NP-MRD: Showing NP-Card for formononetin 7-o-rutinoside (NP0185399)

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Record Information

Version

2.0

Created at

2022-09-04 00:47:24 UTC

Updated at

2022-09-04 00:47:24 UTC

NP-MRD ID

NP0185399

Secondary Accession Numbers

None

Natural Product Identification

Common Name

formononetin 7-o-rutinoside

Description

Derriscanoside A belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Derriscanoside A is an extremely weak basic (essentially neutral) compound (based on its pKa). formononetin 7-o-rutinoside is found in Garcinia dulcis. A 4'-methoxyisoflavone that is the 7-O-rutinosyl derivative of formononetin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309272007382D          

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  3  4  1  0  0  0  0
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M  END

     RDKit          3D

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  Mrv1652309272007382D          

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10001.094110001.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.808610001.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.808610002.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 26  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 33  2  1  0  0  0  0
 31 12  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 36 37  1  0  0  0  0
 36 41  1  0  0  0  0
  1 39  2  0  0  0  0
 37 32  2  0  0  0  0
 35 38  2  0  0  0  0
 40 28  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 14 19  1  0  0  0  0
 18 19  1  0  0  0  0
 18  7  1  1  0  0  0
 17  8  1  6  0  0  0
 16  6  1  1  0  0  0
 15  5  1  1  0  0  0
 14  4  1  6  0  0  0
 20  9  1  1  0  0  0
 21 10  1  6  0  0  0
 22 11  1  1  0  0  0
 23  3  1  6  0  0  0
 25  2  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0185399

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=COC2=CC(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O13/c1-12-20(29)23(32)25(34)27(39-12)38-11-19-22(31)24(33)26(35)28(41-19)40-15-7-8-16-18(9-15)37-10-17(21(16)30)13-3-5-14(36-2)6-4-13/h3-10,12,19-20,22-29,31-35H,11H2,1-2H3/t12-,19+,20-,22+,23+,24-,25+,26+,27+,28+/m0/s1

> <INCHI_KEY>
ZSCRYAYQFLBRDF-ZUTPBCDKSA-N

> <FORMULA>
C28H32O13

> <MOLECULAR_WEIGHT>
576.551

> <EXACT_MASS>
576.18429109

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
57.4301217519487

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
-0.11566200499999914

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.439595923281953

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.912077613782069

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121823516836606

> <JCHEM_POLAR_SURFACE_AREA>
193.82999999999996

> <JCHEM_REFRACTIVITY>
137.1983

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8668.7078667.054   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8663.3848671.690   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8660.7178667.070   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8659.3838666.301   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8656.7168664.761   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8656.7168661.681   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8662.0508661.681   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8659.3838660.141   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8660.7178673.230   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8658.0498671.690   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8658.0498668.610   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8675.3758666.289   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8676.7118667.058   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8659.3838664.760   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8658.0498663.990   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8658.0498662.449   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8659.3838661.680   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8660.7178662.449   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8660.7178663.990   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8660.7178671.690   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8659.3838670.920   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8659.3838669.380   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8660.7178668.610   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8662.0508669.380   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0    8662.0508670.920   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8674.0428668.599   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8672.7088669.368   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8671.3748668.598   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8671.3748667.058   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8672.7088666.288   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8674.0428667.058   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8666.0488671.685   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8664.7148670.915   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8664.7148669.375   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8666.0488668.605   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0    8668.7098671.685   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0    8667.3758670.915   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0    8667.3758669.375   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0    8668.7098668.605   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0    8670.0438669.375   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0    8670.0438670.915   0.000  0.00  0.00           C+0
CONECT    1   39                                                            
CONECT    2   33   25                                                       
CONECT    3    4   23                                                       
CONECT    4    3   14                                                       
CONECT    5   15                                                            
CONECT    6   16                                                            
CONECT    7   18                                                            
CONECT    8   17                                                            
CONECT    9   20                                                            
CONECT   10   21                                                            
CONECT   11   22                                                            
CONECT   12   13   31                                                       
CONECT   13   12                                                            
CONECT   14   15   19    4                                                  
CONECT   15   14   16    5                                                  
CONECT   16   15   17    6                                                  
CONECT   17   16   18    8                                                  
CONECT   18   17   19    7                                                  
CONECT   19   14   18                                                       
CONECT   20   21   25    9                                                  
CONECT   21   20   22   10                                                  
CONECT   22   21   23   11                                                  
CONECT   23   22   24    3                                                  
CONECT   24   23   25                                                       
CONECT   25   20   24    2                                                  
CONECT   26   27   31                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   40                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26   12                                                  
CONECT   32   33   37                                                       
CONECT   33   32   34    2                                                  
CONECT   34   33   35                                                       
CONECT   35   34   38                                                       
CONECT   36   37   41                                                       
CONECT   37   38   36   32                                                  
CONECT   38   37   39   35                                                  
CONECT   39   38   40    1                                                  
CONECT   40   39   41   28                                                  
CONECT   41   40   36                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
4'-Methoxyisoflavone-7-O-[alpha-L-rhamnopyranosyl(1->6)]-beta-D-glucopyranoside	ChEBI
4'-Methoxyisoflavone-7-O-[a-L-rhamnopyranosyl(1->6)]-b-D-glucopyranoside	Generator
4'-Methoxyisoflavone-7-O-[α-L-rhamnopyranosyl(1->6)]-β-D-glucopyranoside	Generator
Derriscanoside a	ChEBI
7-beta-Rutinosyloxy-4'-methoxyisoflavone	PhytoBank
7-β-Rutinosyloxy-4'-methoxyisoflavone	PhytoBank
7-β-Rutinosyloxy-4’-methoxyisoflavone	PhytoBank
Formononetin 7-O-rutinoside	PhytoBank

Chemical Formula

C₂₈H₃₂O₁₃

Average Mass

576.5510 Da

Monoisotopic Mass

576.18429 Da

IUPAC Name

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

Traditional Name

3-(4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=COC2=CC(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2C1=O

InChI Identifier

InChI=1S/C28H32O13/c1-12-20(29)23(32)25(34)27(39-12)38-11-19-22(31)24(33)26(35)28(41-19)40-15-7-8-16-18(9-15)37-10-17(21(16)30)13-3-5-14(36-2)6-4-13/h3-10,12,19-20,22-29,31-35H,11H2,1-2H3/t12-,19+,20-,22+,23+,24-,25+,26+,27+,28+/m0/s1

InChI Key

ZSCRYAYQFLBRDF-ZUTPBCDKSA-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
Garcinia dulcis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavonoid O-glycosides

Direct Parent

Isoflavonoid O-glycosides

Alternative Parents

Substituents

Isoflavonoid-7-o-glycoside
Isoflavonoid o-glycoside
4p-o-methylisoflavone
Isoflavone
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Chromone
1-benzopyran
Benzopyran
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Heteroaromatic compound
Secondary alcohol
Acetal
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

rutinoside (CHEBI:85135 )
disaccharide derivative (CHEBI:85135 )
methoxyisoflavone (CHEBI:85135 )

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	0.5	ALOGPS
logP	-0.12	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	193.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	137.2 m³·mol⁻¹	ChemAxon
Polarizability	57.43 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00010081

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

91666352

PDB ID

Not Available

ChEBI ID

85135

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for formononetin 7-o-rutinoside (NP0185399)

MOL for NP0185399 (formononetin 7-o-rutinoside)

3D MOL for NP0185399 (formononetin 7-o-rutinoside)

3D SDF for NP0185399 (formononetin 7-o-rutinoside)

3D-SDF for NP0185399 (formononetin 7-o-rutinoside)

PDB for NP0185399 (formononetin 7-o-rutinoside)

3D PDB for NP0185399 (formononetin 7-o-rutinoside)

SMILES for NP0185399 (formononetin 7-o-rutinoside)

INCHI for NP0185399 (formononetin 7-o-rutinoside)

Structure for NP0185399 (formononetin 7-o-rutinoside)

3D Structure for NP0185399 (formononetin 7-o-rutinoside)