NP-MRD: Showing NP-Card for Orobol 6-C-(6''-acetylglucoside) (NP0054094)

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Record Information

Version

1.0

Created at

2022-04-28 00:33:33 UTC

Updated at

2022-04-28 00:33:33 UTC

NP-MRD ID

NP0054094

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Orobol 6-C-(6''-acetylglucoside)

Description

Orobol 6-c-(6''-acetylglucoside) belongs to the class of organic compounds known as isoflavonoid c-glycosides. These are c-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Thus, orobol 6-c-(6''-acetylglucoside) is considered to be a flavonoid. Orobol 6-C-(6''-acetylglucoside) is found in Dalbergia monetaria . Based on a literature review very few articles have been published on Orobol 6-c-(6''-acetylglucoside).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202332D          

 35 38  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   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
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   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1 35  1  0  0  0  0
M  END

     RDKit          3D

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    5.4708    0.0946   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4720    1.0652   -1.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6365    1.7713   -1.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7699    1.5086   -0.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9661    2.2065   -0.8805 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8829    0.2186    1.0581 O   0  0  0  0  0  0  0  0  0  0  0  0
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 21 48  1  0
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M  END


  Mrv1652304282202332D          

 35 38  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0054094

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C=C2OC=C(C(=O)C2=C1O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O12/c1-8(24)33-7-15-19(29)21(31)22(32)23(35-15)16-13(27)5-14-17(20(16)30)18(28)10(6-34-14)9-2-3-11(25)12(26)4-9/h2-6,15,19,21-23,25-27,29-32H,7H2,1H3/t15-,19-,21+,22-,23+/m1/s1

> <INCHI_KEY>
ZIKWNNIZDCRJGO-IBUWVLCJSA-N

> <FORMULA>
C23H22O12

> <MOLECULAR_WEIGHT>
490.417

> <EXACT_MASS>
490.111126148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
47.323924970518135

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4R,5R,6S)-6-[3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-6-yl]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
0.45711157333333374

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.679369324572181

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.10809565057765

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6454382028355017

> <JCHEM_POLAR_SURFACE_AREA>
203.43999999999997

> <JCHEM_REFRACTIVITY>
115.93359999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R,6S)-6-[3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-6-yl]-3,4,5-trihydroxyoxan-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       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   35                                                  
CONECT    2    1    3   21                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16                                                            
CONECT   19   15                                                            
CONECT   20    3                                                            
CONECT   21    2   22   26                                                  
CONECT   22   21   23   34                                                  
CONECT   23   22   24   33                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   24                                                            
CONECT   33   23                                                            
CONECT   34   22                                                            
CONECT   35    1                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂O₁₂

Average Mass

490.4170 Da

Monoisotopic Mass

490.11113 Da

IUPAC Name

[(2R,3S,4R,5R,6S)-6-[3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-6-yl]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4R,5R,6S)-6-[3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-6-yl]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C=C2OC=C(C(=O)C2=C1O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C23H22O12/c1-8(24)33-7-15-19(29)21(31)22(32)23(35-15)16-13(27)5-14-17(20(16)30)18(28)10(6-34-14)9-2-3-11(25)12(26)4-9/h2-6,15,19,21-23,25-27,29-32H,7H2,1H3/t15-,19-,21+,22-,23+/m1/s1

InChI Key

ZIKWNNIZDCRJGO-IBUWVLCJSA-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
Dalbergia monetaria	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavonoid c-glycosides. These are c-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 C-glycosides

Direct Parent

Isoflavonoid C-glycosides

Alternative Parents

Substituents

Isoflavonoid c-glycoside
Isoflavonoid-6-c-glycoside
Hydroxyisoflavonoid
Isoflavone
Phenolic glycoside
C-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Pyran
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
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	1.19	ALOGPS
logP	0.46	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	6.11	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.93 m³·mol⁻¹	ChemAxon
Polarizability	47.32 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00006157

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

162882200

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Orobol 6-C-(6''-acetylglucoside) (NP0054094)

MOL for NP0054094 (Orobol 6-C-(6''-acetylglucoside))

3D MOL for NP0054094 (Orobol 6-C-(6''-acetylglucoside))

3D SDF for NP0054094 (Orobol 6-C-(6''-acetylglucoside))

3D-SDF for NP0054094 (Orobol 6-C-(6''-acetylglucoside))

PDB for NP0054094 (Orobol 6-C-(6''-acetylglucoside))

3D PDB for NP0054094 (Orobol 6-C-(6''-acetylglucoside))

SMILES for NP0054094 (Orobol 6-C-(6''-acetylglucoside))

INCHI for NP0054094 (Orobol 6-C-(6''-acetylglucoside))

Structure for NP0054094 (Orobol 6-C-(6''-acetylglucoside))

3D Structure for NP0054094 (Orobol 6-C-(6''-acetylglucoside))