NP-MRD: Showing NP-Card for (1s,2s,9s,11r)-11-[(2r)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0²,¹¹.0³,⁸]tetradeca-3(8),4,6-trien-13-one (NP0311030)

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Record Information

Version

2.0

Created at

2022-09-11 06:44:53 UTC

Updated at

2024-09-12 20:50:04 UTC

NP-MRD ID

NP0311030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,9s,11r)-11-[(2r)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0²,¹¹.0³,⁸]tetradeca-3(8),4,6-trien-13-one

Description

Peyronellone A belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (1s,2s,9s,11r)-11-[(2r)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0²,¹¹.0³,⁸]tetradeca-3(8),4,6-trien-13-one is found in Didymella glomerata. Based on a literature review very few articles have been published on Peyronellone A.

Structure

MOL SDF PDB SMILES InChI

NP0018049
  Mrv2104 05272322453D          

 46 49  0  0  0  0            999 V2000
   -3.6431    0.6832    1.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288    0.9025    0.3252 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2389    0.8942   -0.3666 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3951    2.0732    0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4997   -0.4723   -0.2860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4244   -1.4909   -0.7077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7102   -2.5477   -1.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2143   -3.5716   -1.6223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182   -2.2203   -1.0863 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6096   -2.8434   -2.0507 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2031   -2.6359    0.3456 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1341   -1.3900    1.2370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1371   -0.7428    1.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1735   -0.4204    0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9949   -0.0758   -0.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9311    0.7380   -1.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0316    1.2033   -0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9491    2.0146   -1.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2237    0.8694    0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978    1.4142    1.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599    0.0739    1.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4117   -0.2130    2.7757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700   -0.6735   -1.2356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5183   -0.2437   -2.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3634   -0.3409    2.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760    1.3758    2.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6550    0.8459    2.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2760    0.1511   -0.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1074    1.8694    0.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4696    1.0847   -1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5441    2.2536   -0.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9846    2.9967    0.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0134    1.9103    1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5382   -2.6415   -1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4745   -3.4037    0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2119   -3.0679    0.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2767   -1.6516    2.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8131    1.0162   -2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6859    2.1654   -2.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1413    2.3861    2.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7001    0.7371    2.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2748    1.5332    0.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5382   -0.1600    3.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4471   -0.6605   -3.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2954   -0.5707   -3.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    0.8461   -2.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  6  0  0  0
 13  5  1  0  0  0  0
 21 14  1  0  0  0  0
 23  5  1  0  0  0  0
 23  9  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
  2 28  1  0  0  0  0
  2 29  1  0  0  0  0
  3 30  1  6  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  4 33  1  0  0  0  0
 10 34  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
 12 37  1  1  0  0  0
 16 38  1  0  0  0  0
 18 39  1  0  0  0  0
 20 40  1  0  0  0  0
 20 41  1  0  0  0  0
 20 42  1  0  0  0  0
 22 43  1  0  0  0  0
 24 44  1  0  0  0  0
 24 45  1  0  0  0  0
 24 46  1  0  0  0  0
M  END

