NP-MRD: Showing NP-Card for {3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate (NP0280200)

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Record Information

Version

2.0

Created at

2022-09-09 05:51:27 UTC

Updated at

2022-09-09 05:51:27 UTC

NP-MRD ID

NP0280200

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

Description

{3,4,5-Trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group. {3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate is found in Pimenta dioica. {3,4,5-Trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251509202D          

 39 41  0  0  0  0            999 V2000
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004251509202D          

 39 41  0  0  0  0            999 V2000
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013   -8.6625    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
    6.4302   -6.1875    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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  5  9  2  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  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 17  1  4  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  2  0  0  0  0
 21 31  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 12 36  1  0  0  0  0
 36 37  1  0  0  0  0
 10 38  2  0  0  0  0
  3 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0280200

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CC=C)=CC(OC2OC(COC(=O)C=CC3=CC(OC)=C(O)C(OC)=C3)C(O)C(O)C2O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O12/c1-5-6-14-9-18(36-4)23(30)19(12-14)38-27-26(33)25(32)24(31)20(39-27)13-37-21(28)8-7-15-10-16(34-2)22(29)17(11-15)35-3/h5,7-12,20,24-27,29-33H,1,6,13H2,2-4H3

> <INCHI_KEY>
OMQYRPLKROLHII-UHFFFAOYSA-N

> <FORMULA>
C27H32O12

> <MOLECULAR_WEIGHT>
548.541

> <EXACT_MASS>
548.18937647

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
55.24025288019398

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
2.4539294116666657

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.538831310792085

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.930664923489019

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491103098094584

> <JCHEM_POLAR_SURFACE_AREA>
173.6

> <JCHEM_REFRACTIVITY>
137.38970000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+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       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.003 -14.630   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.337 -16.940   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.337 -18.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.670 -19.250   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.670 -20.790   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      16.004 -21.560   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      17.338 -20.790   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      16.004 -23.100   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.338 -23.870   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.338 -25.410   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.672 -26.180   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.672 -27.720   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      20.005 -28.490   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      21.339 -27.720   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.338 -28.490   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      17.338 -30.030   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      16.004 -27.720   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.670 -28.490   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      13.337 -27.720   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.004 -26.180   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.003 -19.250   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.003 -20.790   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.336 -19.250   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   38                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   36                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   32                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   31                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   21                                                       
CONECT   32   14   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   12   37                                                  
CONECT   37   36                                                            
CONECT   38   10    3   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Value	Source
{3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₇H₃₂O₁₂

Average Mass

548.5410 Da

Monoisotopic Mass

548.18938 Da

IUPAC Name

{3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

Traditional Name

{3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(CC=C)=CC(OC2OC(COC(=O)C=CC3=CC(OC)=C(O)C(OC)=C3)C(O)C(O)C2O)=C1O

InChI Identifier

InChI=1S/C27H32O12/c1-5-6-14-9-18(36-4)23(30)19(12-14)38-27-26(33)25(32)24(31)20(39-27)13-37-21(28)8-7-15-10-16(34-2)22(29)17(11-15)35-3/h5,7-12,20,24-27,29-33H,1,6,13H2,2-4H3

InChI Key

OMQYRPLKROLHII-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
Pimenta dioica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Phenylquinolines

Direct Parent

Phenylquinolines

Alternative Parents

Substituents

Phenylquinoline
2-phenylpyridine
Dihydroquinolone
Dihydroquinoline
Anisole
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyridine
Heteroaromatic compound
Vinylogous amide
Azacycle
Ether
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolines (CHEBI:6082 )
Quinoline alkaloids (C10699 )

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	2.31	ALOGPS
logP	2.45	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.93	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	173.6 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	137.39 m³·mol⁻¹	ChemAxon
Polarizability	55.24 Å³	ChemAxon
Number of Rings	3	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

74342787

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-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate (NP0280200)

MOL for NP0280200 ({3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate)

3D MOL for NP0280200 ({3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate)

3D SDF for NP0280200 ({3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate)

3D-SDF for NP0280200 ({3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate)

PDB for NP0280200 ({3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate)

3D PDB for NP0280200 ({3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate)

SMILES for NP0280200 ({3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate)

INCHI for NP0280200 ({3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate)

Structure for NP0280200 ({3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate)

3D Structure for NP0280200 ({3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate)