NP-MRD: Showing NP-Card for 11-Hydroxyyangonin (NP0336062)

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Record Information

Version

2.0

Created at

2024-09-11 04:33:47 UTC

Updated at

2024-09-11 04:33:47 UTC

NP-MRD ID

NP0336062

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-Hydroxyyangonin

Description

11-Hydroxyyangonin 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. 11-Hydroxyyangonin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 11-Hydroxyyangonin has been detected, but not quantified in, beverages. This could make 11-hydroxyyangonin a potential biomarker for the consumption of these foods. Found in kava (Piper methysticum).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306512D          

 20 21  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    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
    3.5724   -0.4125    0.0000 C   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   -2.8875    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
    2.8579   -1.6500    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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    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    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  7  1  0  0  0  0
 14  6  1  0  0  0  0
 14 13  2  0  0  0  0
 15  9  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  2  0  0  0  0
 18  1  1  0  0  0  0
 18 12  1  0  0  0  0
 19  2  1  0  0  0  0
 19 14  1  0  0  0  0
 20 11  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336062

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)OC(\C=C/C2=CC(O)=C(OC)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c1-18-12-8-11(20-15(17)9-12)5-3-10-4-6-14(19-2)13(16)7-10/h3-9,16H,1-2H3/b5-3-

> <INCHI_KEY>
OCZUPEYJZNWTBK-HYXAFXHYSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.60201226319731

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-4-methoxy-2H-pyran-2-one

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
2.1782532876666663

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.835690226246456

> <JCHEM_PKA_STRONGEST_BASIC>
-4.556035544683389

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
77.1848

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-4-methoxypyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -2.310   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       6.668  -0.770   0.000  0.00  0.00           C+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  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   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       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3    5   10                                                       
CONECT    4    6   10                                                       
CONECT    5    3   11                                                       
CONECT    6    4   14                                                       
CONECT    7   10   13                                                       
CONECT    8   11   12                                                       
CONECT    9   12   15                                                       
CONECT   10    3    4    7                                                  
CONECT   11    5    8   20                                                  
CONECT   12    8    9   18                                                  
CONECT   13    7   14   16                                                  
CONECT   14    6   13   19                                                  
CONECT   15    9   17   20                                                  
CONECT   16   13                                                            
CONECT   17   15                                                            
CONECT   18    1   12                                                       
CONECT   19    2   14                                                       
CONECT   20   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₅

Average Mass

274.2687 Da

Monoisotopic Mass

274.08412 Da

IUPAC Name

6-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-4-methoxy-2H-pyran-2-one

Traditional Name

6-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-4-methoxypyran-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(\C=C/C2=CC(O)=C(OC)C=C2)=C1

InChI Identifier

InChI=1S/C15H14O5/c1-18-12-8-11(20-15(17)9-12)5-3-10-4-6-14(19-2)13(16)7-10/h3-9,16H,1-2H3/b5-3-

InChI Key

OCZUPEYJZNWTBK-HYXAFXHYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.33	ALOGPS
logP	2.18	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.84	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.18 m³·mol⁻¹	ChemAxon
Polarizability	27.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033017

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011009

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751359

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 11-Hydroxyyangonin (NP0336062)

MOL for NP0336062 (11-Hydroxyyangonin)

3D MOL for NP0336062 (11-Hydroxyyangonin)

3D SDF for NP0336062 (11-Hydroxyyangonin)

3D-SDF for NP0336062 (11-Hydroxyyangonin)

PDB for NP0336062 (11-Hydroxyyangonin)

3D PDB for NP0336062 (11-Hydroxyyangonin)

SMILES for NP0336062 (11-Hydroxyyangonin)

INCHI for NP0336062 (11-Hydroxyyangonin)

Structure for NP0336062 (11-Hydroxyyangonin)

3D Structure for NP0336062 (11-Hydroxyyangonin)