NP-MRD: Showing NP-Card for 5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate (NP0281076)

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Record Information

Version

2.0

Created at

2022-09-09 07:12:39 UTC

Updated at

2022-09-09 07:12:39 UTC

NP-MRD ID

NP0281076

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate

Description

5-(Acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. 5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate is found in Cullen corylifolium. 5-(Acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161521252D          

 32 36  0  0  0  0            999 V2000
    0.8547   -2.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5879   -1.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271   -1.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2820   -2.3348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0152   -1.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545   -1.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7877   -0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4818   -1.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2776   -0.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6486   -0.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1960    0.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4723   -0.1992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9249   -0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7486   -0.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2012   -1.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0249   -1.4844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4776   -2.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3012   -2.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1066   -2.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8302   -2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2829   -2.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9119   -3.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9591   -4.5187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2222   -4.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5745   -4.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5204   -3.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0066   -2.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5539   -1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7303   -1.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2142   -2.3166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4426   -2.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7093   -2.4027    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  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  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 15 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  2  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  0  0  0  0
  9 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  8 31  1  0  0  0  0
 31 32  2  0  0  0  0
  5 32  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    8.6505    2.0298   -3.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5201    1.5493   -2.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0567    2.2372   -1.2433 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8982    0.3227   -2.4311 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8410   -0.1069   -1.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0923   -0.8473   -0.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0577   -1.2920    0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7464   -1.0022    0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4668   -0.2659   -1.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5212    0.1685   -1.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1624   -0.1350   -1.1850 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5809   -0.7328   -0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2653   -0.8814    0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7236   -0.3204   -0.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0695   -0.4746   -0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0932    0.1364   -1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6803    1.3934   -0.5008 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6605    1.9573   -1.4780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1033    1.5546   -0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0566    0.4103   -0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4446    2.6761    0.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3187   -1.1755    0.9569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6184   -1.3613    1.3953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0688   -0.4758    2.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4268   -0.5455    2.9583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013    0.4364    2.8217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118   -1.7411    1.7376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0020   -1.5895    1.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9516   -2.1350    2.1075 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2110   -2.0129    1.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0907   -2.5193    2.4767 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5530   -1.3167    0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3130    2.3962   -4.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4166    1.2094   -3.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1729    2.8244   -2.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1305   -1.0653   -0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2610   -1.8728    1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3093    0.7466   -2.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4688    0.2295   -1.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6451    0.3350   -2.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9023   -0.6200   -1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9432    2.2006   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6357    0.4216   -1.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7791    0.4883    0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5935   -0.5688   -0.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4847    3.0425    0.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3263    2.2540    1.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7763    3.5346    0.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1088   -1.0989    2.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8008    0.4403    3.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3863   -1.1608    3.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5388   -2.3019    2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 11  1  0
 11 12  1  0
 12 32  2  0
 32 30  1  0
 30 31  2  0
 30 29  1  0
 29 28  1  0
 28 27  2  0
 27 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 22 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 15 14  1  0
 14 13  2  0
  9 10  2  0
 10  5  1  0
 32  8  1  0
 13 28  1  0
 13 12  1  0
 19 17  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  6 36  1  0
  7 37  1  0
 27 52  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 16 40  1  0
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 17 42  1  1
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 14 39  1  0
 10 38  1  0
M  END


  Mrv1533004161521252D          

 32 36  0  0  0  0            999 V2000
    0.8547   -2.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5879   -1.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271   -1.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2820   -2.3348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0152   -1.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545   -1.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7877   -0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4818   -1.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2776   -0.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6486   -0.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1960    0.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4723   -0.1992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9249   -0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7486   -0.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2012   -1.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0249   -1.4844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4776   -2.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3012   -2.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1066   -2.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8302   -2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2829   -2.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9119   -3.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9591   -4.5187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2222   -4.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5745   -4.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5204   -3.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5539   -1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7303   -1.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2142   -2.3166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4426   -2.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7093   -2.4027    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  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  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
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 17 18  2  0  0  0  0
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 15 20  2  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  2  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  0  0  0  0
  9 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  8 31  1  0  0  0  0
 31 32  2  0  0  0  0
  5 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281076

