NP-MRD: Showing NP-Card for beta-asarone (NP0043122)

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Record Information

Version

1.0

Created at

2021-06-21 00:36:45 UTC

Updated at

2021-08-20 00:00:42 UTC

NP-MRD ID

NP0043122

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-asarone

Provided By

JEOL Database JEOL Logo

Description

Beta-asarone, also known as (Z)-asarone or cis-isoasarone, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. beta-asarone is found in Acorus gramineus, Asarum asperum, Asarum costatum, Asarum forbesii, Asarum heterotropoides, Asarum megacalyx, Asarum sieboldii, Carpesium abrotanoides, Daucus carota , Mosla cavaleriei, Perilla frutescens, Piper cubeba and Rheum australe. It was first documented in 1983 (PMID: 17405096). Based on a literature review a significant number of articles have been published on beta-asarone (PMID: 20460763) (PMID: 20460873) (PMID: 21563811) (PMID: 21621011).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102363D          

 31 31  0  0  0  0            999 V2000
   -1.5536    5.0920   -1.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3478    4.6889    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367    3.5598    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    2.4372    0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    1.7463   -0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5888    0.6637   -0.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188   -0.0576   -2.0803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5423    0.3465   -3.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3581    0.2535    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1405   -0.8194   -0.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1304   -1.2544    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4489    0.9293    1.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3874    2.0172    1.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718    2.7255    2.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6191    2.3918    3.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1403    6.0939   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2013    5.1234   -1.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7152    4.4229   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0758    5.4256    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8507    3.4346    1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    2.0752   -1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375    1.3674   -3.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4169   -0.3195   -3.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5744    0.2441   -2.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -0.4652    0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620   -2.0965    0.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6754   -1.6117    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687    0.6026    2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.3758    4.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271    2.5214    3.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5112    3.0805    4.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  9 10  1  0  0  0  0
  7  8  1  0  0  0  0
  4 13  1  0  0  0  0
 10 11  1  0  0  0  0
  6  5  1  0  0  0  0
 13 14  1  0  0  0  0
 13 12  2  0  0  0  0
  4  3  1  0  0  0  0
 12  9  1  0  0  0  0
  3  2  2  0  0  0  0
  9  6  2  0  0  0  0
 14 15  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  1  0  0  0  0
  5 21  1  0  0  0  0
 12 28  1  0  0  0  0
  8 22  1  0  0  0  0
  8 23  1  0  0  0  0
  8 24  1  0  0  0  0
 11 25  1  0  0  0  0
 11 26  1  0  0  0  0
 11 27  1  0  0  0  0
  3 20  1  0  0  0  0
  2 19  1  0  0  0  0
 15 29  1  0  0  0  0
 15 30  1  0  0  0  0
 15 31  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
M  END

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -1.5536    5.0920   -1.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3478    4.6889    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367    3.5598    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    2.4372    0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    1.7463   -0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5888    0.6637   -0.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188   -0.0576   -2.0803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5423    0.3465   -3.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3581    0.2535    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1405   -0.8194   -0.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1304   -1.2544    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4489    0.9293    1.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3874    2.0172    1.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718    2.7255    2.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6191    2.3918    3.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1403    6.0939   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2013    5.1234   -1.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7152    4.4229   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0758    5.4256    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8507    3.4346    1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    2.0752   -1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375    1.3674   -3.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4169   -0.3195   -3.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5744    0.2441   -2.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -0.4652    0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620   -2.0965    0.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6754   -1.6117    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687    0.6026    2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.3758    4.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271    2.5214    3.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5112    3.0805    4.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
  9 10  1  0
  7  8  1  0
  4 13  1  0
 10 11  1  0
  6  5  1  0
 13 14  1  0
 13 12  2  0
  4  3  1  0
 12  9  1  0
  3  2  2  0
  9  6  2  0
 14 15  1  0
  6  7  1  0
  2  1  1  0
  5 21  1  0
 12 28  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
  3 20  1  0
  2 19  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
M  END


