NP-MRD: Showing NP-Card for scirpyrone A (NP0041855)

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Record Information

Version

2.0

Created at

2021-06-20 23:39:55 UTC

Updated at

2021-06-30 00:16:37 UTC

NP-MRD ID

NP0041855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

scirpyrone A

Provided By

JEOL Database JEOL Logo

Description

6-[(2R,4R)-2-butyl-4-hydroxy-5-oxooxolan-2-yl]-4-methoxy-2H-pyran-2-one 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. scirpyrone A is found in Pestalotiopsis scirpina. scirpyrone A was first documented in 2012 (Li, J., et al.). Based on a literature review very few articles have been published on 6-[(2R,4R)-2-butyl-4-hydroxy-5-oxooxolan-2-yl]-4-methoxy-2H-pyran-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101393D          

 38 39  0  0  0  0            999 V2000
   -0.0641   -3.8526   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -3.4088    0.6084 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7318   -1.9822    0.2076 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0315   -1.5403    0.8977 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5062   -0.1216    0.4911 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4712    0.9349    0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8411    1.7301   -0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762    2.6941    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3286    3.4235   -0.6082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6389    4.4125   -0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033    2.7982    1.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816    1.9354    2.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230    2.0346    3.8986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1941    1.0375    2.2282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8520    0.2320    1.1236 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8473   -0.3915    0.1757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0970    0.2585    0.2562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1150   -0.2511   -1.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6409   -0.2624   -2.2460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7747   -0.1224   -0.9249 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7699   -3.2007    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657   -3.8336   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1884   -4.8744    0.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577   -4.1000    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2276   -3.4693    1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126   -1.3061    0.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8515   -1.9307   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994   -1.5930    1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -2.2741    0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0327    1.6707   -1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642    4.8924   -1.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2039    5.1829    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5163    3.9576    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080    3.4963    2.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0107    1.3189    1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9643   -0.1354    2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9884   -1.4576    0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5808    0.0358   -0.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0  0  0  0
 15  5  1  0  0  0  0
  6  5  1  0  0  0  0
 12 11  1  0  0  0  0
  5  4  1  1  0  0  0
 11  8  2  0  0  0  0
  5 20  1  0  0  0  0
  4  3  1  0  0  0  0
  7  6  2  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
  7  8  1  0  0  0  0
 18 19  2  0  0  0  0
  6 14  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  0  0  0  0
  8  9  1  0  0  0  0
 20 18  1  0  0  0  0
  9 10  1  0  0  0  0
 18 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 34  1  0  0  0  0
 16 37  1  1  0  0  0
 15 35  1  0  0  0  0
 15 36  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
  7 30  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  2 24  1  0  0  0  0
  2 25  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
 10 33  1  0  0  0  0
 17 38  1  0  0  0  0
M  END

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.0641   -3.8526   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -3.4088    0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7318   -1.9822    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0315   -1.5403    0.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062   -0.1216    0.4911 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4712    0.9349    0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8411    1.7301   -0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762    2.6941    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3286    3.4235   -0.6082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6389    4.4125   -0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033    2.7982    1.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816    1.9354    2.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230    2.0346    3.8986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1941    1.0375    2.2282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8520    0.2320    1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8473   -0.3915    0.1757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0970    0.2585    0.2562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1150   -0.2511   -1.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6409   -0.2624   -2.2460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7747   -0.1224   -0.9249 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7699   -3.2007    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657   -3.8336   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1884   -4.8744    0.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577   -4.1000    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2276   -3.4693    1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126   -1.3061    0.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8515   -1.9307   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994   -1.5930    1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -2.2741    0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0327    1.6707   -1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642    4.8924   -1.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2039    5.1829    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5163    3.9576    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080    3.4963    2.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0107    1.3189    1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9643   -0.1354    2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9884   -1.4576    0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5808    0.0358   -0.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15  5  1  0
  6  5  1  0
 12 11  1  0
  5  4  1  1
 11  8  2  0
  5 20  1  0
  4  3  1  0
  7  6  2  0
  3  2  1  0
  2  1  1  0
  7  8  1  0
 18 19  2  0
  6 14  1  0
 12 13  2  0
 14 12  1  0
  8  9  1  0
 20 18  1  0
  9 10  1  0
 18 16  1  0
 16 17  1  0
 11 34  1  0
 16 37  1  1
 15 35  1  0
 15 36  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  3 26  1  0
  3 27  1  0
  2 24  1  0
  2 25  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 17 38  1  0
M  END


