NP-MRD: Showing NP-Card for (3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol (NP0322949)

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Record Information

Version

2.0

Created at

2022-09-12 02:03:07 UTC

Updated at

2022-09-12 02:03:07 UTC

NP-MRD ID

NP0322949

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol

Description

ABACOPTERIN E belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton. (3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol is found in Pronephrium penangianum. (3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol was first documented in 2011 (PMID: 21167928). Based on a literature review very few articles have been published on ABACOPTERIN E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122204032D          

 32 36  0  0  1  0            999 V2000
   -0.4410   -1.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3473   -1.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9521   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7685   -2.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3714   -2.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8336   -0.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3192   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5309   -0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739    0.1693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1097    0.9736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4951    1.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2834    1.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8882    1.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7046    2.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3094    3.2182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9163    2.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115    2.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028    0.6557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2461    1.0136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9894    0.6557    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1730   -0.1486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6586   -0.7937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9613   -0.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661    0.1693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3545   -0.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9592    0.4873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825    0.9736    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9873    1.5348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5942    1.2168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4106    2.0211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 11 19  1  0  0  0  0
 20 19  1  6  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
 23 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END

     RDKit          3D

 58 62  0  0  0  0  0  0  0  0999 V2000
   -3.3303   -3.2875   -0.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9226   -2.7934   -0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459   -3.6882   -0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2692   -5.0220   -0.8735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3602   -3.2524   -0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4216   -4.2254   -0.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6864   -1.9133   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2968   -0.9925   -0.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6116   -1.4543   -0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6981   -0.6481    0.2059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4928    0.6407    0.7557 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7152    1.4447    0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9202    0.8429    1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1199    1.5239    0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1105    2.8262    0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2910    3.5407    0.4954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9240    3.4203    0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109    2.7353    0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448    1.2679    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0970    0.4584    0.1586 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8912    0.8966   -0.7241 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1408    0.7006   -0.2104 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8234   -0.5522   -0.6223 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0778   -1.7145   -0.5363 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0070   -0.6591    0.1220 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8922    0.3623   -0.1715 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1252    0.1390    0.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8135    0.1627    2.0511 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3146    1.7372    0.0843 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2481    2.6793   -0.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0351    1.8419   -0.7183 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4192    3.0622   -0.6007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7167   -3.4725   -1.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9994   -2.5378    0.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4153   -4.2178    0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5361   -5.6769   -1.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3210   -5.1493   -0.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4258   -3.7777   -0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782   -4.4440   -2.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1858    0.5361    1.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9093   -0.1846    1.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0432    1.0589    1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6036    4.0702    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9406    4.4526   -0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8196    3.2328   -0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1220    2.2607    0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5455    1.4500   -1.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2818    0.4992    1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1684    0.7832    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1523   -0.4307   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2304    0.3327   -1.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8510    0.9754    0.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6410   -0.7886    0.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5873    0.5328    2.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0240    1.8484    1.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7712    3.5552   -0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3018    1.5680   -1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2473    3.4444   -1.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7 24  1  0
 24 23  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  9  2  1  0
 18 12  1  0
  8  7  1  0
 22 23  1  0
  8 20  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  6 39  1  0
 23 50  1  6
 26 51  1  6
 27 52  1  0
 27 53  1  0
 28 54  1  0
 29 55  1  1
 30 56  1  0
 31 57  1  6
 32 58  1  0
 22 49  1  1
 20 48  1  1
 19 46  1  0
 19 47  1  0
 11 40  1  1
 13 41  1  0
 14 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
M  END


  Mrv1652309122204032D          

 32 36  0  0  1  0            999 V2000
   -0.4410   -1.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3473   -1.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9521   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7685   -2.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3714   -2.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8336   -0.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3192   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5309   -0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739    0.1693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1097    0.9736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4951    1.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2834    1.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8882    1.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7046    2.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3094    3.2182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9163    2.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115    2.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028    0.6557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2461    1.0136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9894    0.6557    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1730   -0.1486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6586   -0.7937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9613   -0.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661    0.1693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3545   -0.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9592    0.4873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825    0.9736    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9873    1.5348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5942    1.2168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4106    2.0211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 11 19  1  0  0  0  0
 20 19  1  6  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
 23 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0322949

