NP-MRD: Showing NP-Card for Bigelovin (NP0064187)

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Record Information

Version

2.0

Created at

2022-04-28 08:27:21 UTC

Updated at

2022-04-28 08:27:21 UTC

NP-MRD ID

NP0064187

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bigelovin

Description

Bigelovin belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring. Bigelovin is found in Dittrichia graveolens (L.) GREUTER , Helenium scorzoneraefolia and Inula hupehensis. Bigelovin was first documented in 1996 (PMID: 8657753). Bigelovin is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 19107858) (PMID: 23231968) (PMID: 24118350).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041400512D          

 27 29  0  0  1  0            999 V2000
    2.7580    1.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0539   -1.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0634   -2.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8222   -1.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7799    0.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556   -0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9409    0.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1159    0.9680    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9800   -0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2429   -2.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6016    0.3230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4553    0.3230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0769   -0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2717   -0.4813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5284   -0.8393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6013   -0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851   -0.4813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2429   -2.9018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030   -1.7261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4056   -0.5452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5284   -1.6643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2770    0.3970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5549    1.6666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2773    1.0816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7796    1.0816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5188   -1.2684    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0347   -1.4906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  1  1  6  0  0  0
  8  7  1  0  0  0  0
  9  2  2  0  0  0  0
 10  3  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17  4  1  1  0  0  0
 17 11  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 10  2  0  0  0  0
 19 13  2  0  0  0  0
 20 16  2  0  0  0  0
 21 10  1  0  0  0  0
 15 21  1  6  0  0  0
 22 12  1  0  0  0  0
 22 16  1  0  0  0  0
  8 23  1  1  0  0  0
 11 24  1  6  0  0  0
 12 25  1  1  0  0  0
 14 26  1  6  0  0  0
 15 27  1  1  0  0  0
M  END

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    1.7864    3.0718    0.9298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7757    2.7456    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450    3.7379   -0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2255    4.9783   -0.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2685    3.0075   -0.8936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1664    1.6633   -0.3865 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9200    0.7345   -1.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2858   -0.5078   -0.4553 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2301   -1.3815   -1.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0390   -1.2736   -0.1953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3631   -2.6166    0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3321   -2.9927    1.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7140   -1.9864    1.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9238   -2.1624    1.2648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0504   -0.7181    0.7499 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6195   -0.2630    2.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8984    0.3119    0.2062 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7530   -0.3526   -0.7457 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1206   -0.4081   -0.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -1.1232   -1.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7123    0.1043    0.3841 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    1.4837   -0.4730 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5496    2.3855    1.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275    4.1006    1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5391    1.6094    0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8731    1.2257   -1.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854    0.4511   -2.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8505   -0.1801    0.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9323   -0.7190   -1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8367   -2.0219   -0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6503   -2.0336   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5294   -1.4625   -1.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2941   -3.1346    0.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2554   -3.9295    1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017    0.7257    2.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3053   -0.9641    2.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7158   -0.3011    2.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5601    0.6563    1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2946   -1.7686   -2.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5188   -0.3952   -2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6639   -1.8247   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6243    1.5278   -1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 17 22  1  0
 22  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
 22  6  1  0
  5  6  1  0
 15 10  1  0
  6 25  1  1
  7 26  1  0
  7 27  1  0
  8 28  1  1
  9 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  6
 11 33  1  0
 12 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  1
 20 39  1  0
 20 40  1  0
 20 41  1  0
 22 42  1  6
  1 23  1  0
  1 24  1  0
M  END


  Mrv0541 05041400512D          

 27 29  0  0  1  0            999 V2000
    2.7580    1.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0539   -1.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0634   -2.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8222   -1.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7799    0.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556   -0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9409    0.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1159    0.9680    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9800   -0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2429   -2.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6016    0.3230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4553    0.3230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0769   -0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2717   -0.4813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5284   -0.8393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6013   -0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851   -0.4813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2429   -2.9018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030   -1.7261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4056   -0.5452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5284   -1.6643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2770    0.3970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5549    1.6666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2773    1.0816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7796    1.0816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5188   -1.2684    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0347   -1.4906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  1  1  6  0  0  0
  8  7  1  0  0  0  0
  9  2  2  0  0  0  0
 10  3  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17  4  1  1  0  0  0
 17 11  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 10  2  0  0  0  0
 19 13  2  0  0  0  0
 20 16  2  0  0  0  0
 21 10  1  0  0  0  0
 15 21  1  6  0  0  0
 22 12  1  0  0  0  0
 22 16  1  0  0  0  0
  8 23  1  1  0  0  0
 11 24  1  6  0  0  0
 12 25  1  1  0  0  0
 14 26  1  6  0  0  0
 15 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0064187

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@@]([H])(C)[C@]3([H])C=CC(=O)[C@@]3(C)[C@@]([H])(OC(C)=O)[C@]1([H])C(=C)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h5-6,8,11-12,14-15H,2,7H2,1,3-4H3/t8-,11+,12+,14-,15+,17+/m1/s1

> <INCHI_KEY>
DCNRYQODUSSOKC-MMLVVLEOSA-N

> <FORMULA>
C17H20O5

> <MOLECULAR_WEIGHT>
304.3377

> <EXACT_MASS>
304.13107375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.827446267758724

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,4aR,7aR,8R,9aS)-4a,8-dimethyl-3-methylidene-2,5-dioxo-2H,3H,3aH,4H,4aH,5H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-4-yl acetate

