NP-MRD: Showing NP-Card for 14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one (NP0183529)

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Record Information

Version

2.0

Created at

2022-09-03 22:27:20 UTC

Updated at

2022-09-03 22:27:20 UTC

NP-MRD ID

NP0183529

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one

Description

14-Hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]Heptadeca-1(10),3(8),4,6,11,13,15-heptaen-9-one belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. 14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one is found in Hylodesmum podocarpum. 14-Hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]Heptadeca-1(10),3(8),4,6,11,13,15-heptaen-9-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231514482D          

 33 37  0  0  0  0            999 V2000
    0.1596   -1.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9810   -1.8652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585   -2.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7574   -3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769   -3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960   -2.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334   -1.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778   -2.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5969   -2.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3787   -2.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   -3.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3231   -3.7378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4857   -4.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2675   -4.8102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4301   -5.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2119   -5.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8310   -5.3373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8109   -6.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9736   -6.9731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292   -5.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4100   -6.4459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8666   -5.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0848   -4.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9222   -4.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1404   -3.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213   -4.3011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -4.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205   -4.4422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4136   -3.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -3.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146   -3.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933   -3.3650    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
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 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  2  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  6 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
  3 32  2  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
    8.3227   -1.0429   -0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2226    0.2952   -0.1956 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9666    0.8802    0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8309    0.1245   -0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6085    0.7223    0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5100    2.0445    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6551    2.7901    0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9063    2.2003    0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0715    2.9343    0.5724 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2448    2.3422    0.5720 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    1.2871    0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2072    1.0676    0.2758 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6706   -0.0994   -0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7239   -0.2238   -0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3624   -1.3991   -0.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173   -1.5799   -0.3505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7094   -0.6499   -0.0467 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5301   -1.2084    0.9306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5405   -0.3782    1.3348 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0266    0.7306    2.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4480    0.1716    3.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3861    0.1766    0.2410 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4507   -0.6579   -0.0955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6070    0.5458   -0.9956 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5288    0.5417   -2.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5890   -0.5225   -1.2988 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8205   -0.1629   -2.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5508   -2.4649   -0.6829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270   -2.3649   -0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4468   -1.1849   -0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149   -1.0231   -0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5415   -1.9767   -0.6866 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3113    0.2167   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3995   -1.3499   -0.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7817   -1.7406    0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9117   -1.1928   -1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8774   -0.9185   -0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6641    3.8215    0.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9602    2.4903    0.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3351    0.6230    0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3508    0.3512    0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2185   -0.9947    1.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8840    1.3393    2.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3344    1.4055    1.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5234    0.5112    3.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8449    1.1293    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2429   -0.1227   -0.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1398    1.5349   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3786    0.9545   -1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1123   -1.4876   -1.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3301   -0.3978   -3.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0334   -3.4060   -0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4665   -3.2147   -0.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
  6 10  1  0
 10 11  1  0
 11 33  2  0
 33  5  1  0
  5  4  2  0
 33 31  1  0
 31 32  2  0
 31 30  1  0
 30 29  2  0
 29 28  1  0
 28 15  2  0
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 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
  4  3  1  0
 13 30  1  0
  5  6  1  0
 26 17  1  0
 12 11  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  9 39  1  0
  7 38  1  0
  4 37  1  0
 29 53  1  0
 28 52  1  0
 17 41  1  1
 19 42  1  1
 20 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  1
 23 47  1  0
 24 48  1  1
 25 49  1  0
 26 50  1  6
 27 51  1  0
 14 40  1  0
M  END


  Mrv1533004231514482D          

 33 37  0  0  0  0            999 V2000
    0.1596   -1.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9810   -1.8652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585   -2.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7574   -3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769   -3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960   -2.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334   -1.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778   -2.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5969   -2.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3787   -2.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   -3.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3231   -3.7378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4857   -4.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2675   -4.8102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4301   -5.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2119   -5.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8310   -5.3373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8109   -6.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9736   -6.9731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292   -5.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4100   -6.4459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8666   -5.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0848   -4.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9222   -4.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1404   -3.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213   -4.3011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -4.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205   -4.4422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4136   -3.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -3.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146   -3.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933   -3.3650    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 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
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
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 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  2  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  6 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
  3 32  2  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183529