  Mrv1652306212102363D          

 31 31  0  0  0  0            999 V2000
   -1.5536    5.0920   -1.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3478    4.6889    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367    3.5598    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    2.4372    0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    1.7463   -0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5888    0.6637   -0.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188   -0.0576   -2.0803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5423    0.3465   -3.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3581    0.2535    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1405   -0.8194   -0.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1304   -1.2544    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4489    0.9293    1.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3874    2.0172    1.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718    2.7255    2.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6191    2.3918    3.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1403    6.0939   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2013    5.1234   -1.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7152    4.4229   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0758    5.4256    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8507    3.4346    1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    2.0752   -1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375    1.3674   -3.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4169   -0.3195   -3.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5744    0.2441   -2.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -0.4652    0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620   -2.0965    0.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6754   -1.6117    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687    0.6026    2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.3758    4.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271    2.5214    3.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5112    3.0805    4.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  9 10  1  0  0  0  0
  7  8  1  0  0  0  0
  4 13  1  0  0  0  0
 10 11  1  0  0  0  0
  6  5  1  0  0  0  0
 13 14  1  0  0  0  0
 13 12  2  0  0  0  0
  4  3  1  0  0  0  0
 12  9  1  0  0  0  0
  3  2  2  0  0  0  0
  9  6  2  0  0  0  0
 14 15  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  1  0  0  0  0
  5 21  1  0  0  0  0
 12 28  1  0  0  0  0
  8 22  1  0  0  0  0
  8 23  1  0  0  0  0
  8 24  1  0  0  0  0
 11 25  1  0  0  0  0
 11 26  1  0  0  0  0
 11 27  1  0  0  0  0
  3 20  1  0  0  0  0
  2 19  1  0  0  0  0
 15 29  1  0  0  0  0
 15 30  1  0  0  0  0
 15 31  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043122

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(/[H])C([H])([H])[H])C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5-

> <INCHI_KEY>
RKFAZBXYICVSKP-WAYWQWQTSA-N

> <FORMULA>
C12H16O3

> <MOLECULAR_WEIGHT>
208.257

> <EXACT_MASS>
208.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.389829330016397

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,4-trimethoxy-5-[(1Z)-prop-1-en-1-yl]benzene

> <ALOGPS_LOGP>
3.35

> <JCHEM_LOGP>
2.623569081666666

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.395374135558071

> <JCHEM_POLAR_SURFACE_AREA>
27.69

> <JCHEM_REFRACTIVITY>
60.807400000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-asarone

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -1.5536    5.0920   -1.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3478    4.6889    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367    3.5598    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    2.4372    0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    1.7463   -0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5888    0.6637   -0.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188   -0.0576   -2.0803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5423    0.3465   -3.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3581    0.2535    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1405   -0.8194   -0.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1304   -1.2544    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4489    0.9293    1.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3874    2.0172    1.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718    2.7255    2.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6191    2.3918    3.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1403    6.0939   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2013    5.1234   -1.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7152    4.4229   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0758    5.4256    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8507    3.4346    1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    2.0752   -1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375    1.3674   -3.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4169   -0.3195   -3.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5744    0.2441   -2.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -0.4652    0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620   -2.0965    0.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6754   -1.6117    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687    0.6026    2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.3758    4.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271    2.5214    3.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5112    3.0805    4.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
  9 10  1  0
  7  8  1  0
  4 13  1  0
 10 11  1  0
  6  5  1  0
 13 14  1  0
 13 12  2  0
  4  3  1  0
 12  9  1  0
  3  2  2  0
  9  6  2  0
 14 15  1  0
  6  7  1  0
  2  1  1  0
  5 21  1  0
 12 28  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
  3 20  1  0
  2 19  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.554   5.092  -1.061  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.348   4.689   0.140  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.237   3.560   0.859  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.323   2.437   0.588  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.426   1.746  -0.630  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.589   0.664  -0.912  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.619  -0.058  -2.080  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.542   0.347  -3.081  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.358   0.254   0.045  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.141  -0.819  -0.309  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.130  -1.254   0.611  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.449   0.929   1.270  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.387   2.017   1.551  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.372   2.725   2.728  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.619   2.392   3.690  0.00  0.00           C+0
HETATM   16  H   UNK     0      -1.140   6.094  -0.906  0.00  0.00           H+0
HETATM   17  H   UNK     0      -2.201   5.123  -1.942  0.00  0.00           H+0
HETATM   18  H   UNK     0      -0.715   4.423  -1.270  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.076   5.426   0.477  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.851   3.435   1.749  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.176   2.075  -1.342  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.337   1.367  -3.420  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.417  -0.320  -3.940  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.574   0.244  -2.730  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.864  -0.465   0.806  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.662  -2.096   0.157  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.675  -1.612   1.541  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.169   0.603   2.008  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.472   1.376   4.070  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.627   2.521   3.282  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.511   3.080   4.533  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    3    1   19                                                  
CONECT    3    4    2   20                                                  
CONECT    4    5   13    3                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    9    7                                                  
CONECT    7    8    6                                                       
CONECT    8    7   22   23   24                                             
CONECT    9   10   12    6                                                  
CONECT   10    9   11                                                       
CONECT   11   10   25   26   27                                             
CONECT   12   13    9   28                                                  
CONECT   13    4   14   12                                                  
CONECT   14   13   15                                                       
CONECT   15   14   29   30   31                                             
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    2                                                            
CONECT   20    3                                                            
CONECT   21    5                                                            
CONECT   22    8                                                            
CONECT   23    8                                                            
CONECT   24    8                                                            
CONECT   25   11                                                            
CONECT   26   11                                                            
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   15                                                            
CONECT   30   15                                                            
CONECT   31   15                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

