NP-MRD: Showing NP-Card for (2r,4r,6s,7s,12s)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraene-8,14-dione (NP0156247)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 13:25:53 UTC

Updated at

2022-09-02 13:25:54 UTC

NP-MRD ID

NP0156247

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4r,6s,7s,12s)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraene-8,14-dione

Description

(1AR,8S,13S,14S,15aR)-5,13,14-trihydroxy-3-methoxy-8-methyl-8,9,13,14,15,15a-hexahydro-6H-oxireno[k][2]benzoxacyclotetradecine-6,12(1aH)-dione belongs to the class of organic compounds known as zearalenones. (2r,4r,6s,7s,12s)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraene-8,14-dione is found in Aigialus parvus, Hypomyces subiculosus and Trametes versicolor. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene (1aR,8S,13S,14S,15aR)-5,13,14-trihydroxy-3-methoxy-8-methyl-8,9,13,14,15,15a-hexahydro-6H-oxireno[k][2]benzoxacyclotetradecine-6,12(1aH)-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041405202D          

 32 34  0  0  1  0            999 V2000
    1.8073   -2.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4724    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580   -0.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0030   -1.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3290    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0435    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073    2.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -1.4413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0435    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6146    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3290   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0030    2.0827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6116    2.0827    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6146    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580    1.5683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2566    1.5683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2566   -0.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8043    1.0086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3290   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450    2.8260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871    2.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9016   -1.2577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7580    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6116   -1.2577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3796    2.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623   -1.9556    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609    2.8260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499    2.9054    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4464    1.3847    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0724    1.6913    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  2  0  0  0  0
  9  1  1  1  0  0  0
  9  4  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
  5 12  1  4  0  0  0
 13  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  8  1  0  0  0  0
 16 11  2  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 17 14  1  0  0  0  0
 18 11  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 12  2  0  0  0  0
 21 13  1  0  0  0  0
 14 22  1  1  0  0  0
 17 23  1  1  0  0  0
 24 19  2  0  0  0  0
 25  2  1  0  0  0  0
 25 10  1  0  0  0  0
 26  9  1  0  0  0  0
 26 19  1  0  0  0  0
 27 15  1  0  0  0  0
 27 18  1  0  0  0  0
  9 28  1  6  0  0  0
 14 29  1  6  0  0  0
 15 30  1  6  0  0  0
 17 31  1  6  0  0  0
 18 32  1  1  0  0  0
M  END

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
    6.4200   -0.3224    1.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2493   -1.0965    1.1978 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1276   -0.6189    0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1937    0.6215   -0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0915    1.1056   -0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1932    2.3717   -1.2708 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9091    0.3480   -0.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8379   -0.9192   -0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9800   -1.3603    0.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6733   -1.8242   -0.4241 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7565   -2.9319    0.4537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3005   -1.9677    0.5486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5769   -2.5949   -0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248   -2.1988    0.8378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4496   -3.3279    1.2590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6102   -1.2970   -0.0048 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9266   -0.7642   -1.0837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3430   -0.2865    0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0710   -0.7566    1.7322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3071    1.1459    0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2616    1.9401    0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680    1.5270    0.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537    2.0516   -0.0425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2269    3.4160   -0.5867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    1.1359   -1.0674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8186    1.0067   -1.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1631    1.4675   -2.7264 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7590    0.0712    0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1963    0.5200    1.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2554   -0.8979    1.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0951    1.2180    0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0457    2.8854   -1.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9349   -2.3421    0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635   -2.2209   -1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3524   -1.4705    1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5274   -3.7005   -0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6935   -2.2781   -1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4423   -1.6774    1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5032   -4.0059    0.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3789   -1.9985   -0.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5705   -0.6263   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2715    1.6504    0.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3800    3.0259    0.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7250    0.4635    1.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6384    1.9963    1.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813    2.2237    0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1740    3.4388   -1.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1470    4.2059    0.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    3.6483   -1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 26  7  1  0
  7  8  2  0
  8  9  1  0
  9  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 11 12  1  0
  5  7  1  0
 12 35  1  1
 13 36  1  0
 13 37  1  0
 14 38  1  1
 15 39  1  0
 16 40  1  6
 17 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  1
 24 47  1  0
 24 48  1  0
 24 49  1  0
  9 33  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
 10 34  1  6
M  END


  Mrv0541 05041405202D          

 32 34  0  0  1  0            999 V2000
    1.8073   -2.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4724    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580   -0.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0030   -1.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3290    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0435    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073    2.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -1.4413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0435    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6146    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3290   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0030    2.0827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6116    2.0827    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6146    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580    1.5683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2566    1.5683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2566   -0.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8043    1.0086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3290   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450    2.8260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871    2.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9016   -1.2577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7580    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6116   -1.2577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3796    2.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623   -1.9556    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609    2.8260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499    2.9054    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4464    1.3847    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0724    1.6913    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  2  0  0  0  0
  9  1  1  1  0  0  0
  9  4  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
  5 12  1  4  0  0  0
 13  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  8  1  0  0  0  0
 16 11  2  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 17 14  1  0  0  0  0
 18 11  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 12  2  0  0  0  0
 21 13  1  0  0  0  0
 14 22  1  1  0  0  0
 17 23  1  1  0  0  0
 24 19  2  0  0  0  0
 25  2  1  0  0  0  0
 25 10  1  0  0  0  0
 26  9  1  0  0  0  0
 26 19  1  0  0  0  0
 27 15  1  0  0  0  0
 27 18  1  0  0  0  0
  9 28  1  6  0  0  0
 14 29  1  6  0  0  0
 15 30  1  6  0  0  0
 17 31  1  6  0  0  0
 18 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0156247

