NP-MRD: Showing NP-Card for Artecanin (NP0046772)

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Record Information

Version

2.0

Created at

2022-03-17 20:29:18 UTC

Updated at

2022-03-17 20:29:18 UTC

NP-MRD ID

NP0046772

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Artecanin

Description

Artecanin belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Artecanin is found in Achillea clavennae, Achillea clusiana, Achillea ligustica, Achillea millefolium, Achillea nobilis, Achillea santolina, Ajania fastigiata, Artemisia argyi, Artemisia aschurbajewii, Artemisia ashurbajevii, Artemisia cana, Artemisia frigida, Artemisia gilvescens, Artemisia klotzchiana, Artemisia lucentica, Artemisia ludoviciana, Artemisia mexicana, Artemisia xanthochroa, Chrysanthemum x morifolium, Handelia trichophylla, Pentzia calva, Tanacetum macrophyllum, Tanacetum parthenifolium and Chrysanthemum parthenium . Artecanin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221262D          

 20 24  0  0  1  0            999 V2000
   -0.6115   -0.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -0.4711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7874   -1.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6023   -0.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0096   -0.1816    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7027    0.5842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9126    0.8216    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2343    0.3520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4220    0.8519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5268    0.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1493    1.6306    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6755    1.6118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2793    2.3355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4366    1.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3361    1.1127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0345    0.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8003    0.9805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8327   -0.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613   -0.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -1.1886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  2  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  8 10  1  1  0  0  0
  9 11  1  0  0  0  0
 12 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 13  1  1  0  0  0
 12 14  1  6  0  0  0
  6 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  5 18  1  6  0  0  0
 18 19  2  0  0  0  0
  2 20  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0046772

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12O[C@@H]1[C@@H]1O[C@]11[C@H]2[C@H]2OC(=O)C(=C)[C@@H]2CC[C@@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O5/c1-6-7-4-5-13(2,17)15-9(8(7)18-12(6)16)14(3)10(19-14)11(15)20-15/h7-11,17H,1,4-5H2,2-3H3/t7-,8-,9-,10+,11-,13+,14-,15+/m0/s1

> <INCHI_KEY>
KXLUWEYBZBGJRZ-POEOZHCLSA-N

> <FORMULA>
C15H18O5

> <MOLECULAR_WEIGHT>
278.3004

> <EXACT_MASS>
278.115423686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.95490160894991

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5S,9S,10S,11S,13R,14S)-2-hydroxy-2,11-dimethyl-6-methylidene-8,12,15-trioxapentacyclo[8.5.0.0¹,¹⁴.0⁵,⁹.0¹¹,¹³]pentadecan-7-one

> <ALOGPS_LOGP>
0.73

> <JCHEM_LOGP>
0.7688833529999998

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.767612281302565

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3378463881582574

> <JCHEM_POLAR_SURFACE_AREA>
71.59

> <JCHEM_REFRACTIVITY>
66.24390000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.92e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
canin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.141  -0.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.333  -0.879   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.470  -1.919   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.991  -1.678   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.751  -0.339   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.178   1.091   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.704   1.534   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.437   0.657   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.788   1.590   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.983   0.063   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.279   3.044   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.261   3.009   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.521   4.360   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.682   3.603   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.361   2.077   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.664   1.257   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.094   1.830   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.288  -0.236   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.274  -1.418   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.427  -2.219   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8   20                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    2    9   10                                             
CONECT    9    8   10   11                                                  
CONECT   10    9    8                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11    7   13   14                                             
CONECT   13   12   11                                                       
CONECT   14   12                                                            
CONECT   15    6   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    5   19                                                  
CONECT   19   18                                                            
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₅

Average Mass

278.3004 Da

Monoisotopic Mass

278.11542 Da

IUPAC Name

(1R,2R,5S,9S,10S,11S,13R,14S)-2-hydroxy-2,11-dimethyl-6-methylidene-8,12,15-trioxapentacyclo[8.5.0.0¹,¹⁴.0⁵,⁹.0¹¹,¹³]pentadecan-7-one

Traditional Name

canin

CAS Registry Number

24959-84-0

SMILES

C[C@@]12O[C@@H]1[C@@H]1O[C@]11[C@H]2[C@H]2OC(=O)C(=C)[C@@H]2CC[C@@]1(C)O

InChI Identifier

InChI=1S/C15H18O5/c1-6-7-4-5-13(2,17)15-9(8(7)18-12(6)16)14(3)10(19-14)11(15)20-15/h7-11,17H,1,4-5H2,2-3H3/t7-,8-,9-,10+,11-,13+,14-,15+/m0/s1

InChI Key

KXLUWEYBZBGJRZ-POEOZHCLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achillea clavennae	Plant	KNApSAcK
Achillea clusiana	LOTUS Database	35616633
Achillea ligustica	LOTUS Database	35616633
Achillea millefolium	LOTUS Database	35616633
Achillea nobilis	LOTUS Database	35616633
Achillea santolina	LOTUS Database	35616633
Ajania fastigiata	Plant	KNApSAcK
Artemisia argyi	LOTUS Database	35616633
Artemisia aschurbajewii	LOTUS Database	35616633
Artemisia ashurbajevii	Plant	KNApSAcK
Artemisia cana	Plant	KNApSAcK
Artemisia frigida	LOTUS Database	35616633
Artemisia gilvescens	LOTUS Database	35616633
Artemisia klotzchiana	Plant	KNApSAcK
Artemisia lucentica	LOTUS Database	35616633
Artemisia ludoviciana	LOTUS Database	35616633
Artemisia mexicana	Plant	KNApSAcK
Artemisia xanthochroa	LOTUS Database	35616633
Chrysanthemum x morifolium	Plant	KNApSAcK
Handelia trichophylla	Plant	KNApSAcK
Laurus nobilis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pentzia calva	LOTUS Database	35616633
Tanacetum macrophyllum	LOTUS Database	35616633
Tanacetum partheniifolium	LOTUS Database	35616633
Tanacetum parthenium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Sesquiterpenoid
1,4-dioxepane
Dioxepane
Gamma butyrolactone
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpene lactone (CHEBI:3356 )
Guaianolide (C09354 )

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	0.73	ALOGPS
logP	0.77	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	13.77	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.59 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.24 m³·mol⁻¹	ChemAxon
Polarizability	27.95 Å³	ChemAxon
Number of Rings	5	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

FDB005870

KNApSAcK ID

C00000238

Chemspider ID

Not Available

KEGG Compound ID

C09354

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442175

PDB ID

Not Available

ChEBI ID

3356

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Artecanin (NP0046772)

MOL for NP0046772 (Artecanin)

3D MOL for NP0046772 (Artecanin)

3D SDF for NP0046772 (Artecanin)

3D-SDF for NP0046772 (Artecanin)

PDB for NP0046772 (Artecanin)

3D PDB for NP0046772 (Artecanin)

SMILES for NP0046772 (Artecanin)

INCHI for NP0046772 (Artecanin)

Structure for NP0046772 (Artecanin)

3D Structure for NP0046772 (Artecanin)