NP-MRD: Showing NP-Card for gonytolide G (NP0041427)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2021-06-20 23:20:18 UTC

Updated at

2021-06-30 00:15:56 UTC

NP-MRD ID

NP0041427

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gonytolide G

Provided By

JEOL Database JEOL Logo

Description

Methyl (2R)-5-hydroxy-7-(hydroxymethyl)-4-oxo-2-[(2S)-5-oxooxolan-2-yl]-3,4-dihydro-2H-1-benzopyran-2-carboxylate belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety. gonytolide G is found in Gonytrichum sp. It was first documented in 2012 (Kikuchi, H., et al.). Based on a literature review very few articles have been published on methyl (2R)-5-hydroxy-7-(hydroxymethyl)-4-oxo-2-[(2S)-5-oxooxolan-2-yl]-3,4-dihydro-2H-1-benzopyran-2-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101203D          

 40 42  0  0  0  0            999 V2000
    2.8925    2.7533    3.6879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318    2.0566    3.0304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9933    1.9148    1.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9544    2.3454    1.0609 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039    1.1593    1.0448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4098    2.1173    0.9521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1779    3.4171    0.2021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2982    4.2850    0.7254 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4704    3.7629    2.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0493    4.3348    3.0280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115    2.5196    2.2302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4204   -0.0792    1.8612 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5281   -1.0915    1.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777   -1.8787    2.6955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790   -1.1645    0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2288   -2.1630    0.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5546   -3.1144    1.2192 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -2.2334   -0.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5987   -1.3044   -1.9432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2858   -1.3808   -3.2795 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3865   -1.8746   -4.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376   -0.3094   -1.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9938   -0.2293   -0.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0871    0.7854   -0.3199 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9730    3.7752    3.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375    2.2154    3.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6565    2.8001    4.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2268    1.5776    0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2019    3.2961   -0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787    3.8787    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2269    4.1314    0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0195    5.3411    0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4774   -0.5596    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352    0.1600    2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0251   -2.9476    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6219   -3.0196   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6404   -0.3919   -3.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1544   -2.0463   -3.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7897   -2.5039   -3.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023    0.4149   -2.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0  0  0  0
 23 15  2  0  0  0  0
 19 20  1  0  0  0  0
 23 24  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
 16 15  1  0  0  0  0
 24  5  1  0  0  0  0
 16 18  2  0  0  0  0
  5 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 11  6  1  0  0  0  0
 18 19  1  0  0  0  0
  5  3  1  1  0  0  0
 12 13  1  0  0  0  0
  3  4  2  0  0  0  0
 19 22  2  0  0  0  0
  3  2  1  0  0  0  0
 22 23  1  0  0  0  0
  2  1  1  0  0  0  0
  9 10  2  0  0  0  0
 13 14  2  0  0  0  0
  6 28  1  6  0  0  0
 15 13  1  0  0  0  0
 20 21  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 18 36  1  0  0  0  0
 22 40  1  0  0  0  0
 17 35  1  0  0  0  0
 20 37  1  0  0  0  0
 20 38  1  0  0  0  0
  7 29  1  0  0  0  0
  7 30  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 21 39  1  0  0  0  0
M  END

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    2.8925    2.7533    3.6879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318    2.0566    3.0304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9933    1.9148    1.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9544    2.3454    1.0609 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039    1.1593    1.0448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4098    2.1173    0.9521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1779    3.4171    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982    4.2850    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704    3.7629    2.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0493    4.3348    3.0280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115    2.5196    2.2302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4204   -0.0792    1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5281   -1.0915    1.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777   -1.8787    2.6955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790   -1.1645    0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2288   -2.1630    0.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5546   -3.1144    1.2192 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -2.2334   -0.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5987   -1.3044   -1.9432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2858   -1.3808   -3.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3865   -1.8746   -4.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376   -0.3094   -1.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9938   -0.2293   -0.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0871    0.7854   -0.3199 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9730    3.7752    3.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375    2.2154    3.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6565    2.8001    4.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2268    1.5776    0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2019    3.2961   -0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787    3.8787    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2269    4.1314    0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0195    5.3411    0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4774   -0.5596    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352    0.1600    2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0251   -2.9476    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6219   -3.0196   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6404   -0.3919   -3.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1544   -2.0463   -3.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7897   -2.5039   -3.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023    0.4149   -2.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 23 15  2  0
 19 20  1  0
 23 24  1  0
  5  6  1  0
  6  7  1  0
 16 15  1  0
 24  5  1  0
 16 18  2  0
  5 12  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
 11  6  1  0
 18 19  1  0
  5  3  1  1
 12 13  1  0
  3  4  2  0
 19 22  2  0
  3  2  1  0
 22 23  1  0
  2  1  1  0
  9 10  2  0
 13 14  2  0
  6 28  1  6
 15 13  1  0
 20 21  1  0
 12 33  1  0
 12 34  1  0
 18 36  1  0
 22 40  1  0
 17 35  1  0
 20 37  1  0
 20 38  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 21 39  1  0
M  END


