NP-MRD: Showing NP-Card for (5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate (NP0303932)

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Record Information

Version

2.0

Created at

2022-09-10 18:41:01 UTC

Updated at

2022-09-10 18:41:01 UTC

NP-MRD ID

NP0303932

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate

Description

(5-{[2-(Benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate belongs to the class of organic compounds known as cinnamic acid esters. (5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate is found in Viscum articulatum. These are compound containing an ester derivative of cinnamic acid (5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231517522D          

 38 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004231517522D          

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 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 25  1  4  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 21 35  1  0  0  0  0
 18 35  1  0  0  0  0
 35 36  1  0  0  0  0
 16 37  1  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303932

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OCC2=CC=CC=C2)C(O)C(OC2OCC(O)(COC(=O)C=CC3=CC=CC=C3)C2O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O11/c28-13-19-21(30)23(22(31)25(37-19)34-14-18-9-5-2-6-10-18)38-26-24(32)27(33,16-36-26)15-35-20(29)12-11-17-7-3-1-4-8-17/h1-12,19,21-26,28,30-33H,13-16H2

> <INCHI_KEY>
MHNSACWVEAXCGK-UHFFFAOYSA-N

> <FORMULA>
C27H32O11

> <MOLECULAR_WEIGHT>
532.542

> <EXACT_MASS>
532.19446185

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
55.48530602313159

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate

> <ALOGPS_LOGP>
0.83

> <JCHEM_LOGP>
1.1924520609999993

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.350103108825824

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.711023210951273

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810907776490874

> <JCHEM_POLAR_SURFACE_AREA>
164.37

> <JCHEM_REFRACTIVITY>
131.52510000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.56e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0       6.027 -16.396   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.495 -16.557   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.590 -15.311   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.059 -15.472   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.153 -14.226   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.378 -14.387   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.005 -15.794   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.536 -15.955   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.162 -17.362   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.694 -17.523   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.599 -16.277   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.973 -14.870   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.441 -14.709   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.780 -12.819   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.875 -11.574   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.311 -12.658   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.938 -11.252   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.033 -10.006   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.493 -10.006   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.017  -8.541   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.263  -7.636   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.232  -6.491   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.293  -6.491   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.817  -5.027   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.311  -4.707   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.280  -5.851   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.835  -3.242   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.671  -2.922   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.147  -1.457   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.654  -1.137   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.130   0.328   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.099   1.472   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.593   1.152   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.117  -0.313   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.508  -8.541   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.973  -8.065   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.217 -13.904   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.748 -13.743   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    5   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   37                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   35                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   35                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   21   18   36                                                  
CONECT   36   35                                                            
CONECT   37   16    3   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
(5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₂₇H₃₂O₁₁

Average Mass

532.5420 Da

Monoisotopic Mass

532.19446 Da

IUPAC Name

(5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate

Traditional Name

(5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

OCC1OC(OCC2=CC=CC=C2)C(O)C(OC2OCC(O)(COC(=O)C=CC3=CC=CC=C3)C2O)C1O

InChI Identifier

InChI=1S/C27H32O11/c28-13-19-21(30)23(22(31)25(37-19)34-14-18-9-5-2-6-10-18)38-26-24(32)27(33,16-36-26)15-35-20(29)12-11-17-7-3-1-4-8-17/h1-12,19,21-26,28,30-33H,13-16H2

InChI Key

MHNSACWVEAXCGK-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
Viscum articulatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Disaccharide
Glycosyl compound
O-glycosyl compound
Styrene
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organic oxygen compound
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	0.83	ALOGPS
logP	1.19	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.37 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	131.53 m³·mol⁻¹	ChemAxon
Polarizability	55.49 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

75165980

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate (NP0303932)

MOL for NP0303932 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate)

3D MOL for NP0303932 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate)

3D SDF for NP0303932 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate)

3D-SDF for NP0303932 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate)

PDB for NP0303932 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate)

3D PDB for NP0303932 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate)

SMILES for NP0303932 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate)

INCHI for NP0303932 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate)

Structure for NP0303932 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate)

3D Structure for NP0303932 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-phenylprop-2-enoate)