NP-MRD: Showing NP-Card for Artemorin (NP0046773)

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Record Information

Version

2.0

Created at

2022-03-17 20:29:19 UTC

Updated at

2022-03-17 20:29:19 UTC

NP-MRD ID

NP0046773

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Artemorin

Description

Artemorin belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Artemorin is found in Achillea biebersteinii, Achillea micrantha, Artemisia genipi, Artemisia genipy, Artemisia gmelinii, Artemisia ludoviciana, Artemisia mexicana, Artemisia schmidtiana, Artemisia turcomanica, Artemisia verlatorum, Artemisia verlotiorum, Eriocephalus kingesii, Gonospermum elegans, Laurus nobilis, Magnolia grandiflora , Tanacetum parthenium and Tanacetum vulgare. Artemorin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221192D          

 18 19  0  0  1  0            999 V2000
    1.9139    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 10 13  1  6  0  0  0
  5 14  1  6  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  4 18  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0046773

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/[C@H]2OC(=O)C(=C)[C@@H]2CCC(=C)[C@H](O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-4-7-13(16)10(2)5-6-12-11(3)15(17)18-14(12)8-9/h8,12-14,16H,2-7H2,1H3/b9-8+/t12-,13+,14+/m0/s1

> <INCHI_KEY>
JNHKVMWTQCZYHK-CVZWCJCVSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.009157557429205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,7R,11aR)-7-hydroxy-10-methyl-3,6-dimethylidene-2H,3H,3aH,4H,5H,6H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
2.6432892500000005

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.35965208608954

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3292869406839278

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
70.38939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
artemorin

> <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       3.573   1.246   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   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   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.465   2.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.941   3.481   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.910   0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.465  -0.476   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    2                                                       
CONECT   13   10                                                            
CONECT   14    5   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    4                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3175 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(3aS,7R,11aR)-7-hydroxy-10-methyl-3,6-dimethylidene-2H,3H,3aH,4H,5H,6H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one

Traditional Name

artemorin

CAS Registry Number

64845-92-7

SMILES

C\C1=C/[C@H]2OC(=O)C(=C)[C@@H]2CCC(=C)[C@H](O)CC1

InChI Identifier

InChI=1S/C15H20O3/c1-9-4-7-13(16)10(2)5-6-12-11(3)15(17)18-14(12)8-9/h8,12-14,16H,2-7H2,1H3/b9-8+/t12-,13+,14+/m0/s1

InChI Key

JNHKVMWTQCZYHK-CVZWCJCVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achillea biebersteinii	LOTUS Database	35616633
Achillea micrantha	LOTUS Database	35616633
Artemisia genipi	LOTUS Database	35616633
Artemisia genipy	Plant	KNApSAcK
Artemisia gmelinii	LOTUS Database	35616633
Artemisia ludoviciana	LOTUS Database	35616633
Artemisia mexicana	Plant	KNApSAcK
Artemisia schmidtiana	LOTUS Database	35616633
Artemisia turcomanica	LOTUS Database	35616633
Artemisia verlatorum	Plant	KNApSAcK
Artemisia verlotiorum	Plant	KNApSAcK
Eriocephalus kingesii	Plant	KNApSAcK
Gonospermum elegans	Plant	KNApSAcK
Laurus nobilis	LOTUS Database	35616633
Laurus nobilis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Magnolia grandiflora	Plant	KNApSAcK
Tanacetum parthenium	LOTUS Database	35616633
Tanacetum vulgare	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
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

germacranolide (CHEBI:2853 )
Germacrenes (C09345 )
Sesquiterpenoids (C15) (C09345 )

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	2.09	ALOGPS
logP	2.64	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	18.36	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.39 m³·mol⁻¹	ChemAxon
Polarizability	27.01 Å³	ChemAxon
Number of Rings	2	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

FDB005871

KNApSAcK ID

C00003222

Chemspider ID

Not Available

KEGG Compound ID

C09345

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281428

PDB ID

Not Available

ChEBI ID

2853

Good Scents ID

Not Available

References

General References

Showing NP-Card for Artemorin (NP0046773)

MOL for NP0046773 (Artemorin)

3D MOL for NP0046773 (Artemorin)

3D SDF for NP0046773 (Artemorin)

3D-SDF for NP0046773 (Artemorin)

PDB for NP0046773 (Artemorin)

3D PDB for NP0046773 (Artemorin)

SMILES for NP0046773 (Artemorin)

INCHI for NP0046773 (Artemorin)

Structure for NP0046773 (Artemorin)

3D Structure for NP0046773 (Artemorin)