  Mrv1652306212101393D          

 38 39  0  0  0  0            999 V2000
   -0.0641   -3.8526   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -3.4088    0.6084 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7318   -1.9822    0.2076 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0315   -1.5403    0.8977 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5062   -0.1216    0.4911 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4712    0.9349    0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8411    1.7301   -0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762    2.6941    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3286    3.4235   -0.6082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6389    4.4125   -0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033    2.7982    1.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816    1.9354    2.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230    2.0346    3.8986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1941    1.0375    2.2282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8520    0.2320    1.1236 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8473   -0.3915    0.1757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0970    0.2585    0.2562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1150   -0.2511   -1.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6409   -0.2624   -2.2460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7747   -0.1224   -0.9249 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7699   -3.2007    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657   -3.8336   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1884   -4.8744    0.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577   -4.1000    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2276   -3.4693    1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126   -1.3061    0.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8515   -1.9307   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994   -1.5930    1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -2.2741    0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0327    1.6707   -1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642    4.8924   -1.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2039    5.1829    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5163    3.9576    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080    3.4963    2.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0107    1.3189    1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9643   -0.1354    2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9884   -1.4576    0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5808    0.0358   -0.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0  0  0  0
 15  5  1  0  0  0  0
  6  5  1  0  0  0  0
 12 11  1  0  0  0  0
  5  4  1  1  0  0  0
 11  8  2  0  0  0  0
  5 20  1  0  0  0  0
  4  3  1  0  0  0  0
  7  6  2  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
  7  8  1  0  0  0  0
 18 19  2  0  0  0  0
  6 14  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  0  0  0  0
  8  9  1  0  0  0  0
 20 18  1  0  0  0  0
  9 10  1  0  0  0  0
 18 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 34  1  0  0  0  0
 16 37  1  1  0  0  0
 15 35  1  0  0  0  0
 15 36  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
  7 30  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  2 24  1  0  0  0  0
  2 25  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
 10 33  1  0  0  0  0
 17 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041855

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C(=O)O[C@](C2=C([H])C(OC([H])([H])[H])=C([H])C(=O)O2)(C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O6/c1-3-4-5-14(8-10(15)13(17)20-14)11-6-9(18-2)7-12(16)19-11/h6-7,10,15H,3-5,8H2,1-2H3/t10-,14-/m1/s1

> <INCHI_KEY>
HKQVKOAOXNMGFT-QMTHXVAHSA-N

> <FORMULA>
C14H18O6

> <MOLECULAR_WEIGHT>
282.292

> <EXACT_MASS>
282.1103383

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.327531467009614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(2R,4R)-2-butyl-4-hydroxy-5-oxooxolan-2-yl]-4-methoxy-2H-pyran-2-one

