NP-MRD: Showing NP-Card for (2s,3s,4s,5r,6s)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate (NP0253102)

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Record Information

Version

2.0

Created at

2022-09-07 16:52:28 UTC

Updated at

2022-09-07 16:52:28 UTC

NP-MRD ID

NP0253102

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4s,5r,6s)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate

Description

SL 0101-1 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. (2s,3s,4s,5r,6s)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate is found in Zingiber spectabile. SL 0101-1 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041411122D          

 42 45  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 05041411122D          

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 24 20  1  0  0  0  0
 24 21  1  0  0  0  0
 25 20  1  0  0  0  0
 26 11  2  0  0  0  0
 27 12  2  0  0  0  0
 28 14  1  0  0  0  0
 29 15  1  0  0  0  0
 30 16  1  0  0  0  0
 31 19  2  0  0  0  0
 20 32  1  6  0  0  0
 33 10  1  0  0  0  0
 33 25  1  0  0  0  0
 34 11  1  0  0  0  0
 21 34  1  1  0  0  0
 35 12  1  0  0  0  0
 24 35  1  6  0  0  0
 36 17  1  0  0  0  0
 36 22  1  0  0  0  0
 37 23  1  0  0  0  0
 25 37  1  1  0  0  0
 10 38  1  1  0  0  0
 20 39  1  1  0  0  0
 21 40  1  6  0  0  0
 24 41  1  1  0  0  0
 25 42  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0253102

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(C)O[C@@]([H])(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@]([H])(O)[C@]([H])(OC(C)=O)[C@@]1([H])OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O12/c1-10-21(34-11(2)26)24(35-12(3)27)20(32)25(33-10)37-23-19(31)18-16(30)8-15(29)9-17(18)36-22(23)13-4-6-14(28)7-5-13/h4-10,20-21,24-25,28-30,32H,1-3H3/t10-,20+,21-,24-,25-/m0/s1

> <INCHI_KEY>
SXOZSDJHGMAEGZ-IGKKHSBFSA-N

> <FORMULA>
C25H24O12

> <MOLECULAR_WEIGHT>
516.4509

> <EXACT_MASS>
516.126776232

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
49.48158191140891

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
2.0878908130000013

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.440223254210077

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.433890483637724

> <JCHEM_PKA_STRONGEST_BASIC>
-3.96960225673362

> <JCHEM_POLAR_SURFACE_AREA>
178.27999999999994

> <JCHEM_REFRACTIVITY>
124.05389999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   38  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4    6   13                                                       
CONECT    5    7   13                                                       
CONECT    6    4   14                                                       
CONECT    7    5   14                                                       
CONECT    8   15   16                                                       
CONECT    9   15   17                                                       
CONECT   10    1   21   33   38                                             
CONECT   11    2   26   34                                                  
CONECT   12    3   27   35                                                  
CONECT   13    4    5   22                                                  
CONECT   14    6    7   28                                                  
CONECT   15    8    9   29                                                  
CONECT   16    8   18   30                                                  
CONECT   17    9   18   36                                                  
CONECT   18   16   17   19                                                  
CONECT   19   18   23   31                                                  
CONECT   20   24   25   32   39                                             
CONECT   21   10   24   34   40                                             
CONECT   22   13   23   36                                                  
CONECT   23   19   22   37                                                  
CONECT   24   20   21   35   41                                             
CONECT   25   20   33   37   42                                             
CONECT   26   11                                                            
CONECT   27   12                                                            
CONECT   28   14                                                            
CONECT   29   15                                                            
CONECT   30   16                                                            
CONECT   31   19                                                            
CONECT   32   20                                                            
CONECT   33   10   25                                                       
CONECT   34   11   21                                                       
CONECT   35   12   24                                                       
CONECT   36   17   22                                                       
CONECT   37   23   25                                                       
CONECT   38   10                                                            
CONECT   39   20                                                            
CONECT   40   21                                                            
CONECT   41   24                                                            
CONECT   42   25                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
Kaempferol-alpha-L-diacetylrhamnoside	MeSH
(2S,3S,4S,5R,6S)-3-(Acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetic acid	Generator

Chemical Formula

C₂₅H₂₄O₁₂

Average Mass

516.4509 Da

Monoisotopic Mass

516.12678 Da

IUPAC Name

(2S,3S,4S,5R,6S)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate

Traditional Name

(2S,3S,4S,5R,6S)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C)O[C@@]([H])(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@]([H])(O)[C@]([H])(OC(C)=O)[C@@]1([H])OC(C)=O

InChI Identifier

InChI=1S/C25H24O12/c1-10-21(34-11(2)26)24(35-12(3)27)20(32)25(33-10)37-23-19(31)18-16(30)8-15(29)9-17(18)36-22(23)13-4-6-14(28)7-5-13/h4-10,20-21,24-25,28-30,32H,1-3H3/t10-,20+,21-,24-,25-/m0/s1

InChI Key

SXOZSDJHGMAEGZ-IGKKHSBFSA-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
Zingiber spectabile	LOTUS Database	35616633

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
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Monosaccharide
Pyran
Oxane
Vinylogous acid
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
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	3.25	ALOGPS
logP	2.09	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.43	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	178.28 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	124.05 m³·mol⁻¹	ChemAxon
Polarizability	49.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

10459196

PDB ID

SL0

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s,4s,5r,6s)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate (NP0253102)

MOL for NP0253102 ((2s,3s,4s,5r,6s)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

3D MOL for NP0253102 ((2s,3s,4s,5r,6s)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

3D SDF for NP0253102 ((2s,3s,4s,5r,6s)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

3D-SDF for NP0253102 ((2s,3s,4s,5r,6s)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

PDB for NP0253102 ((2s,3s,4s,5r,6s)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

3D PDB for NP0253102 ((2s,3s,4s,5r,6s)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

SMILES for NP0253102 ((2s,3s,4s,5r,6s)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

INCHI for NP0253102 ((2s,3s,4s,5r,6s)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

Structure for NP0253102 ((2s,3s,4s,5r,6s)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

3D Structure for NP0253102 ((2s,3s,4s,5r,6s)-3-(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)