NP-MRD: Showing NP-Card for Neoschaftoside (NP0140292)

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Record Information

Version

2.0

Created at

2022-06-29 21:21:46 UTC

Updated at

2022-06-29 21:21:46 UTC

NP-MRD ID

NP0140292

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Neoschaftoside

Description

Neoschaftoside is found in Apis cerana, Artemisia judaica, Radula complanata and Trichophorum cespitosum. Neoschaftoside was first documented in 1985 (PMID: 24310066).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652307301920002D          

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 18 24  1  0  0  0  0
 18 25  1  6  0  0  0
 21 26  1  0  0  0  0
 21 27  1  0  0  0  0
 22 28  2  0  0  0  0
 23 29  1  0  0  0  0
 24 30  1  6  0  0  0
 26 31  1  0  0  0  0
 27 32  1  0  0  0  0
 27 33  1  6  0  0  0
 28 34  1  0  0  0  0
 31 35  1  0  0  0  0
 31 36  1  1  0  0  0
 32 37  1  1  0  0  0
 34 38  1  0  0  0  0
 35 39  1  6  0  0  0
 36 40  1  0  0  0  0
  7 12  2  0  0  0  0
  9 15  2  0  0  0  0
 20 24  1  0  0  0  0
 29 34  2  0  0  0  0
 32 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140292

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C2=C(OC(=CC2=O)C2=CC=C(O)C=C2)C([C@H]2OC[C@H](O)[C@H](O)[C@H]2O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O14/c27-6-13-18(32)21(35)23(37)26(40-13)15-19(33)14-10(29)5-12(8-1-3-9(28)4-2-8)39-24(14)16(20(15)34)25-22(36)17(31)11(30)7-38-25/h1-5,11,13,17-18,21-23,25-28,30-37H,6-7H2/t11-,13+,17-,18+,21-,22+,23+,25+,26-/m0/s1

> <INCHI_KEY>
MMDUKUSNQNWVET-LQYCTPBQSA-N

> <FORMULA>
C26H28O14

> <MOLECULAR_WEIGHT>
564.496

> <EXACT_MASS>
564.147905582

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.7720665033864

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]-4H-chromen-4-one

> <JCHEM_LOGP>
-2.1776177343333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.630168354527644

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.737643124492441

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6431904735401384

> <JCHEM_POLAR_SURFACE_AREA>
247.05999999999997

> <JCHEM_REFRACTIVITY>
133.18800000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
neoschaftoside

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0      21.900 -18.293   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.567 -17.523   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.900 -19.833   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      23.234 -17.523   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      20.567 -15.983   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.233 -18.293   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.567 -20.603   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.234 -20.603   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.568 -18.293   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.900 -15.213   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      19.233 -15.213   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      19.233 -19.833   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      17.899 -17.523   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      20.567 -22.144   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      24.568 -19.833   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      23.234 -22.144   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      25.901 -17.523   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.900 -13.673   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      23.234 -15.983   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      19.233 -13.673   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.899 -20.603   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.235 -18.293   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.901 -15.983   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.567 -12.903   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      23.234 -12.903   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      16.565 -19.833   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      17.899 -22.144   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      28.569 -17.523   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      27.235 -15.213   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      20.567 -11.363   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      15.232 -20.603   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.565 -22.914   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      19.233 -22.914   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      28.569 -15.983   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.232 -22.144   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.898 -19.833   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      16.565 -24.454   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      29.902 -15.213   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      13.898 -22.914   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      12.564 -20.603   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2   12   13                                                  
CONECT    7    3   14   12                                                  
CONECT    8    3   15   16                                                  
CONECT    9    4   17   15                                                  
CONECT   10    5   18   19                                                  
CONECT   11    5   20                                                       
CONECT   12    6   21    7                                                  
CONECT   13    6                                                            
CONECT   14    7                                                            
CONECT   15    8    9                                                       
CONECT   16    8                                                            
CONECT   17    9   22   23                                                  
CONECT   18   10   24   25                                                  
CONECT   19   10                                                            
CONECT   20   11   24                                                       
CONECT   21   12   26   27                                                  
CONECT   22   17   28                                                       
CONECT   23   17   29                                                       
CONECT   24   18   30   20                                                  
CONECT   25   18                                                            
CONECT   26   21   31                                                       
CONECT   27   21   32   33                                                  
CONECT   28   22   34                                                       
CONECT   29   23   34                                                       
CONECT   30   24                                                            
CONECT   31   26   35   36                                                  
CONECT   32   27   37   35                                                  
CONECT   33   27                                                            
CONECT   34   28   38   29                                                  
CONECT   35   31   39   32                                                  
CONECT   36   31   40                                                       
CONECT   37   32                                                            
CONECT   38   34                                                            
CONECT   39   35                                                            
CONECT   40   36                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
Apigenin 6-C-beta-D-glucopyranosyl-8-C-beta-L-arabinopyranoside	ChEBI
Apigenin 6-C-b-D-glucopyranosyl-8-C-b-L-arabinopyranoside	Generator
Apigenin 6-C-β-D-glucopyranosyl-8-C-β-L-arabinopyranoside	Generator

Chemical Formula

C₂₆H₂₈O₁₄

Average Mass

564.4960 Da

Monoisotopic Mass

564.14791 Da

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]-4H-chromen-4-one

Traditional Name

neoschaftoside

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C2=C(OC(=CC2=O)C2=CC=C(O)C=C2)C([C@H]2OC[C@H](O)[C@H](O)[C@H]2O)=C1O

InChI Identifier

InChI=1S/C26H28O14/c27-6-13-18(32)21(35)23(37)26(40-13)15-19(33)14-10(29)5-12(8-1-3-9(28)4-2-8)39-24(14)16(20(15)34)25-22(36)17(31)11(30)7-38-25/h1-5,11,13,17-18,21-23,25-28,30-37H,6-7H2/t11-,13+,17-,18+,21-,22+,23+,25+,26-/m0/s1

InChI Key

MMDUKUSNQNWVET-LQYCTPBQSA-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
Apis cerana	LOTUS Database	35616633
Artemisia judaica	LOTUS Database	35616633
Radula complanata	LOTUS Database	35616633
Trichophorum cespitosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
C-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Monocyclic benzene moiety
Oxane
Monosaccharide
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Polyol
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Primary alcohol
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:7513 )
flavone C-glycoside (CHEBI:7513 )
flavones (C10110 )
Flavones and Flavonols (C10110 )

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	-2.2	ChemAxon
pKa (Strongest Acidic)	5.74	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	247.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	133.19 m³·mol⁻¹	ChemAxon
Polarizability	53.77 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011641

KNApSAcK ID

C00006382

Chemspider ID

Not Available

KEGG Compound ID

C10110

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442619

PDB ID

Not Available

ChEBI ID

7513

Good Scents ID

Not Available

References

General References

Xie C, Veitch NC, Houghton PJ, Simmonds MS: Flavone C-glycosides from Viola yedoensis MAKINO. Chem Pharm Bull (Tokyo). 2003 Oct;51(10):1204-7. doi: 10.1248/cpb.51.1204. [PubMed:14519932 ]
Kim M, Koh HS, Fukami H: Isolation ofC-glycosylflavones as probing stimulant of planthoppers in rice plant. J Chem Ecol. 1985 Apr;11(4):441-52. doi: 10.1007/BF00989555. [PubMed:24310066 ]

Showing NP-Card for Neoschaftoside (NP0140292)

MOL for NP0140292 (Neoschaftoside)

3D MOL for NP0140292 (Neoschaftoside)

3D SDF for NP0140292 (Neoschaftoside)

3D-SDF for NP0140292 (Neoschaftoside)

PDB for NP0140292 (Neoschaftoside)

3D PDB for NP0140292 (Neoschaftoside)

SMILES for NP0140292 (Neoschaftoside)

INCHI for NP0140292 (Neoschaftoside)

Structure for NP0140292 (Neoschaftoside)

3D Structure for NP0140292 (Neoschaftoside)