NP-MRD: Showing NP-Card for Helichrysetin (NP0054657)

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Record Information

Version

2.0

Created at

2022-04-28 00:56:30 UTC

Updated at

2022-04-28 00:56:30 UTC

NP-MRD ID

NP0054657

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Helichrysetin

Description

1-(2,4-Dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one, also known as helichysetin, belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, 1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one is considered to be a flavonoid lipid molecule. 1-(2,4-Dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. This hydroxylation-of-benzene-ortho-to-edg occurs in humans. It is generated by cyp2c9 and cyp2c19 enzymes via a hydroxylation-of-benzene-ortho-to-edg reaction. Helichrysetin is found in Achyrocline flaccida, Alpinia blepharocalyx , Alpinia roxburghii, Boesenbergia rotunda, Helichrysum heterolasium, Helichrysum odoratissimum , Ononis natrix and Vitex tripinnata. 1-(2,4-Dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.9706   -0.1844   -2.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5538   -0.2217   -1.2124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4265   -0.4550   -0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7630   -0.6554   -0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7260   -0.8953    0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0601   -1.0939    0.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3634   -0.9393    1.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0090   -0.7381    2.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7839   -0.8080    3.4534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397   -0.4969    1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6586   -0.2914    1.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3610   -0.3411    2.7887 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4552   -0.0298    0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6841    0.1408    1.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8483    0.4064    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0975    0.5709    0.9091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356    0.8237    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2069    0.9298   -1.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3714    1.1868   -1.9184 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9837    0.7707   -1.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260    0.5132   -1.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3753   -1.1799   -2.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1950    0.1780   -3.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8272    0.5314   -2.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0868   -0.6269   -1.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6339   -0.2481    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1213   -1.1304    2.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9835   -0.7118    3.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    0.0317   -0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8076    0.0758    2.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1392    0.4903    1.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2063    0.9498    0.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9719    0.4535   -2.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034    0.8443   -2.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785    0.3933   -1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  4  3  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
  9 28  1  0
  7 27  1  0
  6 26  1  0
  4 25  1  0
M  END


  Mrv1652304072021162D          

 21 22  0  0  0  0            999 V2000
 9999.308910000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0234 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.308910001.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.738110000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3089 9998.7624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.880010001.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0234 9999.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4511 9998.7624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.5988 9998.7624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.880010000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.165610000.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1656 9999.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8800 9998.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5945 9999.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.594510000.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.883310000.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.168910000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.454310000.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4543 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1687 9998.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8833 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  2  4  2  0  0  0  0
  5  7  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 10  1  0  0  0  0
  1 15  1  0  0  0  0
 14  5  1  0  0  0  0
 10  6  1  0  0  0  0
 12  8  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 16  1  0  0  0  0
  4 18  1  0  0  0  0
 21  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054657

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-21-15-9-12(18)8-14(20)16(15)13(19)7-4-10-2-5-11(17)6-3-10/h2-9,17-18,20H,1H3/b7-4+

> <INCHI_KEY>
OWGUBYRKZATRIT-QPJJXVBHSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.460257768072342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
3.4719580783333335

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.60957329894507

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.191991341437985

> <JCHEM_PKA_STRONGEST_BASIC>
-4.895833429103171

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
79.2829

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
helichrysetin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-APR-20         0                                  
HETATM    1  C   UNK     0    8665.3778667.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.7108666.666   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8665.3778668.977   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8668.0448667.437   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8665.3778664.356   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8662.7098668.977   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8666.7108665.129   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8660.0428664.356   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8673.3848664.356   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8662.7098667.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8661.3768666.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.3768665.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.7098664.357   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.0438665.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.0438666.667   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8672.0498666.667   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8670.7158667.437   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8669.3818666.667   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8669.3818665.127   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8670.7158664.357   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.0498665.127   0.000  0.00  0.00           C+0
CONECT    1    2    3   15                                                  
CONECT    2    1    4                                                       
CONECT    3    1                                                            
CONECT    4    2   18                                                       
CONECT    5    7   14                                                       
CONECT    6   10                                                            
CONECT    7    5                                                            
CONECT    8   12                                                            
CONECT    9   21                                                            
CONECT   10   11   15    6                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13    8                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15    5                                                  
CONECT   15   14   10    1                                                  
CONECT   16   17   21                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19    4                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16    9                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
Helichysetin	HMDB
1-(2,4-Dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one	HMDB
(2E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one	HMDB
2',4',4-Trihydroxy-6'-methoxychalcone	HMDB
2’,4’,4-Trihydroxy-6’-methoxychalcone	HMDB
4,2',4'-Trihydroxy-6'-methoxychalcone	HMDB
4,2’,4’-Trihydroxy-6’-methoxychalcone	HMDB
Helichrysetin	HMDB

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2830 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

(2E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

helichrysetin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H14O5/c1-21-15-9-12(18)8-14(20)16(15)13(19)7-4-10-2-5-11(17)6-3-10/h2-9,17-18,20H,1H3/b7-4+

InChI Key

OWGUBYRKZATRIT-QPJJXVBHSA-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
Achyrocline flaccida	Plant	KNApSAcK
Alpinia blepharocalyx	Plant	KNApSAcK
Alpinia roxburghii	LOTUS Database	35616633
Boesenbergia rotunda	LOTUS Database	35616633
Helichrysum heterolasium	Plant	KNApSAcK
Helichrysum odoratissimum	Plant	KNApSAcK
Ononis natrix	LOTUS Database	35616633
Vitex tripinnata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Phenol ether
Resorcinol
Styrene
Aryl ketone
Benzoyl
Anisole
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Vinylogous acid
Enone
Alpha,beta-unsaturated ketone
Ketone
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120300 )

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	3.16	ALOGPS
logP	3.47	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.19	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.28 m³·mol⁻¹	ChemAxon
Polarizability	29.46 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

HMDB0132893

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB089950

KNApSAcK ID

Not Available

Chemspider ID

4863252

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6253344

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Helichrysetin (NP0054657)

MOL for NP0054657 (Helichrysetin)

3D MOL for NP0054657 (Helichrysetin)

3D SDF for NP0054657 (Helichrysetin)

3D-SDF for NP0054657 (Helichrysetin)

PDB for NP0054657 (Helichrysetin)

3D PDB for NP0054657 (Helichrysetin)

SMILES for NP0054657 (Helichrysetin)

INCHI for NP0054657 (Helichrysetin)

Structure for NP0054657 (Helichrysetin)

3D Structure for NP0054657 (Helichrysetin)