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C(C)=C2O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O[C@H]3C[C@H](OC1=C23)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O9/c1-9-17(26)10(2)21-16-14(7-13(29-20(9)16)11-3-5-12(25)6-4-11)30-22-19(28)18(27)15(8-24)31-23(22)32-21/h3-6,13-15,18-19,22-28H,7-8H2,1-2H3/t13-,14-,15+,18+,19-,22+,23-/m0/s1

> <INCHI_KEY>
IAQOOCVBIITHOV-USLXRMLJSA-N

> <FORMULA>
C23H26O9

> <MOLECULAR_WEIGHT>
446.452

> <EXACT_MASS>
446.157682417

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
44.72346523099277

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,5R,6S,7S,8R,10S,12S)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0^{3,8}.0^{14,18}]octadeca-1(17),14(18),15-triene-6,7,16-triol

> <JCHEM_LOGP>
1.790449128666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.16996462013234

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.374864381611534

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092557336777

> <JCHEM_POLAR_SURFACE_AREA>
138.07000000000002

> <JCHEM_REFRACTIVITY>
110.84590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,5R,6S,7S,8R,10S,12S)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0^{3,8}.0^{14,18}]octadeca-1(17),14(18),15-triene-6,7,16-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.823  -2.687   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.648  -2.233   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.777  -3.280   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.435  -4.782   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.249  -2.826   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.427  -3.819   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.423  -1.481   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.463  -0.277   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.991  -0.731   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.138   0.316   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.205   1.817   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.924   2.865   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.396   2.411   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.525   3.458   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.182   4.960   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.311   6.007   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.710   5.414   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.581   4.366   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.676   2.271   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.805   1.224   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.193   1.892   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.580   1.224   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.923  -0.277   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.963  -1.481   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.395  -0.731   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.523   0.316   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.995  -0.138   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.124   0.910   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.181   1.817   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.310   2.865   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.709   2.271   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.366   3.773   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   24                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12                                                       
CONECT   19   11   20                                                       
CONECT   20   19    8   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23    7                                                       
CONECT   25   23   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆O₉

Average Mass

446.4520 Da

Monoisotopic Mass

446.15768 Da

IUPAC Name

(3S,5R,6S,7S,8R,10S,12S)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0^{3,8}.0^{14,18}]octadeca-1(17),14(18),15-triene-6,7,16-triol

Traditional Name

(3S,5R,6S,7S,8R,10S,12S)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0^{3,8}.0^{14,18}]octadeca-1(17),14(18),15-triene-6,7,16-triol

CAS Registry Number

Not Available

SMILES

CC1=C(O)C(C)=C2O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O[C@H]3C[C@H](OC1=C23)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C23H26O9/c1-9-17(26)10(2)21-16-14(7-13(29-20(9)16)11-3-5-12(25)6-4-11)30-22-19(28)18(27)15(8-24)31-23(22)32-21/h3-6,13-15,18-19,22-28H,7-8H2,1-2H3/t13-,14-,15+,18+,19-,22+,23-/m0/s1

InChI Key

IAQOOCVBIITHOV-USLXRMLJSA-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
Menisciopsis penangiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Hydroxyflavonoids

Direct Parent

7-hydroxyflavonoids

Alternative Parents

Substituents

4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavan
Chromane
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Acetal
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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	1.79	ChemAxon
pKa (Strongest Acidic)	9.37	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	138.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	110.85 m³·mol⁻¹	ChemAxon
Polarizability	44.72 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

23310895

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23657295

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lei Y, Fu W, Chen J, Xiong C, Wu G, Wei H, Ruan J: Neuroprotective effects of Abacopterin E from Abacopteris penangiana against oxidative stress-induced neurotoxicity. J Ethnopharmacol. 2011 Mar 24;134(2):275-80. doi: 10.1016/j.jep.2010.10.062. Epub 2010 Dec 16. [PubMed:21167928 ]
LOTUS database [Link]

Showing NP-Card for (3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol (NP0322949)

MOL for NP0322949 ((3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol)

3D MOL for NP0322949 ((3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol)

3D SDF for NP0322949 ((3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol)

3D-SDF for NP0322949 ((3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol)

PDB for NP0322949 ((3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol)

3D PDB for NP0322949 ((3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol)

SMILES for NP0322949 ((3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol)

INCHI for NP0322949 ((3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol)

Structure for NP0322949 ((3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol)

3D Structure for NP0322949 ((3s,5r,6s,7s,8r,10s,12s)-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-15,17-dimethyl-2,4,9,13-tetraoxatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),14(18),15-triene-6,7,16-triol)