NP0018049
  Mrv2104 05272322453D          

 46 49  0  0  0  0            999 V2000
   -3.6431    0.6832    1.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288    0.9025    0.3252 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2389    0.8942   -0.3666 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3951    2.0732    0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4997   -0.4723   -0.2860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4244   -1.4909   -0.7077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7102   -2.5477   -1.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2143   -3.5716   -1.6223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182   -2.2203   -1.0863 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6096   -2.8434   -2.0507 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2031   -2.6359    0.3456 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1341   -1.3900    1.2370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1371   -0.7428    1.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1735   -0.4204    0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9949   -0.0758   -0.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9311    0.7380   -1.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0316    1.2033   -0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9491    2.0146   -1.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2237    0.8694    0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978    1.4142    1.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599    0.0739    1.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4117   -0.2130    2.7757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700   -0.6735   -1.2356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5183   -0.2437   -2.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3634   -0.3409    2.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760    1.3758    2.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6550    0.8459    2.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2760    0.1511   -0.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1074    1.8694    0.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4696    1.0847   -1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5441    2.2536   -0.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9846    2.9967    0.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0134    1.9103    1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5382   -2.6415   -1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4745   -3.4037    0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2119   -3.0679    0.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2767   -1.6516    2.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8131    1.0162   -2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6859    2.1654   -2.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1413    2.3861    2.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7001    0.7371    2.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2748    1.5332    0.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5382   -0.1600    3.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4471   -0.6605   -3.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2954   -0.5707   -3.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    0.8461   -2.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  6  0  0  0
 13  5  1  0  0  0  0
 21 14  1  0  0  0  0
 23  5  1  0  0  0  0
 23  9  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
  2 28  1  0  0  0  0
  2 29  1  0  0  0  0
  3 30  1  6  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  4 33  1  0  0  0  0
 10 34  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
 12 37  1  1  0  0  0
 16 38  1  0  0  0  0
 18 39  1  0  0  0  0
 20 40  1  0  0  0  0
 20 41  1  0  0  0  0
 20 42  1  0  0  0  0
 22 43  1  0  0  0  0
 24 44  1  0  0  0  0
 24 45  1  0  0  0  0
 24 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0311030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(O[H])=C1C([H])([H])[H])[C@@]1([H])O[C@@]3(OC(=O)[C@](O[H])(C1([H])[H])[C@]23C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1/C18H22O6/c1-5-8(2)18-16(4)10-6-11(19)9(3)14(20)13(10)12(23-18)7-17(16,22)15(21)24-18/h6,8,12,19-20,22H,5,7H2,1-4H3/t8-,12+,16+,17-,18-/s2

> <INCHI_KEY>
RHIUTYRDTYSZNQ-XBQOJVLQNA-N

> <FORMULA>
C18H22O6

> <MOLECULAR_WEIGHT>
334.368

> <EXACT_MASS>
334.141638428

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
33.87673845745951

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,9S,11R)-11-[(2R)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0^{2,11}.0^{3,8}]tetradeca-3(8),4,6-trien-13-one

> <JCHEM_LOGP>
3.0805789783333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.660106493007412

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.275154339203167

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2677205871755675

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
84.98900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,9S,11R)-11-[(2R)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0^{2,11}.0^{3,8}]tetradeca-3(8),4,6-trien-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: NP0018049                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0      -3.643   0.683   1.831  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.629   0.903   0.325  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.239   0.894  -0.367  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.395   2.073   0.129  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.500  -0.472  -0.286  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.424  -1.491  -0.708  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.710  -2.548  -1.193  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.214  -3.572  -1.622  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.218  -2.220  -1.086  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.610  -2.843  -2.051  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.203  -2.636   0.346  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.134  -1.390   1.237  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.137  -0.743   1.091  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.174  -0.420   0.733  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.995  -0.076  -0.621  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.931   0.738  -1.256  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.032   1.203  -0.531  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.949   2.015  -1.141  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.224   0.869   0.819  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.398   1.414   1.585  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.260   0.074   1.450  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.412  -0.213   2.776  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.270  -0.674  -1.236  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.518  -0.244  -2.692  0.00  0.00           C+0
HETATM   25  H   UNK     0      -3.363  -0.341   2.091  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.976   1.376   2.351  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.655   0.846   2.217  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.276   0.151  -0.143  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.107   1.869   0.121  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.470   1.085  -1.423  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.544   2.254  -0.532  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.985   2.997   0.139  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.013   1.910   1.142  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.538  -2.642  -1.839  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.475  -3.404   0.740  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.212  -3.068   0.357  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.277  -1.652   2.289  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.813   1.016  -2.298  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.686   2.165  -2.063  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.141   2.386   2.018  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.700   0.737   2.390  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.275   1.533   0.940  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.538  -0.160   3.200  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.447  -0.661  -3.096  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.295  -0.571  -3.350  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.587   0.846  -2.781  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    1    3   28   29                                             
CONECT    3    2    4    5   30                                             
CONECT    4    3   31   32   33                                             
CONECT    5    3    6   13   23                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   23                                             
CONECT   10    9   34                                                       
CONECT   11    9   12   35   36                                             
CONECT   12   11   13   14   37                                             
CONECT   13   12    5                                                       
CONECT   14   12   15   21                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17   38                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   39                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19   40   41   42                                             
CONECT   21   19   22   14                                                  
CONECT   22   21   43                                                       
CONECT   23   15   24    5    9                                             
CONECT   24   23   44   45   46                                             
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    2                                                            
CONECT   29    2                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    4                                                            
CONECT   34   10                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   16                                                            
CONECT   39   18                                                            
CONECT   40   20                                                            
CONECT   41   20                                                            
CONECT   42   20                                                            
CONECT   43   22                                                            
CONECT   44   24                                                            
CONECT   45   24                                                            
CONECT   46   24                                                            
MASTER        0    0    0    0    0    0    0    0   46    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₂O₆