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
1.0912709833333336

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.591586411242076

> <JCHEM_PKA_STRONGEST_BASIC>
-3.852240103722715

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
71.6316

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(2R,4R)-2-butyl-4-hydroxy-5-oxooxolan-2-yl]-4-methoxypyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.0641   -3.8526   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -3.4088    0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7318   -1.9822    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0315   -1.5403    0.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062   -0.1216    0.4911 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4712    0.9349    0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8411    1.7301   -0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762    2.6941    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3286    3.4235   -0.6082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6389    4.4125   -0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033    2.7982    1.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816    1.9354    2.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230    2.0346    3.8986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1941    1.0375    2.2282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8520    0.2320    1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8473   -0.3915    0.1757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0970    0.2585    0.2562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1150   -0.2511   -1.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6409   -0.2624   -2.2460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7747   -0.1224   -0.9249 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7699   -3.2007    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657   -3.8336   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1884   -4.8744    0.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577   -4.1000    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2276   -3.4693    1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126   -1.3061    0.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8515   -1.9307   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994   -1.5930    1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -2.2741    0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0327    1.6707   -1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642    4.8924   -1.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2039    5.1829    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5163    3.9576    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080    3.4963    2.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0107    1.3189    1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9643   -0.1354    2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9884   -1.4576    0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5808    0.0358   -0.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15  5  1  0
  6  5  1  0
 12 11  1  0
  5  4  1  1
 11  8  2  0
  5 20  1  0
  4  3  1  0
  7  6  2  0
  3  2  1  0
  2  1  1  0
  7  8  1  0
 18 19  2  0
  6 14  1  0
 12 13  2  0
 14 12  1  0
  8  9  1  0
 20 18  1  0
  9 10  1  0
 18 16  1  0
 16 17  1  0
 11 34  1  0
 16 37  1  1
 15 35  1  0
 15 36  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  3 26  1  0
  3 27  1  0
  2 24  1  0
  2 25  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 17 38  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      -0.064  -3.853  -0.067  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.352  -3.409   0.608  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.732  -1.982   0.208  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.031  -1.540   0.898  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.506  -0.122   0.491  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.471   0.935   0.838  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.841   1.730  -0.039  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.876   2.694   0.417  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.329   3.424  -0.608  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.639   4.412  -0.274  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.603   2.798   1.725  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.282   1.935   2.704  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.023   2.035   3.899  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.194   1.038   2.228  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.852   0.232   1.124  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.847  -0.392   0.176  0.00  0.00           C+0
HETATM   17  O   UNK     0      -7.097   0.259   0.256  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.115  -0.251  -1.144  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.641  -0.262  -2.246  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.775  -0.122  -0.925  0.00  0.00           O+0
HETATM   21  H   UNK     0       0.770  -3.201   0.212  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.166  -3.834  -1.157  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.188  -4.874   0.233  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.158  -4.100   0.335  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.228  -3.469   1.696  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.913  -1.306   0.477  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.851  -1.931  -0.881  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.899  -1.593   1.986  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.805  -2.274   0.639  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.033   1.671  -1.107  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.964   4.892  -1.202  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.204   5.183   0.371  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.516   3.958   0.197  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.108   3.496   2.142  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.011   1.319   1.159  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.964  -0.135   2.150  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.988  -1.458   0.381  0.00  0.00           H+0
HETATM   38  H   UNK     0      -7.581   0.036  -0.563  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    3    1   24   25                                             
CONECT    3    4    2   26   27                                             
CONECT    4    5    3   28   29                                             
CONECT    5   15    6    4   20                                             
CONECT    6    5    7   14                                                  
CONECT    7    6    8   30                                                  
CONECT    8   11    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   31   32   33                                             
CONECT   11   12    8   34                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14    6   12                                                       
CONECT   15   16    5   35   36                                             
CONECT   16   15   18   17   37                                             
CONECT   17   16   38                                                       
CONECT   18   19   20   16                                                  
CONECT   19   18                                                            
CONECT   20    5   18                                                       
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    2                                                            
CONECT   25    2                                                            
CONECT   26    3                                                            
CONECT   27    3                                                            
CONECT   28    4                                                            
CONECT   29    4                                                            
CONECT   30    7                                                            
CONECT   31   10                                                            
CONECT   32   10                                                            
CONECT   33   10                                                            
CONECT   34   11                                                            
CONECT   35   15                                                            
CONECT   36   15                                                            
CONECT   37   16                                                            
CONECT   38   17                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

