NP-MRD: Showing NP-Card for Rufesolide D (NP0044075)

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Record Information

Version

1.0

Created at

2021-11-12 23:48:47 UTC

Updated at

2021-11-26 17:45:09 UTC

NP-MRD ID

NP0044075

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rufesolide D

Description

Rufesolide D belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. It was first documented in 2012 (PMID: 22685350). Based on a literature review very few articles have been published on Rufesolide D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100482D          

 28 29  0  0  1  0            999 V2000
    2.4158    0.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7071    1.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    1.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125    2.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8581    1.1649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7527    0.2594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755   -0.3788    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5668    0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.5267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9037   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7178    0.0221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124   -0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5070   -1.7889    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6929   -1.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8173    0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558    0.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -0.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0298   -2.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3211   -1.6553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1352   -1.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2757    1.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0005    1.0714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 23  1  1  0  0  0
 15 24  1  6  0  0  0
 14 25  1  6  0  0  0
 25 26  1  0  0  0  0
 10 27  1  6  0  0  0
 10 28  1  1  0  0  0
M  END

     RDKit          3D

 58 59  0  0  0  0  0  0  0  0999 V2000
   -2.1581    1.9896   -2.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9180    2.0099   -1.8778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1789    3.2691   -1.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5680    4.4147   -2.0801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9940    3.0194   -1.0020 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1040    1.6425   -0.7454 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4619    1.1308   -1.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3320    0.8442    0.0709 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0091    1.7519    1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4358   -0.6012    0.4010 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2735   -1.3318   -0.7747 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4283   -2.0049   -1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6676   -1.1138    1.5482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2346   -1.2783    1.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285   -0.6969    2.2663 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5562   -2.1187    0.4692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5375   -2.9317    1.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212   -3.1367   -0.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0122   -1.4528   -0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6127   -0.0908   -0.5326 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0098   -0.1141   -0.7239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9079    0.3205    0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062    0.7475    1.3136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3422    0.2680    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9341   -0.2575   -1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1849    0.6914    0.9365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7042    1.2327    2.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135    0.9282   -1.4801 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7157    1.0846   -2.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6719    2.9050   -2.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9131    1.5144    0.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4177    0.2140   -1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9137    1.9086   -1.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3641    1.1809   -0.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540    1.3974    1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9498    1.9067    1.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8061    2.7560    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5285   -0.7924    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2563   -1.2727   -1.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7946   -2.6917   -0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2771   -2.5105   -2.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999   -2.1428    1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0035   -0.5290    2.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1113   -3.8465    1.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3316   -3.1912    0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9714   -2.2615    1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9177   -3.5622    0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8459   -2.1205   -1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6766   -1.3978   -1.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4642    0.3257    0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5269    0.5266   -1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1418   -0.7041   -1.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6386   -1.0972   -0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2588    0.6391    0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1591    0.5136    2.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1022    2.1584    2.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5899    1.5637    2.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3977    0.3945   -2.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 24  2  0
 24 25  1  0
 24 22  1  0
 22 23  2  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 16  1  0
 16 14  1  0
 14 15  2  0
 14 13  1  0
 13 10  1  0
 10  8  1  0
  8  7  1  0
  7  6  1  0
  6 28  1  0
 28  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  8  9  1  0
 10 11  1  0
 11 12  1  0
 16 17  1  0
 16 18  1  6
 28 20  1  0
  5  6  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
 26 54  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 20 50  1  1
 19 48  1  0
 19 49  1  0
 13 42  1  0
 13 43  1  0
 10 38  1  1
  8 34  1  6
  7 32  1  0
  7 33  1  0
  6 31  1  1
 28 58  1  6
  1 29  1  0
  1 30  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
M  END


  Mrv1652311132100482D          

 28 29  0  0  1  0            999 V2000
    2.4158    0.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7071    1.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    1.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125    2.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8581    1.1649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7527    0.2594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755   -0.3788    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5668    0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.5267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9037   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7178    0.0221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124   -0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5070   -1.7889    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6929   -1.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8173    0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558    0.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -0.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0298   -2.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3211   -1.6553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1352   -1.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2757    1.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0005    1.0714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 23  1  1  0  0  0
 15 24  1  6  0  0  0
 14 25  1  6  0  0  0
 25 26  1  0  0  0  0
 10 27  1  6  0  0  0
 10 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044075

