NP-MRD: Showing NP-Card for (1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate (NP0273720)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 20:51:17 UTC

Updated at

2022-09-08 20:51:17 UTC

NP-MRD ID

NP0273720

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate

Description

Aurovertin b belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. (1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate is found in Albatrellus confluens and Calcarisporium arbuscula. (1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate was first documented in 2005 (PMID: 16156519). Based on a literature review a significant number of articles have been published on aurovertin b (PMID: 26013262) (PMID: 19035880) (PMID: 32539922) (PMID: 30144974) (PMID: 22452346) (PMID: 18707016).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082222512D          

 33 35  0  0  1  0            999 V2000
   -1.4463    0.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541    0.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570    0.4916    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1617   -0.3334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8097   -0.8440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5403   -1.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6130   -0.6558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8767   -1.4816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1986    0.0648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1392    0.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8160   -0.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5827   -0.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2299   -0.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9966   -0.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6438   -0.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4104   -0.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5299    0.2636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2966    0.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4161    1.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9438    0.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -0.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4715   -1.2712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2382   -0.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0577   -1.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9382   -1.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6043    0.8308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7990    1.0097    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6321    1.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361    0.0842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7950    0.2732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4566    0.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2730    1.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450    0.6440    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  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 16 24  2  0  0  0  0
 24 25  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
   -5.7303    3.5082   -1.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5909    3.0383   -0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9279    1.6991   -0.1258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1258    0.7135   -1.0444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8561   -0.5198   -0.4751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9013   -1.5471   -0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853   -0.9441   -1.0281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7163   -1.4172   -2.3059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6575    0.3275   -1.0318 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2444    0.0581   -1.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2579    0.2136   -0.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1240   -0.0703   -0.9803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1365    0.0735   -0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5158   -0.1912   -0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5184   -0.0467    0.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8675   -0.3380   -0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0573   -0.7303   -1.3776 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2271   -1.0031   -1.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3798   -1.3900   -3.0737 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3362   -0.8804   -1.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1815   -0.4645    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2515   -0.3216    1.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5455   -0.6119    0.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9159   -0.1884    0.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6899    0.2576    2.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6629    0.9186    0.2004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8721    1.1079    0.7989 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7173    1.8650    2.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5652   -0.2505    1.0112 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6726   -1.2266    1.4425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9882   -1.9926    2.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0752   -3.0582    3.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0646   -1.8262    3.1854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5074    4.0589   -0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2591    2.6615   -2.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3142    4.2368   -2.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6164    3.1666   -1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6035    3.7467    0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8539    1.7795    0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6469   -1.4862    0.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4309   -2.5523   -0.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3369   -1.4349   -1.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0564   -1.6961   -0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2055   -2.2729   -2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0762    0.9562   -1.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0224   -0.2776   -2.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4919    0.5382    0.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180   -0.3971   -1.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8868    0.4045    0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7256   -0.5182   -1.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3589    0.2830    1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3286   -1.1035   -1.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2680   -0.2969    1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6802   -0.0587   -0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5721   -1.7232    0.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0513    1.1824    2.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0891   -0.4916    2.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6109    0.5095    2.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6707    2.2505    2.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3578    2.7730    2.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9758    1.2235    2.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4779   -0.1512    1.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4308   -4.0142    2.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1504   -3.1402    4.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0396   -2.9184    2.7035 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  1
  5 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 29 27  1  0
 27 28  1  1
 27 26  1  0
 26  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 24  2  0
 24 25  1  0
 24 21  1  0
 21 22  1  0
 22 23  1  0
 21 20  2  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
  9  7  1  0
  7  8  1  0
 27  3  1  0
 17 16  1  0
  7  5  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  1
  6 40  1  0
  6 41  1  0
  6 42  1  0
 29 62  1  1
 32 63  1  0
 32 64  1  0
 32 65  1  0
 28 59  1  0
 28 60  1  0
 28 61  1  0
  9 45  1  6
 10 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  0
 14 50  1  0
 15 51  1  0
 25 56  1  0
 25 57  1  0
 25 58  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
 20 52  1  0
  7 43  1  1
  8 44  1  0
M  END