RDKit          3D

38 39  0  0  0  0  0  0  0  0999 V2000
   -0.0641   -3.8526   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -3.4088    0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7318   -1.9822    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0315   -1.5403    0.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062   -0.1216    0.4911 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4712    0.9349    0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8411    1.7301   -0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762    2.6941    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3286    3.4235   -0.6082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6389    4.4125   -0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033    2.7982    1.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816    1.9354    2.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230    2.0346    3.8986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1941    1.0375    2.2282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8520    0.2320    1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8473   -0.3915    0.1757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0970    0.2585    0.2562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1150   -0.2511   -1.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6409   -0.2624   -2.2460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7747   -0.1224   -0.9249 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7699   -3.2007    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657   -3.8336   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1884   -4.8744    0.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577   -4.1000    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2276   -3.4693    1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126   -1.3061    0.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8515   -1.9307   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994   -1.5930    1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -2.2741    0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0327    1.6707   -1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642    4.8924   -1.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2039    5.1829    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5163    3.9576    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080    3.4963    2.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0107    1.3189    1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9643   -0.1354    2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9884   -1.4576    0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5808    0.0358   -0.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15  5  1  0
  6  5  1  0
 12 11  1  0
  5  4  1  1
 11  8  2  0
  5 20  1  0
  4  3  1  0
  7  6  2  0
  3  2  1  0
  2  1  1  0
  7  8  1  0
 18 19  2  0
  6 14  1  0
 12 13  2  0
 14 12  1  0
  8  9  1  0
 20 18  1  0
  9 10  1  0
 18 16  1  0
 16 17  1  0
 11 34  1  0
 16 37  1  1
 15 35  1  0
 15 36  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  3 26  1  0
  3 27  1  0
  2 24  1  0
  2 25  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 17 38  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₈O₆

Average Mass

282.2920 Da

Monoisotopic Mass

282.11034 Da

IUPAC Name

6-[(2R,4R)-2-butyl-4-hydroxy-5-oxooxolan-2-yl]-4-methoxy-2H-pyran-2-one

Traditional Name

6-[(2R,4R)-2-butyl-4-hydroxy-5-oxooxolan-2-yl]-4-methoxypyran-2-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C(=O)O[C@](C2=C([H])C(OC([H])([H])[H])=C([H])C(=O)O2)(C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C1([H])[H]

InChI Identifier

InChI=1S/C14H18O6/c1-3-4-5-14(8-10(15)13(17)20-14)11-6-9(18-2)7-12(16)19-11/h6-7,10,15H,3-5,8H2,1-2H3/t10-,14-/m1/s1

InChI Key

HKQVKOAOXNMGFT-QMTHXVAHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Pestalotiopsis scirpina	JEOL database	Li, J., et al, Eur. J. Org. Chem. 2012, 2445

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

Alkyl aryl ether
Pyranone
Gamma butyrolactone
Heteroaromatic compound
Vinylogous ester
Oxolane
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.39	ALOGPS
logP	1.09	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.59	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.63 m³·mol⁻¹	ChemAxon
Polarizability	28.33 Å³	ChemAxon
Number of Rings	2	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

28289666

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57409271

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li, J., et al. (2012). Li, J., et al, Eur. J. Org. Chem. 2012, 2445. Eur. J. Org. Chem..

Showing NP-Card for scirpyrone A (NP0041855)

MOL for NP0041855 (scirpyrone A)

3D MOL for NP0041855 (scirpyrone A)

3D SDF for NP0041855 (scirpyrone A)

3D-SDF for NP0041855 (scirpyrone A)

PDB for NP0041855 (scirpyrone A)

3D PDB for NP0041855 (scirpyrone A)

SMILES for NP0041855 (scirpyrone A)

INCHI for NP0041855 (scirpyrone A)

Structure for NP0041855 (scirpyrone A)

3D Structure for NP0041855 (scirpyrone A)