NP-MRD: Showing NP-Card for tortuosene B (NP0042830)

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Record Information

Version

1.0

Created at

2021-06-21 00:23:59 UTC

Updated at

2021-06-30 00:18:09 UTC

NP-MRD ID

NP0042830

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tortuosene B

Provided By

JEOL Database JEOL Logo

Description

TortBuosen B belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. tortuosene B is found in Sarcophyton tortuosum. It was first documented in 2021 (PMID: 34130356). Based on a literature review a significant number of articles have been published on TortBuosen B (PMID: 34130335) (PMID: 34130218) (PMID: 34130164) (PMID: 34130154) (PMID: 34130152) (PMID: 34130125).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102243D          

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   -0.8188   -1.3600   -3.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6561   -2.1272   -5.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0846   -0.6019   -6.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026   -0.6270   -5.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8009    1.0310   -4.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5665    0.8760   -2.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8163    1.2372   -3.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6571   -4.2744    2.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8893   -2.5309    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554   -3.5001    3.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844   -3.9395    1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5821    0.1615    2.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9269   -0.9270    3.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4581   -1.1872    4.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6042    0.2548    2.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0531   -0.6804    2.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9611    0.8755    0.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886    0.5533    0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
  8 23  1  0  0  0  0
 27 26  1  0  0  0  0
  7  6  1  0  0  0  0
 21 24  1  0  0  0  0
 26 24  1  0  0  0  0
  6  5  2  0  0  0  0
  5  3  1  0  0  0  0
  5 27  1  0  0  0  0
 12 14  1  0  0  0  0
  8  7  1  0  0  0  0
 14 15  1  0  0  0  0
 11 12  1  0  0  0  0
 14 16  1  0  0  0  0
  8  9  2  0  0  0  0
 17 18  2  0  0  0  0
 21 22  1  1  0  0  0
  9 17  1  0  0  0  0
 12 13  1  1  0  0  0
 11 10  1  0  0  0  0
  7 32  1  1  0  0  0
 17 19  1  0  0  0  0
 24 25  2  0  0  0  0
 12  7  1  0  0  0  0
  3  4  2  0  0  0  0
 23 21  1  0  0  0  0
  3  2  1  0  0  0  0
  9 10  1  0  0  0  0
  2  1  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
  6 31  1  0  0  0  0
 27 54  1  0  0  0  0
 27 55  1  0  0  0  0
 19 45  1  0  0  0  0
 19 46  1  0  0  0  0
 20 47  1  0  0  0  0
 20 48  1  0  0  0  0
 26 52  1  0  0  0  0
 26 53  1  0  0  0  0
 14 38  1  6  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
 15 41  1  0  0  0  0
 16 42  1  0  0  0  0
 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 22 49  1  0  0  0  0
 22 50  1  0  0  0  0
 22 51  1  0  0  0  0
 13 37  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042830

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1(C([H])([H])C([H])([H])C2=C3O[C@](C(=O)C([H])([H])C([H])([H])\C(=C([H])/[C@]13[H])C(=O)OC([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C2=O)C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O6/c1-12(2)21(25)10-7-14-16(22)8-9-20(3)17(23)6-5-13(19(24)26-4)11-15(21)18(14)27-20/h11-12,15,25H,5-10H2,1-4H3/b13-11+/t15-,20+,21+/m0/s1

> <INCHI_KEY>
FXFJOVYKAZVEJS-IMOYLNSISA-N

> <FORMULA>
C21H28O6

> <MOLECULAR_WEIGHT>
376.449

> <EXACT_MASS>
376.188588622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
39.94491860593744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2R,9R,13E)-2-hydroxy-9-methyl-6,10-dioxo-2-(propan-2-yl)-16-oxatricyclo[7.5.2.0^{5,15}]hexadeca-5(15),13-diene-13-carboxylate

