NP-MRD: Showing NP-Card for Tufnelactone A (NP0333192)

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Record Information

Version

2.0

Created at

2024-05-12 08:24:14 UTC

Updated at

2024-09-03 04:21:32 UTC

NP-MRD ID

NP0333192

Natural Product DOI

https://doi.org/10.57994/2517

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tufnelactone A

Description

Tufnelactone A 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. Tufnelactone A was first documented in 2022 (PMID: 35704432). Based on a literature review very few articles have been published on Tufnelactone A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01242311002D          

 54 59  0  0  1  0            999 V2000
    2.2861   -2.9360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7383   -2.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9988   -1.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4511   -0.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6429   -1.0852    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0866   -1.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6647   -1.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3821   -1.7610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0952   -0.4682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2059   -1.2363    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3556    0.3146    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4239    0.7929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9802    0.1837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3105    0.9397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5727   -0.5337    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9902   -1.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152   -1.2395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2327   -1.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0577   -1.9452    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5473   -2.6093    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7415   -2.7864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3301   -2.3488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9471   -2.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7299   -2.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8957   -1.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6785   -1.5675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3468   -3.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1810   -3.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3981   -4.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7812   -3.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3904   -3.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9984   -3.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3814   -3.4174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5986   -3.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4327   -4.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -4.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0330   -4.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1988   -3.3906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841   -5.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0497   -5.0337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6780   -1.2128    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5379   -1.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3243   -1.5238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2775   -0.4916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2227   -0.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8052    0.1894    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2127    0.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0377    0.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1638    0.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0407   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5196    0.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0674   -0.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8069   -1.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  5  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  0  0  0  0
 13 14  1  1  0  0  0
 15 13  1  0  0  0  0
  9 15  1  0  0  0  0
 15  7  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 20 19  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 33 32  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 36 39  2  0  0  0  0
 35 40  2  0  0  0  0
 19 41  1  6  0  0  0
 19 42  1  0  0  0  0
 42 43  1  0  0  0  0
 22 43  1  1  0  0  0
 42 44  2  0  0  0  0
 17 45  1  0  0  0  0
 46 45  1  0  0  0  0
 13 46  1  0  0  0  0
 46 47  1  1  0  0  0
 47 48  1  0  0  0  0
 11 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
  3 54  1  0  0  0  0
M  END


  Mrv2104 01242311002D          

 54 59  0  0  1  0            999 V2000
    2.2861   -2.9360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7383   -2.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9988   -1.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4511   -0.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6429   -1.0852    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0866   -1.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6647   -1.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3821   -1.7610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0952   -0.4682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2059   -1.2363    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3556    0.3146    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4239    0.7929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9802    0.1837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3105    0.9397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5727   -0.5337    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9902   -1.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152   -1.2395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2327   -1.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0577   -1.9452    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5473   -2.6093    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7415   -2.7864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3301   -2.3488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9471   -2.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7299   -2.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8957   -1.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6785   -1.5675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3468   -3.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1810   -3.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3981   -4.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7812   -3.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3904   -3.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9984   -3.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3814   -3.4174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5986   -3.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4327   -4.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -4.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0330   -4.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1988   -3.3906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841   -5.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0497   -5.0337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6780   -1.2128    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5379   -1.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3243   -1.5238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2775   -0.4916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2227   -0.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8052    0.1894    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2127    0.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0377    0.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1638    0.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0407   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5196    0.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0674   -0.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8069   -1.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  5  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  0  0  0  0
 13 14  1  1  0  0  0
 15 13  1  0  0  0  0
  9 15  1  0  0  0  0
 15  7  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 20 19  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 33 32  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 36 39  2  0  0  0  0
 35 40  2  0  0  0  0
 19 41  1  6  0  0  0
 19 42  1  0  0  0  0
 42 43  1  0  0  0  0
 22 43  1  1  0  0  0
 42 44  2  0  0  0  0
 17 45  1  0  0  0  0
 46 45  1  0  0  0  0
 13 46  1  0  0  0  0
 46 47  1  1  0  0  0
 47 48  1  0  0  0  0
 11 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
  3 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CN2C[C@@H](CO)[C@]3(O)O[C@H]4C\C(C)=C\CC\C(CO)=C\[C@H]5OC(=O)[C@]3(C2)[C@]45[H])C(=O)O[C@@H]2\C=C(CO)\CC\C=C(C)\C[C@H](OC(=O)C(=C)CO)[C@@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C38H51NO12/c1-21-6-4-8-24(17-41)12-29-32(28(10-21)48-34(44)23(3)16-40)27(35(45)49-29)15-39-14-26(19-43)38(47)37(20-39)33-30(50-36(37)46)13-25(18-42)9-5-7-22(2)11-31(33)51-38/h6-7,12-13,26-33,40-43,47H,3-5,8-11,14-20H2,1-2H3/b21-6+,22-7+,24-12-,25-13-/t26-,27-,28-,29+,30+,31-,32+,33-,37-,38-/m0/s1

