NP-MRD: Showing NP-Card for [(9r)-9-[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate (NP0180054)

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Record Information

Version

2.0

Created at

2022-09-03 18:21:15 UTC

Updated at

2022-09-03 18:21:15 UTC

NP-MRD ID

NP0180054

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(9r)-9-[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate

Description

[(9R)-9-[(2R,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxo-9,10-dihydroanthracen-2-yl]methyl (2R,3S)-3-hydroxy-2-methylbutanoate belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. [(9r)-9-[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate is found in Aloe littoralis. Based on a literature review very few articles have been published on [(9R)-9-[(2R,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxo-9,10-dihydroanthracen-2-yl]methyl (2R,3S)-3-hydroxy-2-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032220212D          

 41 44  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309032220212D          

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    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  2  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    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915    0.6553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5791    0.5120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9218    0.0233    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6397   -0.7520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7343    0.1665    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2646   -0.4654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  6  0  0  0
  9 11  1  6  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 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  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  6  0  0  0
 24 34  1  0  0  0  0
 34 35  2  0  0  0  0
 20 35  1  0  0  0  0
  9 35  1  0  0  0  0
  8 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
  6 40  1  0  0  0  0
 40 41  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0180054

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)[C@@H](C)C(=O)OCC1=CC(O)=C2C(=O)C3=C(O)C=CC=C3[C@](O)([C@@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O13/c1-11(12(2)29)27(37)40-9-14-7-16-21(18(32)8-14)23(34)20-15(5-4-6-17(20)31)28(16,38)26-25(36)24(35)22(33)19(41-26)10-39-13(3)30/h4-8,11-12,19,22,24-26,29,31-33,35-36,38H,9-10H2,1-3H3/t11-,12+,19-,22-,24+,25-,26-,28-/m1/s1

> <INCHI_KEY>
DNJXORJQFHNALC-NXZNEPAMSA-N

> <FORMULA>
C28H32O13

> <MOLECULAR_WEIGHT>
576.551

> <EXACT_MASS>
576.18429109

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
56.82069196174959

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(9R)-9-[(2R,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxo-9,10-dihydroanthracen-2-yl]methyl (2R,3S)-3-hydroxy-2-methylbutanoate

> <JCHEM_LOGP>
0.7683158193333337

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.823700760772345

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.161125887937876

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7867805631126767

> <JCHEM_POLAR_SURFACE_AREA>
220.50999999999996

> <JCHEM_REFRACTIVITY>
138.8351

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(9R)-9-[(2R,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2R,3S)-3-hydroxy-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0     -12.510  -0.067   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.521   1.113   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0     -12.047   2.560   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0     -10.004   0.846   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -9.014   2.025   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.497   1.758   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.508   2.938   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.991   2.670   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.011   2.670   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668   3.850   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  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.668   8.470   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.464   1.223   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.948   0.956   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -5.454   0.043   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -4.927  -1.404   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -6.971   0.311   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -7.961  -0.869   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   40                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   36                                                  
CONECT    9    8   10   11   35                                             
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   35                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   34                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   24   35                                                       
CONECT   35   34   20    9                                                  
CONECT   36    8   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38    6   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Value	Source
[(9R)-9-[(2R,3R,4S,5S,6R)-6-[(Acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxo-9,10-dihydroanthracen-2-yl]methyl (2R,3S)-3-hydroxy-2-methylbutanoic acid	Generator

Chemical Formula

C₂₈H₃₂O₁₃

Average Mass

576.5510 Da

Monoisotopic Mass

576.18429 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@@H](C)C(=O)OCC1=CC(O)=C2C(=O)C3=C(O)C=CC=C3[C@](O)([C@@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3O)C2=C1

InChI Identifier

InChI=1S/C28H32O13/c1-11(12(2)29)27(37)40-9-14-7-16-21(18(32)8-14)23(34)20-15(5-4-6-17(20)31)28(16,38)26-25(36)24(35)22(33)19(41-26)10-39-13(3)30/h4-8,11-12,19,22,24-26,29,31-33,35-36,38H,9-10H2,1-3H3/t11-,12+,19-,22-,24+,25-,26-,28-/m1/s1

InChI Key

DNJXORJQFHNALC-NXZNEPAMSA-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
Aloe littoralis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Not Available

Direct Parent

Anthracenes

Alternative Parents

Substituents

Anthracene
C-glycosyl compound
Glycosyl compound
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Hydroxy acid
Monosaccharide
Oxane
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Ether
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Polyol
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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

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

162912488

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(9r)-9-[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate (NP0180054)

MOL for NP0180054 ([(9r)-9-[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D MOL for NP0180054 ([(9r)-9-[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D SDF for NP0180054 ([(9r)-9-[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D-SDF for NP0180054 ([(9r)-9-[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

PDB for NP0180054 ([(9r)-9-[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D PDB for NP0180054 ([(9r)-9-[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

SMILES for NP0180054 ([(9r)-9-[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

INCHI for NP0180054 ([(9r)-9-[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

Structure for NP0180054 ([(9r)-9-[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D Structure for NP0180054 ([(9r)-9-[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]-4,5,9-trihydroxy-10-oxoanthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)