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2OC3=C(C2=C1)C(=O)C1=CC=C(OC2OC(CO)C(O)C(O)C2O)C=C1O3

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O11/c1-29-14-5-10-13(6-11(14)24)32-21-16(10)17(25)9-3-2-8(4-12(9)31-21)30-22-20(28)19(27)18(26)15(7-23)33-22/h2-6,15,18-20,22-24,26-28H,7H2,1H3

> <INCHI_KEY>
RXJNCSKYVKCMEZ-UHFFFAOYSA-N

> <FORMULA>
C22H20O11

> <MOLECULAR_WEIGHT>
460.391

> <EXACT_MASS>
460.100561464

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
45.15831730613011

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11,13,15-heptaen-9-one

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
0.17518462733333334

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200306991306306

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.831141084803695

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343722586

> <JCHEM_POLAR_SURFACE_AREA>
168.28

> <JCHEM_REFRACTIVITY>
107.48010000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11,13,15-heptaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       0.298  -3.626   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.831  -3.482   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.723  -4.737   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.256  -4.593   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.147  -5.849   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.677  -6.027   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.833  -5.009   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.529  -3.499   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.292  -5.501   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.448  -4.483   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.907  -4.975   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.210  -6.485   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.670  -6.977   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.973  -8.487   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      15.433  -8.979   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      15.736 -10.489   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.195 -10.981   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      18.351  -9.963   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.580 -11.507   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.884 -13.016   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.121 -11.015   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.965 -12.032   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.818  -9.505   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.358  -9.013   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.055  -7.503   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.595  -7.011   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.440  -8.029   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.980  -7.537   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.638  -8.292   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.505  -7.249   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.972  -7.393   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.081  -6.137   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.547  -6.281   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7   28                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25   12   26                                                       
CONECT   26   25    9   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27    6   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29    5   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31    3   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀O₁₁

Average Mass

460.3910 Da

Monoisotopic Mass

460.10056 Da

IUPAC Name

14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11,13,15-heptaen-9-one

Traditional Name

14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11,13,15-heptaen-9-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2OC3=C(C2=C1)C(=O)C1=CC=C(OC2OC(CO)C(O)C(O)C2O)C=C1O3

InChI Identifier

InChI=1S/C22H20O11/c1-29-14-5-10-13(6-11(14)24)32-21-16(10)17(25)9-3-2-8(4-12(9)31-21)30-22-20(28)19(27)18(26)15(7-23)33-22/h2-6,15,18-20,22-24,26-28H,7H2,1H3

InChI Key

RXJNCSKYVKCMEZ-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
Desmodium podocarpum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Isoflavone
Coumaronochromene
Phenolic glycoside
Hexose monosaccharide
Chromone
Coumarin
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Benzofuran
Furopyran
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Oxane
Benzenoid
Pyran
Monosaccharide
Furan
Heteroaromatic compound
Secondary alcohol
Oxacycle
Polyol
Organoheterocyclic compound
Acetal
Ether
Organic oxide
Organooxygen compound
Primary alcohol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
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	0.88	ALOGPS
logP	0.18	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	8.83	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	168.28 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.48 m³·mol⁻¹	ChemAxon
Polarizability	45.16 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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 14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one (NP0183529)

MOL for NP0183529 (14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one)

3D MOL for NP0183529 (14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one)

3D SDF for NP0183529 (14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one)

3D-SDF for NP0183529 (14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one)

PDB for NP0183529 (14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one)

3D PDB for NP0183529 (14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one)

SMILES for NP0183529 (14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one)

INCHI for NP0183529 (14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one)

Structure for NP0183529 (14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one)

3D Structure for NP0183529 (14-hydroxy-13-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one)