NP-MRD: Showing NP-Card for Œ±-Dihydroartemisinin (NP0137137)

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Record Information

Version

2.0

Created at

2022-05-30 16:42:46 UTC

Updated at

2022-05-30 16:42:46 UTC

NP-MRD ID

NP0137137

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Œ±-Dihydroartemisinin

Description

Alpha-dihydroartemisinin, also known as dihydroqinghaosu, belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins. Alpha-dihydroartemisinin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
   -1.3789   -3.2910   -0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5090   -2.1016   -0.6613 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9032   -2.4761   -0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8354   -1.2662   -0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4014   -0.3359    0.5201 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3436    0.7925    0.7487 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7628    0.3736    0.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1857    1.7832   -0.3806 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5977    1.2928   -1.6016 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9146    2.2730   -0.3473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0845    1.3656   -0.5777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2776    2.0299   -0.4513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0979    1.6362    0.5444 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9738    2.8315    0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0497    0.5771   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1527   -0.3399   -0.8561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9992   -0.8763    0.0092 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0094    0.1542    0.3647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3331    0.7297    1.6206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5511    1.1282    1.6712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0544   -3.6147   -1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0120   -2.9894    0.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7701   -4.1398    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -2.0046   -1.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143   -3.1719   -1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0763   -2.9796    0.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8443   -1.6170   -0.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6768   -0.8548   -1.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4091   -0.9631    1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0257    1.3194    1.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8601   -0.1658    1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1986   -0.1608    0.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3703    1.3124    1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8753    2.6382   -0.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2356    1.9127   -2.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0439    0.9749   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9263    2.8304    0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4182    3.7746    0.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1728    2.8146    2.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5567    0.0085    0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7013    1.1067   -0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8013    0.1215   -1.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7672   -1.2305   -1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186   -1.2026    0.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 19 20  1  0
 17  2  1  0
 18  5  1  0
 18 11  1  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  1
  7 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  1
  9 35  1  0
 11 36  1  6
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  1
M  END


  Mrv0541 06151310242D          

 20 23  0  0  1  0            999 V2000
    4.4084   -0.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360   -0.4388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0337   -0.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4834   -0.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5773    0.5801    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7641    0.8073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2170    0.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4824    1.5790    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7182    1.8342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710    2.0258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9668    1.7616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8776    1.5460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6902    1.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3595    2.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1645    1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6871    0.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8498    0.3887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3022    1.0678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5353    1.9964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2445    2.4460    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  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137137

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14?,15-/m1/s1

> <INCHI_KEY>
BJDCWCLMFKKGEE-KXTPALSWSA-N

> <FORMULA>
C15H24O5

> <MOLECULAR_WEIGHT>
284.3481

> <EXACT_MASS>
284.162373878

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.080427888832986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-ol

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
2.8382655166666666

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.114969558644466

> <JCHEM_PKA_STRONGEST_BASIC>
-4.060712315048911

> <JCHEM_POLAR_SURFACE_AREA>
57.150000000000006

> <JCHEM_REFRACTIVITY>
69.9093

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
artenimol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0       8.229  -1.648   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.974  -0.819   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.663  -1.605   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.636  -0.476   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.811   1.083   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.293   1.507   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.272   0.403   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.767   2.947   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.341   3.424   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.052   3.782   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.538   3.288   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.238   2.886   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.755   3.274   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.004   4.111   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.640   2.002   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.749   0.746   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.186   0.726   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.164   1.993   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.599   3.727   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.923   4.566   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   20                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    2   18                                                  
CONECT   18   17    5   11   19                                             
CONECT   19   18   20                                                       
CONECT   20   19   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
a-Dihydroartemisinin	Generator
Α-dihydroartemisinin	Generator
Dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12alpha,12ar*))-isomer	HMDB
Dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10beta,12alpha,12ar*))-isomer	HMDB
Dihydroartemisinine	HMDB
Dihydroqinghaosu	HMDB
Dihydroquinghaosu	HMDB
Dihydroartemisinin	HMDB
3alpha-Hydroxydeoxydihydroartemisinin	MeSH
9alpha-Hydroxydeoxyartemisinin	MeSH
8alpha-Hydroxydeoxyartemisinin	MeSH

Chemical Formula

C₁₅H₂₄O₅

Average Mass

284.3481 Da

Monoisotopic Mass

284.16237 Da

IUPAC Name

(4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-ol

Traditional Name

artenimol

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4

InChI Identifier

InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14?,15-/m1/s1

InChI Key

BJDCWCLMFKKGEE-KXTPALSWSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Artemisinins

Alternative Parents

Substituents

Artemisinin skeleton
Oxepane
1,2,4-trioxane
Oxane
Dialkyl peroxide
Hemiacetal
Oxacycle
Organoheterocyclic compound
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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
logP	2.25	ALOGPS
logP	2.84	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.11	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.15 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.91 m³·mol⁻¹	ChemAxon
Polarizability	30.08 Å³	ChemAxon
Number of Rings	4	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

HMDB0060593

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

456410

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Œ±-Dihydroartemisinin (NP0137137)

MOL for NP0137137 (Œ±-Dihydroartemisinin)

3D MOL for NP0137137 (Œ±-Dihydroartemisinin)

3D SDF for NP0137137 (Œ±-Dihydroartemisinin)

3D-SDF for NP0137137 (Œ±-Dihydroartemisinin)

PDB for NP0137137 (Œ±-Dihydroartemisinin)

3D PDB for NP0137137 (Œ±-Dihydroartemisinin)

SMILES for NP0137137 (Œ±-Dihydroartemisinin)

INCHI for NP0137137 (Œ±-Dihydroartemisinin)

Structure for NP0137137 (Œ±-Dihydroartemisinin)

3D Structure for NP0137137 (Œ±-Dihydroartemisinin)