NP-MRD: Showing NP-Card for (1r,6r,13r)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one (NP0306009)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 22:13:47 UTC

Updated at

2022-09-10 22:13:47 UTC

NP-MRD ID

NP0306009

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,6r,13r)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

Description

68401-03-6 Belongs to the class of organic compounds known as rotenoid o-glycosides. Rotenoid O-glycosides are compounds containing a carbohydrate moiety glycosidically linked to the rotenoid backbone at the C8-position. (1r,6r,13r)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one is found in Dalbergia monetaria and Dalbergia nitidula. Based on a literature review very few articles have been published on 68401-03-6.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112200132D          

 42 47  0  0  1  0            999 V2000
    6.8359   -1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8484   -0.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5691    0.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2772   -0.3926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9979    0.0089    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0104    0.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7311    1.2354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7436    2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4643    2.4619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4392    0.8121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1599    1.2137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4267   -0.0128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1348   -0.4361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7060   -0.4144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6935   -1.2393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1403    0.0524    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3816   -0.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8390    0.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623    1.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8607    1.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0358    1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125    1.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0141    0.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5908   -0.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7659   -0.3333    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3425   -1.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5176   -1.0288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912   -0.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1104    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9353    0.4376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3587   -0.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129    1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887    1.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3346    2.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378    1.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.3874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9627    1.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876    1.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3860    1.8162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0666    0.8741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16  2  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  2  0  0  0  0
 28 37  1  0  0  0  0
 37 38  1  0  0  0  0
 25 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 22 40  1  0  0  0  0
 40 41  2  0  0  0  0
 19 42  1  0  0  0  0
 16 42  1  0  0  0  0
M  END

     RDKit          3D

 74 79  0  0  0  0  0  0  0  0999 V2000
   -4.3063   -1.9632   -2.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5749   -0.9370   -1.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0348    0.4214   -2.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2730    1.1384   -0.9427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2505    0.6941   -0.1005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4131    1.5264   -0.2535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4450    0.7148    0.2768 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.7803    1.1412   -0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7460    0.3004    0.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3228    0.8750    1.7812 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5691   -0.3236    2.4433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9281    1.3268    2.1602 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7304    2.6792    2.0231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9137    0.5233    1.3301 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0694   -0.8125    1.7564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3269   -1.2736   -1.0603 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0982   -0.7222   -1.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1260   -0.6642   -0.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8664   -0.7196    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1845   -0.6876    1.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1870   -0.6031    1.8561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9009   -0.5475    0.6690 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2547   -0.5781   -0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0340   -0.5188   -1.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3558   -0.0869   -1.7740 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1276   -1.1293   -2.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4956   -0.8437   -2.6573 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1716   -0.4289   -1.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5518   -0.5496   -1.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2606   -0.1469   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6645   -0.2553   -0.3548 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3828   -0.7845   -1.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5750    0.3785    0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3174    0.7768    1.7493 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6209    1.3207    2.8706 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2006    0.4943    0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4661    0.0949   -0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0072    0.2418   -0.4615 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7530    1.6168   -0.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3637   -0.4565    0.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901   -0.9570    1.6541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2185   -0.7982    0.2405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187   -2.9872   -2.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2279   -1.7761   -2.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3818    0.9503   -2.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0260    0.3386   -2.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6266   -0.2843   -0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2536   -0.3564    0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8323    1.1205   -1.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9702    2.1732    0.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9963    0.6899    1.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0478    1.6399    2.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9810   -1.0202    1.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7632    1.0393    3.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1030    2.9305    1.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8883    0.8177    1.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1246   -0.8422    2.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1937   -2.3758   -1.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2292    0.3119   -2.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7534   -1.4035   -2.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7549   -0.7318    2.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7287   -0.5780    2.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3371    0.8300   -2.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7201   -1.0481   -3.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019   -2.1672   -2.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0969   -0.9667   -2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9268   -1.7086   -1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6235   -0.0404   -2.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3870   -1.0896   -1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0615    2.2421    2.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9181    0.5609    3.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3508    1.5679    3.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7312    0.9255    1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857    1.7612    0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 31  1  0
 31 30  1  0
 30 33  2  0
 33 34  1  0
 34 35  1  0
 33 36  1  0
 36 37  2  0
 37 28  1  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 21 20  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  1  0
 16 42  1  0
 16  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 22 40  1  0
 40 41  2  0
 40 38  1  0
 38 39  1  1
 28 29  2  0
 29 30  1  0
 38 37  1  0
 38 25  1  0
 18 23  1  0
 14  5  1  0
 42 19  1  0
 32 67  1  0
 32 68  1  0
 32 69  1  0
 35 70  1  0
 35 71  1  0
 35 72  1  0
 36 73  1  0
 26 64  1  0
 26 65  1  0
 25 63  1  6
 21 62  1  0
 20 61  1  0
 17 59  1  0
 17 60  1  0
 16 58  1  1
  1 43  1  0
  1 44  1  0
  3 45  1  0
  3 46  1  0
  5 47  1  6
  7 48  1  1
  8 49  1  0
  8 50  1  0
  9 51  1  0
 10 52  1  1
 11 53  1  0
 12 54  1  1
 13 55  1  0
 14 56  1  6
 15 57  1  0
 39 74  1  0
 29 66  1  0
M  END


