NP-MRD: Showing NP-Card for 1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene (NP0149575)

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Record Information

Version

2.0

Created at

2022-09-02 05:29:12 UTC

Updated at

2022-09-02 05:29:12 UTC

NP-MRD ID

NP0149575

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Asarone belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. 1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene is found in Acorus calamus, Acorus gramineus, Asarum caudatum, Asarum europaeum, Asarum heterotropoides, Daucus carota, Mosannona depressa, Mosla scabra, Peperomia tetraphylla, Piper cubeba, Piper sarmentosum and Rheum australe. Asarone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
    4.0448    1.7244    1.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6024    1.4686    1.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2282    0.4838    0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8200    0.1944    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2205    0.9310    0.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5492    0.6137    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924    1.3550    0.8804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403    2.4690    1.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8696   -0.4449   -0.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1943   -0.7372   -0.7434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6190   -1.7782   -1.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8216   -1.1829   -0.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -0.8788   -0.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5247   -1.6207   -1.1770 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3835   -2.7234   -2.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2735    2.8075    1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2508    1.3713    2.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6900    1.1407    0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9069    2.1364    1.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975   -0.1541    0.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0298    1.7757    1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6175    2.1696    2.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2611    2.7715    2.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9160    3.3084    1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9267   -1.8214   -2.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5675   -2.7553   -1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6504   -1.5722   -1.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0781   -2.0228   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8285   -2.3734   -2.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8462   -3.5806   -1.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3687   -3.0751   -2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
  3 20  1  0
  2 19  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
M  END


  Mrv1533004161523412D          

 15 15  0  0  0  0            999 V2000
    0.0000    2.4750    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   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 O   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
    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  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
    0.0000    0.0000    0.0000 C   0  0  0  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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  4  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0149575

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C(C=CC)C=C1OC

> <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

> <INCHI_KEY>
RKFAZBXYICVSKP-UHFFFAOYSA-N

> <FORMULA>
C12H16O3

> <MOLECULAR_WEIGHT>
208.257

> <EXACT_MASS>
208.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.22904079430595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,4-trimethoxy-5-(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>
60.8074

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
asarone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   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  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12    3   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
2,4,5-Trimethoxy-1-propenylbenzene	ChEBI
(e)-Asarone	MeSH
(Z)-Asarone	MeSH
Asarone, (e)-isomer	MeSH
cis-Isoelemicin	MeSH
gamma-Asarone	MeSH
Isoasarone	MeSH
beta-Asarone	MeSH
cis-beta-Asarone	MeSH
2,4,5-Trimethoxypropen-1-ylbenzene	MeSH
alpha-Asarone	MeSH
Asarone	MeSH
Asarone, (Z)-isomer	MeSH
cis-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-(prop-1-en-1-yl)benzene

Traditional Name

asarone

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C(C=CC)C=C1OC

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

InChI Key

RKFAZBXYICVSKP-UHFFFAOYSA-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
Acorus calamus	LOTUS Database	35616633
Acorus gramineus	LOTUS Database	35616633
Asarum caudatum	LOTUS Database	35616633
Asarum europaeum	LOTUS Database	35616633
Asarum heterotropoides	LOTUS Database	35616633
Daucus carota	LOTUS Database	35616633
Mosannona depressa	LOTUS Database	35616633
Mosla scabra	LOTUS Database	35616633
Peperomia tetraphylla	LOTUS Database	35616633
Piper cubeba	LOTUS Database	35616633
Piper sarmentosum	LOTUS Database	35616633
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

phenylpropanoid (CHEBI:78308 )
methoxybenzene (CHEBI:78308 )

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	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	23.23 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Asarone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

78308

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene (NP0149575)

MOL for NP0149575 (1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene)

3D MOL for NP0149575 (1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene)

3D SDF for NP0149575 (1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene)

3D-SDF for NP0149575 (1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene)

PDB for NP0149575 (1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene)

3D PDB for NP0149575 (1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene)

SMILES for NP0149575 (1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene)

INCHI for NP0149575 (1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene)

Structure for NP0149575 (1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene)

3D Structure for NP0149575 (1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene)