NP-MRD: Showing NP-Card for {3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate (NP0225825)

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Record Information

Version

1.0

Created at

2022-09-06 04:39:51 UTC

Updated at

2022-09-06 04:39:51 UTC

NP-MRD ID

NP0225825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate

Description

{3,4,5-Trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position. {3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate is found in Protea rubropilosa. {3,4,5-Trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191518052D          

 31 33  0  0  0  0            999 V2000
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 13  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
  3 31  1  0  0  0  0
M  END


  Mrv1533004191518052D          

 31 33  0  0  0  0            999 V2000
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 13  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
  3 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225825

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=CC=C(OC2OC(COC(=O)C=CC3=CC=CC=C3)C(O)C(O)C2O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O9/c23-11-14-6-8-16(15(24)10-14)30-22-21(28)20(27)19(26)17(31-22)12-29-18(25)9-7-13-4-2-1-3-5-13/h1-10,17,19-24,26-28H,11-12H2

> <INCHI_KEY>
HNOZXQFKIYWTHH-UHFFFAOYSA-N

> <FORMULA>
C22H24O9

> <MOLECULAR_WEIGHT>
432.425

> <EXACT_MASS>
432.142032353

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.46856265650172

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.36458803

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20239410709016

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.653426166054036

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8228461594895142

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
108.54780000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.336 -16.170   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002 -18.480   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668 -20.790   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335 -21.560   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668 -23.870   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001 -25.410   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667 -26.180   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667 -27.720   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334 -28.490   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000 -27.720   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000 -26.180   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334 -25.410   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001 -19.250   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.003 -14.630   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   10   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    8   28                                                  
CONECT   28   27                                                            
CONECT   29    6   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    3                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
{3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₂₂H₂₄O₉

Average Mass

432.4250 Da

Monoisotopic Mass

432.14203 Da

IUPAC Name

{3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate

Traditional Name

{3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

OCC1=CC=C(OC2OC(COC(=O)C=CC3=CC=CC=C3)C(O)C(O)C2O)C(O)=C1

InChI Identifier

InChI=1S/C22H24O9/c23-11-14-6-8-16(15(24)10-14)30-22-21(28)20(27)19(26)17(31-22)12-29-18(25)9-7-13-4-2-1-3-5-13/h1-10,17,19-24,26-28H,11-12H2

InChI Key

HNOZXQFKIYWTHH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Protea rubropilosa	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
Catechol
Aryl ketone
Resorcinol
Styrene
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Alpha,beta-unsaturated ketone
Acryloyl-group
Enone
Vinylogous acid
Ketone
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.03	ALOGPS
logP	1.36	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.65	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	108.55 m³·mol⁻¹	ChemAxon
Polarizability	43.47 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate (NP0225825)

MOL for NP0225825 ({3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate)

3D MOL for NP0225825 ({3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate)

3D SDF for NP0225825 ({3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate)

3D-SDF for NP0225825 ({3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate)

PDB for NP0225825 ({3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate)

3D PDB for NP0225825 ({3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate)

SMILES for NP0225825 ({3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate)

INCHI for NP0225825 ({3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate)

Structure for NP0225825 ({3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate)

3D Structure for NP0225825 ({3,4,5-trihydroxy-6-[2-hydroxy-4-(hydroxymethyl)phenoxy]oxan-2-yl}methyl 3-phenylprop-2-enoate)