NP-MRD: Showing NP-Card for Bulbineloneside D (NP0044045)

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Record Information

Version

1.0

Created at

2021-11-12 23:47:04 UTC

Updated at

2021-11-26 17:44:48 UTC

NP-MRD ID

NP0044045

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bulbineloneside D

Description

4'-O-demethylknipholone-4'-O-beta-D-glucopyranoside belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. 4'-O-demethylknipholone-4'-O-beta-D-glucopyranoside is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Bulbineloneside D is found in Bulbine frutescens and Bulbinella floribunda. It was first documented in 2002 (PMID: 12193014). Based on a literature review very few articles have been published on 4'-O-demethylknipholone-4'-O-beta-D-glucopyranoside (PMID: 12828488).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100472D          

 42 46  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652311132100472D          

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  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 20 22  1  1  0  0  0
 22 23  1  0  0  0  0
 19 24  1  6  0  0  0
 18 25  1  1  0  0  0
 17 26  1  6  0  0  0
 10 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  9 30  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  2  0  0  0  0
 34 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 33 40  1  0  0  0  0
 37 41  1  0  0  0  0
  4 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044045

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C(O)C(=C1O)C1=C2C(=O)C3=C(C(O)=CC=C3)C(=O)C2=C(O)C=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C29H26O13/c1-9-6-13(33)21-22(23(35)11-4-3-5-12(32)19(11)26(21)38)17(9)20-14(34)7-15(18(10(2)31)25(20)37)41-29-28(40)27(39)24(36)16(8-30)42-29/h3-7,16,24,27-30,32-34,36-37,39-40H,8H2,1-2H3/t16-,24-,27+,28-,29-/m1/s1

> <INCHI_KEY>
AOJYFODHRHWWEN-GQUXZSRASA-N

> <FORMULA>
C29H26O13

> <MOLECULAR_WEIGHT>
582.514

> <EXACT_MASS>
582.137340897

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
56.695461173890024

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(3-acetyl-2,6-dihydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,5-dihydroxy-2-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
2.8011056429999996

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.912306169398541

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.102215155566199

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923463048447

> <JCHEM_POLAR_SURFACE_AREA>
231.50999999999996

> <JCHEM_REFRACTIVITY>
143.78009999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(3-acetyl-2,6-dihydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.337   9.240   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      12.003  11.550   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.336  13.090   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.668  11.550   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.096   3.556   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   42                                                  
CONECT    5    4    6   35                                                  
CONECT    6    5    7   31                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   30                                                  
CONECT   10    9   11   27                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   26                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   16                                                       
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   19                                                            
CONECT   25   18                                                            
CONECT   26   17                                                            
CONECT   27   10   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    9                                                            
CONECT   31    6   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   40                                                  
CONECT   34   33   35   37                                                  
CONECT   35   34    5   36                                                  
CONECT   36   35                                                            
CONECT   37   34   38   41                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   33                                                       
CONECT   41   37                                                            
CONECT   42    4                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
4'-O-Demethylknipholone-4'-O-b-D-glucopyranoside	Generator
4'-O-Demethylknipholone-4'-O-β-D-glucopyranoside	Generator
4'-O-Demethylknipholone-4'-O-glucopyranoside	MeSH

Chemical Formula

C₂₉H₂₆O₁₃

Average Mass

582.5140 Da

Monoisotopic Mass

582.13734 Da

IUPAC Name

1-(3-acetyl-2,6-dihydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,5-dihydroxy-2-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

1-(3-acetyl-2,6-dihydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

CC(=O)C1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C(O)C(=C1O)C1=C2C(=O)C3=C(C(O)=CC=C3)C(=O)C2=C(O)C=C1C

InChI Identifier

InChI=1S/C29H26O13/c1-9-6-13(33)21-22(23(35)11-4-3-5-12(32)19(11)26(21)38)17(9)20-14(34)7-15(18(10(2)31)25(20)37)41-29-28(40)27(39)24(36)16(8-30)42-29/h3-7,16,24,27-30,32-34,36-37,39-40H,8H2,1-2H3/t16-,24-,27+,28-,29-/m1/s1

InChI Key

AOJYFODHRHWWEN-GQUXZSRASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bulbine frutescens	LOTUS Database	35616633
Bulbinella floribunda	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anthraquinone
9,10-anthraquinone
Phenolic glycoside
Alkyl-phenylketone
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Acetophenone
Phenylketone
Phenol ether
Phenoxy compound
Resorcinol
Aryl ketone
Aryl alkyl ketone
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monosaccharide
Oxane
Monocyclic benzene moiety
Vinylogous acid
Ketone
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Primary alcohol
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:65741 )
polyphenol (CHEBI:65741 )
methyl ketone (CHEBI:65741 )
aromatic ketone (CHEBI:65741 )
anthraquinone (CHEBI:65741 )

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	1.79	ALOGPS
logP	2.8	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.1	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	231.51 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	143.78 m³·mol⁻¹	ChemAxon
Polarizability	56.7 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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8184020

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10008440

PDB ID

Not Available

ChEBI ID

65741

Good Scents ID

Not Available

References

General References

Kuroda M, Mimaki Y, Sakagami H, Sashida Y: Bulbinelonesides A-E, phenylanthraquinone glycosides from the roots of Bulbinella floribunda. J Nat Prod. 2003 Jun;66(6):894-7. doi: 10.1021/np030061l. [PubMed:12828488 ]
Abegaz BM, Bezabih M, Msuta T, Brun R, Menche D, Muhlbacher J, Bringmann G: Gaboroquinones A and B and 4'-O-demethylknipholone-4'-O-beta-D-glucopyranoside, phenylanthraquinones from the roots of Bulbine frutescens. J Nat Prod. 2002 Aug;65(8):1117-21. doi: 10.1021/np0201218. [PubMed:12193014 ]

Showing NP-Card for Bulbineloneside D (NP0044045)

MOL for NP0044045 (Bulbineloneside D)

3D MOL for NP0044045 (Bulbineloneside D)

3D SDF for NP0044045 (Bulbineloneside D)

3D-SDF for NP0044045 (Bulbineloneside D)

PDB for NP0044045 (Bulbineloneside D)

3D PDB for NP0044045 (Bulbineloneside D)

SMILES for NP0044045 (Bulbineloneside D)

INCHI for NP0044045 (Bulbineloneside D)

Structure for NP0044045 (Bulbineloneside D)

3D Structure for NP0044045 (Bulbineloneside D)