NP-MRD: Showing NP-Card for Budlein A (NP0044147)

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Record Information

Version

1.0

Created at

2021-11-12 23:52:39 UTC

Updated at

2021-11-26 17:45:57 UTC

NP-MRD ID

NP0044147

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Budlein A

Description

BUDLEIN A belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Budlein A is found in Aldama bracteata, Aldama excelsa, Centratherum punctatum, Dendroviguiera quinqueradiata, Helianthus schweinitzii, Helianthus tuberosus, Heliomeris multiflora, Lychnophora affinis, Tithonia longiradiata, Viguiera angustifolia, Viguiera buddleiaeformis, Dendroviguiera eriophora, Viguiera eriophora ssp.eriophora, Viguiera linearis, Viguiera robusta, Viguiera schultzii and Dendroviguiera sylvatica. It was first documented in 2007 (PMID: 17320857). Based on a literature review a significant number of articles have been published on BUDLEIN A (PMID: 33022283) (PMID: 32696817) (PMID: 30319413) (PMID: 28879563) (PMID: 28780730) (PMID: 27649126).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100522D          

 27 29  0  0  1  0            999 V2000
   -0.9545   -0.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2015   -1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5371   -2.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069   -1.0949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6204    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8900    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.9049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4337    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887    0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    3.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9060    4.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900   -0.2549    0.0000 C   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  1  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  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  6  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 27  1  6  0  0  0
M  END

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
   -0.8008   -2.3824    2.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2582   -2.0634    0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3326   -2.7615   -0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2091   -3.6392   -0.6418 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6893   -2.2765   -1.1677 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2288   -1.0829   -0.6294 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7005   -1.2786   -0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4869   -0.1969   -0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8380   -0.2622   -1.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8577    0.0255   -0.3550 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0752    1.0773   -0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2566    2.3484   -0.4074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1273    3.1165    0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8795    4.3092   -0.1366 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3699    2.1325    0.9531 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0405    2.8280    2.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1813    1.6200    0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624    0.3229    0.6974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4095   -0.0574   -0.2040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7047   -0.2513    0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0111   -0.0896    1.3742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6928   -0.6385   -0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2991   -0.8222   -2.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9661   -0.8415   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4368   -0.6801    0.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5861   -0.8289    0.6857 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3631    1.1812    1.1792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3960   -3.2829    2.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6864   -1.7996    2.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265   -0.2780   -1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1826   -2.2358   -0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7984    0.4795   -2.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181   -1.2756   -1.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5758   -0.0924    0.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1149    2.6846   -1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8411    2.1407    3.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2050    3.5336    2.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9356    3.4304    2.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3553    1.6200   -0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6423    2.3801    0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8030    0.4196    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0112   -1.4158   -2.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3042   -1.3489   -2.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474    0.1521   -2.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6744   -1.1316   -1.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3021    0.3537    1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9441   -1.4006    1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5248   -0.8930    0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2853   -0.8485    1.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 22  2  0
 22 23  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 13  1  0
 13 14  2  0
 13 12  1  0
 12 11  2  0
 11 27  1  0
 11  8  1  0
  8  7  2  0
  7  6  1  0
  6 26  1  0
 26  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  8  9  1  0
  9 10  1  0
 15 16  1  1
 26 18  1  0
 27 15  1  0
  5  6  1  0
 25 46  1  0
 25 47  1  0
 25 48  1  0
 24 45  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
 18 41  1  1
 17 39  1  0
 17 40  1  0
 12 35  1  0
  7 31  1  0
  6 30  1  6
 26 49  1  1
  1 28  1  0
  1 29  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  END


  Mrv1652311132100522D          

 27 29  0  0  1  0            999 V2000
   -0.9545   -0.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2015   -1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5371   -2.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069   -1.0949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6204    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8900    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.9049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4337    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887    0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    3.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9060    4.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900   -0.2549    0.0000 C   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  1  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  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  6  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044147

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)\C(CO)=C/[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O7/c1-5-10(2)18(23)26-15-8-20(4)16(22)7-13(27-20)12(9-21)6-14-17(15)11(3)19(24)25-14/h5-7,14-15,17,21H,3,8-9H2,1-2,4H3/b10-5-,12-6-/t14-,15-,17+,20-/m1/s1

> <INCHI_KEY>
BMVJFNLJSZHNNS-ZXRHVTAXSA-N

> <FORMULA>
C20H22O7

> <MOLECULAR_WEIGHT>
374.389

> <EXACT_MASS>
374.136553048

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.409854484139444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4R,8R,9R,11R)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
1.7898005923333336

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.021146287600608

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7895506138034767

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000002

> <JCHEM_REFRACTIVITY>
98.0018

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4R,8R,9R,11R)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-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      -1.782  -1.561   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.155  -2.968   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.376  -3.129   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.003  -4.535   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.281  -1.883   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.813  -2.044   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.655  -0.476   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.560   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.025   0.294   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.489   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.395   2.016   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.859   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.395   3.556   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.489   4.802   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.985   2.786   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.025   5.278   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.560   4.802   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.655   3.556   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.810   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.286   0.075   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.715   2.786   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.255   2.786   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.810   4.032   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.025   6.818   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.691   7.588   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.395  -0.476   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15   27                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18    8   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   18                                                       
CONECT   25   16   26                                                       
CONECT   26   25                                                            
CONECT   27   10                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₇