  Mrv1652306212101203D          

 40 42  0  0  0  0            999 V2000
    2.8925    2.7533    3.6879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318    2.0566    3.0304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9933    1.9148    1.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9544    2.3454    1.0609 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039    1.1593    1.0448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4098    2.1173    0.9521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1779    3.4171    0.2021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2982    4.2850    0.7254 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4704    3.7629    2.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0493    4.3348    3.0280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115    2.5196    2.2302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4204   -0.0792    1.8612 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5281   -1.0915    1.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777   -1.8787    2.6955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790   -1.1645    0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2288   -2.1630    0.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5546   -3.1144    1.2192 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -2.2334   -0.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5987   -1.3044   -1.9432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2858   -1.3808   -3.2795 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3865   -1.8746   -4.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376   -0.3094   -1.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9938   -0.2293   -0.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0871    0.7854   -0.3199 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9730    3.7752    3.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375    2.2154    3.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6565    2.8001    4.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2268    1.5776    0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2019    3.2961   -0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787    3.8787    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2269    4.1314    0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0195    5.3411    0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4774   -0.5596    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352    0.1600    2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0251   -2.9476    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6219   -3.0196   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6404   -0.3919   -3.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1544   -2.0463   -3.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7897   -2.5039   -3.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023    0.4149   -2.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0  0  0  0
 23 15  2  0  0  0  0
 19 20  1  0  0  0  0
 23 24  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
 16 15  1  0  0  0  0
 24  5  1  0  0  0  0
 16 18  2  0  0  0  0
  5 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 11  6  1  0  0  0  0
 18 19  1  0  0  0  0
  5  3  1  1  0  0  0
 12 13  1  0  0  0  0
  3  4  2  0  0  0  0
 19 22  2  0  0  0  0
  3  2  1  0  0  0  0
 22 23  1  0  0  0  0
  2  1  1  0  0  0  0
  9 10  2  0  0  0  0
 13 14  2  0  0  0  0
  6 28  1  6  0  0  0
 15 13  1  0  0  0  0
 20 21  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 18 36  1  0  0  0  0
 22 40  1  0  0  0  0
 17 35  1  0  0  0  0
 20 37  1  0  0  0  0
 20 38  1  0  0  0  0
  7 29  1  0  0  0  0
  7 30  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 21 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041427

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C([H])C2=C1C(=O)C([H])([H])[C@](O2)(C(=O)OC([H])([H])[H])[C@@]1([H])OC(=O)C([H])([H])C1([H])[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O8/c1-22-15(21)16(12-2-3-13(20)23-12)6-10(19)14-9(18)4-8(7-17)5-11(14)24-16/h4-5,12,17-18H,2-3,6-7H2,1H3/t12-,16+/m0/s1

> <INCHI_KEY>
RSIDHYMVKNVPPS-BLLLJJGKSA-N

> <FORMULA>
C16H16O8

> <MOLECULAR_WEIGHT>
336.296

> <EXACT_MASS>
336.084517475

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.06922426263547

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R)-5-hydroxy-7-(hydroxymethyl)-4-oxo-2-[(2S)-5-oxooxolan-2-yl]-3,4-dihydro-2H-1-benzopyran-2-carboxylate

