NP-MRD: Showing NP-Card for methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate (NP0212254)

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Record Information

Version

2.0

Created at

2022-09-05 10:52:11 UTC

Updated at

2022-09-05 10:52:11 UTC

NP-MRD ID

NP0212254

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate

Description

Prismatomerin belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate is found in Prismatomeris tetrandra. methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate was first documented in 2007 (PMID: 17784774). Based on a literature review a small amount of articles have been published on prismatomerin (PMID: 17955495) (PMID: 17665951) (PMID: 34533755) (PMID: 34189715).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052212522D          

 27 31  0  0  1  0            999 V2000
   -0.8904   -1.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3264   -1.3580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771   -1.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7165   -2.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0411   -0.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8017   -0.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657    0.4483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1691    0.2609    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8460    0.7326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5037    0.2346    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3286    0.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8266    0.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6452    0.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1432    1.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9618    1.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2824    0.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1010    0.4665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7844   -0.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9658    0.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5680   -0.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3474   -0.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911   -1.0428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334   -0.5448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4728   -1.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7959   -1.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8445   -1.1307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4085   -0.5286    0.0000 C   0  0  2  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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  1  0  0  0
 10 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 25  1  6  0  0  0
  5 26  1  0  0  0  0
 27 26  1  6  0  0  0
  8 27  1  0  0  0  0
 23 27  1  0  0  0  0
M  END

     RDKit          3D

 43 47  0  0  0  0  0  0  0  0999 V2000
    7.4964    0.7566    0.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2006    0.7635    0.2914 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1850   -0.0757    0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4146   -0.8950    1.6114 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -0.0584    0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5392    0.7867   -0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787    0.7921   -1.4067 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7025   -0.5047   -1.6471 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3170   -0.3465   -1.8878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1143    0.1330   -0.6740 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5683   -0.0070   -0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5453    0.7448   -0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9706    0.5323   -0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265    1.6327   -0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0722    1.5153    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7359    0.3110   -0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1033    0.2017    0.1916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9873   -0.7624   -0.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6238   -0.6535   -0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7564   -1.1385    0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7700   -1.4157    1.1883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5525   -1.8652    0.3490 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4680   -0.8865    0.2854 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8255   -0.2905    1.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185   -0.3257    1.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781   -0.9786    0.5982 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7163   -1.3309   -0.3850 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2943    0.9251    0.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5037    1.5201    1.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7240   -0.2113    1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3385    1.4515   -1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -0.9785   -2.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2864    1.1289   -0.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2299    1.5856   -1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2281    2.6019   -0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6857    2.3598    0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7018    0.3941   -0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4966   -1.7130   -0.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0833   -1.5297   -1.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1150    0.1412    2.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6685    0.0607    2.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2628   -1.9427    0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7082   -2.4286   -0.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11 20  1  0
 20 21  2  0
 20 22  1  0
 23 22  1  1
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26  5  1  0
 27  8  1  0
 23 10  1  0
 27 23  1  0
 19 13  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  0
  8 32  1  6
 10 33  1  1
 12 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 24 40  1  0
 25 41  1  0
 26 42  1  1
 27 43  1  6
M  END


  Mrv1652309052212522D          

 27 31  0  0  1  0            999 V2000
   -0.8904   -1.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3264   -1.3580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771   -1.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7165   -2.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0411   -0.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8017   -0.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657    0.4483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1691    0.2609    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8460    0.7326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5037    0.2346    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3286    0.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8266    0.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6452    0.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1432    1.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9618    1.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2824    0.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1010    0.4665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7844   -0.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9658    0.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5680   -0.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3474   -0.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911   -1.0428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334   -0.5448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4728   -1.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7959   -1.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8445   -1.1307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4085   -0.5286    0.0000 C   0  0  2  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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  1  0  0  0
 10 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 25  1  6  0  0  0
  5 26  1  0  0  0  0
 27 26  1  6  0  0  0
  8 27  1  0  0  0  0
 23 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0212254

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H]2O[C@H]3\C(=C\C4=CC=C(O)C=C4)C(=O)O[C@]33C=C[C@H]1[C@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O7/c1-24-17(22)14-9-25-19-15-12(14)6-7-20(15)16(26-19)13(18(23)27-20)8-10-2-4-11(21)5-3-10/h2-9,12,15-16,19,21H,1H3/b13-8-/t12-,15-,16+,19-,20+/m1/s1

> <INCHI_KEY>
CAASUWFDLSGDTI-SRQNPXTGSA-N

> <FORMULA>
C20H16O7

> <MOLECULAR_WEIGHT>
368.341

> <EXACT_MASS>
368.089602855

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
36.959218854079566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,4S,8R,10S,11Z,14S)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0^{1,10}.0^{4,14}]tetradeca-2,5-diene-5-carboxylate

> <JCHEM_LOGP>
2.4426014510000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.338352722721545

> <JCHEM_PKA_STRONGEST_BASIC>
-4.286698340411431

> <JCHEM_POLAR_SURFACE_AREA>
91.29

> <JCHEM_REFRACTIVITY>
92.9524

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,4S,8R,10S,11Z,14S)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0^{1,10}.0^{4,14}]tetradeca-2,5-diene-5-carboxylate

> <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  C   UNK     0      -1.662  -3.659   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.609  -2.535   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.891  -2.885   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.337  -4.358   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.943  -1.761   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.496  -0.287   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.549   0.837   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.049   0.487   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.312   1.368   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.540   0.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.080   0.408   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.010   1.635   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.538   1.444   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.467   2.672   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.995   2.481   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.594   1.062   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      15.122   0.871   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.664  -0.166   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.136   0.025   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.527  -1.066   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.982  -1.571   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.263  -1.947   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.036  -1.017   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.483  -2.491   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.219  -3.371   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.443  -2.111   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.496  -0.987   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13                                                       
CONECT   20   11   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   10   24   27                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    5   27                                                  
CONECT   27   26    8   23                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₆O₇

Average Mass

368.3410 Da

Monoisotopic Mass

368.08960 Da

IUPAC Name

methyl (1S,4S,8R,10S,11Z,14S)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0^{1,10}.0^{4,14}]tetradeca-2,5-diene-5-carboxylate

Traditional Name

methyl (1S,4S,8R,10S,11Z,14S)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0^{1,10}.0^{4,14}]tetradeca-2,5-diene-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H]2O[C@H]3\C(=C\C4=CC=C(O)C=C4)C(=O)O[C@]33C=C[C@H]1[C@H]23

InChI Identifier

InChI=1S/C20H16O7/c1-24-17(22)14-9-25-19-15-12(14)6-7-20(15)16(26-19)13(18(23)27-20)8-10-2-4-11(21)5-3-10/h2-9,12,15-16,19,21H,1H3/b13-8-/t12-,15-,16+,19-,20+/m1/s1

InChI Key

CAASUWFDLSGDTI-SRQNPXTGSA-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
Prismatomeris tetrandra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Iridoid-skeleton
Monoterpenoid
Aromatic monoterpenoid
Furopyran
Furofuran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Pyran
Monosaccharide
Gamma butyrolactone
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tetrahydrofuran
Furan
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.44	ChemAxon
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.95 m³·mol⁻¹	ChemAxon
Polarizability	36.96 Å³	ChemAxon
Number of Rings	5	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

129846269

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stephens PJ, Devlin FJ, Pan JJ: The determination of the absolute configurations of chiral molecules using vibrational circular dichroism (VCD) spectroscopy. Chirality. 2008 May 15;20(5):643-63. doi: 10.1002/chir.20477. [PubMed:17955495 ]
Stephens PJ, Pan JJ, Krohn K: Determination of the absolute configurations of pharmacological natural products via density functional theory calculations of vibrational circular dichroism: the new cytotoxic iridoid prismatomerin. J Org Chem. 2007 Sep 28;72(20):7641-9. doi: 10.1021/jo071183b. Epub 2007 Sep 5. [PubMed:17784774 ]
Krohn K, Gehle D, Dey SK, Nahar N, Mosihuzzaman M, Sultana N, Sohrab MH, Stephens PJ, Pan JJ, Sasse F: Prismatomerin, a new iridoid from Prismatomeris tetrandra. Structure elucidation, determination of absolute configuration, and cytotoxicity. J Nat Prod. 2007 Aug;70(8):1339-43. doi: 10.1021/np070202+. Epub 2007 Aug 1. [PubMed:17665951 ]
Hashim Y, Toume K, Mizukami S, Kitami T, Taniguchi M, Teklemichael AA, Tayama Y, Huy NT, Lami JN, Bodi JM, Hirayama K, Komatsu K: Phenylpropanoid-conjugated iridoid glucosides from leaves of Morinda morindoides. J Nat Med. 2022 Jan;76(1):281-290. doi: 10.1007/s11418-021-01567-1. Epub 2021 Sep 17. [PubMed:34533755 ]
Hashim Y, Toume K, Mizukami S, Ge YW, Taniguchi M, Teklemichael AA, Huy NT, Bodi JM, Hirayama K, Komatsu K: Phenylpropanoid conjugated iridoids with anti-malarial activity from the leaves of Morinda morindoides. J Nat Med. 2021 Sep;75(4):915-925. doi: 10.1007/s11418-021-01541-x. Epub 2021 Jun 29. [PubMed:34189715 ]
LOTUS database [Link]

Showing NP-Card for methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate (NP0212254)

MOL for NP0212254 (methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate)

3D MOL for NP0212254 (methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate)

3D SDF for NP0212254 (methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate)

3D-SDF for NP0212254 (methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate)

PDB for NP0212254 (methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate)

3D PDB for NP0212254 (methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate)

SMILES for NP0212254 (methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate)

INCHI for NP0212254 (methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate)

Structure for NP0212254 (methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate)

3D Structure for NP0212254 (methyl (1s,4s,8r,10s,11z,14s)-11-[(4-hydroxyphenyl)methylidene]-12-oxo-7,9,13-trioxatetracyclo[6.5.1.0¹,¹⁰.0⁴,¹⁴]tetradeca-2,5-diene-5-carboxylate)