NP-MRD: Showing NP-Card for 4,5-Epoxyartemisinic acid (NP0137936)

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Record Information

Version

2.0

Created at

2022-05-31 16:39:53 UTC

Updated at

2022-05-31 16:39:54 UTC

NP-MRD ID

NP0137936

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-Epoxyartemisinic acid

Description

4,5-Epoxyartemisinic acid belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 4,5-Epoxyartemisinic acid is found in Artemisia annua. Based on a literature review very few articles have been published on 4,5-Epoxyartemisinic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    3.0889    0.7243   -1.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5482    0.5734    0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8961    1.5547    1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4152    1.4596    2.2018 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7587    2.6130    0.8095 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6205   -0.5269    0.3845 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4922   -1.4434   -0.7935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4167   -2.4893   -0.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8847   -1.6761   -0.4916 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0127   -2.6573   -0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8066   -0.9681    0.8167 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0901   -0.2866    1.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4569    0.7108    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3591    1.6653   -0.1713 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6746    2.5419   -1.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6934    2.3516    0.8234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0147    1.2878    0.0356 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3013    0.0617    0.8209 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9344    0.0864   -2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7518    1.5569   -1.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4813    3.5099    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154   -1.1062    1.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2289   -0.8909   -1.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4486   -1.9679   -0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5116   -3.0341    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4160   -3.1516   -1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9477   -0.9697   -1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9991   -3.2513    0.3938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0032   -2.2152   -0.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8189   -3.3566   -1.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586   -1.7154    1.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9092   -0.9922    1.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8900    0.2291    2.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3958    1.2587    0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7372    0.1702   -0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9882    3.4120   -1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6990    2.9438   -1.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873    1.9360   -2.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7773    1.7198   -0.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4241    0.3319    1.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 14  1  0
 14 15  1  6
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  2  1  0
  2  1  2  3
  2  3  1  0
  3  5  1  0
  3  4  2  0
  6 18  1  0
 14 17  1  0
 18 11  1  0
 18 17  1  0
 17 39  1  6
 15 36  1  0
 15 37  1  0
 15 38  1  0
 13 34  1  0
 13 35  1  0
 12 32  1  0
 12 33  1  0
 11 31  1  1
  9 27  1  6
 10 28  1  0
 10 29  1  0
 10 30  1  0
  8 25  1  0
  8 26  1  0
  7 23  1  0
  7 24  1  0
  6 22  1  1
  1 19  1  0
  1 20  1  0
  5 21  1  0
 18 40  1  1
M  END


  Mrv1652305312218392D          

 23 25  0  0  1  0            999 V2000
    1.8618    1.2642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3536    0.6018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1731    0.6964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8453   -0.0607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6024   -0.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175   -0.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979   -0.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062   -0.2499    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3866   -0.3446    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8784   -1.0070    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0588   -1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1051    0.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2227    1.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0423    1.1696    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5506    1.8320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3701    1.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8784    2.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1897    2.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175    2.7783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6814    1.3588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5340    0.5071    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0258   -0.1553    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  6  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 15 22  1  0  0  0  0
  2 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0137936

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12O[C@]1(C)CC[C@@]1([H])[C@]([H])(C)CC[C@@]([H])(C(=C)C(O)=O)[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-8-4-5-11(9(2)14(16)17)12-10(8)6-7-15(3)13(12)18-15/h8,10-13H,2,4-7H2,1,3H3,(H,16,17)/t8-,10+,11+,12+,13+,15-/m1/s1

> <INCHI_KEY>
CQNNGKUJKJXDCO-IEFGFUDGSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.338

> <EXACT_MASS>
250.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.089245107073957

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1aR,3aS,4R,7R,7aS,7bS)-1a,4-dimethyl-decahydronaphtho[1,2-b]oxiren-7-yl]prop-2-enoic acid

> <JCHEM_LOGP>
2.875146188666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.783997060216993

> <JCHEM_PKA_STRONGEST_BASIC>
-4.226635531058739

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
67.92660000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1aR,3aS,4R,7R,7aS,7bS)-1a,4-dimethyl-octahydro-2H-naphtho[1,2-b]oxiren-7-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0       3.475   2.360   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       4.393   1.123   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.923   1.300   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.311  -0.113   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724  -0.725   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.699  -1.526   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.169  -1.703   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.252  -0.467   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       0.722  -0.643   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       1.640  -1.880   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       0.110  -2.056   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.196   0.593   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.416   2.007   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.946   2.183   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       1.028   3.420   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       2.558   3.596   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.640   4.833   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.087   3.773   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.699   5.186   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.005   2.537   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.864   0.947   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       3.781  -0.290   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    2    5    6                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   22                                             
CONECT    9    8                                                            
CONECT   10    8   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   22                                             
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   15    2    8   23                                             
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
4,5-Epoxyartemisinate	Generator

Chemical Formula

C₁₅H₂₂O₃

Average Mass

250.3380 Da

Monoisotopic Mass

250.15689 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

92466-31-4

SMILES

[H][C@@]12O[C@]1(C)CC[C@@]1([H])[C@]([H])(C)CC[C@@]([H])(C(=C)C(O)=O)[C@@]21[H]

InChI Identifier

InChI=1S/C15H22O3/c1-8-4-5-11(9(2)14(16)17)12-10(8)6-7-15(3)13(12)18-15/h8,10-13H,2,4-7H2,1,3H3,(H,16,17)/t8-,10+,11+,12+,13+,15-/m1/s1

InChI Key

CQNNGKUJKJXDCO-IEFGFUDGSA-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
Artemisia annua	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Oxepane
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
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

Not Available

Chemspider ID

10184537

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21575635

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 4,5-Epoxyartemisinic acid (NP0137936)

MOL for NP0137936 (4,5-Epoxyartemisinic acid)

3D MOL for NP0137936 (4,5-Epoxyartemisinic acid)

3D SDF for NP0137936 (4,5-Epoxyartemisinic acid)

3D-SDF for NP0137936 (4,5-Epoxyartemisinic acid)

PDB for NP0137936 (4,5-Epoxyartemisinic acid)

3D PDB for NP0137936 (4,5-Epoxyartemisinic acid)

SMILES for NP0137936 (4,5-Epoxyartemisinic acid)

INCHI for NP0137936 (4,5-Epoxyartemisinic acid)

Structure for NP0137936 (4,5-Epoxyartemisinic acid)

3D Structure for NP0137936 (4,5-Epoxyartemisinic acid)