NP-MRD: Showing NP-Card for Demethylwedelolactone 3-O-glucoside (NP0057159)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 02:41:02 UTC

Updated at

2022-04-28 02:41:02 UTC

NP-MRD ID

NP0057159

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Demethylwedelolactone 3-O-glucoside

Description

3,13,14-Trihydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Demethylwedelolactone 3-O-glucoside is found in Eclipta alba . Based on a literature review very few articles have been published on 3,13,14-trihydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204412D          

 33 37  0  0  1  0            999 V2000
    5.9909    0.5068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619    2.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736    1.3045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521   -0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801   -0.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6016   -1.0613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3618    1.2437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9092    1.9334    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2802    2.6703    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1038    2.7174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5565    2.0277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1855    1.2908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3801    2.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7511    2.8117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4748    3.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8275    3.3600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0855    1.8863    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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
 12 19  1  0  0  0  0
  6 19  1  0  0  0  0
  5 20  2  0  0  0  0
 20 21  1  0  0  0  0
  2 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23  1  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 27 29  1  1  0  0  0
 29 30  1  0  0  0  0
 26 31  1  1  0  0  0
 25 32  1  1  0  0  0
 24 33  1  6  0  0  0
M  END

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -3.6440    0.8733    2.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0456    0.5416    1.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7578    0.4070    1.5535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1305    0.0565    0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2521   -0.0526    0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9227   -0.4105   -0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2874   -0.5369   -0.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1472   -0.3299    0.3762 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0551    0.6689   -0.0307 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2841    0.5594    0.5960 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0326    1.8568    0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2563    2.8923    0.8771 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1031   -0.5901   -0.0086 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9272   -0.1254   -1.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0405   -1.5580   -0.5485 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4503   -1.0576   -1.7071 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9707   -1.6184    0.5210 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4981   -1.7582    1.7812 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1754   -0.6510   -1.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1957   -0.5499   -1.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8878   -0.7976   -3.0652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8324   -0.1866   -0.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2050   -0.0536   -0.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1719   -0.1988   -1.5457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3382    0.0399   -1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6349    0.0265   -1.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7316    0.3345   -0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9888    0.3013   -1.2390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5549    0.6674    0.6257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6062    0.9856    1.4865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2496    0.6805    1.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1688    0.3762    0.3085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8005    0.3135    0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7724    0.1455    1.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -0.0404    1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2131    0.4653    1.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0281    1.9901   -0.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0371    1.8661    0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2973    2.6564    0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6478   -1.1512    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5803   -0.8336   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4691   -2.5689   -0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8706   -0.2394   -2.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3416   -2.5048    0.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9541   -1.4110    2.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7436   -0.9328   -2.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8587   -0.7446   -3.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7672   -0.2375   -2.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8365    0.5052   -0.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5632    0.9884    1.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0924    0.9409    2.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 33  2  0
 33 32  1  0
 32 25  2  0
 25 24  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
 33  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  8 17  1  0
 17 18  1  0
 17 15  1  0
 15 16  1  0
 15 13  1  0
 13 14  1  0
 13 10  1  0
  5  6  1  0
  4 22  1  0
 24 23  1  0
 31 32  1  0
 12 39  1  0
 11 37  1  0
 11 38  1  0
 10 36  1  1
  8 35  1  1
 19 46  1  0
 21 47  1  0
 26 48  1  0
 28 49  1  0
 30 50  1  0
 31 51  1  0
  5 34  1  0
 17 44  1  6
 18 45  1  0
 15 42  1  6
 16 43  1  0
 13 40  1  1
 14 41  1  0
M  END


  Mrv1652304282204412D          

 33 37  0  0  1  0            999 V2000
    5.9909    0.5068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619    2.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736    1.3045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521   -0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801   -0.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6016   -1.0613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3618    1.2437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9092    1.9334    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2802    2.6703    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1038    2.7174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5565    2.0277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1855    1.2908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3801    2.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7511    2.8117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4748    3.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8275    3.3600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0855    1.8863    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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
 12 19  1  0  0  0  0
  6 19  1  0  0  0  0
  5 20  2  0  0  0  0
 20 21  1  0  0  0  0
  2 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23  1  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 27 29  1  1  0  0  0
 29 30  1  0  0  0  0
 26 31  1  1  0  0  0
 25 32  1  1  0  0  0
 24 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0057159