Average Mass

334.3680 Da

Monoisotopic Mass

334.14164 Da

IUPAC Name

(1S,2S,9S,11R)-11-[(2R)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0^{2,11}.0^{3,8}]tetradeca-3(8),4,6-trien-13-one

Traditional Name

(1S,2S,9S,11R)-11-[(2R)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0^{2,11}.0^{3,8}]tetradeca-3(8),4,6-trien-13-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C(O[H])=C1C([H])([H])[H])[C@@]1([H])O[C@@]3(OC(=O)[C@](O[H])(C1([H])[H])[C@]23C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1/C18H22O6/c1-5-8(2)18-16(4)10-6-11(19)9(3)14(20)13(10)12(23-18)7-17(16,22)15(21)24-18/h6,8,12,19-20,22H,5,7H2,1-4H3/t8-,12+,16+,17-,18-/s2

InChI Key

RHIUTYRDTYSZNQ-XBQOJVLQNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Didymella glomerata	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthofurans. These are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
2-benzopyran
Tetralin
Isochromane
Benzopyran
Furopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Dioxepane
1,3-dioxepane
Benzenoid
Pyran
Oxane
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Furan
Lactone
Carboxylic acid ester
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
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	3.08	ChemAxon
pKa (Strongest Acidic)	9.28	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	84.99 m³·mol⁻¹	ChemAxon
Polarizability	33.88 Å³	ChemAxon
Number of Rings	4	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,9s,11r)-11-[(2r)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0²,¹¹.0³,⁸]tetradeca-3(8),4,6-trien-13-one (NP0311030)

MOL for NP0311030 ((1s,2s,9s,11r)-11-[(2r)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0²,¹¹.0³,⁸]tetradeca-3(8),4,6-trien-13-one)

3D MOL for NP0311030 ((1s,2s,9s,11r)-11-[(2r)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0²,¹¹.0³,⁸]tetradeca-3(8),4,6-trien-13-one)

3D SDF for NP0311030 ((1s,2s,9s,11r)-11-[(2r)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0²,¹¹.0³,⁸]tetradeca-3(8),4,6-trien-13-one)

3D-SDF for NP0311030 ((1s,2s,9s,11r)-11-[(2r)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0²,¹¹.0³,⁸]tetradeca-3(8),4,6-trien-13-one)

PDB for NP0311030 ((1s,2s,9s,11r)-11-[(2r)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0²,¹¹.0³,⁸]tetradeca-3(8),4,6-trien-13-one)

3D PDB for NP0311030 ((1s,2s,9s,11r)-11-[(2r)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0²,¹¹.0³,⁸]tetradeca-3(8),4,6-trien-13-one)

SMILES for NP0311030 ((1s,2s,9s,11r)-11-[(2r)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0²,¹¹.0³,⁸]tetradeca-3(8),4,6-trien-13-one)

INCHI for NP0311030 ((1s,2s,9s,11r)-11-[(2r)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0²,¹¹.0³,⁸]tetradeca-3(8),4,6-trien-13-one)

Structure for NP0311030 ((1s,2s,9s,11r)-11-[(2r)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0²,¹¹.0³,⁸]tetradeca-3(8),4,6-trien-13-one)

3D Structure for NP0311030 ((1s,2s,9s,11r)-11-[(2r)-butan-2-yl]-1,5,7-trihydroxy-2,6-dimethyl-10,12-dioxatetracyclo[7.4.1.0²,¹¹.0³,⁸]tetradeca-3(8),4,6-trien-13-one)