  Mrv1652309082222512D          

 33 35  0  0  1  0            999 V2000
   -1.4463    0.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541    0.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570    0.4916    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1617   -0.3334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8097   -0.8440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5403   -1.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6130   -0.6558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8767   -1.4816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1986    0.0648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1392    0.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8160   -0.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5827   -0.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2299   -0.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9966   -0.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6438   -0.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4104   -0.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5299    0.2636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2966    0.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4161    1.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9438    0.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -0.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4715   -1.2712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2382   -0.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0577   -1.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9382   -1.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6043    0.8308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7990    1.0097    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6321    1.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361    0.0842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7950    0.2732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4566    0.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2730    1.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450    0.6440    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  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 16 24  2  0  0  0  0
 24 25  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0273720

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1O[C@]2(C)[C@@H](OC(C)=O)[C@@]1(C)O[C@@H](\C=C\C=C\C=C\C1=C(C)C(OC)=CC(=O)O1)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O8/c1-7-20-24(4)23(30-16(3)26)25(5,33-20)22(28)18(32-24)13-11-9-8-10-12-17-15(2)19(29-6)14-21(27)31-17/h8-14,18,20,22-23,28H,7H2,1-6H3/b9-8+,12-10+,13-11+/t18-,20+,22-,23-,24-,25-/m0/s1

> <INCHI_KEY>
QXCOFYWOWZJFEA-DWUHWWJMSA-N

> <FORMULA>
C25H32O8

> <MOLECULAR_WEIGHT>
460.523

> <EXACT_MASS>
460.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
50.261825334162154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,4S,5S,7R,8R)-7-ethyl-4-hydroxy-3-[(1E,3E,5E)-6-(4-methoxy-5-methyl-2-oxo-2H-pyran-6-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate

> <JCHEM_LOGP>
2.5531159653333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.9124340730191

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7119013364614455

> <JCHEM_POLAR_SURFACE_AREA>
100.52000000000001

> <JCHEM_REFRACTIVITY>
125.50259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,4S,5S,7R,8R)-7-ethyl-4-hydroxy-3-[(1E,3E,5E)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.700   0.964   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.221   1.544   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.293   0.918   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.302  -0.622   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.511  -1.576   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.008  -3.112   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.011  -1.224   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.503  -2.766   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.104   0.121   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.860   0.171   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.123  -0.828   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.554  -0.259   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.762  -1.214   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.194  -0.645   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.402  -1.600   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.833  -1.032   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.056   0.492   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      15.487   1.061   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      15.710   2.585   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      16.695   0.106   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.472  -1.418   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      17.680  -2.373   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      19.111  -1.804   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.041  -1.987   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.818  -3.510   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.995   1.551   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.491   1.885   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.180   3.473   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.934   0.157   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.351   0.510   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.586   1.656   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.243   3.157   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.057   1.202   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   29                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   16   25                                                  
CONECT   25   24                                                            
CONECT   26    9   27                                                       
CONECT   27   26    3   28   29                                             
CONECT   28   27                                                            
CONECT   29   27    5   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₈

Average Mass

460.5230 Da

Monoisotopic Mass

460.20972 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@H]1O[C@]2(C)[C@@H](OC(C)=O)[C@@]1(C)O[C@@H](\C=C\C=C\C=C\C1=C(C)C(OC)=CC(=O)O1)[C@@H]2O

InChI Identifier

InChI=1S/C25H32O8/c1-7-20-24(4)23(30-16(3)26)25(5,33-20)22(28)18(32-24)13-11-9-8-10-12-17-15(2)19(29-6)14-21(27)31-17/h8-14,18,20,22-23,28H,7H2,1-6H3/b9-8+,12-10+,13-11+/t18-,20+,22-,23-,24-,25-/m0/s1

InChI Key

QXCOFYWOWZJFEA-DWUHWWJMSA-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
Albatrellus confluens	LOTUS Database	35616633
Calcarisporium arbuscula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
Pyranone
Dioxepane
Alkyl aryl ether
1,4-dioxepane
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Vinylogous ester
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
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