RDKit          3D

31 31  0  0  0  0  0  0  0  0999 V2000
   -1.5536    5.0920   -1.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3478    4.6889    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367    3.5598    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    2.4372    0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    1.7463   -0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5888    0.6637   -0.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188   -0.0576   -2.0803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5423    0.3465   -3.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3581    0.2535    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1405   -0.8194   -0.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1304   -1.2544    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4489    0.9293    1.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3874    2.0172    1.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718    2.7255    2.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6191    2.3918    3.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1403    6.0939   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2013    5.1234   -1.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7152    4.4229   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0758    5.4256    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8507    3.4346    1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    2.0752   -1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375    1.3674   -3.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4169   -0.3195   -3.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5744    0.2441   -2.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -0.4652    0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620   -2.0965    0.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6754   -1.6117    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687    0.6026    2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.3758    4.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271    2.5214    3.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5112    3.0805    4.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
  9 10  1  0
  7  8  1  0
  4 13  1  0
 10 11  1  0
  6  5  1  0
 13 14  1  0
 13 12  2  0
  4  3  1  0
 12  9  1  0
  3  2  2  0
  9  6  2  0
 14 15  1  0
  6  7  1  0
  2  1  1  0
  5 21  1  0
 12 28  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
  3 20  1  0
  2 19  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
M  END

View in JSmol

Synonyms

Value	Source
(Z)-1,2,4-Trimethoxy-5-(1-propenyl)benzene	ChEBI
(Z)-Asarone	ChEBI
cis-2,4,5-Trimethoxyphenylpropene	ChEBI
cis-Asarone	ChEBI
cis-Isoasarone	ChEBI
cis-Isoelemicin	ChEBI
(Z)-1-(2,4,5-Trimethoxyphenyl)-1-propene	Kegg
b-Asarone	Generator
Β-asarone	Generator
(e)-Asarone	MeSH
2,4,5-Trimethoxypropen-1-ylbenzene	MeSH
alpha-Asarone	MeSH
Asarone	MeSH
Asarone, (e)-isomer	MeSH
Asarone, (Z)-isomer	MeSH
cis-beta-Asarone	MeSH
gamma-Asarone	MeSH
Isoasarone	MeSH
trans-Asarone	MeSH

Chemical Formula

C₁₂H₁₆O₃

Average Mass

208.2570 Da

Monoisotopic Mass

208.10994 Da

IUPAC Name

1,2,4-trimethoxy-5-[(1Z)-prop-1-en-1-yl]benzene

Traditional Name

β-asarone

CAS Registry Number

Not Available

SMILES

[H]\C(=C(/[H])C([H])([H])[H])C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1OC([H])([H])[H]

