NP-MRD: Showing NP-Card for (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(1s,12s)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol (NP0239418)

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Record Information

Version

2.0

Created at

2022-09-06 23:01:00 UTC

Updated at

2022-09-06 23:01:00 UTC

NP-MRD ID

NP0239418

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(1s,12s)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol

Description

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(1S,12S)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]Icosa-2(10),3,5(9),13(18),14,16-hexaen-16-yloxy]oxane-3,4,5-triol belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(1s,12s)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol is found in Trifolium pratense. Based on a literature review very few articles have been published on (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(1S,12S)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]Icosa-2(10),3,5(9),13(18),14,16-hexaen-16-yloxy]oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072201012D          

 32 37  0  0  1  0            999 V2000
   -0.3143    0.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2240   -0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0481   -1.0914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4903   -1.7165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2181   -2.4954    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7565   -3.1205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5670   -2.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1054   -3.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9160   -3.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1881   -2.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6498   -2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8392   -2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9219   -1.2554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7325   -1.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2709   -1.7268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0957   -1.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6611   -1.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4641   -1.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7017   -2.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1363   -2.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3333   -2.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6553   -3.0052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9987   -2.5057    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5329   -3.4477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3435   -3.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4478   -2.4756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925   -2.6491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8646   -3.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1308   -2.0239    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9414   -2.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8587   -1.2451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3971   -0.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  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
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  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
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 10 23  1  0  0  0  0
 15 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  6  0  0  0
M  END

     RDKit          3D

 54 59  0  0  0  0  0  0  0  0999 V2000
   -5.8268    1.4442    2.5403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7431    1.2708    1.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1236    1.3894    0.2418 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0734    1.2216   -0.6122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4858   -0.0428   -0.5948 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4989   -0.1674    0.3737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1573   -0.4018    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5316   -0.5619   -0.9937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8239   -0.7972   -1.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6394   -0.8847    0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0219   -0.7257    1.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3185   -0.4942    1.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8317   -0.8111    2.3846 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1537   -0.3026    2.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8397   -1.0844    1.1467 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1079   -0.4296    0.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3307   -0.2220    1.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3557    0.4433    0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2062    0.9270   -0.5323 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0051    0.7336   -1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9714    0.0576   -0.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7001   -0.2240   -1.0172 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0877   -1.1410   -0.1276 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1329    1.3113   -2.4243 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2379    2.1980   -2.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0495    1.6241   -1.4103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5256   -1.1498   -0.5140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1213   -2.2370   -1.3182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8068   -0.5820   -1.0855 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7822   -1.5580   -1.2496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2815    0.4470   -0.0475 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3868    1.1012   -0.5411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6616    1.6739    2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2757    0.3074    1.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9969    2.0542    1.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5187    2.4153    0.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0354   -0.1621   -1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1553   -0.4966   -1.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2752   -0.9169   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7876   -0.3724    2.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1857    0.7628    1.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7399   -0.4331    3.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0523   -2.0884    1.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4375   -0.6054    2.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3131    0.6095    1.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1668   -2.1900   -0.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7758    2.1877   -3.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8846    3.1934   -2.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6621   -1.5496    0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2667   -2.6044   -0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5485   -0.0681   -2.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3558   -2.3698   -1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5347   -0.1401    0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8637    0.4413   -1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  2  0
 20 24  1  0
 24 25  1  0
 25 26  1  0
 26 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
  5 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31  3  1  0
 12  7  1  0
 11 10  1  0
 15 23  1  0
 16 21  1  0
 19 20  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  1
  5 37  1  6
  8 38  1  0
  9 39  1  0
 23 46  1  6
 25 47  1  0
 25 48  1  0
 18 45  1  0
 17 44  1  0
 15 43  1  1
 14 41  1  0
 14 42  1  0
 12 40  1  0
 27 49  1  1
 28 50  1  0
 29 51  1  6
 30 52  1  0
 31 53  1  1
 32 54  1  0
M  END


