NP-MRD: Showing NP-Card for Achillin (NP0051834)

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Record Information

Version

2.0

Created at

2022-04-27 23:03:03 UTC

Updated at

2022-04-27 23:03:03 UTC

NP-MRD ID

NP0051834

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Achillin

Description

Achillin belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Achillin is an extremely weak basic (essentially neutral) compound (based on its pKa). Achillin is found in Achillea collina , Achillea lanulosa, Achillea millefolium , Achillea pseudopectinata, Artemisia assoana, Artemisia copa, Artemisia lagocephala, Artemisia lancea, Artemisia ludoviciana, Artemisia princeps, Artemisia reptans, Artemisia rutifolia, Artemisia spp. , Helminthotheca echioides (L.) Holub, Hypochaeris setosus Rusby and Tanacetum parthenium. Achillin was first documented in 1999 (PMID: 10418323). A sesquiterpene lactone that is (3R,3aS,9aS,9bS)-3,3a,4,5,9a,9b-hexahydroazulenofuran-2,7-dione carrying three additional methyl substituents at positions 3, 6 and 9 (PMID: 12889533) (PMID: 25227949).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -1.9411   -2.8530   -0.9388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9678   -1.5589   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8283   -1.2727    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6023    0.0615    1.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2315    0.6639    2.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4760    0.5965    0.5391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9701    1.8017    0.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6263    2.6004    1.7926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1880    2.4204   -0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117    1.5008    0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275    0.3471   -0.8301 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3999   -0.7747   -0.2357 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7510   -1.8668   -1.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0119   -1.6879   -1.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6308   -2.4727   -2.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5246   -0.3751   -1.1270 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3029   -0.6505    0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0386   -0.4466   -0.4490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0608   -2.6754   -2.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8226   -3.4882   -0.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0049   -3.3911   -0.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6008   -1.9261    1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1173    3.6087    1.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6948    2.8383    1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5104    2.1786    2.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4224    3.3594    0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906    2.5964   -1.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2762    2.1073   -0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5012    1.2044    1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8097    0.7111   -1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6930   -0.9221    0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1345    0.1440   -1.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -1.0463   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3745    0.2232    0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814   -1.5049    0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1439   -0.0509   -1.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  1  0
  7  6  2  0
  6 18  1  0
 18 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 18  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
 14 16  1  0
 12 11  1  0
  4  6  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 16 32  1  6
 11 30  1  6
 10 28  1  0
 10 29  1  0
  9 26  1  0
  9 27  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
 18 36  1  6
 12 31  1  1
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
M  END


  Mrv1652301212022253D          

 18 20  0  0  0  0            999 V2000
   -1.9402    2.8611   -0.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8896   -3.0403    0.9771 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8140   -0.0791   -0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2410    1.8103   -1.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3537    1.3261   -0.4417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0679   -0.8852    0.8030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0846    1.6657   -0.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9861   -1.5907    0.5694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5459   -0.8630   -0.0642 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3313   -0.1486   -0.4465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9463    0.4842    0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6146    0.5592   -0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910   -0.7821   -0.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3066   -0.5847    0.6138 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2241   -1.5356    1.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7862    1.4142    0.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0516   -1.8584    2.1103 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8526   -1.7217    1.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  0  0  0  0
  9  3  1  1  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
 10  5  1  1  0  0  0
  6  8  2  0  0  0  0
  6 11  1  0  0  0  0
  7 12  2  0  0  0  0
 13  8  1  1  0  0  0
  9 10  1  0  0  0  0
  9 15  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 18  1  6  0  0  0
 15 17  2  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051834

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H]2CCC(C)=C3[C@@H]([C@H]2OC1=O)C(C)=CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,9-10,13-14H,4-5H2,1-3H3/t9-,10+,13+,14+/m1/s1

> <INCHI_KEY>
BJPSSVHNEGMBDQ-OAACRXHESA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.306

> <EXACT_MASS>
246.12559444

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.890628480309648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aS,9aS,9bS)-3,6,9-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
2.4665371326666667

