NP-MRD: Showing NP-Card for Morachalcone A (NP0049611)

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Record Information

Version

2.0

Created at

2022-03-17 21:15:15 UTC

Updated at

2022-03-17 21:15:15 UTC

NP-MRD ID

NP0049611

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Morachalcone A

Description

Morachalcone A belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position. Thus, morachalcone a is considered to be a flavonoid lipid molecule. Morachalcone A is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Morachalcone A has been detected, but not quantified in, breadfruits and fruits. Morachalcone A is found in Artocarpus integer, Broussonetia papyrifera, Glycyrrhiza glabra, Maclura pomifera, Morus alba , Morus mesozygia and Morus nigra. This could make morachalcone a a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061311442D          

 25 26  0  0  0  0            999 V2000
   -5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -5.3625    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
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -6.1875    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
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    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
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  8  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  2  0  0  0  0
 13  4  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 14 11  2  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 17 16  1  0  0  0  0
 18 10  1  0  0  0  0
 18 15  2  0  0  0  0
 19 11  1  0  0  0  0
 19 13  2  0  0  0  0
 20 15  1  0  0  0  0
 20 16  2  0  0  0  0
 21 14  1  0  0  0  0
 22 17  2  0  0  0  0
 23 18  1  0  0  0  0
 24 19  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049611

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C=CC(C(=O)\C=C\C2=C(O)C=C(O)C=C2)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O5/c1-12(2)3-7-15-18(23)10-8-16(20(15)25)17(22)9-5-13-4-6-14(21)11-19(13)24/h3-6,8-11,21,23-25H,7H2,1-2H3/b9-5+

> <INCHI_KEY>
NXBYIJSAISXPKJ-WEVVVXLNSA-N

> <FORMULA>
C20H20O5

> <MOLECULAR_WEIGHT>
340.3698

> <EXACT_MASS>
340.13107375

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.149107512465086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(2,4-dihydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
5.054631021666667

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.508218810522584

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.553792942427394

> <JCHEM_PKA_STRONGEST_BASIC>
-5.970314157670516

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
99.04339999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
morachalcone A

> <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     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -13.337 -12.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0     -13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3    7   12                                                       
CONECT    4    6   13                                                       
CONECT    5    9   13                                                       
CONECT    6    4   14                                                       
CONECT    7    3   15                                                       
CONECT    8   10   16                                                       
CONECT    9    5   17                                                       
CONECT   10    8   18                                                       
CONECT   11   14   19                                                       
CONECT   12    1    2    3                                                  
CONECT   13    4    5   19                                                  
CONECT   14    6   11   21                                                  
CONECT   15    7   18   20                                                  
CONECT   16    8   17   20                                                  
CONECT   17    9   16   22                                                  
CONECT   18   10   15   23                                                  
CONECT   19   11   13   24                                                  
CONECT   20   15   16   25                                                  
CONECT   21   14                                                            
CONECT   22   17                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
CONECT   25   20                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀O₅

Average Mass

340.3698 Da

Monoisotopic Mass

340.13107 Da

IUPAC Name

(2E)-1-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(2,4-dihydroxyphenyl)prop-2-en-1-one

Traditional Name

morachalcone A

CAS Registry Number

76472-88-3

SMILES

CC(C)=CCC1=C(O)C=CC(C(=O)\C=C\C2=C(O)C=C(O)C=C2)=C1O

InChI Identifier

InChI=1S/C20H20O5/c1-12(2)3-7-15-18(23)10-8-16(20(15)25)17(22)9-5-13-4-6-14(21)11-19(13)24/h3-6,8-11,21,23-25H,7H2,1-2H3/b9-5+

InChI Key

NXBYIJSAISXPKJ-WEVVVXLNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artocarpus altilis	FooDB	KNAPSACK
Artocarpus champeden	LOTUS Database	35616633
Broussonetia papyrifera	LOTUS Database	35616633
Glycyrrhiza glabra	LOTUS Database	35616633
Maclura pomifera	LOTUS Database	35616633
Morus alba	Plant	KNApSAcK
Morus mesozygia	LOTUS Database	35616633
Morus nigra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

3-prenylated chalcones

Alternative Parents

Substituents

3-prenylated chalcone
2'-hydroxychalcone
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Benzoyl
Aryl ketone
Resorcinol
Styrene
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Ketone
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120119 )

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	3.37	ALOGPS
logP	5.05	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	7.55	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.04 m³·mol⁻¹	ChemAxon
Polarizability	37.15 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0040306

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020029

KNApSAcK ID

C00007091

Chemspider ID

8038465

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9862769

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Morachalcone A (NP0049611)

MOL for NP0049611 (Morachalcone A)

3D MOL for NP0049611 (Morachalcone A)

3D SDF for NP0049611 (Morachalcone A)

3D-SDF for NP0049611 (Morachalcone A)

PDB for NP0049611 (Morachalcone A)

3D PDB for NP0049611 (Morachalcone A)

SMILES for NP0049611 (Morachalcone A)

INCHI for NP0049611 (Morachalcone A)

Structure for NP0049611 (Morachalcone A)

3D Structure for NP0049611 (Morachalcone A)