21,23-25,27H,9-11H2,1-3H3/t19-,21-,22+/m0/s1

InChI Key

XHEQMBRUWDPYAQ-ILWGZMRPSA-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
Rubia oncotricha	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
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
1-naphthol
O-glycosyl compound
Naphthalene
Pentose monosaccharide
Salicylic acid or derivatives
Monosaccharide
Benzenoid
Methyl ester
Oxolane
Vinylogous acid
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.96	ChemAxon
pKa (Strongest Acidic)	9.62	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	109.14 m³·mol⁻¹	ChemAxon
Polarizability	43.4 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101600458

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate (NP0203671)

MOL for NP0203671 (methyl 4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate)

3D MOL for NP0203671 (methyl 4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate)

3D SDF for NP0203671 (methyl 4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate)

3D-SDF for NP0203671 (methyl 4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate)

PDB for NP0203671 (methyl 4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate)

3D PDB for NP0203671 (methyl 4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate)

SMILES for NP0203671 (methyl 4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate)

INCHI for NP0203671 (methyl 4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate)

Structure for NP0203671 (methyl 4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate)

3D Structure for NP0203671 (methyl 4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-2-carboxylate)