NP-MRD: Showing NP-Card for 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2h,5h,6h,7h,8h-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid (NP0161886)

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Record Information

Version

2.0

Created at

2022-09-02 20:10:53 UTC

Updated at

2022-09-02 20:10:53 UTC

NP-MRD ID

NP0161886

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2h,5h,6h,7h,8h-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

Description

8-Hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2H,5H,6H,7H,8H-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid belongs to the class of organic compounds known as 9,9p-dihydroxyaryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9'- position. 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2h,5h,6h,7h,8h-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid is found in Juniperus thurifera. 8-Hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2H,5H,6H,7H,8H-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161508402D          

 31 34  0  0  0  0            999 V2000
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    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
    2.1434   -2.8875    0.0000 C   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
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -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  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
    0.7145   -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 O   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
    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
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   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
    0.0000   -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   -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
  4  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  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  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
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 13 28  1  0  0  0  0
 20 28  1  0  0  0  0
 14 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    3.6801   -1.9623    3.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0817   -1.1219    2.0380 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1137   -0.5903    1.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777   -0.8766    1.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7868   -0.3708    0.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6461   -0.6855    0.8098 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4989    0.5122    0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098    1.5908    1.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726    2.7232    1.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0348    2.7695    0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3019    1.6745   -0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5251    0.5268   -0.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378   -0.6540   -1.0895 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2398   -0.6689   -1.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3973   -1.9346   -0.5040 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4551   -2.3807    0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1559   -3.6592    0.9675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0291   -1.9086    0.1242 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0059   -2.3447   -0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386   -3.4398   -0.6448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3797   -1.6799   -1.9828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6316    4.0293    0.5610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6971    4.8657    1.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9155    3.9611    2.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2043    0.4557   -0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5239    0.7761   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8663    1.5920   -1.7353 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0330    2.1955   -2.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4809    0.2388    0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8117    0.5769   -0.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5388   -0.2832   -0.9890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5424   -2.3460    3.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0200   -1.4078    3.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1134   -2.8398    2.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4989   -1.5168    2.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813   -0.8970    1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3874    1.5881    2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1182    1.7096   -1.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4311   -0.4706   -2.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739   -0.2429   -0.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3817   -2.7125   -1.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5444   -1.6473    1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4263   -2.4506   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2892   -4.2876    0.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0889   -2.7471    0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1498   -1.0552   -2.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0128    5.3601    0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2700    5.5373    1.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4596    0.8977   -1.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268    1.4903   -3.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4506    3.0785   -3.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1248    2.5660   -2.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9788   -1.2268   -1.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5329   -0.5364   -0.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7319    0.2299   -1.9552 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
  4  5  1  0
  5 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  2  0
 29 30  1  0
 30 31  1  0
  5  6  1  0
  6 18  1  0
 18 15  1  0
 15 16  1  0
 16 17  1  0
 15 13  1  0
 13 14  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9 24  1  0
 24 23  1  0
 23 22  1  0
  9  8  1  0
  8  7  2  0
 18 19  1  0
 19 21  1  0
 19 20  2  0
 29  3  1  0
  7  6  1  0
  7 12  1  0
 22 10  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
 25 49  1  0
 28 50  1  0
 28 51  1  0
 28 52  1  0
 31 53  1  0
 31 54  1  0
 31 55  1  0
  6 36  1  1
 18 45  1  1
 15 41  1  6
 16 42  1  0
 16 43  1  0
 17 44  1  0
 13 39  1  6
 14 40  1  0
 11 38  1  0
 23 47  1  0
 23 48  1  0
  8 37  1  0
 21 46  1  0
M  END


  Mrv1533004161508402D          

 31 34  0  0  0  0            999 V2000
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    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
    2.1434   -2.8875    0.0000 C   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
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -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  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
    0.7145   -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 O   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
    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
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   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
    0.0000   -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   -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
  4  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  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  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
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 13 28  1  0  0  0  0
 20 28  1  0  0  0  0
 14 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0161886

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C1C(C(CO)C(O)C2=CC3=C(OCO3)C=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O9/c1-27-16-4-10(5-17(28-2)21(16)29-3)18-11-6-14-15(31-9-30-14)7-12(11)20(24)13(8-23)19(18)22(25)26/h4-7,13,18-20,23-24H,8-9H2,1-3H3,(H,25,26)

> <INCHI_KEY>
XRBSKUSTLXISAB-UHFFFAOYSA-N

> <FORMULA>
C22H24O9

> <MOLECULAR_WEIGHT>
432.425

> <EXACT_MASS>
432.142032353

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.230928541001106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2H,5H,6H,7H,8H-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
0.9583271446666664

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.027037993596995

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5599616732594757

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6470008380486503

> <JCHEM_POLAR_SURFACE_AREA>
123.91000000000001

> <JCHEM_REFRACTIVITY>
107.3972

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2H,5H,6H,7H,8H-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14   28                                                  
CONECT   14   13   15   29                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   13   20                                                  
CONECT   29   14   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
8-Hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2H,5H,6H,7H,8H-naphtho[2,3-D][1,3]dioxole-6-carboxylate	Generator

Chemical Formula

C₂₂H₂₄O₉

Average Mass

432.4250 Da

Monoisotopic Mass

432.14203 Da

IUPAC Name

8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2H,5H,6H,7H,8H-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

Traditional Name

8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2H,5H,6H,7H,8H-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)C1C(C(CO)C(O)C2=CC3=C(OCO3)C=C12)C(O)=O

InChI Identifier

InChI=1S/C22H24O9/c1-27-16-4-10(5-17(28-2)21(16)29-3)18-11-6-14-15(31-9-30-14)7-12(11)20(24)13(8-23)19(18)22(25)26/h4-7,13,18-20,23-24H,8-9H2,1-3H3,(H,25,26)

InChI Key

XRBSKUSTLXISAB-UHFFFAOYSA-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
Juniperus thurifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 9,9p-dihydroxyaryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9'- position.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

9,9p-dihydroxyaryltetralin lignans

Direct Parent

9,9p-dihydroxyaryltetralin lignans

Alternative Parents

Substituents

9,9p-dihydroxyaryltetralin lignan
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
Tetralin
Benzodioxole
Methoxybenzene
Phenol ether
Phenoxy compound
Anisole
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Organic oxygen compound
Carbonyl group
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
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	1.35	ALOGPS
logP	0.96	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.56	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	123.91 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	107.4 m³·mol⁻¹	ChemAxon
Polarizability	43.23 Å³	ChemAxon
Number of Rings	4	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

411658

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2h,5h,6h,7h,8h-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid (NP0161886)

MOL for NP0161886 (8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2h,5h,6h,7h,8h-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid)

3D MOL for NP0161886 (8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2h,5h,6h,7h,8h-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid)

3D SDF for NP0161886 (8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2h,5h,6h,7h,8h-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid)

3D-SDF for NP0161886 (8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2h,5h,6h,7h,8h-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid)

PDB for NP0161886 (8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2h,5h,6h,7h,8h-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid)

3D PDB for NP0161886 (8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2h,5h,6h,7h,8h-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid)

SMILES for NP0161886 (8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2h,5h,6h,7h,8h-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid)

INCHI for NP0161886 (8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2h,5h,6h,7h,8h-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid)

Structure for NP0161886 (8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2h,5h,6h,7h,8h-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid)

3D Structure for NP0161886 (8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2h,5h,6h,7h,8h-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid)