NP-MRD: Showing NP-Card for Kawain (NP0051729)

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Record Information

Version

2.0

Created at

2022-04-27 22:59:09 UTC

Updated at

2022-04-27 22:59:09 UTC

NP-MRD ID

NP0051729

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kawain

Description

Kawain, also known as kavain or kavaform, belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton. Kawain is found in Piper methysticum . Kawain is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
    4.0064    1.9833   -0.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    1.2173   -1.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4784    0.0700   -0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933   -0.0717    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2617   -1.2786    1.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4670   -1.4175    2.8066 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6255   -2.2503    0.8060 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637   -1.9796   -0.4413 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3849   -1.6208   -0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7619   -0.3746   -0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1280    0.0429   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1355   -0.8500    0.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4405   -0.4051    0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7351    0.9394    0.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7137    1.8578    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4248    1.4068   -0.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8026   -0.9573   -1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9576    1.3999   -0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0916    2.8072   -1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9265    2.4413    0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1898    0.6881    1.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0910   -2.9366   -1.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0605   -2.4346   -0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0316    0.3643   -0.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9572   -1.9119    0.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2362   -1.1232    0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7562    1.2961    0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9156    2.9285    0.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6222    2.1003   -0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0839   -0.4799   -1.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6140   -1.4519   -1.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  2  0
  9  8  1  0
  8 17  1  0
 17  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  7  8  1  0
 16 11  1  0
 10 24  1  0
  9 23  1  0
  8 22  1  6
 17 30  1  0
 17 31  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
M  END


  Mrv1572004221603552D          

 20 21  0  0  1  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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   -0.0000    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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  1  0  0  0
 12  9  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 14  2  0  0  0  0
 16  1  1  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 17 14  1  0  0  0  0
 18  7  1  0  0  0  0
 19  8  1  0  0  0  0
 12 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051729

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])[C@@]1([H])CC(OC)=CC(=O)O1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7+/t12-/m0/s1

> <INCHI_KEY>
XEAQIWGXBXCYFX-GUOLPTJISA-N

> <FORMULA>
C14H14O3

> <MOLECULAR_WEIGHT>
230.263

> <EXACT_MASS>
230.094294311

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.868517511188575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6R)-4-methoxy-6-[(E)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
2.4327116786666663

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.541493371180767

> <JCHEM_PKA_STRONGEST_BASIC>
-4.788416686866828

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
67.35770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
kavain

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   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  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0       4.001  -2.310   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.000  -3.080   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
CONECT    1   16                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    8   11   18                                                  
CONECT    8    7   12   19                                                  
CONECT    9   12   13                                                       
CONECT   10   13   14                                                       
CONECT   11    5    6    7                                                  
CONECT   12    8    9   17   20                                             
CONECT   13    9   10   16                                                  
CONECT   14   10   15   17                                                  
CONECT   15   14                                                            
CONECT   16    1   13                                                       
CONECT   17   12   14                                                       
CONECT   18    7                                                            
CONECT   19    8                                                            
CONECT   20   12                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Kavain	Kegg
Kavaform	Kegg
Kavaine	MeSH
Kavain, (R)-(e)-isomer	MeSH
Cavain	MeSH
Kavain, (R)-isomer	MeSH
Neuronica	MeSH
Kavain, (e)-(+-)-isomer	MeSH
Kavain, (+-)-isomer	MeSH
Neuronika	MeSH
Kawain	MeSH

Chemical Formula

C₁₄H₁₄O₃

Average Mass

230.2630 Da

Monoisotopic Mass

230.09429 Da

IUPAC Name

(6R)-4-methoxy-6-[(E)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one

Traditional Name

kavain

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])[C@@]1([H])CC(OC)=CC(=O)O1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7+/t12-/m0/s1

InChI Key

XEAQIWGXBXCYFX-GUOLPTJISA-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
Piper methysticum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Kavalactones

Sub Class

Not Available

Direct Parent

Kavalactones

Alternative Parents

Substituents

Kavalactone
Styrene
Dihydropyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Vinylogous ester
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:6117 )
2-pyranones (CHEBI:6117 )
Polyketides (C09947 )
alpha-Pyrones (C09947 )

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	2.96	ALOGPS
logP	2.43	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	16.54	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	67.36 m³·mol⁻¹	ChemAxon
Polarizability	24.87 Å³	ChemAxon
Number of Rings	2	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

C00003000

Chemspider ID

Not Available

KEGG Compound ID

C09947

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281565

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Kawain (NP0051729)

MOL for NP0051729 (Kawain)

3D MOL for NP0051729 (Kawain)

3D SDF for NP0051729 (Kawain)

3D-SDF for NP0051729 (Kawain)

PDB for NP0051729 (Kawain)

3D PDB for NP0051729 (Kawain)

SMILES for NP0051729 (Kawain)

INCHI for NP0051729 (Kawain)

Structure for NP0051729 (Kawain)

3D Structure for NP0051729 (Kawain)