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@]([H])(O)[C@]([H])(O)C(=O)C=CC[C@]([H])(C)OC(=O)C3=C(C=C(OC)C=C3O)[C@@]1([H])O2

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O8/c1-9-4-3-5-12(20)17(23)14(22)8-15-18(27-15)11-6-10(25-2)7-13(21)16(11)19(24)26-9/h3,5-7,9,14-15,17-18,21-23H,4,8H2,1-2H3/t9-,14-,15+,17+,18+/m0/s1

> <INCHI_KEY>
SSNQAUBBJYCSMY-LWQPPDATSA-N

> <FORMULA>
C19H22O8

> <MOLECULAR_WEIGHT>
378.3732

> <EXACT_MASS>
378.13146768

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
37.572458190891126

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,4R,6S,7S,12S)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(15),9,16,18-tetraene-8,14-dione

> <ALOGPS_LOGP>
0.95

> <JCHEM_LOGP>
1.6343301726666666

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.425224435229335

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.474741354591858

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2662629454875995

> <JCHEM_POLAR_SURFACE_AREA>
125.82000000000002

> <JCHEM_REFRACTIVITY>
94.9755

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4R,6S,7S,12S)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(15),9,16,18-tetraene-8,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    9                                                            
CONECT    2   25                                                            
CONECT    3    4    5                                                       
CONECT    4    3    9                                                       
CONECT    5    3   12                                                       
CONECT    6   10   11                                                       
CONECT    7   10   13                                                       
CONECT    8   14   15                                                       
CONECT    9    1    4   26   28                                             
CONECT   10    6    7   25                                                  
CONECT   11    6   16   18                                                  
CONECT   12    5   17   20                                                  
CONECT   13    7   16   21                                                  
CONECT   14    8   17   22   29                                             
CONECT   15    8   18   27   30                                             
CONECT   16   11   13   19                                                  
CONECT   17   12   14   23   31                                             
CONECT   18   11   15   27   32                                             
CONECT   19   16   24   26                                                  
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22   14                                                            
CONECT   23   17                                                            
CONECT   24   19                                                            
CONECT   25    2   10                                                       
CONECT   26    9   19                                                       
CONECT   27   15   18                                                       
CONECT   28    9                                                            
CONECT   29   14                                                            
CONECT   30   15                                                            
CONECT   31   17                                                            
CONECT   32   18                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₈

Average Mass

378.3732 Da

Monoisotopic Mass

378.13147 Da

IUPAC Name

(2R,4R,6S,7S,12S)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(15),9,16,18-tetraene-8,14-dione

Traditional Name

(2R,4R,6S,7S,12S)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(15),9,16,18-tetraene-8,14-dione

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@]([H])(O)[C@]([H])(O)C(=O)C=CC[C@]([H])(C)OC(=O)C3=C(C=C(OC)C=C3O)[C@@]1([H])O2

InChI Identifier

InChI=1S/C19H22O8/c1-9-4-3-5-12(20)17(23)14(22)8-15-18(27-15)11-6-10(25-2)7-13(21)16(11)19(24)26-9/h3,5-7,9,14-15,17-18,21-23H,4,8H2,1-2H3/t9-,14-,15+,17+,18+/m0/s1

InChI Key

SSNQAUBBJYCSMY-LWQPPDATSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aigialus parvus	LOTUS Database	35616633
Hypomyces subiculosus	LOTUS Database	35616633
Trametes Versicolor	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Zearalenones

Direct Parent

Zearalenones

Alternative Parents

Substituents

Zearalenone-skeleton
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
1,2-diol
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.95	ALOGPS
logP	1.63	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	125.82 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.98 m³·mol⁻¹	ChemAxon
Polarizability	37.57 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

DB07905

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131676399

PDB ID

HMY

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,4r,6s,7s,12s)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraene-8,14-dione (NP0156247)

MOL for NP0156247 ((2r,4r,6s,7s,12s)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraene-8,14-dione)

3D MOL for NP0156247 ((2r,4r,6s,7s,12s)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraene-8,14-dione)

3D SDF for NP0156247 ((2r,4r,6s,7s,12s)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraene-8,14-dione)

3D-SDF for NP0156247 ((2r,4r,6s,7s,12s)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraene-8,14-dione)

PDB for NP0156247 ((2r,4r,6s,7s,12s)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraene-8,14-dione)

3D PDB for NP0156247 ((2r,4r,6s,7s,12s)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraene-8,14-dione)

SMILES for NP0156247 ((2r,4r,6s,7s,12s)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraene-8,14-dione)

INCHI for NP0156247 ((2r,4r,6s,7s,12s)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraene-8,14-dione)

Structure for NP0156247 ((2r,4r,6s,7s,12s)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraene-8,14-dione)

3D Structure for NP0156247 ((2r,4r,6s,7s,12s)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraene-8,14-dione)