NP-MRD: Showing NP-Card for 6-[(1e,3e,5e)-6-[(1r,3s,4r,5s,7r,8s)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one (NP0283388)

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Record Information

Version

2.0

Created at

2022-09-09 10:37:51 UTC

Updated at

2022-09-09 10:37:51 UTC

NP-MRD ID

NP0283388

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(1e,3e,5e)-6-[(1r,3s,4r,5s,7r,8s)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one

Description

Isocitreoviridinol belongs to the class of organic compounds known as 1,4-dioxepanes. These are dioxepanes with the two ring oxygen atoms at position 1 and 4, respectively. 6-[(1e,3e,5e)-6-[(1r,3s,4r,5s,7r,8s)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one is found in Penicillium pedemontanum. Based on a literature review very few articles have been published on Isocitreoviridinol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092212372D          

 30 32  0  0  1  0            999 V2000
    6.9342    6.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2892    6.1700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4121    5.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1801    5.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3031    4.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0710    3.9356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6581    3.7226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8901    4.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2451    3.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3680    2.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7230    2.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8460    1.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010    0.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330    1.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    0.6363    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4330    0.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    1.5632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4421    2.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.6363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5690    0.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -0.2905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4421   -1.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    0.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    1.0488    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2374    1.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300   -0.1070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9444   -0.7520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7671    4.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9992    5.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  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  2  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  6  0  0  0
 22 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  1  0  0  0
  8 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
   10.1727   -0.9044    0.6983 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8138   -1.2205    0.6950 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7981   -0.3926    0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0003    0.8791   -0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9268    1.6457   -0.6165 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1554    2.7904   -1.0476 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7075    1.1567   -0.5382 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4455   -0.0472   -0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0729   -0.5291   -0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0986    0.2399   -0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7266   -0.2309   -0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6937    0.4945   -0.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724    0.0400   -0.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087    0.7620   -1.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0865    0.1521   -0.9712 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1081   -0.9270   -2.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9834    1.1139   -1.2267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0324    1.3081   -0.4099 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6918    2.6307   -0.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7069    1.0907    1.0780 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8101    1.3905    1.8308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5329   -0.4351    0.9662 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6066   -1.1084    2.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4476   -0.8616    0.0369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1007    0.2098   -0.5064 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6291    0.0319   -1.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447   -0.5441    0.3340 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2784    0.0329    1.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5019   -0.8469    0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1719   -2.2001    0.8330 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6367   -1.3383    1.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3843    0.1802    0.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7373   -1.3128   -0.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9902    1.2787   -0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8944   -1.5149    0.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2945    1.2182   -0.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4975   -1.2285    0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8963    1.4878   -1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8699   -0.9543   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5564    1.7520   -1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109   -0.5071   -2.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735   -1.7733   -1.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0991   -1.3397   -2.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1880    3.4504   -0.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7682    2.5898   -0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6896    2.8701   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7829    1.5843    1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6535    1.2124    2.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6243   -1.5160    2.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3763   -0.4147    3.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8959   -1.9699    2.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8992    0.5215    0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6121    0.5499   -2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8902    0.4250   -2.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8166   -1.0433   -2.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8225   -1.6058    0.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -0.6332    1.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7660   -2.8644    0.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5051   -2.1368    1.7055 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1264   -2.6883    1.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 15 14  1  1
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  1
 18 25  1  0
 25 26  1  0
 25 24  1  0
 24 22  1  0
 22 23  1  1
 22 20  1  0
 20 21  1  0
 22 27  1  0
 27 28  1  0
  8 29  2  0
 29 30  1  0
 29  3  1  0
 27 15  1  0
 20 18  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 25 52  1  1
 26 53  1  0
 26 54  1  0
 26 55  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 20 47  1  1
 21 48  1  0
 27 56  1  6
 28 57  1  0
 30 58  1  0
 30 59  1  0
 30 60  1  0
M  END


  Mrv1652309092212372D          

 30 32  0  0  1  0            999 V2000
    6.9342    6.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2892    6.1700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4121    5.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1801    5.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3031    4.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0710    3.9356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6581    3.7226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8901    4.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2451    3.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3680    2.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7230    2.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8460    1.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010    0.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330    1.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    0.6363    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4330    0.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    1.5632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4421    2.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.6363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5690    0.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -0.2905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4421   -1.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    0.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    1.0488    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2374    1.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300   -0.1070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9444   -0.7520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7671    4.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9992    5.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  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  2  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  6  0  0  0
 22 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  1  0  0  0
  8 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283388

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)OC(\C=C\C=C\C=C\[C@]2(C)O[C@@]3(C)[C@@H](C)O[C@](C)([C@@H]3O)[C@@H]2O)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O7/c1-14-16(28-18(24)13-17(14)27-6)11-9-7-8-10-12-21(3)19(25)23(5)20(26)22(4,30-21)15(2)29-23/h7-13,15,19-20,25-26H,1-6H3/b8-7+,11-9+,12-10+/t15-,19-,20-,21+,22+,23+/m1/s1