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(O)=C3C4=C(C5=C(O4)C=C(O)C(O)=C5)C(=O)OC3=C2)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O12/c22-5-13-16(26)17(27)18(28)21(33-13)30-6-1-10(25)15-12(2-6)32-20(29)14-7-3-8(23)9(24)4-11(7)31-19(14)15/h1-4,13,16-18,21-28H,5H2/t13-,16+,17+,18-,21-/m1/s1

> <INCHI_KEY>
HKFFFIWYFPSUML-KMYJYHJKSA-N

> <FORMULA>
C21H18O12

> <MOLECULAR_WEIGHT>
462.363

> <EXACT_MASS>
462.07982602

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
43.854472248904734

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,13,14-trihydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
-0.4778774143333334

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.311254384056701

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.575681814927255

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343758667

> <JCHEM_POLAR_SURFACE_AREA>
199.51

> <JCHEM_REFRACTIVITY>
105.72569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,13,14-trihydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0      11.183   0.946   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.645   0.858   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.800   2.146   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.263   2.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.570   0.682   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.033   0.594   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.188   1.881   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.881   3.257   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.036   4.544   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.418   3.345   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.702   1.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.629  -0.063   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.260  -0.768   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.035   0.064   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.038   1.603   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.407   2.308   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.257   2.435   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.404  -0.641   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.070  -0.607   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.415  -0.606   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.953  -0.517   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.723  -1.981   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.875   2.322   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.030   3.609   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.723   4.985   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.261   5.073   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.105   3.785   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.413   2.410   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      15.643   3.873   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.335   5.249   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      13.953   6.448   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      10.878   6.272   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.493   3.521   0.000  0.00  0.00           O+0
CONECT    1    2   23                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6   20                                                  
CONECT    6    5    7   19                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4                                                       
CONECT   11    7   12   16                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15                                                            
CONECT   18   14                                                            
CONECT   19   12    6                                                       
CONECT   20    5   21   22                                                  
CONECT   21   20    2                                                       
CONECT   22   20                                                            
CONECT   23    1   24   28                                                  
CONECT   24   23   25   33                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   26                                                            
CONECT   32   25                                                            
CONECT   33   24                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₁₈O₁₂

Average Mass

462.3630 Da

Monoisotopic Mass

462.07983 Da

IUPAC Name

3,13,14-trihydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

Traditional Name

3,13,14-trihydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC(O)=C3C4=C(C5=C(O4)C=C(O)C(O)=C5)C(=O)OC3=C2)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H18O12/c22-5-13-16(26)17(27)18(28)21(33-13)30-6-1-10(25)15-12(2-6)32-20(29)14-7-3-8(23)9(24)4-11(7)31-19(14)15/h1-4,13,16-18,21-28H,5H2/t13-,16+,17+,18-,21-/m1/s1

InChI Key

HKFFFIWYFPSUML-KMYJYHJKSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Eclipta alba	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Phenolic glycoside
Furanocoumarin
Angular furanocoumarin
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Coumarin
1-benzopyran
Benzopyran
Furopyran
Benzofuran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Furan
Secondary alcohol
Lactone
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	0.52	ALOGPS
logP	-0.48	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	6.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	199.51 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.73 m³·mol⁻¹	ChemAxon
Polarizability	43.85 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

163036243

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Demethylwedelolactone 3-O-glucoside (NP0057159)

MOL for NP0057159 (Demethylwedelolactone 3-O-glucoside)

3D MOL for NP0057159 (Demethylwedelolactone 3-O-glucoside)

3D SDF for NP0057159 (Demethylwedelolactone 3-O-glucoside)

3D-SDF for NP0057159 (Demethylwedelolactone 3-O-glucoside)

PDB for NP0057159 (Demethylwedelolactone 3-O-glucoside)

3D PDB for NP0057159 (Demethylwedelolactone 3-O-glucoside)

SMILES for NP0057159 (Demethylwedelolactone 3-O-glucoside)

INCHI for NP0057159 (Demethylwedelolactone 3-O-glucoside)

Structure for NP0057159 (Demethylwedelolactone 3-O-glucoside)

3D Structure for NP0057159 (Demethylwedelolactone 3-O-glucoside)