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.413396323654869

> <JCHEM_PKA_STRONGEST_BASIC>
-5.144736140763016

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
68.71629999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
achillin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-20         0                                  
HETATM    1  C   UNK     0      -1.940   2.861  -0.770  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.890  -3.040   0.977  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.814  -0.079  -0.014  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.241   1.810  -1.368  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.354   1.326  -0.442  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.068  -0.885   0.803  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.085   1.666  -0.782  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.986  -1.591   0.569  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.546  -0.863  -0.064  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.331  -0.149  -0.447  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.946   0.484   0.331  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.615   0.559  -0.244  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.991  -0.782  -0.114  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.307  -0.585   0.614  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.224  -1.536   1.214  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.786   1.414   0.393  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.052  -1.858   2.110  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.853  -1.722   1.198  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    5    7                                                       
CONECT    5    4   10                                                       
CONECT    6    8   11                                                       
CONECT    7    1    4   12                                                  
CONECT    8    2    6   13                                                  
CONECT    9    3   10   15                                                  
CONECT   10    5    9   14                                                  
CONECT   11    6   12   16                                                  
CONECT   12    7   11   13                                                  
CONECT   13    8   12   14                                                  
CONECT   14   10   13   18                                                  
CONECT   15    9   17   18                                                  
CONECT   16   11                                                            
CONECT   17   15                                                            
CONECT   18   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₃

Average Mass

246.3060 Da

Monoisotopic Mass

246.12559 Da

IUPAC Name

(3R,3aS,9aS,9bS)-3,6,9-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

Traditional Name

achillin

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H]2CCC(C)=C3[C@@H]([C@H]2OC1=O)C(C)=CC3=O

InChI Identifier

InChI=1S/C15H18O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,9-10,13-14H,4-5H2,1-3H3/t9-,10+,13+,14+/m1/s1

InChI Key

BJPSSVHNEGMBDQ-OAACRXHESA-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
Achillea collina	Plant	KNApSAcK
Achillea lanulosa	Plant	KNApSAcK
Achillea millefolium	Plant	KNApSAcK
Achillea pseudopectinata	LOTUS Database	35616633
Artemisia assoana	LOTUS Database	35616633
Artemisia copa	LOTUS Database	35616633
Artemisia lagocephala	LOTUS Database	35616633
Artemisia lancea	LOTUS Database	35616633
Artemisia ludoviciana	LOTUS Database	35616633
Artemisia princeps	LOTUS Database	35616633
Artemisia reptans	LOTUS Database	35616633
Artemisia rutifolia	LOTUS Database	35616633
Artemisia spp.	Plant	KNApSAcK
Helminthia echioides	Plant	KNApSAcK
Hypochaeris setosus Rusby	Plant	KNApSAcK
Tanacetum parthenium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

azulenofuran (CHEBI:2425 )
sesquiterpene lactone (CHEBI:2425 )
Guaianolide (C09287 )

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	2.18	ALOGPS
logP	2.47	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	15.41	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.72 m³·mol⁻¹	ChemAxon
Polarizability	26.89 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

C00003205

Chemspider ID

Not Available

KEGG Compound ID

C09287

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442139

PDB ID

Not Available

ChEBI ID

2425

Good Scents ID

Not Available

References

General References

Kang TH, Pae HO, Jeong SJ, Yoo JC, Choi BM, Jun CD, Chung HT, Miyamoto T, Higuchi R, Kim YC: Scopoletin: an inducible nitric oxide synthesis inhibitory active constituent from Artemisia feddei. Planta Med. 1999 Jun;65(5):400-3. doi: 10.1055/s-1999-14014. [PubMed:10418323 ]
Glasl S, Mucaji P, Werner I, Jurenitsch J: TLC and HPLC characteristics of desacetylmatricarin, leucodin, achillin and their 8alpha-angeloxy-derivatives. Pharmazie. 2003 Jul;58(7):487-90. [PubMed:12889533 ]
Zaghloul AM, Yusufoglu HS, Salkini MA, Alam A: New cytotoxic sesquiterpene lactones from Anthemis scrobicularis. J Asian Nat Prod Res. 2014;16(9):922-9. doi: 10.1080/10286020.2014.931377. Epub 2014 Sep 17. [PubMed:25227949 ]

Showing NP-Card for Achillin (NP0051834)

MOL for NP0051834 (Achillin)

3D MOL for NP0051834 (Achillin)

3D SDF for NP0051834 (Achillin)

3D-SDF for NP0051834 (Achillin)

PDB for NP0051834 (Achillin)

3D PDB for NP0051834 (Achillin)

SMILES for NP0051834 (Achillin)

INCHI for NP0051834 (Achillin)

Structure for NP0051834 (Achillin)

3D Structure for NP0051834 (Achillin)