NP-MRD: Showing NP-Card for rugosachromenone A (NP0043727)

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Record Information

Version

2.0

Created at

2021-06-21 01:03:21 UTC

Updated at

2021-06-30 00:19:35 UTC

NP-MRD ID

NP0043727

Secondary Accession Numbers

None

Natural Product Identification

Common Name

rugosachromenone A

Provided By

JEOL Database JEOL Logo

Description

Rugosachromenone A belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. rugosachromenone A is found in Rosa rugosa. rugosachromenone A was first documented in 2013 (PMID: 24063567). Based on a literature review very few articles have been published on Rugosachromenone A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212103033D          

 39 41  0  0  0  0            999 V2000
   -0.9017   -5.1368    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -4.6873   -0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6068   -3.4519   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2577   -2.7627    0.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -3.0345   -1.1741 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6810   -3.8575   -2.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3572   -1.6075   -1.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653   -0.4778   -1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5943    0.7792   -1.7246 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578    0.9239   -2.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168    2.3160   -2.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569    3.2187   -3.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6263    4.5450   -3.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837    4.9758   -3.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    6.2586   -3.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624    4.1060   -2.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304    2.7810   -2.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4257   -0.1165   -2.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0486   -1.4609   -2.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260   -2.4441   -2.5686 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027   -0.4521   -0.7412 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853   -1.3032   -1.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2226   -2.6319   -1.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0376   -3.3178   -0.4599 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3353   -4.7244   -0.5281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7614   -4.4595    0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912   -5.2246    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2355   -6.1260    0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -3.8821   -2.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866    2.8934   -3.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4000    5.2177   -3.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2699    6.7511   -3.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6811    4.4584   -2.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1109    2.1258   -2.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3860   -0.0395   -3.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1462   -0.7622   -1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0679   -3.2354   -1.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9966   -3.0610    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0019   -5.0099   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0  0  0  0
  8  7  2  0  0  0  0
 11 12  2  0  0  0  0
  7 19  1  0  0  0  0
 12 13  1  0  0  0  0
  7  5  1  0  0  0  0
 13 14  2  0  0  0  0
 19 18  1  0  0  0  0
 14 16  1  0  0  0  0
  8 21  1  0  0  0  0
 16 17  2  0  0  0  0
 17 11  1  0  0  0  0
 18 10  2  0  0  0  0
 14 15  1  0  0  0  0
  5 24  1  0  0  0  0
 19 20  2  0  0  0  0
 10  9  1  0  0  0  0
  5  3  1  0  0  0  0
 21 22  1  0  0  0  0
  3  2  1  0  0  0  0
  3  4  2  0  0  0  0
 24 23  1  0  0  0  0
  2  1  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  1  0  0  0  0
  8  9  1  0  0  0  0
  5  6  1  6  0  0  0
 18 35  1  0  0  0  0
 24 38  1  1  0  0  0
 22 36  1  0  0  0  0
 23 37  1  0  0  0  0
 12 30  1  0  0  0  0
 13 31  1  0  0  0  0
 16 33  1  0  0  0  0
 17 34  1  0  0  0  0
 15 32  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 25 39  1  0  0  0  0
  6 29  1  0  0  0  0
M  END

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.9017   -5.1368    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -4.6873   -0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6068   -3.4519   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2577   -2.7627    0.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -3.0345   -1.1741 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6810   -3.8575   -2.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3572   -1.6075   -1.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653   -0.4778   -1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5943    0.7792   -1.7246 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578    0.9239   -2.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168    2.3160   -2.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569    3.2187   -3.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6263    4.5450   -3.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837    4.9758   -3.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    6.2586   -3.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624    4.1060   -2.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304    2.7810   -2.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4257   -0.1165   -2.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0486   -1.4609   -2.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260   -2.4441   -2.5686 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027   -0.4521   -0.7412 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853   -1.3032   -1.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2226   -2.6319   -1.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0376   -3.3178   -0.4599 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3353   -4.7244   -0.5281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7614   -4.4595    0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912   -5.2246    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2355   -6.1260    0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -3.8821   -2.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866    2.8934   -3.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4000    5.2177   -3.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2699    6.7511   -3.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6811    4.4584   -2.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1109    2.1258   -2.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3860   -0.0395   -3.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1462   -0.7622   -1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0679   -3.2354   -1.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9966   -3.0610    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0019   -5.0099   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  8  7  2  0
 11 12  2  0
  7 19  1  0
 12 13  1  0
  7  5  1  0
 13 14  2  0
 19 18  1  0
 14 16  1  0
  8 21  1  0
 16 17  2  0
 17 11  1  0
 18 10  2  0
 14 15  1  0
  5 24  1  0
 19 20  2  0
 10  9  1  0
  5  3  1  0
 21 22  1  0
  3  2  1  0
  3  4  2  0
 24 23  1  0
  2  1  1  0
 22 23  2  0
 24 25  1  0
  8  9  1  0
  5  6  1  6
 18 35  1  0
 24 38  1  1
 22 36  1  0
 23 37  1  0
 12 30  1  0
 13 31  1  0
 16 33  1  0
 17 34  1  0
 15 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 25 39  1  0
  6 29  1  0
M  END


