NP-MRD: Showing NP-Card for (3s,7r)-11-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one (NP0300552)

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Record Information

Version

2.0

Created at

2022-09-10 13:00:09 UTC

Updated at

2022-09-10 13:00:10 UTC

NP-MRD ID

NP0300552

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,7r)-11-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one

Description

6-(4-O-Methyl-beta-L-arabinopyranosyloxy)-8-hydroxy-3abeta,12cbeta-dihydro-7H-furo[3',2':4,5]Furo[2,3-c]xanthene-7-one belongs to the class of organic compounds known as sterigmatocystins. These are a group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. And Bipolaris spp. (3s,7r)-11-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one is found in Aschersonia coffeae. Based on a literature review very few articles have been published on 6-(4-O-Methyl-beta-L-arabinopyranosyloxy)-8-hydroxy-3abeta,12cbeta-dihydro-7H-furo[3',2':4,5]Furo[2,3-c]xanthene-7-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102215002D          

 33 38  0  0  1  0            999 V2000
    2.0336  -10.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5779   -9.5428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9457   -8.8043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4900   -8.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8577   -7.3781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812   -7.3273    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0489   -6.5888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -5.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698   -5.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3141   -5.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6819   -4.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5053   -4.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8731   -3.7363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6965   -3.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0643   -2.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8877   -2.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3434   -3.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9756   -4.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4313   -5.0103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1522   -4.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7844   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2401   -5.7995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9610   -5.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0932   -3.9476    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9566   -3.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1406   -3.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2272   -3.7510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3616   -4.3289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4981   -5.1425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1368   -8.0150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9603   -7.9643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691   -8.7535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2248   -9.4413    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  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  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
 12 13  1  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
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  8 23  2  0  0  0  0
 12 23  1  0  0  0  0
 24 11  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  1  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
 10 29  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END

     RDKit          3D

 53 58  0  0  0  0  0  0  0  0999 V2000
    6.9065   -0.6705   -0.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0670   -0.1782    0.4135 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7699   -0.0123    0.0435 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7670   -0.7878    0.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8908    0.0044    1.5527 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0735    0.7908    0.7496 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9284    0.1558    0.3157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3807    0.4830    0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7652    1.5634    1.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1218    1.8373    1.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0546    1.0070    0.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6990   -0.0989    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6104   -0.8779   -0.3703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2946   -1.9216   -1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2600   -2.7313   -1.6573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9678   -3.8352   -2.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6608   -4.1542   -2.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6393   -3.3626   -2.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3717   -3.7424   -2.3917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9636   -2.2719   -1.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0107   -1.4470   -0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1981   -1.6883   -0.9642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3590   -0.3443   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3824    1.5257    1.3087 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9086    2.5155    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2390    3.6116    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9835    3.4621    2.3616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0899    2.4001    2.5006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7638    2.8633    2.2316 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8702    1.3821   -0.4251 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8018    0.4563   -1.4479 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3130    1.4455    0.0641 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2375    1.9344    1.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6324   -1.6586   -0.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9191   -0.7876   -0.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0500    0.0901   -1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6732   -0.3319   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418   -1.4613    0.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3028   -1.4305    1.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8084    1.6702    1.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0530    2.2311    1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2954   -2.4792   -1.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7469   -4.4610   -2.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4415   -5.0211   -3.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5202   -3.4580   -2.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1122    0.7254    1.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0234    2.4115   -0.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6602    4.5411    0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1607    1.8760    3.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5145    2.3817   -0.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4921    0.8415   -2.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9402    2.0785   -0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2015    2.9284    1.2804 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  1  0
  8 23  2  0
 23 21  1  0
 21 22  2  0
 21 20  1  0
 20 18  2  0
 18 19  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 10  1  0
 10  9  2  0
  6 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32  3  1  0
  9  8  1  0
 12 23  1  0
 10 11  1  0
 14 20  1  0
 28 24  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  6
  4 38  1  0
  4 39  1  0
  6 40  1  1
 19 45  1  0
 17 44  1  0
 16 43  1  0
 15 42  1  0
 24 46  1  1
 25 47  1  0
 26 48  1  0
 28 49  1  1
  9 41  1  0
 30 50  1  6
 31 51  1  0
 32 52  1  6
 33 53  1  0
M  END


  Mrv1652309102215002D          

 33 38  0  0  1  0            999 V2000
    2.0336  -10.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5779   -9.5428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9457   -8.8043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4900   -8.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8577   -7.3781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812   -7.3273    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0489   -6.5888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -5.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698   -5.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3141   -5.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6819   -4.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5053   -4.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8731   -3.7363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6965   -3.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0643   -2.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8877   -2.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3434   -3.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9756   -4.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4313   -5.0103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1522   -4.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7844   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2401   -5.7995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9610   -5.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0932   -3.9476    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9566   -3.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1406   -3.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2272   -3.7510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3616   -4.3289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4981   -5.1425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1368   -8.0150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9603   -7.9643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691   -8.7535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2248   -9.4413    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  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
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 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
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 14 20  1  0  0  0  0
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 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  8 23  2  0  0  0  0
 12 23  1  0  0  0  0
 24 11  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  1  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
 10 29  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0300552

