NP-MRD: Showing NP-Card for Patuletin 3-(6''-acetylglucoside) (NP0053973)

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Record Information

Version

2.0

Created at

2022-04-28 00:28:26 UTC

Updated at

2022-04-28 00:28:26 UTC

NP-MRD ID

NP0053973

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Patuletin 3-(6''-acetylglucoside)

Description

Patuletin 3-(6''-acetylglucoside) belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Thus, patuletin 3-(6''-acetylglucoside) is considered to be a flavonoid. Patuletin 3-(6''-acetylglucoside) is found in Arnica chamissonis, Arnica mollis and Lagascea mollis. Based on a literature review very few articles have been published on Patuletin 3-(6''-acetylglucoside).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202282D          

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M  END

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  Mrv1652304282202282D          

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M  END
> <DATABASE_ID>
NP0053973

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O[C@@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3O)C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O14/c1-8(25)35-7-14-16(29)19(32)20(33)24(37-14)38-23-18(31)15-13(6-12(28)22(34-2)17(15)30)36-21(23)9-3-4-10(26)11(27)5-9/h3-6,14,16,19-20,24,26-30,32-33H,7H2,1-2H3/t14-,16-,19+,20-,24+/m1/s1

> <INCHI_KEY>
UZMXXPUWSOLRLS-ZWOIFGKBSA-N

> <FORMULA>
C24H24O14

> <MOLECULAR_WEIGHT>
536.442

> <EXACT_MASS>
536.116605453

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
50.44015828052473

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
0.13861884866666657

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.22403764523841

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.896426175528175

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491028644426606

> <JCHEM_POLAR_SURFACE_AREA>
221.89999999999995

> <JCHEM_REFRACTIVITY>
124.89020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   38                                                  
CONECT    2    1    3   36                                                  
CONECT    3    2    4   35                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   26                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   16                                                            
CONECT   25   15                                                            
CONECT   26   14                                                            
CONECT   27    8   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31   27                                                       
CONECT   33   31                                                            
CONECT   34   30                                                            
CONECT   35    3                                                            
CONECT   36    2   37                                                       
CONECT   37   36                                                            
CONECT   38    1                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₄O₁₄

Average Mass

536.4420 Da

Monoisotopic Mass

536.11661 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O[C@@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3O)C(=O)C2=C1O

InChI Identifier

InChI=1S/C24H24O14/c1-8(25)35-7-14-16(29)19(32)20(33)24(37-14)38-23-18(31)15-13(6-12(28)22(34-2)17(15)30)36-21(23)9-3-4-10(26)11(27)5-9/h3-6,14,16,19-20,24,26-30,32-33H,7H2,1-2H3/t14-,16-,19+,20-,24+/m1/s1

InChI Key

UZMXXPUWSOLRLS-ZWOIFGKBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Arnica chamissonis	Plant	KNApSAcK
Arnica mollis	Plant	KNApSAcK
Lagascea mollis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
6-methoxyflavonoid-skeleton
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
O-glycosyl compound
Glycosyl compound
Chromone
Benzopyran
1-benzopyran
Anisole
Catechol
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Polyol
Acetal
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.44	ALOGPS
logP	0.14	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.9	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	221.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	124.89 m³·mol⁻¹	ChemAxon
Polarizability	50.44 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

C00006021

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

13940612

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Patuletin 3-(6''-acetylglucoside) (NP0053973)

MOL for NP0053973 (Patuletin 3-(6''-acetylglucoside))

3D MOL for NP0053973 (Patuletin 3-(6''-acetylglucoside))

3D SDF for NP0053973 (Patuletin 3-(6''-acetylglucoside))

3D-SDF for NP0053973 (Patuletin 3-(6''-acetylglucoside))

PDB for NP0053973 (Patuletin 3-(6''-acetylglucoside))

3D PDB for NP0053973 (Patuletin 3-(6''-acetylglucoside))

SMILES for NP0053973 (Patuletin 3-(6''-acetylglucoside))

INCHI for NP0053973 (Patuletin 3-(6''-acetylglucoside))

Structure for NP0053973 (Patuletin 3-(6''-acetylglucoside))

3D Structure for NP0053973 (Patuletin 3-(6''-acetylglucoside))