> <ALOGPS_LOGP>
0.81

> <JCHEM_LOGP>
0.8402337546666667

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.83220153832351

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.3981503519105

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9038581859543857

> <JCHEM_POLAR_SURFACE_AREA>
119.36

> <JCHEM_REFRACTIVITY>
78.4341

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R)-5-hydroxy-7-(hydroxymethyl)-4-oxo-2-[(2S)-5-oxooxolan-2-yl]-3H-1-benzopyran-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    2.8925    2.7533    3.6879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318    2.0566    3.0304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9933    1.9148    1.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9544    2.3454    1.0609 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039    1.1593    1.0448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4098    2.1173    0.9521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1779    3.4171    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982    4.2850    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704    3.7629    2.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0493    4.3348    3.0280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115    2.5196    2.2302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4204   -0.0792    1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5281   -1.0915    1.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777   -1.8787    2.6955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790   -1.1645    0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2288   -2.1630    0.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5546   -3.1144    1.2192 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -2.2334   -0.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5987   -1.3044   -1.9432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2858   -1.3808   -3.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3865   -1.8746   -4.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376   -0.3094   -1.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9938   -0.2293   -0.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0871    0.7854   -0.3199 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9730    3.7752    3.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375    2.2154    3.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6565    2.8001    4.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2268    1.5776    0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2019    3.2961   -0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787    3.8787    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2269    4.1314    0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0195    5.3411    0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4774   -0.5596    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352    0.1600    2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0251   -2.9476    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6219   -3.0196   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6404   -0.3919   -3.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1544   -2.0463   -3.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7897   -2.5039   -3.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023    0.4149   -2.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 23 15  2  0
 19 20  1  0
 23 24  1  0
  5  6  1  0
  6  7  1  0
 16 15  1  0
 24  5  1  0
 16 18  2  0
  5 12  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
 11  6  1  0
 18 19  1  0
  5  3  1  1
 12 13  1  0
  3  4  2  0
 19 22  2  0
  3  2  1  0
 22 23  1  0
  2  1  1  0
  9 10  2  0
 13 14  2  0
  6 28  1  6
 15 13  1  0
 20 21  1  0
 12 33  1  0
 12 34  1  0
 18 36  1  0
 22 40  1  0
 17 35  1  0
 20 37  1  0
 20 38  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 21 39  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       2.893   2.753   3.688  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.832   2.057   3.030  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.993   1.915   1.687  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.954   2.345   1.061  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.804   1.159   1.045  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.410   2.117   0.952  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.178   3.417   0.202  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.298   4.285   0.725  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.470   3.763   2.121  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.049   4.335   3.028  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.912   2.520   2.230  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.420  -0.079   1.861  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.528  -1.091   1.787  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.778  -1.879   2.696  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.279  -1.165   0.524  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.229  -2.163   0.292  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.555  -3.114   1.219  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.887  -2.233  -0.934  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.599  -1.304  -1.943  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.286  -1.381  -3.280  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.386  -1.875  -4.262  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.638  -0.309  -1.703  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.994  -0.229  -0.468  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.087   0.785  -0.320  0.00  0.00           O+0
HETATM   25  H   UNK     0       2.973   3.775   3.305  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.837   2.215   3.564  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.656   2.800   4.755  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.227   1.578   0.450  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.202   3.296  -0.885  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.779   3.879   0.470  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.227   4.131   0.169  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.020   5.341   0.730  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.477  -0.560   1.454  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.235   0.160   2.914  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.025  -2.948   2.032  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.622  -3.020  -1.096  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.640  -0.392  -3.588  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.154  -2.046  -3.242  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.790  -2.504  -3.822  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.402   0.415  -2.482  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5    6   24   12    3                                             
CONECT    6    5    7   11   28                                             
CONECT    7    6    8   29   30                                             
CONECT    8    7    9   31   32                                             
CONECT    9    8   11   10                                                  
CONECT   10    9                                                            
CONECT   11    9    6                                                       
CONECT   12    5   13   33   34                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   23   16   13                                                  
CONECT   16   17   15   18                                                  
CONECT   17   16   35                                                       
CONECT   18   16   19   36                                                  
CONECT   19   20   18   22                                                  
CONECT   20   19   21   37   38                                             
CONECT   21   20   39                                                       
CONECT   22   19   23   40                                                  
CONECT   23   15   24   22                                                  
CONECT   24   23    5                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    8                                                            
CONECT   33   12                                                            
CONECT   34   12                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   20                                                            
CONECT   38   20                                                            
CONECT   39   21                                                            
CONECT   40   22                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

RDKit          3D

40 42  0  0  0  0  0  0  0  0999 V2000
    2.8925    2.7533    3.6879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318    2.0566    3.0304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9933    1.9148    1.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9544    2.3454    1.0609 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039    1.1593    1.0448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4098    2.1173    0.9521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1779    3.4171    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982    4.2850    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704    3.7629    2.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0493    4.3348    3.0280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115    2.5196    2.2302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4204   -0.0792    1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5281   -1.0915    1.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777   -1.8787    2.6955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790   -1.1645    0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2288   -2.1630    0.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5546   -3.1144    1.2192 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -2.2334   -0.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5987   -1.3044   -1.9432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2858   -1.3808   -3.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3865   -1.8746   -4.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376   -0.3094   -1.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9938   -0.2293   -0.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0871    0.7854   -0.3199 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9730    3.7752    3.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375    2.2154    3.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6565    2.8001    4.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2268    1.5776    0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2019    3.2961   -0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787    3.8787    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2269    4.1314    0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0195    5.3411    0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4774   -0.5596    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352    0.1600    2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0251   -2.9476    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6219   -3.0196   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6404   -0.3919   -3.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1544   -2.0463   -3.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7897   -2.5039   -3.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023    0.4149   -2.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 23 15  2  0
 19 20  1  0
 23 24  1  0
  5  6  1  0
  6  7  1  0
 16 15  1  0
 24  5  1  0
 16 18  2  0
  5 12  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
 11  6  1  0
 18 19  1  0
  5  3  1  1
 12 13  1  0
  3  4  2  0
 19 22  2  0
  3  2  1  0
 22 23  1  0
  2  1  1  0
  9 10  2  0
 13 14  2  0
  6 28  1  6
 15 13  1  0
 20 21  1  0
 12 33  1  0
 12 34  1  0
 18 36  1  0
 22 40  1  0
 17 35  1  0
 20 37  1  0
 20 38  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 21 39  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl (2R)-5-hydroxy-7-(hydroxymethyl)-4-oxo-2-[(2S)-5-oxooxolan-2-yl]-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid	Generator

Chemical Formula

C₁₆H₁₆O₈

Average Mass

336.2960 Da

Monoisotopic Mass

336.08452 Da

IUPAC Name

methyl (2R)-5-hydroxy-7-(hydroxymethyl)-4-oxo-2-[(2S)-5-oxooxolan-2-yl]-3,4-dihydro-2H-1-benzopyran-2-carboxylate

Traditional Name

methyl (2R)-5-hydroxy-7-(hydroxymethyl)-4-oxo-2-[(2S)-5-oxooxolan-2-yl]-3H-1-benzopyran-2-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(=C([H])C2=C1C(=O)C([H])([H])[C@](O2)(C(=O)OC([H])([H])[H])[C@@]1([H])OC(=O)C([H])([H])C1([H])[H])C([H])([H])O[H]

InChI Identifier

InChI=1S/C16H16O8/c1-22-15(21)16(12-2-3-13(20)23-12)6-10(19)14-9(18)4-8(7-17)5-11(14)24-16/h4-5,12,17-18H,2-3,6-7H2,1H3/t12-,16+/m0/s1

InChI Key

RSIDHYMVKNVPPS-BLLLJJGKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Gonytrichum sp.	JEOL database	Kikuchi, H., et al, Tetrahedron 68, 6218 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromones

Alternative Parents

Substituents

Chromone
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Dicarboxylic acid or derivatives
Gamma butyrolactone
Benzenoid
Methyl ester
Vinylogous acid
Oxolane
Carboxylic acid ester
Ketone
Lactone
Oxacycle
Carboxylic acid derivative
Ether
Alcohol
Organic oxide
Primary alcohol
Aromatic alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
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	0.81	ALOGPS
logP	0.84	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	8.4	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.43 m³·mol⁻¹	ChemAxon
Polarizability	32.07 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

78437434

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60170335

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kikuchi, H., et al. (2012). Kikuchi, H., et al, Tetrahedron 68, 6218 (2012). Tetrahedron.

Showing NP-Card for gonytolide G (NP0041427)

MOL for NP0041427 (gonytolide G)

3D MOL for NP0041427 (gonytolide G)

3D SDF for NP0041427 (gonytolide G)

3D-SDF for NP0041427 (gonytolide G)

PDB for NP0041427 (gonytolide G)

3D PDB for NP0041427 (gonytolide G)

SMILES for NP0041427 (gonytolide G)

INCHI for NP0041427 (gonytolide G)

Structure for NP0041427 (gonytolide G)

3D Structure for NP0041427 (gonytolide G)