NP-MRD: Showing NP-Card for (3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate (NP0182723)

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Record Information

Version

2.0

Created at

2022-09-03 21:30:09 UTC

Updated at

2022-09-03 21:30:09 UTC

NP-MRD ID

NP0182723

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate

Description

Arnicolide D belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring. (3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate is found in Arnica acaulis, Arnica montana and Centipeda minima. (3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate was first documented in 2019 (PMID: 31202878). Based on a literature review a small amount of articles have been published on Arnicolide D (PMID: 33402084) (PMID: 34487850) (PMID: 32669950) (PMID: 31408803).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
    4.0802   -1.4236   -1.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0506   -0.3666   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3575    0.1893    0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7823    0.2296    0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    1.2196    0.9162 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5894   -0.3046   -0.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3044    0.2329    0.0994 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3424    0.6981   -1.1141 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1527    2.1105   -1.4445 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1454    3.0518   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8753    2.5298   -2.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7253    3.1893   -3.4716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0755    2.0406   -1.9371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7846    0.8120   -1.2446 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6476    0.7680   -0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8625   -0.6443    0.4497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8711   -1.2779   -0.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5997   -1.4067    0.3303 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6865   -2.7050    1.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4932   -3.0367    1.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4423   -1.9837    1.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6744   -2.1037    1.1466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886   -0.7802    0.9402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7485   -0.2152    2.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0085   -1.8749   -1.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1235   -1.8274   -1.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1547    1.0268    0.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9651    0.5738   -0.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9251   -0.5696    0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5425    1.1021    0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0380    0.1022   -2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1688    2.0813   -1.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062    4.0554   -0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1737    3.2954    0.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5011    2.8318    0.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2001    0.0278   -1.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3771    1.3802    0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6730    1.1276   -0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3477   -0.6320    1.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4374   -0.5152   -1.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5612   -1.9571    0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3507   -1.9136   -1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4457   -1.6604   -0.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5744   -3.3234    1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3079   -3.9553    2.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0261   -0.5829    3.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7369   -0.5198    2.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5949    0.9040    2.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  1
 23  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11  9  1  0
  7  8  1  0
 23 18  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
  9 32  1  6
  8 31  1  6
 14 36  1  6
 15 37  1  0
 15 38  1  0
 16 39  1  1
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  6
 19 44  1  0
 20 45  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
  7 30  1  1
  3 27  1  0
  3 28  1  0
  3 29  1  0
  1 25  1  0
  1 26  1  0
M  END


  Mrv1652309032223302D          

 24 26  0  0  1  0            999 V2000
    3.5284    2.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2429    2.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9574    2.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2429    1.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9574    1.2533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5284    1.2533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5284    0.4283    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2717    0.0703    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9800    0.4935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3042    1.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6013   -0.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4056    0.1343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2770   -0.8079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4553   -0.7340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9409   -1.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1159   -1.3790    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7580   -2.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6016   -0.7340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7799   -0.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556   -0.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769    0.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030    1.3152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851    0.0703    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8222    0.8945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  6  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  7 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0182723

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H]2[C@@H](C[C@@H](C)[C@@H]3C=CC(=O)[C@@]3(C)[C@H]2OC(=O)C(C)=C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O5/c1-9(2)17(21)24-16-15-11(4)18(22)23-13(15)8-10(3)12-6-7-14(20)19(12,16)5/h6-7,10-13,15-16H,1,8H2,2-5H3/t10-,11+,12+,13-,15-,16+,19+/m1/s1

> <INCHI_KEY>
NZESEVTYUVXOTC-APDQSUQKSA-N

> <FORMULA>
C19H24O5

> <MOLECULAR_WEIGHT>
332.396

> <EXACT_MASS>
332.162373873

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
34.79405647174953

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.5315544570000004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.949645212861732