> <INCHI_KEY>
BHMIDMOHWXULQB-MUIQRTEUSA-N

> <FORMULA>
C23H30O7

> <MOLECULAR_WEIGHT>
418.486

> <EXACT_MASS>
418.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
45.67711983281907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1E,3E,5E)-6-[(1R,3S,4R,5S,7R,8S)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methyl-2H-pyran-2-one

> <JCHEM_LOGP>
1.8700448283333329

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.178080754795229

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.479778017324247

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7655671114840272

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
116.46529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1E,3E,5E)-6-[(1R,3S,4R,5S,7R,8S)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      12.944  12.477   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.740  11.517   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.969   9.994   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.403   9.432   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.632   7.909   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      15.066   7.346   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      12.428   6.949   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.995   7.512   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.791   6.551   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.020   5.029   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.816   4.068   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.046   2.546   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.842   1.585   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.408   2.148   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.204   1.188   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.408   0.228   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.536   2.575   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.035   2.918   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.692   4.419   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.602   1.188   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.062   1.188   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.035  -0.542   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.692  -2.044   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.831   0.418   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.831   1.958   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.443   2.626   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.536  -0.200   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.496  -1.404   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.765   9.034   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.332   9.597   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   27                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20   25                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   27                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   18   26                                                  
CONECT   26   25                                                            
CONECT   27   22   15   28                                                  
CONECT   28   27                                                            
CONECT   29    8    3   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀O₇

Average Mass

418.4860 Da

Monoisotopic Mass

418.19915 Da

IUPAC Name

6-[(1E,3E,5E)-6-[(1R,3S,4R,5S,7R,8S)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methyl-2H-pyran-2-one

Traditional Name

6-[(1E,3E,5E)-6-[(1R,3S,4R,5S,7R,8S)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(\C=C\C=C\C=C\[C@]2(C)O[C@@]3(C)[C@@H](C)O[C@](C)([C@@H]3O)[C@@H]2O)=C1C

InChI Identifier

InChI=1S/C23H30O7/c1-14-16(28-18(24)13-17(14)27-6)11-9-7-8-10-12-21(3)19(25)23(5)20(26)22(4,30-21)15(2)29-23/h7-13,15,19-20,25-26H,1-6H3/b8-7+,11-9+,12-10+/t15-,19-,20-,21+,22+,23+/m1/s1

InChI Key

BHMIDMOHWXULQB-MUIQRTEUSA-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
Penicillium pedemontanum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-dioxepanes. These are dioxepanes with the two ring oxygen atoms at position 1 and 4, respectively.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dioxepanes

Sub Class

1,4-dioxepanes

Direct Parent

1,4-dioxepanes

Alternative Parents

Substituents

1,4-dioxepane
Alkyl aryl ether
Pyranone
Oxane
Pyran
Oxolane
Heteroaromatic compound
Vinylogous ester
Lactone
Secondary alcohol
Ether
Dialkyl ether
Oxacycle
Alcohol
Organic oxygen compound
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	1.87	ChemAxon
pKa (Strongest Acidic)	12.48	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	116.47 m³·mol⁻¹	ChemAxon
Polarizability	45.68 Å³	ChemAxon
Number of Rings	3	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

68026561

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101288315

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[(1e,3e,5e)-6-[(1r,3s,4r,5s,7r,8s)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one (NP0283388)

MOL for NP0283388 (6-[(1e,3e,5e)-6-[(1r,3s,4r,5s,7r,8s)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one)

3D MOL for NP0283388 (6-[(1e,3e,5e)-6-[(1r,3s,4r,5s,7r,8s)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one)

3D SDF for NP0283388 (6-[(1e,3e,5e)-6-[(1r,3s,4r,5s,7r,8s)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one)

3D-SDF for NP0283388 (6-[(1e,3e,5e)-6-[(1r,3s,4r,5s,7r,8s)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one)

PDB for NP0283388 (6-[(1e,3e,5e)-6-[(1r,3s,4r,5s,7r,8s)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one)

3D PDB for NP0283388 (6-[(1e,3e,5e)-6-[(1r,3s,4r,5s,7r,8s)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one)

SMILES for NP0283388 (6-[(1e,3e,5e)-6-[(1r,3s,4r,5s,7r,8s)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one)

INCHI for NP0283388 (6-[(1e,3e,5e)-6-[(1r,3s,4r,5s,7r,8s)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one)

Structure for NP0283388 (6-[(1e,3e,5e)-6-[(1r,3s,4r,5s,7r,8s)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one)

3D Structure for NP0283388 (6-[(1e,3e,5e)-6-[(1r,3s,4r,5s,7r,8s)-4,8-dihydroxy-1,3,5,7-tetramethyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]hexa-1,3,5-trien-1-yl]-4-methoxy-5-methylpyran-2-one)