Average Mass

374.3890 Da

Monoisotopic Mass

374.13655 Da

IUPAC Name

(2Z,4R,8R,9R,11R)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(2Z,4R,8R,9R,11R)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)\C(CO)=C/[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C20H22O7/c1-5-10(2)18(23)26-15-8-20(4)16(22)7-13(27-20)12(9-21)6-14-17(15)11(3)19(24)25-14/h5-7,14-15,17,21H,3,8-9H2,1-2,4H3/b10-5-,12-6-/t14-,15-,17+,20-/m1/s1

InChI Key

BMVJFNLJSZHNNS-ZXRHVTAXSA-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

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aldama bracteata	LOTUS Database	35616633
Aldama excelsa	LOTUS Database	35616633
Centratherum punctatum	Plant	KNApSAcK
Dendroviguiera quinqueradiata	LOTUS Database	35616633
Helianthus schweinitzii	LOTUS Database	35616633
Helianthus tuberosus	LOTUS Database	35616633
Heliomeris multiflora	LOTUS Database	35616633
Lychnophora affinis	Plant	KNApSAcK
Tithonia longiradiata	LOTUS Database	35616633
Viguiera angustifolia	Plant	KNApSAcK
Viguiera buddleiaeformis	Plant	KNApSAcK
Viguiera eriophora	LOTUS Database	35616633
Viguiera eriophora ssp.eriophora	Plant	KNApSAcK
Viguiera linearis	LOTUS Database	35616633
Viguiera robusta	Plant	KNApSAcK
Viguiera schultzii	LOTUS Database	35616633
Viguiera sylvatica	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
Sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
3-furanone
Gamma butyrolactone
Fatty acyl
Dihydrofuran
Vinylogous ester
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:3208 )
Germacrenes (C09351 )

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	1.19	ALOGPS
logP	1.79	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	15.02	ChemAxon
pKa (Strongest Basic)	-2.8	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	98 m³·mol⁻¹	ChemAxon
Polarizability	37.41 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