  Mrv1652306212103033D          

 39 41  0  0  0  0            999 V2000
   -0.9017   -5.1368    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -4.6873   -0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6068   -3.4519   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2577   -2.7627    0.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -3.0345   -1.1741 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6810   -3.8575   -2.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3572   -1.6075   -1.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653   -0.4778   -1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5943    0.7792   -1.7246 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578    0.9239   -2.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168    2.3160   -2.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569    3.2187   -3.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6263    4.5450   -3.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837    4.9758   -3.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    6.2586   -3.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624    4.1060   -2.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304    2.7810   -2.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4257   -0.1165   -2.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0486   -1.4609   -2.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260   -2.4441   -2.5686 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027   -0.4521   -0.7412 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853   -1.3032   -1.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2226   -2.6319   -1.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0376   -3.3178   -0.4599 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3353   -4.7244   -0.5281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7614   -4.4595    0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912   -5.2246    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2355   -6.1260    0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -3.8821   -2.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866    2.8934   -3.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4000    5.2177   -3.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2699    6.7511   -3.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6811    4.4584   -2.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1109    2.1258   -2.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3860   -0.0395   -3.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1462   -0.7622   -1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0679   -3.2354   -1.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9966   -3.0610    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0019   -5.0099   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0  0  0  0
  8  7  2  0  0  0  0
 11 12  2  0  0  0  0
  7 19  1  0  0  0  0
 12 13  1  0  0  0  0
  7  5  1  0  0  0  0
 13 14  2  0  0  0  0
 19 18  1  0  0  0  0
 14 16  1  0  0  0  0
  8 21  1  0  0  0  0
 16 17  2  0  0  0  0
 17 11  1  0  0  0  0
 18 10  2  0  0  0  0
 14 15  1  0  0  0  0
  5 24  1  0  0  0  0
 19 20  2  0  0  0  0
 10  9  1  0  0  0  0
  5  3  1  0  0  0  0
 21 22  1  0  0  0  0
  3  2  1  0  0  0  0
  3  4  2  0  0  0  0
 24 23  1  0  0  0  0
  2  1  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  1  0  0  0  0
  8  9  1  0  0  0  0
  5  6  1  6  0  0  0
 18 35  1  0  0  0  0
 24 38  1  1  0  0  0
 22 36  1  0  0  0  0
 23 37  1  0  0  0  0
 12 30  1  0  0  0  0
 13 31  1  0  0  0  0
 16 33  1  0  0  0  0
 17 34  1  0  0  0  0
 15 32  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 25 39  1  0  0  0  0
  6 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043727

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(=O)C2=C(O1)OC([H])=C([H])[C@]([H])(O[H])[C@@]2(O[H])C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O8/c1-23-16(21)17(22)13(20)6-7-24-15-14(17)11(19)8-12(25-15)9-2-4-10(18)5-3-9/h2-8,13,18,20,22H,1H3/t13-,17-/m0/s1

> <INCHI_KEY>
WEMFCNJAKPAGGS-GUYCJALGSA-N

> <FORMULA>
C17H14O8

> <MOLECULAR_WEIGHT>
346.291

> <EXACT_MASS>
346.068867411

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.177747496156165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (5R,6S)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H,5H,6H-pyrano[2,3-b]oxepine-5-carboxylate