InChI Identifier

InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5-

InChI Key

RKFAZBXYICVSKP-WAYWQWQTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acorus calamus	KNApSAcK Database	22123792
Acorus calanus L.	KNApSAcK Database	22123792
Acorus gramineus	LOTUS Database	35616633
Asarum asperum	LOTUS Database	35616633
Asarum costatum	LOTUS Database	35616633
Asarum europaeum	KNApSAcK Database	22123792
Asarum forbesii	LOTUS Database	35616633
Asarum heterotropoides	LOTUS Database	35616633
Asarum megacalyx	LOTUS Database	35616633
Asarum sieboldii	LOTUS Database	35616633
Carpesium abrotanoides	LOTUS Database	35616633
Daucus carota	Plant	KNApSAcK
Mosla cavaleriei	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Piper angustifolium	KNApSAcK Database	22123792
Piper cubeba	Plant	KNApSAcK
Rheum australe	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Methoxybenzene
Styrene
Anisole
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

asarone (CHEBI:10353 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	62.00 to 63.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	264.00 to 267.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	101.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.406 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	3.35	ALOGPS
logP	2.62	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	60.81 m³·mol⁻¹	ChemAxon
Polarizability	23.39 Å³	ChemAxon
Number of Rings	1	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

C00002715

Chemspider ID

4445072

KEGG Compound ID

C10430

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281758

PDB ID

Not Available

ChEBI ID

10353

Good Scents ID

rw1230211

References

General References

Keller K, Stahl E: [Composition of the essential oil from beta-Asarone free calamus.]. Planta Med. 1983 Feb;47(2):71-4. doi: 10.1055/s-2007-969954. [PubMed:17405096 ]
Geng Y, Li C, Liu J, Xing G, Zhou L, Dong M, Li X, Niu Y: Beta-asarone improves cognitive function by suppressing neuronal apoptosis in the beta-amyloid hippocampus injection rats. Biol Pharm Bull. 2010;33(5):836-43. doi: 10.1248/bpb.33.836. [PubMed:20460763 ]
Liu J, Li C, Xing G, Zhou L, Dong M, Geng Y, Li X, Li J, Wang G, Zou D, Niu Y: Beta-asarone attenuates neuronal apoptosis induced by Beta amyloid in rat hippocampus. Yakugaku Zasshi. 2010 May;130(5):737-46. doi: 10.1248/yakushi.130.737. [PubMed:20460873 ]
Zaugg J, Eickmeier E, Ebrahimi SN, Baburin I, Hering S, Hamburger M: Positive GABA(A) receptor modulators from Acorus calamus and structural analysis of (+)-dioxosarcoguaiacol by 1D and 2D NMR and molecular modeling. J Nat Prod. 2011 Jun 24;74(6):1437-43. doi: 10.1021/np200181d. Epub 2011 May 12. [PubMed:21563811 ]
Qiu D, Hou L, Chen Y, Zhou X, Yuan W, Rong W, Zhu L, Wang J: Beta-asarone inhibits synaptic inputs to airway preganglionic parasympathetic motoneurons. Respir Physiol Neurobiol. 2011 Aug 15;177(3):313-9. doi: 10.1016/j.resp.2011.05.010. Epub 2011 May 17. [PubMed:21621011 ]
Patra, A., et al. (1981). Patra, A., et al, J. Nat. Prod. 44, 668 (1981). J. Nat. Prod..

Showing NP-Card for beta-asarone (NP0043122)

MOL for NP0043122 (beta-asarone)

3D MOL for NP0043122 (beta-asarone)

3D SDF for NP0043122 (beta-asarone)

3D-SDF for NP0043122 (beta-asarone)

PDB for NP0043122 (beta-asarone)

3D PDB for NP0043122 (beta-asarone)

SMILES for NP0043122 (beta-asarone)

INCHI for NP0043122 (beta-asarone)

Structure for NP0043122 (beta-asarone)

3D Structure for NP0043122 (beta-asarone)