NP-MRD: Showing NP-Card for (2r,3r,4r,5r,6r)-2-{[(3s,5r)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0190955)

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Record Information

Version

2.0

Created at

2022-09-04 07:44:05 UTC

Updated at

2022-09-04 07:44:05 UTC

NP-MRD ID

NP0190955

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4r,5r,6r)-2-{[(3s,5r)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

CHEMBL1159484 belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. (2r,3r,4r,5r,6r)-2-{[(3s,5r)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Betula platyphylla. Based on a literature review very few articles have been published on CHEMBL1159484.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042209442D          

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M  END

     RDKit          3D

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  Mrv1652309042209442D          

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M  END
> <DATABASE_ID>
NP0190955

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@@H](CCC2=CC=C(O)C=C2)C[C@H](O)CCC2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O9/c26-14-21-22(30)23(31)24(32)25(34-21)33-20(12-6-16-3-9-18(28)10-4-16)13-19(29)11-5-15-1-7-17(27)8-2-15/h1-4,7-10,19-32H,5-6,11-14H2/t19-,20+,21-,22+,23-,24-,25-/m1/s1

> <INCHI_KEY>
WRUJLWFLDOUUHV-QVQNJILUSA-N

> <FORMULA>
C25H34O9

> <MOLECULAR_WEIGHT>
478.538

> <EXACT_MASS>
478.220282675

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
51.08169278662362

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4R,5R,6R)-2-{[(3S,5R)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
1.5082544839999996

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.589217555002948

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.992346215642518

> <JCHEM_PKA_STRONGEST_BASIC>
-2.726148052844894

> <JCHEM_POLAR_SURFACE_AREA>
160.07

> <JCHEM_REFRACTIVITY>
123.0717

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R,5R,6R)-2-{[(3S,5R)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10                                                       
CONECT   17    7   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22                                                       
CONECT   29    5   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    3   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₄O₉

Average Mass

478.5380 Da

Monoisotopic Mass

478.22028 Da

IUPAC Name

(2R,3R,4R,5R,6R)-2-{[(3S,5R)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4R,5R,6R)-2-{[(3S,5R)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@@H](CCC2=CC=C(O)C=C2)C[C@H](O)CCC2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C25H34O9/c26-14-21-22(30)23(31)24(32)25(34-21)33-20(12-6-16-3-9-18(28)10-4-16)13-19(29)11-5-15-1-7-17(27)8-2-15/h1-4,7-10,19-32H,5-6,11-14H2/t19-,20+,21-,22+,23-,24-,25-/m1/s1

InChI Key

WRUJLWFLDOUUHV-QVQNJILUSA-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
Betula platyphylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Curcuminoids

Alternative Parents

Substituents

Bis-desmethoxycurcumin
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Fatty alcohol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Primary 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	1.51	ChemAxon
pKa (Strongest Acidic)	9.99	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	160.07 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	123.07 m³·mol⁻¹	ChemAxon
Polarizability	51.08 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

25056619

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46905138

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4r,5r,6r)-2-{[(3s,5r)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0190955)

MOL for NP0190955 ((2r,3r,4r,5r,6r)-2-{[(3s,5r)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0190955 ((2r,3r,4r,5r,6r)-2-{[(3s,5r)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0190955 ((2r,3r,4r,5r,6r)-2-{[(3s,5r)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0190955 ((2r,3r,4r,5r,6r)-2-{[(3s,5r)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0190955 ((2r,3r,4r,5r,6r)-2-{[(3s,5r)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0190955 ((2r,3r,4r,5r,6r)-2-{[(3s,5r)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0190955 ((2r,3r,4r,5r,6r)-2-{[(3s,5r)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0190955 ((2r,3r,4r,5r,6r)-2-{[(3s,5r)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0190955 ((2r,3r,4r,5r,6r)-2-{[(3s,5r)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0190955 ((2r,3r,4r,5r,6r)-2-{[(3s,5r)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)