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

62988833

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101995634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang F, Luo DQ, Liu JK: Aurovertin E, a new polyene pyrone from the basidiomycete Albatrellus confluens. J Antibiot (Tokyo). 2005 Jun;58(6):412-5. doi: 10.1038/ja.2005.53. [PubMed:16156519 ]
Mao XM, Xu W, Li D, Yin WB, Chooi YH, Li YQ, Tang Y, Hu Y: Epigenetic genome mining of an endophytic fungus leads to the pleiotropic biosynthesis of natural products. Angew Chem Int Ed Engl. 2015 Jun 22;54(26):7592-6. doi: 10.1002/anie.201502452. Epub 2015 May 27. [PubMed:26013262 ]
Grover GJ, Malm J: Pharmacological profile of the selective mitochondrial F1F0 ATP hydrolase inhibitor BMS-199264 in myocardial ischemia. Cardiovasc Ther. 2008 Winter;26(4):287-96. doi: 10.1111/j.1755-5922.2008.00065.x. [PubMed:19035880 ]
Wu R, Yang X, Zhou Q, Yu W, Li M, Wo J, Shan W, Zhao H, Chen Y, Zhan Z: Aurovertin B exerts potent antitumor activity against triple-negative breast cancer in vivo and in vitro via regulating ATP synthase activity and DUSP1 expression. Pharmazie. 2020 Jun 1;75(6):261-265. doi: 10.1691/ph.2020.0380. [PubMed:32539922 ]
Zhu H, Wang F, Ju X, Kong L, An T, Zhao Z, Liu J, Li Y: Aurovertin B sensitizes colorectal cancer cells to NK cell recognition and lysis. Biochem Biophys Res Commun. 2018 Sep 18;503(4):3057-3063. doi: 10.1016/j.bbrc.2018.08.093. Epub 2018 Aug 23. [PubMed:30144974 ]
Cumero S, Fogolari F, Domenis R, Zucchi R, Mavelli I, Contessi S: Mitochondrial F(0) F(1) -ATP synthase is a molecular target of 3-iodothyronamine, an endogenous metabolite of thyroid hormone. Br J Pharmacol. 2012 Aug;166(8):2331-47. doi: 10.1111/j.1476-5381.2012.01958.x. [PubMed:22452346 ]
Grover GJ, Marone PA, Koetzner L, Seto-Young D: Energetic signalling in the control of mitochondrial F1F0 ATP synthase activity in health and disease. Int J Biochem Cell Biol. 2008;40(12):2698-701. doi: 10.1016/j.biocel.2008.06.013. Epub 2008 Jul 30. [PubMed:18707016 ]
Huang TC, Chang HY, Hsu CH, Kuo WH, Chang KJ, Juan HF: Targeting therapy for breast carcinoma by ATP synthase inhibitor aurovertin B. J Proteome Res. 2008 Apr;7(4):1433-44. doi: 10.1021/pr700742h. Epub 2008 Feb 15. [PubMed:18275135 ]
Belogrudov GI: Bovine factor B: cloning, expression, and characterization. Arch Biochem Biophys. 2006 Jul 1;451(1):68-78. doi: 10.1016/j.abb.2006.02.021. Epub 2006 Mar 13. [PubMed:16579955 ]
Gledhill JR, Walker JE: Inhibition sites in F1-ATPase from bovine heart mitochondria. Biochem J. 2005 Mar 15;386(Pt 3):591-8. doi: 10.1042/BJ20041513. [PubMed:15537385 ]
LOTUS database [Link]

Showing NP-Card for (1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate (NP0273720)

MOL for NP0273720 ((1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

3D MOL for NP0273720 ((1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

3D SDF for NP0273720 ((1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

3D-SDF for NP0273720 ((1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

PDB for NP0273720 ((1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

3D PDB for NP0273720 ((1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

SMILES for NP0273720 ((1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

INCHI for NP0273720 ((1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

Structure for NP0273720 ((1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

3D Structure for NP0273720 ((1s,3s,4s,5s,7r,8r)-7-ethyl-4-hydroxy-3-[(1e,3e,5e)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)