> <INCHI_KEY>
FUPNQSIRYTXGJK-STBIJNLUSA-N

> <FORMULA>
C38H51NO12

> <MOLECULAR_WEIGHT>
713.821

> <EXACT_MASS>
713.341126086

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
75.05641336143503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,3aR,4S,11aR)-3-{[(1S,3S,4S,8S,11R,12Z,16E,19R)-3-hydroxy-4,13-bis(hydroxymethyl)-17-methyl-9-oxo-2,10-dioxa-6-azatetracyclo[9.7.1.0^{3,8}.0^{8,19}]nonadeca-12,16-dien-6-yl]methyl}-10-(hydroxymethyl)-6-methyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

> <JCHEM_LOGP>
0.8789070536765681

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.504761132995753

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.090150899003792

> <JCHEM_PKA_STRONGEST_BASIC>
9.108481841156403

> <JCHEM_POLAR_SURFACE_AREA>
192.51999999999998

> <JCHEM_REFRACTIVITY>
186.70650000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aR,4S,11aR)-3-{[(1S,3S,4S,8S,11R,12Z,16E,19R)-3-hydroxy-4,13-bis(hydroxymethyl)-17-methyl-9-oxo-2,10-dioxa-6-azatetracyclo[9.7.1.0^{3,8}.0^{8,19}]nonadeca-12,16-dien-6-yl]methyl}-10-(hydroxymethyl)-6-methyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JAN-23         0                                  
HETATM    1  O   UNK     0       4.267  -5.481   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.245  -4.329   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.731  -2.868   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.709  -1.716   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.200  -2.026   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.162  -3.163   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.241  -2.527   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.580  -3.287   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.178  -0.874   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      -0.384  -2.308   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       0.664   0.587   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.791   1.480   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.830   0.343   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.446   1.754   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.069  -0.996   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.848  -2.324   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -3.388  -2.314   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -4.168  -3.642   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.708  -3.631   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.622  -4.871   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      -5.118  -5.201   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      -8.083  -4.384   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.235  -5.407   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.696  -4.921   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.005  -3.412   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0     -12.467  -2.926   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0     -11.847  -5.943   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -11.538  -7.452   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -10.077  -7.938   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.925  -6.915   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.062  -5.877   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -7.464  -7.402   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.312  -6.379   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.851  -6.865   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.541  -8.374   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.080  -8.860   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.928  -7.838   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -2.238  -6.329   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.770 -10.369   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -5.693  -9.396   0.000  0.00  0.00           O+0
HETATM   41  H   UNK     0      -4.999  -2.264   0.000  0.00  0.00           H+0
HETATM   42  C   UNK     0      -6.604  -2.379   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -8.072  -2.845   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -6.118  -0.918   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -4.149  -0.975   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -3.370   0.354   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -4.130   1.693   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -5.670   1.703   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       2.172   0.897   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       3.195  -0.255   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       1.943  -1.151   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.703   0.055   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       5.726  -1.097   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       5.240  -2.558   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   54                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7                                                            
CONECT    9    5   10   11   15                                             
CONECT   10    9                                                            
CONECT   11    9   12   49                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   46                                             
CONECT   14   13                                                            
CONECT   15   13    9    7   16                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   45                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   41   42                                             
CONECT   20   19   21   22   33                                             
CONECT   21   20                                                            
CONECT   22   20   23   43                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   20   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   36                                                            
CONECT   40   35                                                            
CONECT   41   19                                                            
CONECT   42   19   43   44                                                  
CONECT   43   42   22                                                       
CONECT   44   42                                                            
CONECT   45   17   46                                                       
CONECT   46   45   13   47                                                  
CONECT   47   46   48                                                       
CONECT   48   47                                                            
CONECT   49   11   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53    3                                                       
MASTER        0    0    0    0    0    0    0    0   54    0  118    0
END