  Mrv1652309112200132D          

 42 47  0  0  1  0            999 V2000
    6.8359   -1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8484   -0.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5691    0.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2772   -0.3926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9979    0.0089    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0104    0.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7311    1.2354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7436    2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4643    2.4619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4392    0.8121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1599    1.2137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4267   -0.0128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1348   -0.4361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7060   -0.4144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6935   -1.2393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1403    0.0524    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3816   -0.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8390    0.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623    1.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8607    1.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0358    1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125    1.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0141    0.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5908   -0.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7659   -0.3333    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3425   -1.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5176   -1.0288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912   -0.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1104    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9353    0.4376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3587   -0.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129    1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887    1.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3346    2.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378    1.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.3874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9627    1.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876    1.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3860    1.8162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0666    0.8741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16  2  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  2  0  0  0  0
 28 37  1  0  0  0  0
 37 38  1  0  0  0  0
 25 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 22 40  1  0  0  0  0
 40 41  2  0  0  0  0
 19 42  1  0  0  0  0
 16 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306009

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C2C(OC[C@H]3OC4=C(C=CC5=C4C[C@@H](O5)C(=C)CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(=O)[C@@]23O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H32O13/c1-12(10-39-28-25(33)24(32)23(31)21(9-30)41-28)17-6-14-16(40-17)5-4-13-26(14)42-22-11-38-18-8-20(37-3)19(36-2)7-15(18)29(22,35)27(13)34/h4-5,7-8,17,21-25,28,30-33,35H,1,6,9-11H2,2-3H3/t17-,21-,22-,23-,24+,25-,28-,29-/m1/s1

> <INCHI_KEY>
MLGRWAZPBZFAGL-ZHVRRYISSA-N

> <FORMULA>
C29H32O13

> <MOLECULAR_WEIGHT>
588.562

> <EXACT_MASS>
588.18429109

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
58.604798774366955

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,6R,13R)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

> <JCHEM_LOGP>
-0.32294665100000064

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.237960421615995

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.044565880533524

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98108355234298

> <JCHEM_POLAR_SURFACE_AREA>
182.82999999999998

> <JCHEM_REFRACTIVITY>
141.1463

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6R,13R)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      12.760  -2.232   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.784  -0.692   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.129   0.057   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      15.451  -0.733   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      16.796   0.017   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      16.819   1.557   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      18.165   2.306   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.188   3.846   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      19.533   4.596   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      19.487   1.516   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      20.832   2.266   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      19.463  -0.024   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      20.785  -0.814   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      18.118  -0.774   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      18.094  -2.313   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.462   0.098   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.046  -0.507   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.033   0.653   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.823   1.975   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.073   3.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.534   3.343   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.743   2.022   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.493   0.676   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.703  -0.645   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.163  -0.622   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.373  -1.944   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.833  -1.920   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.083  -0.575   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.543  -0.552   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.206   0.793   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.746   0.817   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.536  -0.505   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.584   2.115   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.166   3.460   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.625   4.782   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.124   2.092   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.874   0.747   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.413   0.723   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.664   2.068   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.204   2.045   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       4.454   3.390   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      11.324   1.632   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15                                                  
CONECT   15   14                                                            
CONECT   16    2   17   42                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   42                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   40                                                  
CONECT   23   22   18   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   38                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   37                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37                                                       
CONECT   37   36   28   38                                                  
CONECT   38   37   25   39   40                                             
CONECT   39   38                                                            
CONECT   40   38   22   41                                                  
CONECT   41   40                                                            
CONECT   42   19   16                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₂O₁₃

Average Mass

588.5620 Da

Monoisotopic Mass

588.18429 Da

IUPAC Name

(1R,6R,13R)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C2C(OC[C@H]3OC4=C(C=CC5=C4C[C@@H](O5)C(=C)CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(=O)[C@@]23O)=C1

InChI Identifier

InChI=1S/C29H32O13/c1-12(10-39-28-25(33)24(32)23(31)21(9-30)41-28)17-6-14-16(40-17)5-4-13-26(14)42-22-11-38-18-8-20(37-3)19(36-2)7-15(18)29(22,35)27(13)34/h4-5,7-8,17,21-25,28,30-33,35H,1,6,9-11H2,2-3H3/t17-,21-,22-,23-,24+,25-,28-,29-/m1/s1

InChI Key

MLGRWAZPBZFAGL-ZHVRRYISSA-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
Dalbergia monetaria	LOTUS Database	35616633
Dalbergia nitidula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rotenoid o-glycosides. Rotenoid O-glycosides are compounds containing a carbohydrate moiety glycosidically linked to the rotenoid backbone at the C8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Rotenoid O-glycosides

Alternative Parents

Substituents

Rotenoid-8p-o-glycoside
Rotenone or derivatives
8-prenylated isoflavanone
Chromeno-3,4b-chromene
Rotenoid
Isoflavanone
Isoflavan
Isoflavonoid
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
1-benzopyran
Chromane
Benzopyran
Coumaran
Aryl alkyl ketone
Aryl ketone
Anisole
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Tertiary alcohol
Secondary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Ether
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Alcohol
Organic oxygen compound
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	-0.32	ChemAxon
pKa (Strongest Acidic)	11.04	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	182.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	141.15 m³·mol⁻¹	ChemAxon
Polarizability	58.6 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

C00010181

Chemspider ID

10289965

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21676234

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,6r,13r)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one (NP0306009)

MOL for NP0306009 ((1r,6r,13r)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

3D MOL for NP0306009 ((1r,6r,13r)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

3D SDF for NP0306009 ((1r,6r,13r)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

3D-SDF for NP0306009 ((1r,6r,13r)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

PDB for NP0306009 ((1r,6r,13r)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

3D PDB for NP0306009 ((1r,6r,13r)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

SMILES for NP0306009 ((1r,6r,13r)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

INCHI for NP0306009 ((1r,6r,13r)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

Structure for NP0306009 ((1r,6r,13r)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

3D Structure for NP0306009 ((1r,6r,13r)-13-hydroxy-16,17-dimethoxy-6-(3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)