> <JCHEM_PKA_STRONGEST_BASIC>
-5.1042493116089656

> <JCHEM_POLAR_SURFACE_AREA>
69.67000000000002

> <JCHEM_REFRACTIVITY>
87.97599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       6.586   5.419   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.920   4.649   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.254   5.419   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.920   3.109   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.254   2.339   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       6.586   2.339   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.586   0.799   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.974   0.131   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.296   0.921   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.901   2.337   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.456  -0.092   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.957   0.251   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       9.850  -1.508   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.317  -1.370   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.356  -2.574   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.816  -2.574   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.148  -3.962   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.856  -1.370   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.322  -1.508   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.717  -0.092   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.877   0.921   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.739   2.455   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.199   0.131   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.268   1.670   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    7   18   24                                             
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₄O₅

Average Mass

332.3960 Da

Monoisotopic Mass

332.16237 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H]2[C@@H](C[C@@H](C)[C@@H]3C=CC(=O)[C@@]3(C)[C@H]2OC(=O)C(C)=C)OC1=O

InChI Identifier

InChI=1S/C19H24O5/c1-9(2)17(21)24-16-15-11(4)18(22)23-13(15)8-10(3)12-6-7-14(20)19(12,16)5/h6-7,10-13,15-16H,1,8H2,2-5H3/t10-,11+,12+,13-,15-,16+,19+/m1/s1

InChI Key

NZESEVTYUVXOTC-APDQSUQKSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Arnica acaulis	LOTUS Database	35616633
Arnica montana	LOTUS Database	35616633
Centipeda minima	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

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00021129

Chemspider ID

158463

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

182199

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chan CO, Xie XJ, Wan SW, Zhou GL, Yuen AC, Mok DK, Chen SB: Qualitative and quantitative analysis of sesquiterpene lactones in Centipeda minima by UPLC-Orbitrap-MS & UPLC-QQQ-MS. J Pharm Biomed Anal. 2019 Sep 10;174:360-366. doi: 10.1016/j.jpba.2019.05.067. Epub 2019 May 30. [PubMed:31202878 ]
Huang DN, Wang S, Sooranna SR, Miao JH: The efficacy of natural bioactive compounds for the treatment of nasopharyngeal carcinoma. Mini Rev Med Chem. 2021 Jan 4. pii: MRMC-EPUB-113051. doi: 10.2174/1389557521666210105113831. [PubMed:33402084 ]
Yao J, Shen Q, Huang M, Ding M, Guo Y, Chen W, Lin Y, Zheng Y, Yu S, Yan W, Su T, Liu Z, Lu L: Screening tumor specificity targeted by arnicolide D, the active compound of Centipeda minima and molecular mechanism underlying by integrative pharmacology. J Ethnopharmacol. 2022 Jan 10;282:114583. doi: 10.1016/j.jep.2021.114583. Epub 2021 Sep 4. [PubMed:34487850 ]
Qu Z, Lin Y, Mok DK, Bian Q, Tai WC, Chen S: Arnicolide D Inhibits Triple Negative Breast Cancer Cell Proliferation by Suppression of Akt/mTOR and STAT3 Signaling Pathways. Int J Med Sci. 2020 Jun 15;17(11):1482-1490. doi: 10.7150/ijms.46925. eCollection 2020. [PubMed:32669950 ]
Zhu P, Zheng Z, Fu X, Li J, Yin C, Chou J, Wang Y, Liu Y, Chen Y, Bai J, Wu J, Chen S, Yu ZL: Arnicolide D exerts anti-melanoma effects and inhibits the NF-kappaB pathway. Phytomedicine. 2019 Nov;64:153065. doi: 10.1016/j.phymed.2019.153065. Epub 2019 Aug 2. [PubMed:31408803 ]
LOTUS database [Link]

Showing NP-Card for (3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate (NP0182723)

MOL for NP0182723 ((3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate)

3D MOL for NP0182723 ((3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate)

3D SDF for NP0182723 ((3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate)

3D-SDF for NP0182723 ((3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate)

PDB for NP0182723 ((3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate)

3D PDB for NP0182723 ((3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate)

SMILES for NP0182723 ((3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate)

INCHI for NP0182723 ((3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate)

Structure for NP0182723 ((3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate)

3D Structure for NP0182723 ((3s,3ar,4s,4ar,7ar,8r,9ar)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylprop-2-enoate)