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1=CC=C2C(OC3=C2C(=O)OC2=CC(OC(C)=O)=C(CC4OC4(C)C)C=C32)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H20O8/c1-11(25)28-14-5-6-15-18(9-14)30-22-16-7-13(8-20-24(3,4)32-20)17(29-12(2)26)10-19(16)31-23(27)21(15)22/h5-7,9-10,20H,8H2,1-4H3

> <INCHI_KEY>
XNDLQQWPZJMYLA-UHFFFAOYSA-N

> <FORMULA>
C24H20O8

> <MOLECULAR_WEIGHT>
436.416

> <EXACT_MASS>
436.115817604

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
44.82270890344717

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11,13,15-heptaen-14-yl acetate

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
2.9688056753333325

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.065735704016652

> <JCHEM_POLAR_SURFACE_AREA>
104.57000000000001

> <JCHEM_REFRACTIVITY>
111.00280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11,13,15-heptaen-14-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       1.595  -4.232   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.964  -3.526   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.037  -1.988   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.260  -4.358   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.628  -3.653   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.702  -2.114   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.070  -1.409   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.366  -2.241   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.852  -1.835   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.544  -0.460   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.699   0.828   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      12.082  -0.372   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.927  -1.659   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.464  -1.571   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.309  -2.859   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      16.846  -2.771   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      17.691  -4.058   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      19.229  -3.970   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      16.999  -5.434   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.616  -4.234   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.461  -5.522   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.769  -6.897   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.857  -8.435   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.481  -7.742   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.272  -8.696   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.171  -6.933   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.079  -4.322   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.234  -3.035   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.697  -3.123   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.733  -4.324   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.293  -3.779   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.924  -4.485   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10   29                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   24                                                       
CONECT   24   23   22   25   26                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   20   28                                                       
CONECT   28   27   13   29                                                  
CONECT   29   28    9   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30    8   32                                                  
CONECT   32   31    5                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
5-(Acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0,.0,]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetic acid	Generator
5-(Acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetic acid	Generator

Chemical Formula

C₂₄H₂₀O₈

Average Mass

436.4160 Da

Monoisotopic Mass

436.11582 Da

IUPAC Name

5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11,13,15-heptaen-14-yl acetate

Traditional Name

5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11,13,15-heptaen-14-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1=CC=C2C(OC3=C2C(=O)OC2=CC(OC(C)=O)=C(CC4OC4(C)C)C=C32)=C1

InChI Identifier

InChI=1S/C24H20O8/c1-11(25)28-14-5-6-15-18(9-14)30-22-16-7-13(8-20-24(3,4)32-20)17(29-12(2)26)10-19(16)31-23(27)21(15)22/h5-7,9-10,20H,8H2,1-4H3

InChI Key

XNDLQQWPZJMYLA-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
Cullen corylifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular furanocoumarin
Furanocoumarin
Coumarin
Benzopyran
1-benzopyran
Benzofuran
Furopyran
Pyranone
Dicarboxylic acid or derivatives
Benzenoid
Pyran
Furan
Heteroaromatic compound
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen 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	4.14	ALOGPS
logP	2.97	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	104.57 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	111 m³·mol⁻¹	ChemAxon
Polarizability	44.82 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	Yes	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 5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate (NP0281076)

MOL for NP0281076 (5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate)

3D MOL for NP0281076 (5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate)

3D SDF for NP0281076 (5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate)

3D-SDF for NP0281076 (5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate)

PDB for NP0281076 (5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate)

3D PDB for NP0281076 (5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate)

SMILES for NP0281076 (5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate)

INCHI for NP0281076 (5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate)

Structure for NP0281076 (5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate)

3D Structure for NP0281076 (5-(acetyloxy)-4-[(3,3-dimethyloxiran-2-yl)methyl]-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl acetate)