NP-MRD: Showing NP-Card for Haploside A (NP0053986)

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Record Information

Version

2.0

Created at

2022-04-28 00:28:59 UTC

Updated at

2022-04-28 00:28:59 UTC

NP-MRD ID

NP0053986

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Haploside A

Description

[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-{[3,5,8-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl acetate belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Haploside A is found in Haplophyllum acutifolium, Haplophyllum latifolium and Haplophyllum perforatum. Based on a literature review very few articles have been published on [(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-{[3,5,8-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202292D          

 38 41  0  0  1  0            999 V2000
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    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282202292D          

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M  END
> <DATABASE_ID>
NP0053986

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1=C(O)C(=O)C2=C(O)C=C(O[C@@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@@H]3O)C(O)=C2O1

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

> <INCHI_KEY>
JEXCKOGBYYLXKD-JHGAMKDOSA-N

> <FORMULA>
C24H24O14

> <MOLECULAR_WEIGHT>
536.442

> <EXACT_MASS>
536.116605453

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
51.01054891387521

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-{[3,5,8-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
0.17168551533333323

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.721013281400566

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.55686110529503

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491028351998587

> <JCHEM_POLAR_SURFACE_AREA>
221.89999999999998

> <JCHEM_REFRACTIVITY>
124.62129999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-{[3,5,8-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-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       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -10.669   0.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   24                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13   10                                                            
CONECT   14    9   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17                                                            
CONECT   23    3                                                            
CONECT   24    1   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   38                                                  
CONECT   27   26   28   37                                                  
CONECT   28   27   29   36                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   25                                                       
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   28                                                            
CONECT   37   27                                                            
CONECT   38   26                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5S,6S)-3,4,5-Trihydroxy-6-{[3,5,8-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₄H₂₄O₁₄

Average Mass

536.4420 Da

Monoisotopic Mass

536.11661 Da

IUPAC Name

[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-{[3,5,8-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-{[3,5,8-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1=C(O)C(=O)C2=C(O)C=C(O[C@@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@@H]3O)C(O)=C2O1

InChI Identifier

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

InChI Key

JEXCKOGBYYLXKD-JHGAMKDOSA-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
Haplophyllum acutifolium	LOTUS Database	35616633
Haplophyllum latifolium	Plant	KNApSAcK
Haplophyllum perforatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3p-methoxyflavonoid-skeleton
3-hydroxyflavone
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
8-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
Methoxyphenol
1-benzopyran
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
Pyranone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyran
Oxane
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Acetal
Polyol
Ether
Oxacycle
Carbonyl group
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
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	1.43	ALOGPS
logP	0.17	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.56	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	221.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	124.62 m³·mol⁻¹	ChemAxon
Polarizability	51.01 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

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

162951885

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Haploside A (NP0053986)

MOL for NP0053986 (Haploside A)

3D MOL for NP0053986 (Haploside A)

3D SDF for NP0053986 (Haploside A)

3D-SDF for NP0053986 (Haploside A)

PDB for NP0053986 (Haploside A)

3D PDB for NP0053986 (Haploside A)

SMILES for NP0053986 (Haploside A)

INCHI for NP0053986 (Haploside A)

Structure for NP0053986 (Haploside A)

3D Structure for NP0053986 (Haploside A)