NP-MRD: Showing NP-Card for 4',7-bis-(beta-Cymaropyranosyl)genistein (NP0062432)

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Record Information

Version

2.0

Created at

2022-04-28 07:05:40 UTC

Updated at

2022-04-28 07:05:40 UTC

NP-MRD ID

NP0062432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4',7-bis-(beta-Cymaropyranosyl)genistein

Description

5-Hydroxy-7-{[(2S,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3-(4-{[(2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}phenyl)-4H-chromen-4-one 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. 4',7-bis-(beta-Cymaropyranosyl)genistein is found in Actinomycete isolate HKI 129-L. Based on a literature review very few articles have been published on 5-hydroxy-7-{[(2S,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3-(4-{[(2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}phenyl)-4H-chromen-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209052D          

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M  END

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M  END


  Mrv1652304282209052D          

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    7.1447   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  1  0  0  0
  4  9  1  1  0  0  0
  9 10  1  0  0  0  0
  2 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 26 29  1  0  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 34 36  1  6  0  0  0
 36 37  1  0  0  0  0
 33 38  1  6  0  0  0
 32 39  1  6  0  0  0
 14 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C[C@@H](OC2=CC=C(C=C2)C2=COC3=CC(O[C@H]4C[C@@H](OC)[C@@H](O)[C@@H](C)O4)=CC(O)=C3C2=O)O[C@H](C)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O11/c1-14-27(31)22(34-3)11-24(37-14)39-17-7-5-16(6-8-17)19-13-36-21-10-18(9-20(30)26(21)29(19)33)40-25-12-23(35-4)28(32)15(2)38-25/h5-10,13-15,22-25,27-28,30-32H,11-12H2,1-4H3/t14-,15-,22-,23-,24-,25+,27+,28+/m1/s1

> <INCHI_KEY>
CSNBBXYKBRNMIS-QYNVYTKESA-N

> <FORMULA>
C29H34O11

> <MOLECULAR_WEIGHT>
558.58

> <EXACT_MASS>
558.210111915

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
58.24454457778677

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-7-{[(2S,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3-(4-{[(2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}phenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
3.7220852696666658

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.914070353977646

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.285703403160196

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5795154422913162

> <JCHEM_POLAR_SURFACE_AREA>
142.37

> <JCHEM_REFRACTIVITY>
139.36530000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-7-{[(2S,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3-(4-{[(2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}phenyl)chromen-4-one

> <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  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   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  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    4   10                                                       
CONECT   10    9                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   40                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   15   22                                                  
CONECT   22   21                                                            
CONECT   23   20   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   26   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34   38                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34   30                                                       
CONECT   36   34   37                                                       
CONECT   37   36                                                            
CONECT   38   33                                                            
CONECT   39   32                                                            
CONECT   40   14                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄O₁₁

Average Mass

558.5800 Da

Monoisotopic Mass

558.21011 Da

IUPAC Name

5-hydroxy-7-{[(2S,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3-(4-{[(2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}phenyl)-4H-chromen-4-one

Traditional Name

5-hydroxy-7-{[(2S,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3-(4-{[(2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}phenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C[C@@H](OC2=CC=C(C=C2)C2=COC3=CC(O[C@H]4C[C@@H](OC)[C@@H](O)[C@@H](C)O4)=CC(O)=C3C2=O)O[C@H](C)[C@@H]1O

InChI Identifier

InChI=1S/C29H34O11/c1-14-27(31)22(34-3)11-24(37-14)39-17-7-5-16(6-8-17)19-13-36-21-10-18(9-20(30)26(21)29(19)33)40-25-12-23(35-4)28(32)15(2)38-25/h5-10,13-15,22-25,27-28,30-32H,11-12H2,1-4H3/t14-,15-,22-,23-,24-,25+,27+,28+/m1/s1

InChI Key

CSNBBXYKBRNMIS-QYNVYTKESA-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
Actinomycete isolate HKI 129-L	-	KNApSAcK

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-4p-o-glycoside
Isoflavonoid-7-o-glycoside
Isoflavonoid o-glycoside
Hydroxyisoflavonoid
Isoflavone
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Oxane
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	2.48	ALOGPS
logP	3.72	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.29	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	142.37 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	139.37 m³·mol⁻¹	ChemAxon
Polarizability	58.24 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

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

162938937

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4',7-bis-(beta-Cymaropyranosyl)genistein (NP0062432)

MOL for NP0062432 (4',7-bis-(beta-Cymaropyranosyl)genistein)

3D MOL for NP0062432 (4',7-bis-(beta-Cymaropyranosyl)genistein)

3D SDF for NP0062432 (4',7-bis-(beta-Cymaropyranosyl)genistein)

3D-SDF for NP0062432 (4',7-bis-(beta-Cymaropyranosyl)genistein)

PDB for NP0062432 (4',7-bis-(beta-Cymaropyranosyl)genistein)

3D PDB for NP0062432 (4',7-bis-(beta-Cymaropyranosyl)genistein)

SMILES for NP0062432 (4',7-bis-(beta-Cymaropyranosyl)genistein)

INCHI for NP0062432 (4',7-bis-(beta-Cymaropyranosyl)genistein)

Structure for NP0062432 (4',7-bis-(beta-Cymaropyranosyl)genistein)

3D Structure for NP0062432 (4',7-bis-(beta-Cymaropyranosyl)genistein)