NP-MRD: Showing NP-Card for Arteannuin B (NP0061884)

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Record Information

Version

2.0

Created at

2022-04-28 06:34:55 UTC

Updated at

2022-04-28 06:34:55 UTC

NP-MRD ID

NP0061884

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arteannuin B

Description

Arteannuin B belongs to the class of organic compounds known as cadinanolides. These are sesquiterpene lactones based on 2-dioxonaphtho[4a,4-b]furan. Arteannuin B is found in Artemisia annua . Arteannuin B was first documented in 2020 (PMID: 32786284). Based on a literature review a small amount of articles have been published on Arteannuin B (PMID: 34527599) (PMID: 35286922) (PMID: 34655840) (PMID: 34452197).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
   -1.5005    3.5677   -0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1209    2.4736   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2714    2.3791   -1.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1232    3.3604   -2.5512 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0094    1.0102   -2.0577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0735    0.4461   -0.7615 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4079    1.0798   -0.3319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6394    0.7215    1.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0345   -0.7611    1.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9043   -1.5647    0.4878 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3900   -2.9795    0.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2778   -1.0253   -0.7491 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0491   -1.7153   -0.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0599   -1.3358    0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1743    0.1347    0.2998 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1125    0.5152    1.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3030    0.9337   -0.8100 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752    0.9380    0.0331 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1842    4.5206   -0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1199    3.5400    0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1839    0.6545   -0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3972    1.3102    1.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7059    0.7552    1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2698   -1.1290    2.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9298   -0.8070    0.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1568   -1.6763    1.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098   -3.2544   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8857   -3.7402    0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977   -3.0466    0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9281   -1.2922   -1.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840   -1.4695   -1.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8592   -2.8109   -0.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8627   -1.8085    1.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0397   -1.7916   -0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558   -0.1934    1.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4937    0.5531    2.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209    1.5497    1.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665    1.9580    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  6  5  1  6
  6 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  1  1
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
  6  7  1  0
 12  6  1  0
 15 18  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 10 26  1  1
  9 24  1  0
  9 25  1  0
  8 22  1  0
  8 23  1  0
  7 21  1  6
  1 19  1  0
  1 20  1  0
 18 38  1  1
 16 35  1  0
 16 36  1  0
 16 37  1  0
 14 33  1  0
 14 34  1  0
 13 31  1  0
 13 32  1  0
 12 30  1  6
M  END


  Mrv1652304282208342D          

 18 21  0  0  1  0            999 V2000
    0.3998   -0.3501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1033    0.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2114    1.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0291    1.1751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5323    0.5213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2176   -0.2413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7207   -0.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5385   -0.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532   -0.0237    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3949    0.5224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1679    0.7389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6158   -0.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3096    0.7977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2869    1.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9407    2.1255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4955    1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2191    2.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851   -1.1128    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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
  9 11  1  0  0  0  0
  9 12  1  1  0  0  0
  5 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  4 16  1  1  0  0  0
 16 17  2  0  0  0  0
  1 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0061884

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H]2C(=C)C(=O)O[C@@]22[C@@H]3O[C@]3(C)CC[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-4-5-11-9(2)12(16)17-15(11)10(8)6-7-14(3)13(15)18-14/h8,10-11,13H,2,4-7H2,1,3H3/t8-,10+,11+,13-,14-,15-/m1/s1

> <INCHI_KEY>
QWQSMEDUZQDVLA-KPHNHPKPSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.013885952246056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.0^{1,5}.0^{12,14}]tetradecan-3-one

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.8475120716666664

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.244929433355257

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
65.7315

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.0^{1,5}.0^{12,14}]tetradecan-3-one

> <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       0.746  -0.654   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.193   0.567   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.395   1.990   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.921   2.194   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.860   0.973   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.273  -0.450   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.212  -1.671   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.739  -1.468   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.326  -0.044   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.470   0.975   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.913   1.379   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.750  -0.632   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.311   1.489   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.269   3.029   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.489   3.968   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.792   3.464   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.276   4.915   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.159  -2.077   0.000  0.00  0.00           C+0
CONECT    1    2    6   18                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6   10   13                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9    5   11                                                  
CONECT   11   10    9                                                       
CONECT   12    9                                                            
CONECT   13    5   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    4   17                                                  
CONECT   17   16                                                            
CONECT   18    1                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.0^{1,5}.0^{12,14}]tetradecan-3-one

Traditional Name

(1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.0^{1,5}.0^{12,14}]tetradecan-3-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@H]2C(=C)C(=O)O[C@@]22[C@@H]3O[C@]3(C)CC[C@@H]12

InChI Identifier

InChI=1S/C15H20O3/c1-8-4-5-11-9(2)12(16)17-15(11)10(8)6-7-14(3)13(15)18-14/h8,10-11,13H,2,4-7H2,1,3H3/t8-,10+,11+,13-,14-,15-/m1/s1

InChI Key

QWQSMEDUZQDVLA-KPHNHPKPSA-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 cadinanolides. These are sesquiterpene lactones based on 2-dioxonaphtho[4a,4-b]furan.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Cadinanolides

Alternative Parents

Substituents

Cadinanolide skeleton
Sesquiterpenoid
Oxepane
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
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	2.65	ALOGPS
logP	2.85	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.73 m³·mol⁻¹	ChemAxon
Polarizability	27.01 Å³	ChemAxon
Number of Rings	4	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

C00017523

Chemspider ID

5023987

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6543478

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hu Y, Liu M, Qin H, Lin H, An X, Shi Z, Song L, Yang X, Fan H, Tong Y: Artemether, Artesunate, Arteannuin B, Echinatin, Licochalcone B and Andrographolide Effectively Inhibit SARS-CoV-2 and Related Viruses In Vitro. Front Cell Infect Microbiol. 2021 Aug 30;11:680127. doi: 10.3389/fcimb.2021.680127. eCollection 2021. [PubMed:34527599 ]
Rasool JU, Mir KB, Shaikh M, Bhat AH, Nalli Y, Khalid A, Ahmad SM, Goswami A, Ali A: Palladium catalyzed migratory heck coupling of arteannuin B and boronic acids: An approach towards the synthesis of antiproliferative agents in breast and lung cancer cells. Bioorg Chem. 2022 May;122:105694. doi: 10.1016/j.bioorg.2022.105694. Epub 2022 Feb 28. [PubMed:35286922 ]
Ur Rasool J, Sawhney G, Shaikh M, Nalli Y, Madishetti S, Ahmed Z, Ali A: Site selective synthesis and anti-inflammatory evaluation of Spiro-isoxazoline stitched adducts of arteannuin B. Bioorg Chem. 2021 Dec;117:105408. doi: 10.1016/j.bioorg.2021.105408. Epub 2021 Oct 9. [PubMed:34655840 ]
Wang Y, Huang W, Wang N, Ouyang D, Xiao L, Zhang S, Ou X, He T, Yu R, Song L: Development of Arteannuin B Sustained-Release Microspheres for Anti-Tumor Therapy by Integrated Experimental and Molecular Modeling Approaches. Pharmaceutics. 2021 Aug 11;13(8). pii: pharmaceutics13081236. doi: 10.3390/pharmaceutics13081236. [PubMed:34452197 ]
Cao R, Hu H, Li Y, Wang X, Xu M, Liu J, Zhang H, Yan Y, Zhao L, Li W, Zhang T, Xiao D, Guo X, Li Y, Yang J, Hu Z, Wang M, Zhong W: Anti-SARS-CoV-2 Potential of Artemisinins In Vitro. ACS Infect Dis. 2020 Sep 11;6(9):2524-2531. doi: 10.1021/acsinfecdis.0c00522. Epub 2020 Aug 18. [PubMed:32786284 ]

Showing NP-Card for Arteannuin B (NP0061884)

MOL for NP0061884 (Arteannuin B)

3D MOL for NP0061884 (Arteannuin B)

3D SDF for NP0061884 (Arteannuin B)

3D-SDF for NP0061884 (Arteannuin B)

PDB for NP0061884 (Arteannuin B)

3D PDB for NP0061884 (Arteannuin B)

SMILES for NP0061884 (Arteannuin B)

INCHI for NP0061884 (Arteannuin B)

Structure for NP0061884 (Arteannuin B)

3D Structure for NP0061884 (Arteannuin B)