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1CC(=O)[C@](C)(O)C[C@H](OC(=O)C(\C)=C/C)[C@@H]2[C@@H](C[C@H]1C)OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O7/c1-7-11(2)19(23)28-16-10-21(5,25)17(22)9-14(26-6)12(3)8-15-18(16)13(4)20(24)27-15/h7,12,14-16,18,25H,4,8-10H2,1-3,5-6H3/b11-7-/t12-,14-,15-,16+,18+,21-/m1/s1

> <INCHI_KEY>
SRKXZENOIPHTOL-SGQSMADDSA-N

> <FORMULA>
C21H30O7

> <MOLECULAR_WEIGHT>
394.464

> <EXACT_MASS>
394.199153306

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.983158127560806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,4S,6R,9R,10R,11aR)-6-hydroxy-9-methoxy-6,10-dimethyl-3-methylidene-2,7-dioxo-dodecahydrocyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
2.8521318883333335

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.71138245684997

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.184337077839885

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5927434009483594

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
102.2453

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,4S,6R,9R,10R,11aR)-6-hydroxy-9-methoxy-6,10-dimethyl-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       4.509   1.426   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.053   2.867   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.573   3.116   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.117   4.557   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.549   1.925   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.068   2.174   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.005   0.484   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.981  -0.707   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.525   0.734   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.044   0.983   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.020  -0.208   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.540   0.041   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.476  -1.649   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.957  -1.898   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.413  -3.339   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.893  -3.589   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.917  -2.397   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.461  -0.957   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.259   0.006   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.331   1.544   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.972  -0.840   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.531  -0.296   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.379  -2.326   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.389  -4.531   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.933  -3.090   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.452  -2.840   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.848   2.511   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.201   2.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   27   28                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17    8   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   17                                                       
CONECT   24   15                                                            
CONECT   25   14   26                                                       
CONECT   26   25                                                            
CONECT   27   10                                                            
CONECT   28   10                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₇

Average Mass

394.4640 Da

Monoisotopic Mass

394.19915 Da

IUPAC Name

(3aS,4S,6R,9R,10R,11aR)-6-hydroxy-9-methoxy-6,10-dimethyl-3-methylidene-2,7-dioxo-dodecahydrocyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(3aS,4S,6R,9R,10R,11aR)-6-hydroxy-9-methoxy-6,10-dimethyl-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CO[C@@H]1CC(=O)[C@](C)(O)C[C@H](OC(=O)C(\C)=C/C)[C@@H]2[C@@H](C[C@H]1C)OC(=O)C2=C

InChI Identifier

InChI=1S/C21H30O7/c1-7-11(2)19(23)28-16-10-21(5,25)17(22)9-14(26-6)12(3)8-15-18(16)13(4)20(24)27-15/h7,12,14-16,18,25H,4,8-10H2,1-3,5-6H3/b11-7-/t12-,14-,15-,16+,18+,21-/m1/s1

InChI Key

SRKXZENOIPHTOL-SGQSMADDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Piptocoma rufescens

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Fatty acid ester
Acyloin
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Oxolane
Enoate ester
Tertiary alcohol
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
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	1.92	ALOGPS
logP	2.85	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.18	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	102.25 m³·mol⁻¹	ChemAxon
Polarizability	40.98 Å³	ChemAxon
Number of Rings	2	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

57386241

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ren Y, Acuna UM, Jimenez F, Garcia R, Mejia M, Chai H, Gallucci JC, Farnsworth NR, Soejarto DD, Carcache de Blanco EJ, Kinghorn AD: Cytotoxic and NF-kappaB inhibitory sesquiterpene lactones from Piptocoma rufescens. Tetrahedron. 2012 Mar 25;68(12):2671-2678. doi: 10.1016/j.tet.2012.01.061. Epub 2012 Jan 26. [PubMed:22685350 ]

Showing NP-Card for Rufesolide D (NP0044075)

MOL for NP0044075 (Rufesolide D)

3D MOL for NP0044075 (Rufesolide D)

3D SDF for NP0044075 (Rufesolide D)

3D-SDF for NP0044075 (Rufesolide D)

PDB for NP0044075 (Rufesolide D)

3D PDB for NP0044075 (Rufesolide D)

SMILES for NP0044075 (Rufesolide D)

INCHI for NP0044075 (Rufesolide D)

Structure for NP0044075 (Rufesolide D)

3D Structure for NP0044075 (Rufesolide D)