C00003226

Chemspider ID

4444777

KEGG Compound ID

C09351

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281430

PDB ID

Not Available

ChEBI ID

3208

Good Scents ID

Not Available

References

General References

Wang XZ, Feng Y, Han YF, Bian Y, Liang J, Wen HM, Wu H: Budlein A methylacrylate demonstrates potent activity against triple-negative breast cancer by targeting IkappaBalpha kinase and exportin-1. Toxicol Appl Pharmacol. 2020 Dec 1;408:115263. doi: 10.1016/j.taap.2020.115263. Epub 2020 Oct 3. [PubMed:33022283 ]
Seregheti TMQ, Pinto APR, Goncalves MDC, Antunes ADS, Almeida WADS, Machado RS, Silva JN, Ferreira PMP, Pessoa C, Santos VMRD, Nascimento AMD: Antiproliferative and photoprotective activities of the extracts and compounds from Calea fruticosa. Braz J Med Biol Res. 2020;53(9):e9375. doi: 10.1590/1414-431x20209375. Epub 2020 Jul 17. [PubMed:32696817 ]
Fattori V, Zarpelon AC, Staurengo-Ferrari L, Borghi SM, Zaninelli TH, Da Costa FB, Alves-Filho JC, Cunha TM, Cunha FQ, Casagrande R, Arakawa NS, Verri WA Jr: Budlein A, a Sesquiterpene Lactone From Viguiera robusta, Alleviates Pain and Inflammation in a Model of Acute Gout Arthritis in Mice. Front Pharmacol. 2018 Sep 25;9:1076. doi: 10.3389/fphar.2018.01076. eCollection 2018. [PubMed:30319413 ]
Zarpelon AC, Fattori V, Souto FO, Pinto LG, Pinho-Ribeiro FA, Ruiz-Miyazawa KW, Turato WM, Cunha TM, Da Costa FB, Cunha FQ, Casagrande R, Arakawa NS, Verri WA Jr: Erratum to: The Sesquiterpene Lactone, Budlein A, Inhibits Antigen-Induced Arthritis in Mice: Role of NF-kappaB and Cytokines. Inflammation. 2017 Dec;40(6):2174. doi: 10.1007/s10753-017-0663-9. [PubMed:28879563 ]
Zarpelon AC, Fattori V, Souto FO, Pinto LG, Pinho-Ribeiro FA, Ruiz-Miyazawa KW, Turato WM, Cunha TM, da Costa FB, Cunha FQ, Casagrande R, Arakawa NS, Verri WA Jr: The Sesquiterpene Lactone, Budlein A, Inhibits Antigen-Induced Arthritis in Mice: Role of NF-kappaB and Cytokines. Inflammation. 2017 Dec;40(6):2020-2032. doi: 10.1007/s10753-017-0642-1. [PubMed:28780730 ]
Nogueira MS, Da Costa FB, Brun R, Kaiser M, Schmidt TJ: ent-Pimarane and ent-Kaurane Diterpenes from Aldama discolor (Asteraceae) and Their Antiprotozoal Activity. Molecules. 2016 Sep 15;21(9). pii: molecules21091237. doi: 10.3390/molecules21091237. [PubMed:27649126 ]
Knob CD, Silva M, Gasparoto TH, Oliveira CE, Amor NG, Arakawa NS, Costa FB, Campanelli AP: Effects of budlein A on human neutrophils and lymphocytes. J Appl Oral Sci. 2016 May-Jun;24(3):271-7. doi: 10.1590/1678-775720150540. [PubMed:27383709 ]
Bombo AB, Appezzato-da-Gloria B, Aschenbrenner AK, Spring O: Capitate glandular trichomes in Aldama discolor (Heliantheae - Asteraceae): morphology, metabolite profile and sesquiterpene biosynthesis. Plant Biol (Stuttg). 2016 May;18(3):455-62. doi: 10.1111/plb.12423. Epub 2015 Dec 23. [PubMed:26642998 ]
Sass DC, Morais GO, Miranda RA, Magalhaes LG, Cunha WR, dos Santos RA, Arakawa NS, Da Costa FB, Constantino MG, Heleno VC: Structurally modified natural sesquiterpene lactones constitute effective and less toxic schistosomicidal compounds. Org Biomol Chem. 2014 Oct 28;12(40):7957-64. doi: 10.1039/c4ob00426d. [PubMed:25030079 ]
Sartori LR, Vessecchi R, Humpf HU, Da Costa FB, Lopes NP: A systematic investigation of the fragmentation pattern of two furanoheliangolide C-8 stereoisomers using electrospray ionization mass spectrometry. Rapid Commun Mass Spectrom. 2014 Apr 15;28(7):723-30. doi: 10.1002/rcm.6839. [PubMed:24573803 ]
Schmidt TJ, Da Costa FB, Lopes NP, Kaiser M, Brun R: In Silico prediction and experimental evaluation of furanoheliangolide sesquiterpene lactones as potent agents against Trypanosoma brucei rhodesiense. Antimicrob Agents Chemother. 2014;58(1):325-32. doi: 10.1128/AAC.01263-13. Epub 2013 Oct 28. [PubMed:24165182 ]
Arakawa NS, Gobbo-Neto L, Ambrosio SR, Antonucci GA, Sampaio SV, Pupo MT, Said S, Schmidt TJ, Da Costa FB: Unusual biotransformation products of the sesquiterpene lactone budlein A by Aspergillus species. Phytochemistry. 2013 Dec;96:92-100. doi: 10.1016/j.phytochem.2013.09.022. Epub 2013 Oct 14. [PubMed:24135634 ]
Nicolete R, Arakawa NS, Rius C, Nomizo A, Jose PJ, Da Costa FB, Sanz MJ, Faccioli LH: Budlein A from Viguiera robusta inhibits leukocyte-endothelial cell interactions, adhesion molecule expression and inflammatory mediators release. Phytomedicine. 2009 Oct;16(10):904-15. doi: 10.1016/j.phymed.2009.04.002. Epub 2009 Jun 12. [PubMed:19524419 ]
Arakawa NS, Schorr K, Ambrosio SR, Merfort I, Da Costa FB: Further sesquiterpene lactones from Viguiera robusta and the potential anti-inflammatory activity of a heliangolide: inhibition of human neutrophil elastase release. Z Naturforsch C J Biosci. 2008 Jul-Aug;63(7-8):533-8. doi: 10.1515/znc-2008-7-811. [PubMed:18810997 ]
Valerio DA, Cunha TM, Arakawa NS, Lemos HP, Da Costa FB, Parada CA, Ferreira SH, Cunha FQ, Verri WA Jr: Anti-inflammatory and analgesic effects of the sesquiterpene lactone budlein A in mice: inhibition of cytokine production-dependent mechanism. Eur J Pharmacol. 2007 May 7;562(1-2):155-63. doi: 10.1016/j.ejphar.2007.01.029. Epub 2007 Feb 1. [PubMed:17320857 ]
Guillermo Delgado, Alfonso Romo de Vivar, Werner Herz (1982). Sesquiterpene lactones from Viguiera species. Phytochemistry, Volume 21, Issue 6, 1982, Pages 1305-1308. DOI: 10.1016/0031-9422(82)80130-1. Phytochemistry.

Showing NP-Card for Budlein A (NP0044147)

MOL for NP0044147 (Budlein A)

3D MOL for NP0044147 (Budlein A)

3D SDF for NP0044147 (Budlein A)

3D-SDF for NP0044147 (Budlein A)

PDB for NP0044147 (Budlein A)

3D PDB for NP0044147 (Budlein A)

SMILES for NP0044147 (Budlein A)

INCHI for NP0044147 (Budlein A)

Structure for NP0044147 (Budlein A)

3D Structure for NP0044147 (Budlein A)