NP-MRD: Showing NP-Card for (1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione (NP0189094)

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Record Information

Version

2.0

Created at

2022-09-04 05:31:32 UTC

Updated at

2022-09-04 05:31:32 UTC

NP-MRD ID

NP0189094

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione

Description

ASATONE belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. (1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione is found in Asarum fauriei and Asarum sakawanum. (1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione was first documented in 2019 (PMID: 31683670). Based on a literature review a small amount of articles have been published on ASATONE (PMID: 35609322) (PMID: 33577041) (PMID: 33165354) (PMID: 32644793).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042207312D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042207312D          

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M  END
> <DATABASE_ID>
NP0189094

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C[C@@]2(CC=C)[C@H]([C@H]3C(CC=C)=CC2(OC)C(=O)C3(OC)OC)C(OC)(OC)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O8/c1-9-11-15-13-22(28-4)20(26)23(29-5,30-6)17(15)18-21(22,12-10-2)14-16(27-3)19(25)24(18,31-7)32-8/h9-10,13-14,17-18H,1-2,11-12H2,3-8H3/t17-,18+,21+,22?/m1/s1

> <INCHI_KEY>
XBKKBTPYPCCCKA-LWJBKALKSA-N

> <FORMULA>
C24H32O8

> <MOLECULAR_WEIGHT>
448.512

> <EXACT_MASS>
448.20971799

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.27924212340962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,7S)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0^{2,7}]dodeca-5,11-diene-4,9-dione

> <JCHEM_LOGP>
3.352683611333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.610244645600527

> <JCHEM_POLAR_SURFACE_AREA>
89.52000000000002

> <JCHEM_REFRACTIVITY>
119.91209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,7S)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0^{2,7}]dodeca-5,11-diene-4,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.439  -0.892   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.224   0.055   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.700  -0.563   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.053   0.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.250   1.920   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.417   2.283   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.152   4.046   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.186   5.374   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.702   1.435   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.985   2.904   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.610  -0.103   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.679   0.592   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.719  -0.802   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.693  -2.049   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.329  -3.333   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.233  -0.792   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.550   0.218   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.836  -0.630   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.936  -2.047   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.318  -3.781   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.562  -2.055   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.101  -2.561   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.213   0.059   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.945   0.582   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.305   1.596   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.970   2.308   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.739   3.721   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.020   2.444   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.642   1.755   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.162   1.254   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.548   2.957   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.075   3.154   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9   29                                             
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14   16                                             
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14                                                            
CONECT   16   11    4   17                                                  
CONECT   17   16   18   29                                                  
CONECT   18   17   19   21   23                                             
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21                                                            
CONECT   23   18   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28   17    6   30                                             
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₈

Average Mass

448.5120 Da

Monoisotopic Mass

448.20972 Da

IUPAC Name

(1S,2S,7S)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0^{2,7}]dodeca-5,11-diene-4,9-dione

Traditional Name

(1S,2S,7S)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0^{2,7}]dodeca-5,11-diene-4,9-dione

CAS Registry Number

Not Available

SMILES

COC1=C[C@@]2(CC=C)[C@H]([C@H]3C(CC=C)=CC2(OC)C(=O)C3(OC)OC)C(OC)(OC)C1=O

InChI Identifier

InChI=1S/C24H32O8/c1-9-11-15-13-22(28-4)20(26)23(29-5,30-6)17(15)18-21(22,12-10-2)14-16(27-3)19(25)24(18,31-7)32-8/h9-10,13-14,17-18H,1-2,11-12H2,3-8H3/t17-,18+,21+,22?/m1/s1

InChI Key

XBKKBTPYPCCCKA-LWJBKALKSA-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
Asarum fauriei	LOTUS Database	35616633
Asarum sakawanum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Cyclohexenone
Cyclic ketone
Ketone
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.35	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	89.52 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	119.91 m³·mol⁻¹	ChemAxon
Polarizability	46.28 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000508

Chemspider ID

71041976

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134714897

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang C, Liang H, Li Y, Tang Z, Zhang Y: Chemokine (C-C motif) ligand 18/membrane-associated 3/forkhead box O1 axis promotes the proliferation, migration, and invasion of intrahepatic cholangiocarcinoma. Bioengineered. 2022 May;13(5):12738-12748. doi: 10.1080/21655979.2022.2069383. [PubMed:35609322 ]
Song L, Luan B, Xu QR, Wang XF: Effect of TLR7 gene expression mediating NF-kappaB signaling pathway on the pathogenesis of bronchial asthma in mice and the intervention role of IFN-gamma. Eur Rev Med Pharmacol Sci. 2021 Jan;25(2):866-879. doi: 10.26355/eurrev_202101_24655. [PubMed:33577041 ]
Wu J, Liu Y, Hu J, Xie J, Nie Z, Yin W: Protective activity of asatone against ovalbumin-induced allergic asthma. Int J Clin Exp Pathol. 2020 Oct 1;13(10):2487-2494. eCollection 2020. [PubMed:33165354 ]
Wu L, Liu X, Huang Y, Lu C, Zhou J, Ren P, Huang X: Antidepressant-like Effect of Merazin Hydrate Depends on NO/ERK by Suppressing Its Downstream NF-kappaB or Nonactivating CREB/BDNF in Mouse Hippocampus. ACS Chem Neurosci. 2020 Aug 19;11(16):2472-2481. doi: 10.1021/acschemneuro.0c00246. Epub 2020 Jul 9. [PubMed:32644793 ]
Ling R, Yang R, Li P, Zhang X, Shen T, Li X, Yang Q, Sun L, Yan J: Asatone and Isoasatone A Against Spodoptera litura Fab. by Acting on Cytochrome P450 Monoxygenases and Glutathione Transferases. Molecules. 2019 Oct 31;24(21):3940. doi: 10.3390/molecules24213940. [PubMed:31683670 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione (NP0189094)

MOL for NP0189094 ((1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione)

3D MOL for NP0189094 ((1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione)

3D SDF for NP0189094 ((1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione)

3D-SDF for NP0189094 ((1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione)

PDB for NP0189094 ((1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione)

3D PDB for NP0189094 ((1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione)

SMILES for NP0189094 ((1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione)

INCHI for NP0189094 ((1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione)

Structure for NP0189094 ((1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione)

3D Structure for NP0189094 ((1s,2s,7s)-3,3,5,8,10,10-hexamethoxy-7,11-bis(prop-2-en-1-yl)tricyclo[6.2.2.0²,⁷]dodeca-5,11-diene-4,9-dione)