NP-MRD: Showing NP-Card for Arteannuic acid (NP0061882)

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Record Information

Version

2.0

Created at

2022-04-28 06:34:49 UTC

Updated at

2022-04-28 06:34:50 UTC

NP-MRD ID

NP0061882

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arteannuic acid

Description

(+)-Artemisinic acid, also known as artemisate, belongs to the class of organic compounds known as sesquiterpenoids. Arteannuic acid is found in Artemisia annua and Solanum lycopersicum. Arteannuic acid was first documented in 1996 (PMID: 17252486). These are terpenes with three consecutive isoprene units (+)-artemisinic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 16612385) (PMID: 19194910) (PMID: 20050663) (PMID: 22396222).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    2.7886    1.5837    0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6850    0.2866    0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9372   -0.4265   -0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542    0.1962   -0.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0308   -1.7737   -0.2980 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4418   -0.4728    0.3290 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1431   -1.3164   -0.9066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -2.3551   -0.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1319   -1.5761   -0.1825 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3196   -2.4336    0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9957   -0.4917    0.8542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2704    0.2960    0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810    1.7904    1.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1483    2.1258   -0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5511    3.2132   -1.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0503    1.4105   -0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2265    0.3506    0.6855 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7571    2.0454    0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9656    2.1940    0.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9782   -2.4887    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596   -1.2172    1.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -0.6665   -1.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0027   -1.7999   -1.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0359   -3.1566   -1.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4547   -2.7405    0.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3618   -1.0536   -1.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9951   -3.4816    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1205   -2.3662   -0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7992   -2.1018    1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9577   -1.0244    1.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0105   -0.0694    1.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7071    0.2317   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4426    1.9332    2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9532    2.2908    1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2248    4.1766   -0.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0889    3.1411   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6693    3.3023   -1.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6111    1.5973   -1.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4460    0.8467    1.6406 H   0  0  0  0  0  0  0  0  0  0  0  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 17  1  0
 17 16  1  0
 16 14  2  0
 14 15  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
 11 17  1  0
  9 26  1  6
 10 27  1  0
 10 28  1  0
 10 29  1  0
  8 24  1  0
  8 25  1  0
  7 22  1  0
  7 23  1  0
  6 21  1  1
  1 18  1  0
  1 19  1  0
  5 20  1  0
 17 39  1  1
 16 38  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 13 33  1  0
 13 34  1  0
 12 31  1  0
 12 32  1  0
 11 30  1  1
M  END

  Mrv0541 09041212512D          

 21 22  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  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    3.7125    0.0000 C   0  0  0  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
    3.5724    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    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  2  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  4  1  0  0  0  0
  9  8  2  0  0  0  0
 10  2  1  1  0  0  0
 10  5  1  0  0  0  0
 11  3  2  0  0  0  0
 12  6  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  6  0  0  0
 14  8  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 11  1  0  0  0  0
 16 15  2  0  0  0  0
 17 15  1  0  0  0  0
 10 18  1  6  0  0  0
 12 19  1  1  0  0  0
 13 20  1  1  0  0  0
 14 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0061882

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-9-4-6-12-10(2)5-7-13(14(12)8-9)11(3)15(16)17/h8,10,12-14H,3-7H2,1-2H3,(H,16,17)/t10-,12+,13+,14+/m1/s1

> <INCHI_KEY>
PLQMEXSCSAIXGB-SAXRGWBVSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.142088143014888

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
3.6979739670000003

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.049922561410144

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
69.2431

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
artemisinic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   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   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    6    9                                                       
CONECT    5    7   10                                                       
CONECT    6    4   12                                                       
CONECT    7    5   13                                                       
CONECT    8    9   14                                                       
CONECT    9    1    4    8                                                  
CONECT   10    2    5   12   18                                             
CONECT   11    3   13   15                                                  
CONECT   12    6   10   14   19                                             
CONECT   13    7   11   14   20                                             
CONECT   14    8   12   13   21                                             
CONECT   15   11   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   10                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
Artemisic acid	ChEBI
Artemisinic acid	ChEBI
Artemisate	Generator
Artemisinate	Generator
(+)-Artemisinate	Generator

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3340 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

2-[(1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid

Traditional Name

artemisinic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H22O2/c1-9-4-6-12-10(2)5-7-13(14(12)8-9)11(3)15(16)17/h8,10,12-14H,3-7H2,1-2H3,(H,16,17)/t10-,12+,13+,14+/m1/s1

InChI Key

PLQMEXSCSAIXGB-SAXRGWBVSA-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
Artemisia annua	Plant	KNApSAcK
Solanum lycopersicum	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
Cadinane sesquiterpenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:63749 )
sesquiterpenoid (CHEBI:63749 )
carbobicyclic compound (CHEBI:63749 )

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	3.2	ALOGPS
logP	3.7	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	5.05	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.24 m³·mol⁻¹	ChemAxon
Polarizability	27.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C20309

BioCyc ID

CPD-13248

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10922465

PDB ID

Not Available

ChEBI ID

63749

Good Scents ID

Not Available

References

General References

Ro DK, Paradise EM, Ouellet M, Fisher KJ, Newman KL, Ndungu JM, Ho KA, Eachus RA, Ham TS, Kirby J, Chang MC, Withers ST, Shiba Y, Sarpong R, Keasling JD: Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Nature. 2006 Apr 13;440(7086):940-3. doi: 10.1038/nature04640. [PubMed:16612385 ]
Kim SU, Han J, Lim YH: Revised assignment of 1H-NMR signals of artemisinic acid. Planta Med. 1996 Oct;62(5):480-1. doi: 10.1055/s-2006-957948. [PubMed:17252486 ]
Lenihan JR, Tsuruta H, Diola D, Renninger NS, Regentin R: Developing an industrial artemisinic acid fermentation process to support the cost-effective production of antimalarial artemisinin-based combination therapies. Biotechnol Prog. 2008 Sep-Oct;24(5):1026-32. doi: 10.1002/btpr.27. [PubMed:19194910 ]
Ferreira JF, Luthria DL: Drying affects artemisinin, dihydroartemisinic acid, artemisinic acid, and the antioxidant capacity of Artemisia annua L. leaves. J Agric Food Chem. 2010 Feb 10;58(3):1691-8. doi: 10.1021/jf903222j. [PubMed:20050663 ]
Lee J, Kim MH, Lee JH, Jung E, Yoo ES, Park D: Artemisinic acid is a regulator of adipocyte differentiation and C/EBP delta expression. J Cell Biochem. 2012 Jul;113(7):2488-99. doi: 10.1002/jcb.24124. [PubMed:22396222 ]

Showing NP-Card for Arteannuic acid (NP0061882)

MOL for NP0061882 (Arteannuic acid)

3D MOL for NP0061882 (Arteannuic acid)

3D SDF for NP0061882 (Arteannuic acid)

3D-SDF for NP0061882 (Arteannuic acid)

PDB for NP0061882 (Arteannuic acid)

3D PDB for NP0061882 (Arteannuic acid)

SMILES for NP0061882 (Arteannuic acid)

INCHI for NP0061882 (Arteannuic acid)

Structure for NP0061882 (Arteannuic acid)

3D Structure for NP0061882 (Arteannuic acid)