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
2.2880323316666678

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.389850123985926

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.559888673200341

> <JCHEM_PKA_STRONGEST_BASIC>
-5.104194195013178

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
78.77459999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,4aR,7aR,8R,9aS)-4a,8-dimethyl-3-methylidene-2,5-dioxo-3aH,4H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   17                                                            
CONECT    5    6   11                                                       
CONECT    6    5   13                                                       
CONECT    7    8   12                                                       
CONECT    8    1    7   11   23                                             
CONECT    9    2   14   16                                                  
CONECT   10    3   18   21                                                  
CONECT   11    5    8   17   24                                             
CONECT   12    7   14   22   25                                             
CONECT   13    6   17   19                                                  
CONECT   14    9   12   15   26                                             
CONECT   15   14   17   21   27                                             
CONECT   16    9   20   22                                                  
CONECT   17    4   11   13   15                                             
CONECT   18   10                                                            
CONECT   19   13                                                            
CONECT   20   16                                                            
CONECT   21   10   15                                                       
CONECT   22   12   16                                                       
CONECT   23    8                                                            
CONECT   24   11                                                            
CONECT   25   12                                                            
CONECT   26   14                                                            
CONECT   27   15                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
6alpha,8alpha-Dihydroxy-4-oxo-ambrosa-2,11(13)-dien-12-Oic acid-12,8-lactone acetate	ChEBI
6a,8a-Dihydroxy-4-oxo-ambrosa-2,11(13)-dien-12-Oate-12,8-lactone acetate	Generator
6a,8a-Dihydroxy-4-oxo-ambrosa-2,11(13)-dien-12-Oic acid-12,8-lactone acetic acid	Generator
6alpha,8alpha-Dihydroxy-4-oxo-ambrosa-2,11(13)-dien-12-Oate-12,8-lactone acetate	Generator
6alpha,8alpha-Dihydroxy-4-oxo-ambrosa-2,11(13)-dien-12-Oic acid-12,8-lactone acetic acid	Generator
6Α,8α-dihydroxy-4-oxo-ambrosa-2,11(13)-dien-12-Oate-12,8-lactone acetate	Generator
6Α,8α-dihydroxy-4-oxo-ambrosa-2,11(13)-dien-12-Oic acid-12,8-lactone acetic acid	Generator

Chemical Formula

C₁₇H₂₀O₅

Average Mass

304.3377 Da

Monoisotopic Mass

304.13107 Da

IUPAC Name

(3aR,4S,4aR,7aR,8R,9aS)-4a,8-dimethyl-3-methylidene-2,5-dioxo-2H,3H,3aH,4H,4aH,5H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-4-yl acetate

Traditional Name

(3aR,4S,4aR,7aR,8R,9aS)-4a,8-dimethyl-3-methylidene-2,5-dioxo-3aH,4H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-4-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@]([H])(C)[C@]3([H])C=CC(=O)[C@@]3(C)[C@@]([H])(OC(C)=O)[C@]1([H])C(=C)C(=O)O2

InChI Identifier

InChI=1S/C17H20O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h5-6,8,11-12,14-15H,2,7H2,1,3-4H3/t8-,11+,12+,14-,15+,17+/m1/s1

InChI Key

DCNRYQODUSSOKC-MMLVVLEOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Dittrichia graveolens	Plant	KNApSAcK
Helenium scorzoneraefolia	Plant	KNApSAcK
Inula hupehensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Sesquiterpene lactones

Alternative Parents

Substituents

Helenalin-skeleton
Ambrosanolide
Pseudoguaiane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Enoate ester
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:69337 )
organic heterotricyclic compound (CHEBI:69337 )
acetate ester (CHEBI:69337 )
gamma-lactone (CHEBI:69337 )
sesquiterpene lactone (CHEBI:69337 )

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	1.13	ALOGPS
logP	2.29	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.56	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.77 m³·mol⁻¹	ChemAxon
Polarizability	30.83 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

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

3080597

PDB ID

Not Available

ChEBI ID

69337

Good Scents ID

Not Available

References

General References

Zeng GZ, Tan NH, Ji CJ, Fan JT, Huang HQ, Han HJ, Zhou GB: Apoptosis inducement of bigelovin from Inula helianthus-aquatica on human Leukemia U937 cells. Phytother Res. 2009 Jun;23(6):885-91. doi: 10.1002/ptr.2671. [PubMed:19107858 ]
Yue GG, Chan BC, Kwok HF, Wong YL, Leung HW, Ji CJ, Fung KP, Leung PC, Tan NH, Lau CB: Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica. Eur J Med Chem. 2013 Jan;59:243-52. doi: 10.1016/j.ejmech.2012.11.029. Epub 2012 Nov 24. [PubMed:23231968 ]
Liu JL, Zeng GZ, Liu XL, Liu YQ, Hu ZG, Liu Y, Tan NH, Zhou GB: Small compound bigelovin exerts inhibitory effects and triggers proteolysis of E2F1 in multiple myeloma cells. Cancer Sci. 2013 Dec;104(12):1697-704. doi: 10.1111/cas.12295. Epub 2013 Nov 8. [PubMed:24118350 ]
Wang Q, Zhou BN, Zhang RW, Lin YY, Lin LZ, Gil RR, Cordell GA: Cytotoxicity and NMR spectral assignments of ergolide and bigelovin. Planta Med. 1996 Apr;62(2):166-8. doi: 10.1055/s-2006-957843. [PubMed:8657753 ]

Showing NP-Card for Bigelovin (NP0064187)

MOL for NP0064187 (Bigelovin)

3D MOL for NP0064187 (Bigelovin)

3D SDF for NP0064187 (Bigelovin)

3D-SDF for NP0064187 (Bigelovin)

PDB for NP0064187 (Bigelovin)

3D PDB for NP0064187 (Bigelovin)

SMILES for NP0064187 (Bigelovin)

INCHI for NP0064187 (Bigelovin)

Structure for NP0064187 (Bigelovin)

3D Structure for NP0064187 (Bigelovin)