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
2.357197854333333

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.260759183257743

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.499976157719556

> <JCHEM_PKA_STRONGEST_BASIC>
-3.175727153444937

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
101.04669999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2R,9R,13E)-2-hydroxy-2-isopropyl-9-methyl-6,10-dioxo-16-oxatricyclo[7.5.2.0^{5,15}]hexadeca-5(15),13-diene-13-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -5.1351   -1.2779    0.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7780   -0.8383    0.5096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0319   -1.4978   -0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4422   -2.3694   -1.1630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6225   -0.9902   -0.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752   -1.5501   -1.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6784   -1.1773   -1.5278 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5654   -1.8818   -0.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -2.9325   -0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3652   -3.5330   -2.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786   -2.9353   -3.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468   -1.4250   -3.0157 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3950   -0.7365   -3.2385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1457   -0.8463   -4.0814 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6148   -1.0640   -5.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1099    0.6586   -3.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3496   -3.5412    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -4.1809   -0.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454   -3.3624    1.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8131   -3.2144    2.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2560   -1.7836    1.9065 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8330   -0.8929    3.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6937   -1.1802    0.6857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2879   -1.7985    2.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9030   -2.8453    2.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0649   -0.4905    2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2234    0.0633    0.6032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6393   -0.7006    1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1830   -2.3379    0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6447   -1.0943   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1589   -2.3548   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8131   -0.1009   -1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3755   -3.4064   -2.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1862   -4.6137   -2.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7876   -3.1363   -4.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271   -3.4768   -3.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0380   -0.9995   -2.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188   -1.3600   -3.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6561   -2.1272   -5.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0846   -0.6019   -6.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026   -0.6270   -5.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8009    1.0310   -4.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5665    0.8760   -2.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8163    1.2372   -3.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6571   -4.2744    2.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8893   -2.5309    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554   -3.5001    3.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844   -3.9395    1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5821    0.1615    2.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9269   -0.9270    3.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4581   -1.1872    4.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6042    0.2548    2.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0531   -0.6804    2.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9611    0.8755    0.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886    0.5533    0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0
 21 20  1  0
  8 23  1  0
 27 26  1  0
  7  6  1  0
 21 24  1  0
 26 24  1  0
  6  5  2  0
  5  3  1  0
  5 27  1  0
 12 14  1  0
  8  7  1  0
 14 15  1  0
 11 12  1  0
 14 16  1  0
  8  9  2  0
 17 18  2  0
 21 22  1  1
  9 17  1  0
 12 13  1  1
 11 10  1  0
  7 32  1  1
 17 19  1  0
 24 25  2  0
 12  7  1  0
  3  4  2  0
 23 21  1  0
  3  2  1  0
  9 10  1  0
  2  1  1  0
 11 35  1  0
 11 36  1  0
 10 33  1  0
 10 34  1  0
  6 31  1  0
 27 54  1  0
 27 55  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 26 52  1  0
 26 53  1  0
 14 38  1  6
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 13 37  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.135  -1.278   0.577  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.778  -0.838   0.510  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.032  -1.498  -0.411  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.442  -2.369  -1.163  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.623  -0.990  -0.398  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.775  -1.550  -1.287  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.678  -1.177  -1.528  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.565  -1.882  -0.497  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.342  -2.933  -0.831  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.365  -3.533  -2.216  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.379  -2.935  -3.222  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.147  -1.425  -3.016  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.395  -0.737  -3.239  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.146  -0.846  -4.081  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.615  -1.064  -5.530  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.110   0.659  -3.894  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.350  -3.541   0.098  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.292  -4.181  -0.376  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.245  -3.362   1.594  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.813  -3.214   2.083  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.256  -1.784   1.907  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.833  -0.893   3.026  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.694  -1.180   0.686  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.288  -1.799   2.089  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.903  -2.845   2.320  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.065  -0.491   2.016  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.223   0.063   0.603  0.00  0.00           C+0
HETATM   28  H   UNK     0      -5.639  -0.701   1.357  0.00  0.00           H+0
HETATM   29  H   UNK     0      -5.183  -2.338   0.846  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.645  -1.094  -0.374  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.159  -2.355  -1.916  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.813  -0.101  -1.360  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.376  -3.406  -2.628  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.186  -4.614  -2.153  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.788  -3.136  -4.218  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.427  -3.477  -3.159  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.038  -1.000  -2.558  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.819  -1.360  -3.987  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.656  -2.127  -5.783  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.085  -0.602  -6.236  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.603  -0.627  -5.708  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.801   1.031  -4.658  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.567   0.876  -2.924  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.816   1.237  -3.973  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.657  -4.274   2.045  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.889  -2.531   1.893  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.755  -3.500   3.142  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.184  -3.939   1.549  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.582   0.162   2.865  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.927  -0.927   3.050  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.458  -1.187   4.013  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.604   0.255   2.670  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.053  -0.680   2.453  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.961   0.876   0.607  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.289   0.553   0.316  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5    6    3   27                                                  
CONECT    6    7    5   31                                                  
CONECT    7    6    8   32   12                                             
CONECT    8   23    7    9                                                  
CONECT    9    8   17   10                                                  
CONECT   10   11    9   33   34                                             
CONECT   11   12   10   35   36                                             
CONECT   12   14   11   13    7                                             
CONECT   13   12   37                                                       
CONECT   14   12   15   16   38                                             
CONECT   15   14   39   40   41                                             
CONECT   16   14   42   43   44                                             
CONECT   17   18    9   19                                                  
CONECT   18   17                                                            
CONECT   19   20   17   45   46                                             
CONECT   20   19   21   47   48                                             
CONECT   21   20   24   22   23                                             
CONECT   22   21   49   50   51                                             
CONECT   23    8   21                                                       
CONECT   24   21   26   25                                                  
CONECT   25   24                                                            
CONECT   26   27   24   52   53                                             
CONECT   27   26    5   54   55                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33   10                                                            
CONECT   34   10                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   13                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
CONECT   41   15                                                            
CONECT   42   16                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   19                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   20                                                            
CONECT   49   22                                                            
CONECT   50   22                                                            
CONECT   51   22                                                            
CONECT   52   26                                                            
CONECT   53   26                                                            
CONECT   54   27                                                            
CONECT   55   27                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
   -5.1351   -1.2779    0.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7780   -0.8383    0.5096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0319   -1.4978   -0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4422   -2.3694   -1.1630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6225   -0.9902   -0.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752   -1.5501   -1.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6784   -1.1773   -1.5278 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5654   -1.8818   -0.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -2.9325   -0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3652   -3.5330   -2.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786   -2.9353   -3.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468   -1.4250   -3.0157 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3950   -0.7365   -3.2385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1457   -0.8463   -4.0814 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6148   -1.0640   -5.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1099    0.6586   -3.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3496   -3.5412    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -4.1809   -0.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454   -3.3624    1.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8131   -3.2144    2.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2560   -1.7836    1.9065 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8330   -0.8929    3.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6937   -1.1802    0.6857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2879   -1.7985    2.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9030   -2.8453    2.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0649   -0.4905    2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2234    0.0633    0.6032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6393   -0.7006    1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1830   -2.3379    0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6447   -1.0943   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1589   -2.3548   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8131   -0.1009   -1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3755   -3.4064   -2.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1862   -4.6137   -2.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7876   -3.1363   -4.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271   -3.4768   -3.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0380   -0.9995   -2.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188   -1.3600   -3.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6561   -2.1272   -5.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0846   -0.6019   -6.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026   -0.6270   -5.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8009    1.0310   -4.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5665    0.8760   -2.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8163    1.2372   -3.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6571   -4.2744    2.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8893   -2.5309    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554   -3.5001    3.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844   -3.9395    1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5821    0.1615    2.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9269   -0.9270    3.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4581   -1.1872    4.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6042    0.2548    2.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0531   -0.6804    2.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9611    0.8755    0.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886    0.5533    0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0
 21 20  1  0
  8 23  1  0
 27 26  1  0
  7  6  1  0
 21 24  1  0
 26 24  1  0
  6  5  2  0
  5  3  1  0
  5 27  1  0
 12 14  1  0
  8  7  1  0
 14 15  1  0
 11 12  1  0
 14 16  1  0
  8  9  2  0
 17 18  2  0
 21 22  1  1
  9 17  1  0
 12 13  1  1
 11 10  1  0
  7 32  1  1
 17 19  1  0
 24 25  2  0
 12  7  1  0
  3  4  2  0
 23 21  1  0
  3  2  1  0
  9 10  1  0
  2  1  1  0
 11 35  1  0
 11 36  1  0
 10 33  1  0
 10 34  1  0
  6 31  1  0
 27 54  1  0
 27 55  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 26 52  1  0
 26 53  1  0
 14 38  1  6
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 13 37  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₆