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1CO[C@H](OC2=C3C(=O)C4=C(O)C=CC=C4OC3=C3[C@@H]4C=CO[C@@H]4OC3=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O10/c1-28-14-8-30-23(20(27)18(14)25)33-13-7-12-15(9-5-6-29-22(9)32-12)21-17(13)19(26)16-10(24)3-2-4-11(16)31-21/h2-7,9,14,18,20,22-25,27H,8H2,1H3/t9-,14-,18-,20+,22+,23+/m0/s1

> <INCHI_KEY>
FTRIBOHVBCUNQE-ZLRXVCEVSA-N

> <FORMULA>
C23H20O10

> <MOLECULAR_WEIGHT>
456.403

> <EXACT_MASS>
456.105646844

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
44.18857525965417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,7R)-11-{[(2R,3R,4R,5S)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1,4,9,11,14,16,18-heptaen-13-one

> <JCHEM_LOGP>
1.9580909873333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.268828791958779

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.38147134001997

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5233654523830897

> <JCHEM_POLAR_SURFACE_AREA>
133.14000000000001

> <JCHEM_REFRACTIVITY>
110.15339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,7R)-11-{[(2R,3R,4R,5S)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1,4,9,11,14,16,18-heptaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       3.796 -19.097   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.945 -17.813   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.632 -16.435   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.781 -15.151   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.468 -13.772   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.005 -13.678   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.691 -12.299   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.841 -11.015   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.304 -11.110   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.453  -9.826   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.139  -8.448   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.677  -8.353   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.363  -6.974   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.900  -6.880   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.587  -5.501   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.124  -5.406   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.974  -6.690   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.288  -8.069   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.138  -9.352   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.751  -8.163   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.064  -9.542   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.915 -10.826   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.527  -9.637   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.041  -7.369   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.786  -5.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.262  -5.623   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.424  -7.002   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.675  -8.081   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.930  -9.599   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.855 -14.961   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.393 -14.867   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.169 -16.340   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.020 -17.624   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                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12   24                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    8   12                                                  
CONECT   24   11   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24   29                                                  
CONECT   29   28   10                                                       
CONECT   30    6   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    3   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Value	Source
6-(4-O-Methyl-b-L-arabinopyranosyloxy)-8-hydroxy-3abeta,12cbeta-dihydro-7H-furo[3',2':4,5]furo[2,3-c]xanthene-7-one	Generator
6-(4-O-Methyl-β-L-arabinopyranosyloxy)-8-hydroxy-3abeta,12cbeta-dihydro-7H-furo[3',2':4,5]furo[2,3-c]xanthene-7-one	Generator

Chemical Formula

C₂₃H₂₀O₁₀

Average Mass

456.4030 Da

Monoisotopic Mass

456.10565 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@H]1CO[C@H](OC2=C3C(=O)C4=C(O)C=CC=C4OC3=C3[C@@H]4C=CO[C@@H]4OC3=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C23H20O10/c1-28-14-8-30-23(20(27)18(14)25)33-13-7-12-15(9-5-6-29-22(9)32-12)21-17(13)19(26)16-10(24)3-2-4-11(16)31-21/h2-7,9,14,18,20,22-25,27H,8H2,1H3/t9-,14-,18-,20+,22+,23+/m0/s1

InChI Key

FTRIBOHVBCUNQE-ZLRXVCEVSA-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
Aschersonia coffeae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sterigmatocystins. These are a group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. And Bipolaris spp.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Sterigmatocystins

Sub Class

Not Available

Direct Parent

Sterigmatocystins

Alternative Parents

Substituents

Sterigmatocystin backbone
Xanthone
Phenolic glycoside
Dibenzopyran
Xanthene
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Oxane
Pyran
Monosaccharide
Benzenoid
Dihydrofuran
Vinylogous ester
Vinylogous acid
Heteroaromatic compound
1,2-diol
Secondary alcohol
Organoheterocyclic compound
Ether
Oxacycle
Dialkyl ether
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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

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

78437803

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71473602

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,7r)-11-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one (NP0300552)

MOL for NP0300552 ((3s,7r)-11-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

3D MOL for NP0300552 ((3s,7r)-11-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

3D SDF for NP0300552 ((3s,7r)-11-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

3D-SDF for NP0300552 ((3s,7r)-11-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

PDB for NP0300552 ((3s,7r)-11-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

3D PDB for NP0300552 ((3s,7r)-11-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

SMILES for NP0300552 ((3s,7r)-11-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

INCHI for NP0300552 ((3s,7r)-11-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

Structure for NP0300552 ((3s,7r)-11-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

3D Structure for NP0300552 ((3s,7r)-11-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxy}-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)