NP-MRD: Showing NP-Card for (6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate (NP0218379)

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Record Information

Version

2.0

Created at

2022-09-05 19:02:05 UTC

Updated at

2022-09-05 19:02:05 UTC

NP-MRD ID

NP0218379

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate

Description

(6-{[8,20-Dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]Icosa-6(11),7,9,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. (6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate is found in Trigonotis peduncularis. They include 1-aryltetralin lactones (6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]Icosa-6(11),7,9,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171523402D          

 52 57  0  0  0  0            999 V2000
    0.8503    1.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089    1.0712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167    0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1753    0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9831   -0.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5322    0.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2736    1.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4658    1.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2072    2.3025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -0.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0495   -0.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5986   -0.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3400    0.4002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4064   -0.5509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650   -1.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1159   -1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3638   -2.2891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3745   -2.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253   -3.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0176   -3.1814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5669   -2.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0069   -2.7371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3081   -1.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7590   -2.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9512   -2.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4020   -2.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5943   -2.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0451   -3.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3037   -4.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3356   -1.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279   -1.7270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8848   -1.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6926   -1.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2137   -2.5512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3814   -1.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8702   -1.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6901   -1.1698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2031   -1.8173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5501   -2.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718   -2.6395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7187   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5404   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0151   -2.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8368   -2.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1838   -3.6094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3116   -2.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2440   -4.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5909   -4.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4223   -3.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9475   -4.6637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0753   -3.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2536   -3.1667    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  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 11 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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 10 33  1  0  0  0  0
 25 33  1  0  0  0  0
 18 34  1  0  0  0  0
 34 35  1  0  0  0  0
 15 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 41 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 39 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END


  Mrv1533004171523402D          

 52 57  0  0  0  0            999 V2000
    0.8503    1.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089    1.0712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167    0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1753    0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9831   -0.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5322    0.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2736    1.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4658    1.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2072    2.3025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -0.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0495   -0.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5986   -0.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3400    0.4002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4064   -0.5509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650   -1.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1159   -1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3638   -2.2891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3745   -2.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253   -3.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0176   -3.1814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5669   -2.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0069   -2.7371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3081   -1.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7590   -2.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9512   -2.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4020   -2.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5943   -2.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0451   -3.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3037   -4.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3356   -1.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279   -1.7270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8848   -1.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6926   -1.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2137   -2.5512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3814   -1.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8702   -1.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6901   -1.1698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2031   -1.8173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5501   -2.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718   -2.6395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7187   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5404   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0151   -2.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8368   -2.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1838   -3.6094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3116   -2.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2440   -4.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5909   -4.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4223   -3.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9475   -4.6637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0753   -3.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2536   -3.1667    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  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 11 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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 10 33  1  0  0  0  0
 25 33  1  0  0  0  0
 18 34  1  0  0  0  0
 34 35  1  0  0  0  0
 15 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 41 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 39 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218379

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1C2C(=CC3=CC(OC)=C(O)C=C13)C(=O)OCC1OC(CO)(OC3OC(COC(C)=O)C(O)C(O)C3O)C(OC2=O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C34H38O18/c1-13(36)47-10-22-26(39)28(41)29(42)33(49-22)52-34(12-35)30-27(40)23(51-34)11-48-31(43)17-6-15-8-21(46-3)19(38)9-16(15)24(25(17)32(44)50-30)14-4-5-18(37)20(7-14)45-2/h4-9,22-30,33,35,37-42H,10-12H2,1-3H3

> <INCHI_KEY>
XOMTWRCRDIWSSU-UHFFFAOYSA-N

> <FORMULA>
C34H38O18

> <MOLECULAR_WEIGHT>
734.66

> <EXACT_MASS>
734.205814384

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
71.48589776709765

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate

> <ALOGPS_LOGP>
0.79

> <JCHEM_LOGP>
-0.22300732699999823

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.151004733849323

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.531780042927336

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4565504872811488

> <JCHEM_POLAR_SURFACE_AREA>
266.65999999999997

> <JCHEM_REFRACTIVITY>
169.36890000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       1.587   3.462   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.070   1.999   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.578   1.686   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.061   0.224   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.568  -0.089   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.593   1.060   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.111   2.523   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.603   2.836   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.120   4.298   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.051  -1.551   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.559  -1.865   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.584  -0.715   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.101   0.747   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      10.092  -1.028   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.575  -2.491   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.550  -3.640   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.146  -4.273   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.032  -5.102   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.007  -6.252   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.499  -5.939   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.658  -3.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.613  -5.109   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.042  -3.327   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.017  -4.476   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.509  -4.163   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.484  -5.312   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.976  -4.999   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.951  -6.149   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.434  -7.611   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.493  -3.537   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.985  -3.224   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.518  -2.388   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.026  -2.701   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.599  -4.762   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.912  -3.254   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.824  -2.014   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.355  -2.184   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      13.446  -3.392   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      14.093  -4.789   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      15.627  -4.927   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      16.275  -6.324   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      17.809  -6.462   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      18.695  -5.203   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      20.229  -5.340   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      20.876  -6.737   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      21.115  -4.081   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      15.389  -7.584   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      16.036  -8.981   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      13.855  -7.446   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      12.969  -8.706   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      13.207  -6.049   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      11.673  -5.911   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   33                                                  
CONECT   11   10   12   23                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   35                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   34                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   11   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   10   25                                                  
CONECT   34   18   35                                                       
CONECT   35   34   15   36   38                                             
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   39                                                       
CONECT   39   38   40   51                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   47                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   41   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   39   52                                                  
CONECT   52   51                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  114    0
END

View in JSmol

Synonyms

Value	Source
(6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0,.0,]icosa-6(11),7,9,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetic acid	Generator
(6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6(11),7,9,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetic acid	Generator

Chemical Formula

C₃₄H₃₈O₁₈

Average Mass

734.6600 Da

Monoisotopic Mass

734.20581 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1C2C(=CC3=CC(OC)=C(O)C=C13)C(=O)OCC1OC(CO)(OC3OC(COC(C)=O)C(O)C(O)C3O)C(OC2=O)C1O

InChI Identifier

InChI=1S/C34H38O18/c1-13(36)47-10-22-26(39)28(41)29(42)33(49-22)52-34(12-35)30-27(40)23(51-34)11-48-31(43)17-6-15-8-21(46-3)19(38)9-16(15)24(25(17)32(44)50-30)14-4-5-18(37)20(7-14)45-2/h4-9,22-30,33,35,37-42H,10-12H2,1-3H3

InChI Key

XOMTWRCRDIWSSU-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
Trigonotis peduncularis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Lignan lactone
1-aryltetralin lignan
O-glycosyl compound
Disaccharide
Glycosyl compound
Naphthalene
Methoxyphenol
Tricarboxylic acid or derivatives
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Ketal
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Oxane
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Lactone
Polyol
Acetal
Carboxylic acid derivative
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Primary 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	0.79	ALOGPS
logP	-0.22	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.53	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	266.66 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	169.37 m³·mol⁻¹	ChemAxon
Polarizability	71.49 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate (NP0218379)

MOL for NP0218379 ((6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D MOL for NP0218379 ((6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D SDF for NP0218379 ((6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D-SDF for NP0218379 ((6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

PDB for NP0218379 ((6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D PDB for NP0218379 ((6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

SMILES for NP0218379 ((6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

INCHI for NP0218379 ((6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

Structure for NP0218379 ((6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D Structure for NP0218379 ((6-{[8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.0⁴,¹³.0⁶,¹¹]icosa-6,8,10,12-tetraen-19-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)