Average Mass

376.4490 Da

Monoisotopic Mass

376.18859 Da

IUPAC Name

methyl (1R,2R,9R,13E)-2-hydroxy-9-methyl-6,10-dioxo-2-(propan-2-yl)-16-oxatricyclo[7.5.2.0^{5,15}]hexadeca-5(15),13-diene-13-carboxylate

Traditional Name

methyl (1R,2R,9R,13E)-2-hydroxy-2-isopropyl-9-methyl-6,10-dioxo-16-oxatricyclo[7.5.2.0^{5,15}]hexadeca-5(15),13-diene-13-carboxylate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1(C([H])([H])C([H])([H])C2=C3O[C@](C(=O)C([H])([H])C([H])([H])\C(=C([H])/[C@]13[H])C(=O)OC([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C2=O)C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H28O6/c1-12(2)21(25)10-7-14-16(22)8-9-20(3)17(23)6-5-13(19(24)26-4)11-15(21)18(14)27-20/h11-12,15,25H,5-10H2,1-4H3/b13-11+/t15-,20+,21+/m0/s1

InChI Key

FXFJOVYKAZVEJS-IMOYLNSISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Sarcophyton tortuosum	JEOL database	Lin, K.-H., et al, Org. Lett. 16, 1314 (2014)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Tertiary alcohol
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carbonyl group
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.94	ALOGPS
logP	2.36	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	5.5	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.05 m³·mol⁻¹	ChemAxon
Polarizability	39.94 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

