NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate (NP0243928)

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Record Information

Version

2.0

Created at

2022-09-07 04:35:39 UTC

Updated at

2022-09-07 04:35:39 UTC

NP-MRD ID

NP0243928

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate

Description

3,4,5-Trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate belongs to the class of organic compounds known as o-cinnamoyl glycosides. These are o-glycoside derivatives of cinnamic acid. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. 3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate is found in Fragaria chiloensis and Melia azedarach. 3,4,5-Trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -3.5522   -1.8107    1.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062   -0.3063    1.0752 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3102    0.1318    1.0097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6906   -0.0610   -0.2212 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2852    0.0118   -0.1025 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5348   -1.0778   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0447   -2.1323   -0.7367 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9876   -1.0174   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5896    0.0705    0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0315    0.1722    0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5819    1.3948    0.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241    1.5587    0.7936 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7819    0.4985    0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2814   -0.7132    0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096   -0.8506   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2343    0.8827   -1.2730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5103    2.0516   -1.3588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6889    1.1368   -0.8955 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8263    2.1530    0.0154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2730   -0.1331   -0.2699 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6453   -0.0658   -0.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5411   -2.1593    1.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2717   -2.2938    0.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7936   -1.9701    2.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1599    0.2292    1.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9383   -1.0906   -0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5506   -1.9039   -0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9795    0.9611    0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9152    2.2085    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2984    2.5327    1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8358    0.7020    0.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9497   -1.5253   -0.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5296   -1.8070   -0.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2261    0.3712   -2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3152    2.4523   -0.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3115    1.3598   -1.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5376    1.9992    0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9404   -0.9906   -0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9785   -0.9694    0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  2  1  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  1
  4 26  1  6
  8 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  6
 17 35  1  0
 18 36  1  6
 19 37  1  0
 20 38  1  6
 21 39  1  0
M  END


  Mrv1533004181500252D          

 21 22  0  0  0  0            999 V2000
    0.7145   -2.8875    0.0000 C   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 O   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
    2.1434   -5.3625    0.0000 O   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
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    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
    4.2868   -6.6000    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
    5.7158   -6.6000    0.0000 C   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
    5.0013   -7.8375    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
    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 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
   -0.7145   -5.3625    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  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
 10 15  1  0  0  0  0
  4 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
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243928

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC(=O)C=CC2=CC=CC=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O6/c1-9-12(17)13(18)14(19)15(20-9)21-11(16)8-7-10-5-3-2-4-6-10/h2-9,12-15,17-19H,1H3

> <INCHI_KEY>
DQIXENSCQIXIKS-UHFFFAOYSA-N

> <FORMULA>
C15H18O6

> <MOLECULAR_WEIGHT>
294.303

> <EXACT_MASS>
294.1103383

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.65371998057757

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate

> <ALOGPS_LOGP>
0.55

> <JCHEM_LOGP>
1.1482614666666668

> <ALOGPS_LOGS>
-1.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.267083513889851

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.209079774686577

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6122030173621544

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
73.9474

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    4   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    2   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₁₅H₁₈O₆

Average Mass

294.3030 Da

Monoisotopic Mass

294.11034 Da

IUPAC Name

3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate

Traditional Name

3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC1OC(OC(=O)C=CC2=CC=CC=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C15H18O6/c1-9-12(17)13(18)14(19)15(20-9)21-11(16)8-7-10-5-3-2-4-6-10/h2-9,12-15,17-19H,1H3

InChI Key

DQIXENSCQIXIKS-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
Fragaria chiloensis	LOTUS Database	35616633
Melia azedarach	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-cinnamoyl glycosides. These are o-glycoside derivatives of cinnamic acid. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

O-cinnamoyl glycosides

Alternative Parents

Substituents

O-cinnamoyl glycoside
Hexose monosaccharide
Styrene
Fatty acid ester
Monocyclic benzene moiety
Monosaccharide
Fatty acyl
Oxane
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	0.55	ALOGPS
logP	1.15	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.95 m³·mol⁻¹	ChemAxon
Polarizability	29.65 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

73004101

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-methyloxan-2-yl 3-phenylprop-2-enoate (NP0243928)

MOL for NP0243928 (3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate)

3D MOL for NP0243928 (3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate)

3D SDF for NP0243928 (3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate)

3D-SDF for NP0243928 (3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate)

PDB for NP0243928 (3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate)

3D PDB for NP0243928 (3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate)

SMILES for NP0243928 (3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate)

INCHI for NP0243928 (3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate)

Structure for NP0243928 (3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate)

3D Structure for NP0243928 (3,4,5-trihydroxy-6-methyloxan-2-yl 3-phenylprop-2-enoate)