NP-MRD: Showing NP-Card for 2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione (NP0200629)

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Record Information

Version

2.0

Created at

2022-09-04 19:30:51 UTC

Updated at

2022-09-04 19:30:52 UTC

NP-MRD ID

NP0200629

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione

Description

2-(1-{[5-(1,2-Dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxy-9,10-dihydroanthracene-9,10-dione belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. 2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione is found in Staphylotrichum boninense. Based on a literature review very few articles have been published on 2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxy-9,10-dihydroanthracene-9,10-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042221302D          

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M  END

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M  END


  Mrv1652309042221302D          

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 14 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 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
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  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
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 30 37  1  0  0  0  0
 37 38  1  0  0  0  0
 24 38  1  0  0  0  0
 38 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0200629

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CCCC(OC1OC(C(O)CO)C(O)C1O)C1=C(O)C=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O13/c1-9(28)3-2-4-16(38-26-24(37)23(36)25(39-26)15(32)8-27)19-14(31)7-12-18(22(19)35)21(34)17-11(20(12)33)5-10(29)6-13(17)30/h5-7,15-16,23-27,29-32,35-37H,2-4,8H2,1H3

> <INCHI_KEY>
AWPZQTIGVJBSTI-UHFFFAOYSA-N

> <FORMULA>
C26H28O13

> <MOLECULAR_WEIGHT>
548.497

> <EXACT_MASS>
548.152990962

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.568685021669225

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxy-9,10-dihydroanthracene-9,10-dione

> <JCHEM_LOGP>
1.3038778823333343

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.457931278885501

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.772694285940504

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9745069773523056

> <JCHEM_POLAR_SURFACE_AREA>
231.50999999999996

> <JCHEM_REFRACTIVITY>
131.66509999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  -8.470   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.337  -6.160   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.091  -5.255   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.567  -3.790   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.662  -2.544   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.130  -2.705   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.288  -1.137   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.383   0.108   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.107  -3.790   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      15.012  -2.544   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.583  -5.255   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.047  -5.731   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669 -10.780   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003 -13.090   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.337 -10.780   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.670 -13.090   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      16.004 -12.320   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.004 -15.400   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      17.338 -14.630   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.670 -17.710   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      14.670 -19.250   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.337 -15.400   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      10.669 -15.400   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   11   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19                                                  
CONECT   19   18                                                            
CONECT   20    7   21   26                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   38                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   20   27                                                  
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   37                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   30   38                                                  
CONECT   38   37   24   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₁₃

Average Mass

548.4970 Da

Monoisotopic Mass

548.15299 Da

IUPAC Name

2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxy-9,10-dihydroanthracene-9,10-dione

Traditional Name

2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

CC(=O)CCCC(OC1OC(C(O)CO)C(O)C1O)C1=C(O)C=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C26H28O13/c1-9(28)3-2-4-16(38-26-24(37)23(36)25(39-26)15(32)8-27)19-14(31)7-12-18(22(19)35)21(34)17-11(20(12)33)5-10(29)6-13(17)30/h5-7,15-16,23-27,29-32,35-37H,2-4,8H2,1H3

InChI Key

AWPZQTIGVJBSTI-UHFFFAOYSA-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
Staphylotrichum boninense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Pentose monosaccharide
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Monosaccharide
Vinylogous acid
Tetrahydrofuran
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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	1.3	ChemAxon
pKa (Strongest Acidic)	6.77	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	9	ChemAxon
Refractivity	131.67 m³·mol⁻¹	ChemAxon
Polarizability	53.57 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	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

163081624

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione (NP0200629)

MOL for NP0200629 (2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione)

3D MOL for NP0200629 (2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione)

3D SDF for NP0200629 (2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione)

3D-SDF for NP0200629 (2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione)

PDB for NP0200629 (2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione)

3D PDB for NP0200629 (2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione)

SMILES for NP0200629 (2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione)

INCHI for NP0200629 (2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione)

Structure for NP0200629 (2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione)

3D Structure for NP0200629 (2-(1-{[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-oxohexyl)-1,3,6,8-tetrahydroxyanthracene-9,10-dione)