NP-MRD: Showing NP-Card for 2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate (NP0217328)

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Record Information

Version

2.0

Created at

2022-09-05 17:38:36 UTC

Updated at

2022-09-05 17:38:37 UTC

NP-MRD ID

NP0217328

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

Description

2,4,5-Trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). 2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate is found in Premna microphylla. 2,4,5-Trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191519502D          

 24 25  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   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
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -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
    1.4289   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   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
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217328

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=CC(=O)OC2C(O)OC(C)C(O)C2O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O8/c1-8-13(19)14(20)15(16(21)23-8)24-12(18)6-4-9-3-5-11(22-2)10(17)7-9/h3-8,13-17,19-21H,1-2H3

> <INCHI_KEY>
UGNCQBJDUPXVHT-UHFFFAOYSA-N

> <FORMULA>
C16H20O8

> <MOLECULAR_WEIGHT>
340.328

> <EXACT_MASS>
340.115817604

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
34.13066316429739

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
0.6870248793333337

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.3196002808162

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.80890203739639

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6129035822228994

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
82.39150000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-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  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667 -18.480   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334 -20.790   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.000 -18.480   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334 -19.250   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.000 -16.940   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   12   21                                                  
CONECT   21   20                                                            
CONECT   22    6   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
2,4,5-Trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₁₆H₂₀O₈

Average Mass

340.3280 Da

Monoisotopic Mass

340.11582 Da

IUPAC Name

2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

Traditional Name

2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=CC(=O)OC2C(O)OC(C)C(O)C2O)C=C1O

InChI Identifier

InChI=1S/C16H20O8/c1-8-13(19)14(20)15(16(21)23-8)24-12(18)6-4-9-3-5-11(22-2)10(17)7-9/h3-8,13-17,19-21H,1-2H3

InChI Key

UGNCQBJDUPXVHT-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Premna microphylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depsidone
Diaryl ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
1,4-dioxepine
Alkyl aryl ether
Dioxepine
Aryl chloride
Aryl halide
Benzenoid
Carboxylic acid ester
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.31	ALOGPS
logP	0.69	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.81	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.39 m³·mol⁻¹	ChemAxon
Polarizability	34.13 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

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 2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate (NP0217328)

MOL for NP0217328 (2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

3D MOL for NP0217328 (2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

3D SDF for NP0217328 (2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0217328 (2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

PDB for NP0217328 (2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

3D PDB for NP0217328 (2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

SMILES for NP0217328 (2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

INCHI for NP0217328 (2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

Structure for NP0217328 (2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)

3D Structure for NP0217328 (2,4,5-trihydroxy-6-methyloxan-3-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate)