NP-MRD: Showing NP-Card for Artemisinic aldehyde (NP0073825)

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Record Information

Version

2.0

Created at

2022-04-28 19:02:56 UTC

Updated at

2022-04-28 19:02:56 UTC

NP-MRD ID

NP0073825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Artemisinic aldehyde

Description

Artemisinic aldehyde belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Artemisinic aldehyde is found in Artemisia annua . Artemisinic aldehyde was first documented in 2018 (PMID: 29868094). Based on a literature review a small amount of articles have been published on artemisinic aldehyde (PMID: 34273542) (PMID: 32258005) (PMID: 32326167) (PMID: 30822491).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -2.1346   -2.6517    1.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6876   -1.6538    0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7915   -1.7697   -0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900   -0.8893   -1.6034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0816   -0.4696    1.2160 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9412    0.7195    1.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8831    1.6265    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548    1.9262   -0.3761 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2727    3.4094   -0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    1.1126    0.1168 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5414    0.9485   -1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6819    0.0492   -0.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0354   -1.3116   -0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6898   -2.4316   -1.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9037   -1.3781    0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3216   -0.1715    0.7749 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5855   -3.5409    0.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0527   -2.5963    2.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2323   -2.6463   -1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9670   -0.8231    2.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0199    0.3654    1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7624    1.2293    2.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3962    2.5899    0.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6264    1.2710   -0.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6524    1.8067   -1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6243    3.6572   -0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0441    3.5854    0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1357    4.0233   -0.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1759    1.8041    0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0529    0.4688   -1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665    1.9333   -1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5006    0.0882   -1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0359    0.3402    0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5400   -3.3699   -0.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7966   -2.2253   -1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3568   -2.5710   -2.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3859   -2.3007    0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9268   -0.1542    1.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5 16  1  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
  5  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
 10  8  1  0
 10 16  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
  8 25  1  6
  7 23  1  0
  7 24  1  0
  6 21  1  0
  6 22  1  0
  5 20  1  1
 16 38  1  1
 15 37  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 12 32  1  0
 12 33  1  0
 11 30  1  0
 11 31  1  0
 10 29  1  1
  1 17  1  0
  1 18  1  0
  3 19  1  0
M  END


  Mrv1652304282221022D          

 16 17  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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  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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   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
    2.1434   -0.4125    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
    1.4289   -1.6500    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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  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
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  1  0  0  0
 12 15  1  0  0  0  0
  3 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0073825

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-10-4-6-13-11(2)5-7-14(12(3)9-16)15(13)8-10/h8-9,11,13-15H,3-7H2,1-2H3/t11-,13+,14+,15+/m1/s1

> <INCHI_KEY>
SVAPNGMAOHQQFJ-UNQGMJICSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.34

> <EXACT_MASS>
218.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.20977429917383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <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-enal

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
3.539357714666668

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.548903360866666

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
68.3177

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.37e-03 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   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   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -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  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9                                                            
CONECT   11    5   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    4                                                       
CONECT   15   12                                                            
CONECT   16    3                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
(+)-Artemisinic aldehyde	ChEBI
Amporph-4,11-diene-12-al	ChEBI
Artemisic aldehyde	ChEBI

Chemical Formula

C₁₅H₂₂O

Average Mass

218.3400 Da

Monoisotopic Mass

218.16707 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H22O/c1-10-4-6-13-11(2)5-7-14(12(3)9-16)15(13)8-10/h8-9,11,13-15H,3-7H2,1-2H3/t11-,13+,14+,15+/m1/s1

InChI Key

SVAPNGMAOHQQFJ-UNQGMJICSA-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

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
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

aldehyde (CHEBI:64688 )
sesquiterpenoid (CHEBI:64688 )
carbobicyclic compound (CHEBI:64688 )

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	3.28	ALOGPS
logP	3.54	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.32 m³·mol⁻¹	ChemAxon
Polarizability	26.21 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

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15983961

PDB ID

Not Available

ChEBI ID

64688

Good Scents ID

Not Available

References

General References

Czechowski T, Larson TR, Catania TM, Harvey D, Wei C, Essome M, Brown GD, Graham IA: Detailed Phytochemical Analysis of High- and Low Artemisinin-Producing Chemotypes of Artemisia annua. Front Plant Sci. 2018 May 18;9:641. doi: 10.3389/fpls.2018.00641. eCollection 2018. [PubMed:29868094 ]
Feng X, Fan S, Lv G, Yan M, Wu G, Jin Y, Yang Z: Expression, purification and X-ray crystal diffraction analysis of alcohol dehydrogenase 1 from Artemisia annua L. Protein Expr Purif. 2021 Nov;187:105943. doi: 10.1016/j.pep.2021.105943. Epub 2021 Jul 14. [PubMed:34273542 ]
Zeng BX, Yao MD, Wang Y, Xiao WH, Yuan YJ: Metabolic Engineering of Saccharomyces cerevisiae for Enhanced Dihydroartemisinic Acid Production. Front Bioeng Biotechnol. 2020 Mar 17;8:152. doi: 10.3389/fbioe.2020.00152. eCollection 2020. [PubMed:32258005 ]
Firsov A, Mitiouchkina T, Shaloiko L, Pushin A, Vainstein A, Dolgov S: Agrobacterium-Mediated Transformation of Chrysanthemum with Artemisinin Biosynthesis Pathway Genes. Plants (Basel). 2020 Apr 21;9(4):537. doi: 10.3390/plants9040537. [PubMed:32326167 ]
Beyraghdar Kashkooli A, van der Krol AR, Rabe P, Dickschat JS, Bouwmeester H: Substrate promiscuity of enzymes from the sesquiterpene biosynthetic pathways from Artemisia annua and Tanacetum parthenium allows for novel combinatorial sesquiterpene production. Metab Eng. 2019 Jul;54:12-23. doi: 10.1016/j.ymben.2019.01.007. Epub 2019 Feb 26. [PubMed:30822491 ]

Showing NP-Card for Artemisinic aldehyde (NP0073825)

MOL for NP0073825 (Artemisinic aldehyde)

3D MOL for NP0073825 (Artemisinic aldehyde)

3D SDF for NP0073825 (Artemisinic aldehyde)

3D-SDF for NP0073825 (Artemisinic aldehyde)

PDB for NP0073825 (Artemisinic aldehyde)

3D PDB for NP0073825 (Artemisinic aldehyde)

SMILES for NP0073825 (Artemisinic aldehyde)

INCHI for NP0073825 (Artemisinic aldehyde)

Structure for NP0073825 (Artemisinic aldehyde)

3D Structure for NP0073825 (Artemisinic aldehyde)