NP-MRD: Showing NP-Card for (1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one (NP0216776)

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Record Information

Version

2.0

Created at

2022-09-05 16:52:29 UTC

Updated at

2022-09-05 16:52:29 UTC

NP-MRD ID

NP0216776

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one

Description

Preussomerin E belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. (1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one is found in Preussia isomera. (1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one was first documented in 2008 (PMID: 18234248). Based on a literature review a small amount of articles have been published on Preussomerin E (PMID: 19697340) (PMID: 24689520).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052218522D          

 27 33  0  0  1  0            999 V2000
    1.2982    0.9090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9519    0.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8446   -0.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -0.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4223   -0.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9173   -1.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5487   -2.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3506   -1.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5039   -0.9534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.6401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1232   -0.3283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8289   -0.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5781   -0.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2647   -0.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2078   -1.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4551   -2.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7359   -1.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9355   -2.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0341   -2.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7532   -3.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4633   -2.9008    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1825   -3.3051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0686   -2.3080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6187   -1.3706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3780    0.2198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4835    1.0381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7222    0.7204    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 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
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  1  0  0  0
 18 23  1  0  0  0  0
  8 23  1  0  0  0  0
 18 24  1  1  0  0  0
 10 24  1  1  0  0  0
 10 25  1  0  0  0  0
 25 26  1  1  0  0  0
 27 26  1  1  0  0  0
  2 27  1  0  0  0  0
 25 27  1  0  0  0  0
M  END

     RDKit          3D

 39 45  0  0  0  0  0  0  0  0999 V2000
   -4.8886   -0.6728   -1.2502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7558   -0.1707   -1.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613    0.1246    0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9469    0.2960    1.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3191    0.2079    1.2388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3142    0.5691    2.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9610    0.6632    2.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1454    0.4940    1.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675    0.2260    0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8881    0.0461   -0.9061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3390   -1.2845   -0.9218 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0179   -1.4670   -0.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6789   -2.6341   -1.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0291   -2.7554   -0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7068   -1.7238   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0672   -0.5350    0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269   -0.4717   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9804    0.7582    0.2800 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8858    1.9070    0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1683    1.8280    0.7258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8446    0.5255    0.8721 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0492    0.6259    0.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2392    0.5836    1.5001 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1169    1.0047   -0.7982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5914    0.2038   -2.2189 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3549    1.4765   -2.2870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9735    0.1424   -2.3278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9286    0.0405    0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9317    0.6991    3.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4224    0.8760    3.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0971   -3.4230   -1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5226   -3.6732   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7596   -1.8362    0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4518    2.9185    0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7503    2.7787    0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0318    0.2585    1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9558    1.2988   -0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9365    0.1452   -3.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4543   -0.0506   -3.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 23  1  1
 23  8  1  0
  8  9  2  0
  9  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  3  2  1  0
  2  1  2  0
  2 27  1  0
 27 26  1  0
 26 25  1  0
 25 10  1  0
 10 11  1  6
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 24  1  0
 16 21  1  0
 17 18  1  0
 24 18  1  0
  7  8  1  0
 25 27  1  0
 17 12  1  0
 10  9  1  0
 22 37  1  0
 21 36  1  1
 20 35  1  0
 19 34  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
 27 39  1  6
 25 38  1  6
 13 31  1  0
 14 32  1  0
 15 33  1  0
M  END


  Mrv1652309052218522D          

 27 33  0  0  1  0            999 V2000
    1.2982    0.9090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9519    0.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8446   -0.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -0.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4223   -0.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9173   -1.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5487   -2.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3506   -1.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5039   -0.9534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.6401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1232   -0.3283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8289   -0.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5781   -0.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2647   -0.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2078   -1.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4551   -2.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7359   -1.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9355   -2.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0341   -2.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7532   -3.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4633   -2.9008    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1825   -3.3051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0686   -2.3080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6187   -1.3706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3780    0.2198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4835    1.0381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7222    0.7204    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 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
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  1  0  0  0
 18 23  1  0  0  0  0
  8 23  1  0  0  0  0
 18 24  1  1  0  0  0
 10 24  1  1  0  0  0
 10 25  1  0  0  0  0
 25 26  1  1  0  0  0
 27 26  1  1  0  0  0
  2 27  1  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216776

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1C=C[C@]23OC4=C5C(=C(O)C=C4)C(=O)[C@H]4O[C@H]4[C@@]5(OC4=CC=CC1=C24)O3

> <INCHI_IDENTIFIER>
InChI=1S/C20H12O7/c21-9-6-7-19-14-8(9)2-1-3-11(14)26-20(27-19)15-12(25-19)5-4-10(22)13(15)16(23)17-18(20)24-17/h1-7,9,17-18,21-22H/t9-,17+,18+,19+,20-/m0/s1

> <INCHI_KEY>
OBZXRUYSZXAANO-NDMITINESA-N

> <FORMULA>
C20H12O7

> <MOLECULAR_WEIGHT>
364.309

> <EXACT_MASS>
364.058302726

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
34.51735053089662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4S,12R,15S)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1^{1,6}.1^{12,16}.0^{2,4}.0^{10,24}.0^{20,23}]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one

> <JCHEM_LOGP>
3.342215490666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.809144785950089

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.675737325265926

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2915172907751122

> <JCHEM_POLAR_SURFACE_AREA>
97.75000000000001

> <JCHEM_REFRACTIVITY>
90.06680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,12R,15S)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1^{1,6}.1^{12,16}.0^{2,4}.0^{10,24}.0^{20,23}]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0       2.423   1.697   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.644   0.757   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.443  -0.785   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.970  -1.317   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.788  -0.330   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.712  -2.846   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.891  -3.852   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.388  -3.361   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.674  -1.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.204  -1.195   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.697  -0.613   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.014  -1.458   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.412  -0.764   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.694  -1.627   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.588  -3.169   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.183  -3.861   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.840  -3.062   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.346  -3.814   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.530  -5.411   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.873  -6.203   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.198  -5.415   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.541  -6.169   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.728  -4.308   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.755  -2.559   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.306   0.410   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.503   1.938   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.081   1.345   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11   24   25                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17   19   23   24                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21                                                            
CONECT   23   18    8                                                       
CONECT   24   18   10                                                       
CONECT   25   10   26   27                                                  
CONECT   26   25   27                                                       
CONECT   27   26    2   25                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₂O₇

Average Mass

364.3090 Da

Monoisotopic Mass

364.05830 Da

IUPAC Name

(1S,2R,4S,12R,15S)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1^{1,6}.1^{12,16}.0^{2,4}.0^{10,24}.0^{20,23}]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one

Traditional Name

(1S,2R,4S,12R,15S)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1^{1,6}.1^{12,16}.0^{2,4}.0^{10,24}.0^{20,23}]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one

CAS Registry Number

Not Available

SMILES

O[C@H]1C=C[C@]23OC4=C5C(=C(O)C=C4)C(=O)[C@H]4O[C@H]4[C@@]5(OC4=CC=CC1=C24)O3

InChI Identifier

InChI=1S/C20H12O7/c21-9-6-7-19-14-8(9)2-1-3-11(14)26-20(27-19)15-12(25-19)5-4-10(22)13(15)16(23)17-18(20)24-17/h1-7,9,17-18,21-22H/t9-,17+,18+,19+,20-/m0/s1

InChI Key

OBZXRUYSZXAANO-NDMITINESA-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
Preussia isomera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Naphthalene
Tetralin
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Ketal
Vinylogous acid
Ketone
Secondary alcohol
Acetal
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Alcohol
Aldehyde
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	3.34	ChemAxon
pKa (Strongest Acidic)	8.68	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.75 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.07 m³·mol⁻¹	ChemAxon
Polarizability	34.52 Å³	ChemAxon
Number of Rings	7	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

C00034170

Chemspider ID

8559583

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10384141

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Macias-Rubalcava ML, Hernandez-Bautista BE, Jimenez-Estrada M, Gonzalez MC, Glenn AE, Hanlin RT, Hernandez-Ortega S, Saucedo-Garcia A, Muria-Gonzalez JM, Anaya AL: Naphthoquinone spiroketal with allelochemical activity from the newly discovered endophytic fungus Edenia gomezpompae. Phytochemistry. 2008 Mar;69(5):1185-96. doi: 10.1016/j.phytochem.2007.12.006. Epub 2008 Jan 29. [PubMed:18234248 ]
Dong JY, Wang LM, Song HC, Shen KZ, Zhou YP, Wang L, Zhang KQ: Colomitides A and B: novel ketals with an unusual 2,7-dioxabicyclo[3.2.1]octane ring system from the aquatic fungus YMF 1.01029. Chem Biodivers. 2009 Aug;6(8):1216-23. doi: 10.1002/cbdv.200800184. [PubMed:19697340 ]
Macias-Rubalcava ML, Ruiz-Velasco Sobrino ME, Melendez-Gonzalez C, Hernandez-Ortega S: Naphthoquinone spiroketals and organic extracts from the endophytic fungus Edenia gomezpompae as potential herbicides. J Agric Food Chem. 2014 Apr 23;62(16):3553-62. doi: 10.1021/jf500965k. Epub 2014 Apr 11. [PubMed:24689520 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one (NP0216776)

MOL for NP0216776 ((1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one)

3D MOL for NP0216776 ((1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one)

3D SDF for NP0216776 ((1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one)

3D-SDF for NP0216776 ((1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one)

PDB for NP0216776 ((1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one)

3D PDB for NP0216776 ((1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one)

SMILES for NP0216776 ((1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one)

INCHI for NP0216776 ((1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one)

Structure for NP0216776 ((1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one)

3D Structure for NP0216776 ((1s,2r,4s,12r,15s)-7,15-dihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]tetracosa-6,8,10(24),13,16(23),17,19-heptaen-5-one)