  Mrv1652309072201012D          

 32 37  0  0  1  0            999 V2000
   -0.3143    0.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2240   -0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0481   -1.0914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4903   -1.7165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2181   -2.4954    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7565   -3.1205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5670   -2.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1054   -3.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9160   -3.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1881   -2.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6498   -2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8392   -2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9219   -1.2554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7325   -1.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2709   -1.7268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0957   -1.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6611   -1.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4641   -1.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7017   -2.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1363   -2.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3333   -2.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6553   -3.0052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9987   -2.5057    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5329   -3.4477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3435   -3.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4478   -2.4756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925   -2.6491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8646   -3.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1308   -2.0239    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9414   -2.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8587   -1.2451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3971   -0.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  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
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  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
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 10 23  1  0  0  0  0
 15 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0239418

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C3[C@H]4OC5=C6OCOC6=CC=C5[C@H]4COC3=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O10/c23-6-15-16(24)17(25)18(26)22(31-15)30-9-1-2-11-14(5-9)27-7-12-10-3-4-13-21(29-8-28-13)20(10)32-19(11)12/h1-5,12,15-19,22-26H,6-8H2/t12-,15-,16-,17+,18-,19-,22-/m1/s1

> <INCHI_KEY>
FCRUGSNPZLERNO-VIDNIUHMSA-N

> <FORMULA>
C22H22O10

> <MOLECULAR_WEIGHT>
446.408

> <EXACT_MASS>
446.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.11045763054893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(1S,12S)-6,8,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{5,9}.0^{13,18}]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol

> <JCHEM_LOGP>
0.022060036333333283

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.196090792974335

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200140018647128

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923437225645

> <JCHEM_POLAR_SURFACE_AREA>
136.3

> <JCHEM_REFRACTIVITY>
104.5092

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(1S,12S)-6,8,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{5,9}.0^{13,18}]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0      -0.587   0.583   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.418  -0.584   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.090  -2.037   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.915  -3.204   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.407  -4.658   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.412  -5.825   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.925  -5.538   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.930  -6.705   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.443  -6.418   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.951  -4.964   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.946  -3.797   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.433  -4.084   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.454  -2.343   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.967  -2.057   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.972  -3.223   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.512  -3.257   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.567  -2.136   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.066  -2.489   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.510  -3.964   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.454  -5.085   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.955  -4.732   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.690  -5.610   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.464  -4.677   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.195  -6.436   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      13.708  -6.149   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.902  -4.621   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.106  -4.945   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.614  -6.399   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.111  -3.778   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.624  -4.065   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.603  -2.324   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.608  -1.157   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   10   15                                                  
CONECT   24   20   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   19                                                       
CONECT   27    5   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    3   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₁₀

Average Mass

446.4080 Da

Monoisotopic Mass

446.12130 Da

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(1S,12S)-6,8,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{5,9}.0^{13,18}]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol

Traditional Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(1S,12S)-6,8,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{5,9}.0^{13,18}]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=C3[C@H]4OC5=C6OCOC6=CC=C5[C@H]4COC3=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C22H22O10/c23-6-15-16(24)17(25)18(26)22(31-15)30-9-1-2-11-14(5-9)27-7-12-10-3-4-13-21(29-8-28-13)20(10)32-19(11)12/h1-5,12,15-19,22-26H,6-8H2/t12-,15-,16-,17+,18-,19-,22-/m1/s1

InChI Key

FCRUGSNPZLERNO-VIDNIUHMSA-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
Trifolium pratense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Isoflavan
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Coumaran
Benzodioxole
Benzofuran
Alkyl aryl ether
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Polyol
Ether
Acetal
Organoheterocyclic compound
Oxacycle
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
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	0.022	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	136.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	104.51 m³·mol⁻¹	ChemAxon
Polarizability	44.11 Å³	ChemAxon
Number of Rings	6	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

163029154

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(1s,12s)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol (NP0239418)

MOL for NP0239418 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(1s,12s)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol)

3D MOL for NP0239418 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(1s,12s)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol)

3D SDF for NP0239418 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(1s,12s)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol)

3D-SDF for NP0239418 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(1s,12s)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol)

PDB for NP0239418 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(1s,12s)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol)

3D PDB for NP0239418 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(1s,12s)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol)

SMILES for NP0239418 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(1s,12s)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol)

INCHI for NP0239418 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(1s,12s)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol)

Structure for NP0239418 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(1s,12s)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol)

3D Structure for NP0239418 ((2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(1s,12s)-6,8,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁵,⁹.0¹³,¹⁸]icosa-2,4,9,13,15,17-hexaen-16-yloxy]oxane-3,4,5-triol)