NP-MRD: Showing NP-Card for Stercurensin (NP0054741)

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Record Information

Version

2.0

Created at

2022-04-28 00:59:52 UTC

Updated at

2022-04-28 00:59:52 UTC

NP-MRD ID

NP0054741

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Stercurensin

Description

Stercurensin 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, stercurensin is considered to be a flavonoid lipid molecule. Stercurensin is found in Comptonia peregrina , Sterculia urens , Syzygium nervosum and Syzygium samarangense. Stercurensin was first documented in 2011 (PMID: 21268076). Stercurensin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    2.8626   -3.7573   -1.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9285   -2.7578   -0.9106 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3306   -1.4526   -0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6777   -1.1947   -0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1137    0.0804   -0.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4585    0.3845   -0.1881 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1808    1.0275    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5915    2.4023    0.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8130    0.7389    0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9076    1.6989    0.4315 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3563   -0.5123   -0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0244   -0.9294   -0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2718   -2.1436   -0.6155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -0.1230    0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4118   -0.6193   -0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232    0.1326    0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8484   -0.5323    0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0348    0.1197    0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0667    1.4441    0.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8535    2.0926    0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6626    1.4327    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5647   -4.0114   -0.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4627   -3.3995   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937   -4.6665   -1.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4267   -1.9214   -0.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8563    1.2634    0.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6367    2.4354    0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679    2.7125    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5669    3.1308   -0.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1778    2.6267    0.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1393    0.9093    0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4887   -1.6671   -0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9165   -1.5774   -0.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9859   -0.4008    0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0232    1.9091    0.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8719    3.1318    1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7636    1.9931    0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 11  9  1  0
  9 10  1  0
  9  7  2  0
  7  8  1  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  4  3  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 10 30  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  6 26  1  0
  4 25  1  0
M  END


  Mrv0541 05061309482D          

 21 22  0  0  0  0            999 V2000
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    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
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  2  0  0  0  0
 11  1  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 16 13  1  0  0  0  0
 16 15  2  0  0  0  0
 17 11  2  0  0  0  0
 17 16  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  1  0  0  0  0
 20 17  1  0  0  0  0
 21  2  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054741

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O4/c1-11-14(19)10-15(21-2)16(17(11)20)13(18)9-8-12-6-4-3-5-7-12/h3-10,19-20H,1-2H3/b9-8+

> <INCHI_KEY>
JUZVHLGKYJTCKP-CMDGGOBGSA-N

> <FORMULA>
C17H16O4

> <MOLECULAR_WEIGHT>
284.3065

> <EXACT_MASS>
284.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.383007711253413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(2,4-dihydroxy-6-methoxy-3-methylphenyl)-3-phenylprop-2-en-1-one

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
4.288944789333333

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.427628877945073

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.223800043226133

> <JCHEM_PKA_STRONGEST_BASIC>
-4.884649367568723

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
82.34319999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
stercurensin

> <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  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  11.550   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  13.860   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002  13.860   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   21                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   12                                                       
CONECT    7    5   12                                                       
CONECT    8    9   12                                                       
CONECT    9    8   13                                                       
CONECT   10   14   15                                                       
CONECT   11    1   14   17                                                  
CONECT   12    6    7    8                                                  
CONECT   13    9   16   18                                                  
CONECT   14   10   11   19                                                  
CONECT   15   10   16   21                                                  
CONECT   16   13   15   17                                                  
CONECT   17   11   16   20                                                  
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   17                                                            
CONECT   21    2   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
1-(2,4-Dihydroxy-6-methoxy-3-methylphenyl)-3-phenyl-2-propen-1-one	HMDB
2',4'-Dihydroxy-6'-methoxy-3'-methylchalcone	HMDB

Chemical Formula

C₁₇H₁₆O₄

Average Mass

284.3065 Da

Monoisotopic Mass

284.10486 Da

IUPAC Name

(2E)-1-(2,4-dihydroxy-6-methoxy-3-methylphenyl)-3-phenylprop-2-en-1-one

Traditional Name

stercurensin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H16O4/c1-11-14(19)10-15(21-2)16(17(11)20)13(18)9-8-12-6-4-3-5-7-12/h3-10,19-20H,1-2H3/b9-8+

InChI Key

JUZVHLGKYJTCKP-CMDGGOBGSA-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
Comptonia peregrina	Plant	KNApSAcK
Sterculia urens	Plant	KNApSAcK
Syzygium nervosum	LOTUS Database	35616633
Syzygium samarangense	Plant	KNApSAcK

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
Methoxyphenol
O-cresol
Phenol ether
Resorcinol
Styrene
Phenoxy compound
Aryl ketone
Benzoyl
Anisole
Methoxybenzene
Toluene
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
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

resorcinols (CHEBI:70659 )
monomethoxybenzene (CHEBI:70659 )
chalcones (CHEBI:70659 )
Chalcones and dihydrochalcones (LMPK12120223 )

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	3.64	ALOGPS
logP	4.29	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.22	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.34 m³·mol⁻¹	ChemAxon
Polarizability	30.38 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

HMDB0037485

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016556

KNApSAcK ID

C00007042

Chemspider ID

9953283

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11778601

PDB ID

Not Available

ChEBI ID

70659

Good Scents ID

Not Available

References

General References

Kim YJ, Kim HC, Ko H, Amor EC, Lee JW, Yang HO: Stercurensin inhibits nuclear factor-kappaB-dependent inflammatory signals through attenuation of TAK1-TAB1 complex formation. J Cell Biochem. 2011 Feb;112(2):548-58. doi: 10.1002/jcb.22945. [PubMed:21268076 ]

Showing NP-Card for Stercurensin (NP0054741)

MOL for NP0054741 (Stercurensin)

3D MOL for NP0054741 (Stercurensin)

3D SDF for NP0054741 (Stercurensin)

3D-SDF for NP0054741 (Stercurensin)

PDB for NP0054741 (Stercurensin)

3D PDB for NP0054741 (Stercurensin)

SMILES for NP0054741 (Stercurensin)

INCHI for NP0054741 (Stercurensin)

Structure for NP0054741 (Stercurensin)

3D Structure for NP0054741 (Stercurensin)