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
0.35967901233333355

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.500011818214315

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.693300534788321

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5975076883007686

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
95.16629999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (5R,6S)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-6H-pyrano[2,3-b]oxepine-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.9017   -5.1368    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -4.6873   -0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6068   -3.4519   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2577   -2.7627    0.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -3.0345   -1.1741 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6810   -3.8575   -2.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3572   -1.6075   -1.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653   -0.4778   -1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5943    0.7792   -1.7246 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578    0.9239   -2.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168    2.3160   -2.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569    3.2187   -3.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6263    4.5450   -3.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837    4.9758   -3.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    6.2586   -3.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624    4.1060   -2.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304    2.7810   -2.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4257   -0.1165   -2.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0486   -1.4609   -2.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260   -2.4441   -2.5686 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027   -0.4521   -0.7412 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853   -1.3032   -1.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2226   -2.6319   -1.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0376   -3.3178   -0.4599 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3353   -4.7244   -0.5281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7614   -4.4595    0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912   -5.2246    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2355   -6.1260    0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -3.8821   -2.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866    2.8934   -3.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4000    5.2177   -3.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2699    6.7511   -3.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6811    4.4584   -2.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1109    2.1258   -2.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3860   -0.0395   -3.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1462   -0.7622   -1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0679   -3.2354   -1.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9966   -3.0610    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0019   -5.0099   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8  7  2  0
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  7  5  1  0
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 19 18  1  0
 14 16  1  0
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 10  9  1  0
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  1 26  1  0
  1 27  1  0
  1 28  1  0
 25 39  1  0
  6 29  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.902  -5.137   0.486  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.102  -4.687  -0.423  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.607  -3.452  -0.133  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.258  -2.763   0.820  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.683  -3.034  -1.174  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.681  -3.857  -2.366  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.357  -1.607  -1.580  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.065  -0.478  -1.367  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.594   0.779  -1.725  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.358   0.924  -2.319  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.017   2.316  -2.633  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.957   3.219  -3.092  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.626   4.545  -3.388  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.684   4.976  -3.219  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.052   6.259  -3.493  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.662   4.106  -2.757  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.330   2.781  -2.461  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.426  -0.117  -2.614  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.049  -1.461  -2.272  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.626  -2.444  -2.569  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.303  -0.452  -0.741  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.285  -1.303  -1.172  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.223  -2.632  -1.065  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.038  -3.318  -0.460  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.335  -4.724  -0.528  0.00  0.00           O+0
HETATM   26  H   UNK     0      -1.761  -4.460   0.473  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.491  -5.225   1.497  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.236  -6.126   0.161  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.744  -3.882  -2.662  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.987   2.893  -3.229  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.400   5.218  -3.744  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.270   6.751  -3.790  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.681   4.458  -2.620  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.111   2.126  -2.081  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.386  -0.040  -3.106  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.146  -0.762  -1.543  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.068  -3.235  -1.382  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.997  -3.061   0.606  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.002  -5.010  -1.405  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    7   24    3    6                                             
CONECT    6    5   29                                                       
CONECT    7    8   19    5                                                  
CONECT    8    7   21    9                                                  
CONECT    9   10    8                                                       
CONECT   10   11   18    9                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   30                                                  
CONECT   13   12   14   31                                                  
CONECT   14   13   16   15                                                  
CONECT   15   14   32                                                       
CONECT   16   14   17   33                                                  
CONECT   17   16   11   34                                                  
CONECT   18   19   10   35                                                  
CONECT   19    7   18   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22                                                       
CONECT   22   21   23   36                                                  
CONECT   23   24   22   37                                                  
CONECT   24    5   23   25   38                                             
CONECT   25   24   39                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    6                                                            
CONECT   30   12                                                            
CONECT   31   13                                                            
CONECT   32   15                                                            
CONECT   33   16                                                            
CONECT   34   17                                                            
CONECT   35   18                                                            
CONECT   36   22                                                            
CONECT   37   23                                                            
CONECT   38   24                                                            
CONECT   39   25                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

RDKit          3D

39 41  0  0  0  0  0  0  0  0999 V2000
   -0.9017   -5.1368    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -4.6873   -0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6068   -3.4519   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2577   -2.7627    0.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -3.0345   -1.1741 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6810   -3.8575   -2.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3572   -1.6075   -1.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653   -0.4778   -1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5943    0.7792   -1.7246 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578    0.9239   -2.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168    2.3160   -2.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569    3.2187   -3.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6263    4.5450   -3.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837    4.9758   -3.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    6.2586   -3.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624    4.1060   -2.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304    2.7810   -2.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4257   -0.1165   -2.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0486   -1.4609   -2.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260   -2.4441   -2.5686 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027   -0.4521   -0.7412 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853   -1.3032   -1.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2226   -2.6319   -1.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0376   -3.3178   -0.4599 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3353   -4.7244   -0.5281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7614   -4.4595    0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912   -5.2246    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2355   -6.1260    0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -3.8821   -2.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866    2.8934   -3.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4000    5.2177   -3.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2699    6.7511   -3.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6811    4.4584   -2.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1109    2.1258   -2.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3860   -0.0395   -3.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1462   -0.7622   -1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0679   -3.2354   -1.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9966   -3.0610    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0019   -5.0099   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  8  7  2  0
 11 12  2  0
  7 19  1  0
 12 13  1  0
  7  5  1  0
 13 14  2  0
 19 18  1  0
 14 16  1  0
  8 21  1  0
 16 17  2  0
 17 11  1  0
 18 10  2  0
 14 15  1  0
  5 24  1  0
 19 20  2  0
 10  9  1  0
  5  3  1  0
 21 22  1  0
  3  2  1  0
  3  4  2  0
 24 23  1  0
  2  1  1  0
 22 23  2  0
 24 25  1  0
  8  9  1  0
  5  6  1  6
 18 35  1  0
 24 38  1  1
 22 36  1  0
 23 37  1  0
 12 30  1  0
 13 31  1  0
 16 33  1  0
 17 34  1  0
 15 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 25 39  1  0
  6 29  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₄O₈

Average Mass

346.2910 Da

Monoisotopic Mass

346.06887 Da

IUPAC Name

methyl (5R,6S)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H,5H,6H-pyrano[2,3-b]oxepine-5-carboxylate

Traditional Name

methyl (5R,6S)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-6H-pyrano[2,3-b]oxepine-5-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(=O)C2=C(O1)OC([H])=C([H])[C@]([H])(O[H])[C@@]2(O[H])C(=O)OC([H])([H])[H]

InChI Identifier

InChI=1S/C17H14O8/c1-23-16(21)17(22)13(20)6-7-24-15-14(17)11(19)8-12(25-15)9-2-4-10(18)5-3-9/h2-8,13,18,20,22H,1H3/t13-,17-/m0/s1

InChI Key

WEMFCNJAKPAGGS-GUYCJALGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rosa rugosa	JEOL database	Hu, Q. -F., et al, J. Nat. Prod. 76, 1866 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Hydroxy acid
Heteroaromatic compound
Vinylogous ester
Methyl ester
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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
logP	1.41	ALOGPS
logP	0.36	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.69	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.17 m³·mol⁻¹	ChemAxon
Polarizability	33.18 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

30829872

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72701620

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hu QF, Zhou B, Huang JM, Jiang ZY, Huang XZ, Yang LY, Gao XM, Yang GY, Che CT: Cytotoxic oxepinochromenone and flavonoids from the flower buds of Rosa rugosa. J Nat Prod. 2013 Oct 25;76(10):1866-71. doi: 10.1021/np4004068. Epub 2013 Sep 24. [PubMed:24063567 ]
Hu, Q. -F., et al. (2013). Hu, Q. -F., et al, J. Nat. Prod. 76, 1866 (2013). J. Nat. Prod..

Showing NP-Card for rugosachromenone A (NP0043727)

MOL for NP0043727 (rugosachromenone A)

3D MOL for NP0043727 (rugosachromenone A)

3D SDF for NP0043727 (rugosachromenone A)

3D-SDF for NP0043727 (rugosachromenone A)

PDB for NP0043727 (rugosachromenone A)

3D PDB for NP0043727 (rugosachromenone A)

SMILES for NP0043727 (rugosachromenone A)

INCHI for NP0043727 (rugosachromenone A)

Structure for NP0043727 (rugosachromenone A)

3D Structure for NP0043727 (rugosachromenone A)