NP-MRD: Showing NP-Card for 5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate (NP0269596)

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Record Information

Version

2.0

Created at

2022-09-08 15:09:11 UTC

Updated at

2022-09-08 15:09:11 UTC

NP-MRD ID

NP0269596

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate

Description

5-(1,2-Dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate 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. 5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate is found in Staphylotrichum boninense. Based on a literature review very few articles have been published on 5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082217092D          

 41 44  0  0  0  0            999 V2000
   -0.5230   -6.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 40 41  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309082217092D          

 41 44  0  0  0  0            999 V2000
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    3.1895   -1.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    1.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -0.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -1.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -1.7901    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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  8 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
 19 21  2  0  0  0  0
  6 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 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
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  0  0  0  0
 26 40  1  0  0  0  0
 40 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0269596

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(OC1OC(C(O)CO)C(O)C1OC(C)=O)C1=C(O)C=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O13/c1-3-4-5-6-18(40-28-27(39-11(2)30)25(38)26(41-28)17(34)10-29)21-16(33)9-14-20(24(21)37)23(36)19-13(22(14)35)7-12(31)8-15(19)32/h7-9,17-18,25-29,31-34,37-38H,3-6,10H2,1-2H3

> <INCHI_KEY>
RUWRWSMREJGOBH-UHFFFAOYSA-N

> <FORMULA>
C28H32O13

> <MOLECULAR_WEIGHT>
576.551

> <EXACT_MASS>
576.18429109

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
58.12195774351157

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate

> <JCHEM_LOGP>
3.180188199999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.457935981458421

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.772696660004103

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9745072612323424

> <JCHEM_POLAR_SURFACE_AREA>
220.51

> <JCHEM_REFRACTIVITY>
140.20109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.976 -11.344   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564 -11.344   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644  -8.676   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184  -8.676   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.954 -10.010   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.184 -11.344   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.652 -11.505   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.332 -13.011   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.925 -13.637   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.679 -12.732   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.764 -15.169   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.357 -15.795   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.666 -13.781   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.827 -15.313   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.810 -12.751   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.316 -13.071   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.347 -11.926   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.853 -12.246   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.871 -10.462   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.954  -7.343   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.494  -7.343   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.264  -8.676   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.264  -6.009   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.494  -4.675   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.954  -4.675   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.184  -6.009   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.644  -6.009   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.184  -3.342   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.644  -3.342   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.954  -2.008   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.184  -0.674   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.644  -0.674   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.954   0.659   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.494   0.659   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.264   1.993   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.264  -0.674   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.494  -2.008   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.264  -3.342   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       9.804  -3.342   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   10   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    8   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    6   23   28                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   40                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   22   29                                                  
CONECT   29   28                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   39                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   32   40                                                  
CONECT   40   39   26   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Value	Source
5-(1,2-Dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₂O₁₃

Average Mass

576.5510 Da

Monoisotopic Mass

576.18429 Da

IUPAC Name

5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate

Traditional Name

5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CCCCCC(OC1OC(C(O)CO)C(O)C1OC(C)=O)C1=C(O)C=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C28H32O13/c1-3-4-5-6-18(40-28-27(39-11(2)30)25(38)26(41-28)17(34)10-29)21-16(33)9-14-20(24(21)37)23(36)19-13(22(14)35)7-12(31)8-15(19)32/h7-9,17-18,25-29,31-34,37-38H,3-6,10H2,1-2H3

InChI Key

RUWRWSMREJGOBH-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
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Monosaccharide
Vinylogous acid
Tetrahydrofuran
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
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	3.18	ChemAxon
pKa (Strongest Acidic)	6.77	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	220.51 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	140.2 m³·mol⁻¹	ChemAxon
Polarizability	58.12 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

162930490

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate (NP0269596)

MOL for NP0269596 (5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate)

3D MOL for NP0269596 (5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate)

3D SDF for NP0269596 (5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate)

3D-SDF for NP0269596 (5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate)

PDB for NP0269596 (5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate)

3D PDB for NP0269596 (5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate)

SMILES for NP0269596 (5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate)

INCHI for NP0269596 (5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate)

Structure for NP0269596 (5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate)

3D Structure for NP0269596 (5-(1,2-dihydroxyethyl)-4-hydroxy-2-{[1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate)