NP-MRD: Showing NP-Card for 2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol (NP0268876)

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Record Information

Version

2.0

Created at

2022-09-08 14:08:52 UTC

Updated at

2022-09-08 14:08:53 UTC

NP-MRD ID

NP0268876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Description

2-[(3-{3-[1,3-Dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups. 2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol is found in Bidens parviflora. 2-[(3-{3-[1,3-Dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241509092D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004241509092D          

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    0.0000  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -11.1375    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 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  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  4  0  0  0
 18 19  2  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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  2  0  0  0  0
 15 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0268876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C(O)CC(O)C1=CC(C=CCOC2OC(CO)C(O)C(O)C2O)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O12/c1-35-19-10-14(5-6-16(19)28)17(29)11-18(30)15-8-13(9-20(36-2)22(15)31)4-3-7-37-26-25(34)24(33)23(32)21(12-27)38-26/h3-6,8-10,17-18,21,23-34H,7,11-12H2,1-2H3

> <INCHI_KEY>
XSWHADNOBPLVSA-UHFFFAOYSA-N

> <FORMULA>
C26H34O12

> <MOLECULAR_WEIGHT>
538.546

> <EXACT_MASS>
538.205026535

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.887731906406295

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.10

> <JCHEM_LOGP>
-0.4309818813333331

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.488016740109286

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.778311794123738

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835511361624

> <JCHEM_POLAR_SURFACE_AREA>
198.75999999999996

> <JCHEM_REFRACTIVITY>
134.4206

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001 -16.170   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  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000 -16.940   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000 -18.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667 -18.480   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334 -20.790   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001 -25.410   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335 -26.180   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.668 -25.410   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.002 -26.180   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.336 -25.410   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669 -26.180   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.003 -25.410   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.337 -26.180   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.669 -27.720   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.003 -28.490   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.336 -28.490   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.336 -30.030   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.002 -27.720   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.668 -28.490   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334 -23.870   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000 -23.100   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.334 -23.870   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000 -21.560   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.334 -20.790   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   37                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   33                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
CONECT   33   17   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34   15   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₁₂

Average Mass

538.5460 Da

Monoisotopic Mass

538.20503 Da

IUPAC Name

2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C(O)CC(O)C1=CC(C=CCOC2OC(CO)C(O)C(O)C2O)=CC(OC)=C1O

InChI Identifier

InChI=1S/C26H34O12/c1-35-19-10-14(5-6-16(19)28)17(29)11-18(30)15-8-13(9-20(36-2)22(15)31)4-3-7-37-26-25(34)24(33)23(32)21(12-27)38-26/h3-6,8-10,17-18,21,23-34H,7,11-12H2,1-2H3

InChI Key

XSWHADNOBPLVSA-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
Bidens parviflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Cinnamylphenols

Direct Parent

Cinnamylphenols

Alternative Parents

Substituents

Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Cinnamylphenol
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Oxane
Fatty acyl
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Primary alcohol
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Aromatic alcohol
Organooxygen 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	-0.1	ALOGPS
logP	-0.43	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	198.76 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	134.42 m³·mol⁻¹	ChemAxon
Polarizability	55.89 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

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-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol (NP0268876)

MOL for NP0268876 (2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0268876 (2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0268876 (2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0268876 (2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0268876 (2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0268876 (2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0268876 (2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0268876 (2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0268876 (2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0268876 (2-[(3-{3-[1,3-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-4-hydroxy-5-methoxyphenyl}prop-2-en-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)