32674810

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102232568

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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Li N, Yamamoto G, Fuji H, Kisseleva T: Interleukin-17 in Liver Disease Pathogenesis. Semin Liver Dis. 2021 Jun 15. doi: 10.1055/s-0041-1730926. [PubMed:34130335 ]
Narita K, Suganuma K, Murata T, Kondo R, Satoh H, Watanabe K, Sasaki K, Inoue N, Yoshimura Y: Synthesis and evaluation of trypanocidal activity of derivatives of naturally occurring 2,5-diphenyloxazoles. Bioorg Med Chem. 2021 Jul 15;42:116253. doi: 10.1016/j.bmc.2021.116253. Epub 2021 Jun 12. [PubMed:34130218 ]
Aparicio JD, Espindola D, Montesinos VN, Litter MI, Donati E, Benimeli CS, Polti MA: Evaluation of the sequential coupling of a bacterial treatment with a physicochemical process for the remediation of wastewater containing Cr and organic pollutants. J Hazard Mater. 2021 Jun 6;418:126307. doi: 10.1016/j.jhazmat.2021.126307. [PubMed:34130164 ]
Pandolfi EC, Hunt TJ, Goldsmith S, Hurlbut K, Silber SJ, Clark AT: Generation of three human induced pluripotent stem cell sublines (UCLAi005-A, UCLAi005-B and UCLAi005-C) for reproductive science research. Stem Cell Res. 2021 Jul;54:102409. doi: 10.1016/j.scr.2021.102409. Epub 2021 Jun 8. [PubMed:34130154 ]
Ahmadi TS, Mousavi Gargari SL, Talei D: Anti-flagellin IgY antibodies protect against Pseudomonas aeruginosa infection in both acute pneumonia and burn wound murine models in a non-type-specific mode. Mol Immunol. 2021 Aug;136:118-127. doi: 10.1016/j.molimm.2021.06.002. Epub 2021 Jun 12. [PubMed:34130152 ]
Thilo FJ, Hahn S, Halfens RJ, Heckemann B, Schols JM: Facilitating the use of personal safety alerting device with older adults: The views, experiences and roles of relatives and health care professionals. Geriatr Nurs. 2021 Jul-Aug;42(4):935-942. doi: 10.1016/j.gerinurse.2021.05.005. Epub 2021 Jun 12. [PubMed:34130125 ]
de la Fourniere S, Paoletta MS, Guillemi EC, Sarmiento NF, Donati PA, Wilkowsky SE, Farber MD: Development of highly sensitive one step-PCR tests for improved detection of B. bigemina and B. bovis. Vet Parasitol. 2021 Aug;296:109493. doi: 10.1016/j.vetpar.2021.109493. Epub 2021 Jun 8. [PubMed:34130095 ]
Katayoshi T, Nakajo T, Tsuji-Naito K: Restoring NAD(+) by NAMPT is essential for the SIRT1/p53-mediated survival of UVA- and UVB-irradiated epidermal keratinocytes. J Photochem Photobiol B. 2021 Aug;221:112238. doi: 10.1016/j.jphotobiol.2021.112238. Epub 2021 Jun 12. [PubMed:34130091 ]
Paidi SK, Raj P, Bordett R, Zhang C, Karandikar SH, Pandey R, Barman I: Raman and quantitative phase imaging allow morpho-molecular recognition of malignancy and stages of B-cell acute lymphoblastic leukemia. Biosens Bioelectron. 2021 Oct 15;190:113403. doi: 10.1016/j.bios.2021.113403. Epub 2021 Jun 12. [PubMed:34130086 ]
Alves O, Calado L, Panizio RM, Goncalves M, Monteiro E, Brito P: Techno-economic study for a gasification plant processing residues of sewage sludge and solid recovered fuels. Waste Manag. 2021 Jul 15;131:148-162. doi: 10.1016/j.wasman.2021.05.026. Epub 2021 Jun 12. [PubMed:34130077 ]
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Showing NP-Card for tortuosene B (NP0042830)

MOL for NP0042830 (tortuosene B)

3D MOL for NP0042830 (tortuosene B)

3D SDF for NP0042830 (tortuosene B)

3D-SDF for NP0042830 (tortuosene B)

PDB for NP0042830 (tortuosene B)

3D PDB for NP0042830 (tortuosene B)

SMILES for NP0042830 (tortuosene B)

INCHI for NP0042830 (tortuosene B)

Structure for NP0042830 (tortuosene B)

3D Structure for NP0042830 (tortuosene B)