View in JSmol

Synonyms

Value	Source
(3R,3AR,4S,11ar)-3-{[(1S,3R,4S,8R,11R,12Z,16Z,19R)-3-hydroxy-4,13-bis(hydroxymethyl)-17-methyl-9-oxo-2,10-dioxa-6-azatetracyclo[9.7.1.0,.0,]nonadeca-12,16-dien-6-yl]methyl}-10-(hydroxymethyl)-6-methyl-2-oxo-3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl 2-(hydroxymethyl)prop-2-enoic acid	Generator

Chemical Formula

C₃₈H₅₁NO₁₂

Average Mass

713.8210 Da

Monoisotopic Mass

713.34113 Da

IUPAC Name

(3R,3aR,4S,11aR)-3-{[(1S,3S,4S,8S,11R,12Z,16E,19R)-3-hydroxy-4,13-bis(hydroxymethyl)-17-methyl-9-oxo-2,10-dioxa-6-azatetracyclo[9.7.1.0^{3,8}.0^{8,19}]nonadeca-12,16-dien-6-yl]methyl}-10-(hydroxymethyl)-6-methyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

Traditional Name

(3R,3aR,4S,11aR)-3-{[(1S,3S,4S,8S,11R,12Z,16E,19R)-3-hydroxy-4,13-bis(hydroxymethyl)-17-methyl-9-oxo-2,10-dioxa-6-azatetracyclo[9.7.1.0^{3,8}.0^{8,19}]nonadeca-12,16-dien-6-yl]methyl}-10-(hydroxymethyl)-6-methyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CN2C[C@@H](CO)[C@]3(O)O[C@H]4C\C(C)=C\CC\C(CO)=C\[C@H]5OC(=O)[C@]3(C2)[C@]45[H])C(=O)O[C@@H]2\C=C(CO)\CC\C=C(C)\C[C@H](OC(=O)C(=C)CO)[C@@]12[H]

InChI Identifier

InChI=1S/C38H51NO12/c1-21-6-4-8-24(17-41)12-29-32(28(10-21)48-34(44)23(3)16-40)27(35(45)49-29)15-39-14-26(19-43)38(47)37(20-39)33-30(50-36(37)46)13-25(18-42)9-5-7-22(2)11-31(33)51-38/h6-7,12-13,26-33,40-43,47H,3-5,8-11,14-20H2,1-2H3/b21-6+,22-7+,24-12-,25-13-/t26-,27-,28-,29+,30+,31-,32+,33-,37-,38-/m0/s1

InChI Key

FUPNQSIRYTXGJK-STBIJNLUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C3D6O, experimental)	opatz@uni-mainz.de	Not Available	Not Available	2024-05-12	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
tufnelliae		Not Available

Chemical Taxonomy

Description

This compound 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
Farsesane sesquiterpenoid
Sesquiterpenoid
Germacrane sesquiterpenoid
Furanoid amino acid
Azaspirodecane
Tricarboxylic acid or derivatives
Piperidinecarboxylic acid
Furofuran
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Piperidine
Hydroxy acid
Hemiketal
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
1,3-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Lactone
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
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	0.88	ChemAxon
pKa (Strongest Acidic)	11.09	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	192.52 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	186.71 m³·mol⁻¹	ChemAxon
Polarizability	75.06 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

168290067

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bitchagno GTM, Schuffler A, Gross J, Krumb M, Tane P, Opatz T: Sesquiterpene Lactones from Vernonia tufnelliae: Structural Characterization and Biological Evaluation. J Nat Prod. 2022 Jul 22;85(7):1681-1690. doi: 10.1021/acs.jnatprod.2c00055. Epub 2022 Jun 15. [PubMed:35704432 ]

Showing NP-Card for Tufnelactone A (NP0333192)

MOL for NP0333192 (Tufnelactone A)

3D MOL for NP0333192 (Tufnelactone A)

3D SDF for NP0333192 (Tufnelactone A)

3D-SDF for NP0333192 (Tufnelactone A)

PDB for NP0333192 (Tufnelactone A)

3D PDB for NP0333192 (Tufnelactone A)

SMILES for NP0333192 (Tufnelactone A)

INCHI for NP0333192 (Tufnelactone A)

Structure for NP0333192 (Tufnelactone A)

3D Structure for NP0333192 (Tufnelactone A)