NP-MRD: Showing NP-Card for [(9r)-4,5,9-trihydroxy-10-oxo-9-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate (NP0235364)

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Record Information

Version

2.0

Created at

2022-09-06 17:56:53 UTC

Updated at

2022-09-06 17:56:53 UTC

NP-MRD ID

NP0235364

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(9r)-4,5,9-trihydroxy-10-oxo-9-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate

Description

[(9R)-4,5,9-trihydroxy-10-oxo-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-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)-4,5,9-trihydroxy-10-oxo-9-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-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)-4,5,9-trihydroxy-10-oxo-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracen-2-yl]methyl (2R,3S)-3-hydroxy-2-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062219562D          

 38 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309062219562D          

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  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  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  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  1  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  6  0  0  0
 17 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 30 36  1  0  0  0  0
 36 37  1  0  0  0  0
 14 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0235364

> <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](CO)[C@@H](O)[C@H](O)[C@H]3O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O12/c1-10(11(2)28)25(35)37-9-12-6-14-19(16(30)7-12)21(32)18-13(4-3-5-15(18)29)26(14,36)24-23(34)22(33)20(31)17(8-27)38-24/h3-7,10-11,17,20,22-24,27-31,33-34,36H,8-9H2,1-2H3/t10-,11+,17-,20-,22+,23-,24-,26-/m1/s1

> <INCHI_KEY>
LHIPKJMQYMTREZ-LIEJRACDSA-N

> <FORMULA>
C26H30O12

> <MOLECULAR_WEIGHT>
534.514

> <EXACT_MASS>
534.173726406

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.1799275958395

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
0.3271904089999996

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.82370025100455

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.161125746327999

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7867805631126767

> <JCHEM_POLAR_SURFACE_AREA>
214.43999999999997

> <JCHEM_REFRACTIVITY>
129.6836

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(9R)-4,5,9-trihydroxy-10-oxo-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2R,3S)-3-hydroxy-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.807  -3.757   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.183  -2.043   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.710  -0.595   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.226  -0.328   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.753   1.119   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.270   1.387   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.216  -1.508   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.733  -1.240   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.689  -2.955   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.679  -4.135   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.173  -3.222   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.646  -4.669   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   37                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   10                                                       
CONECT   17   15   18   19   30                                             
CONECT   18   17                                                            
CONECT   19   17   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   19   29                                                  
CONECT   29   28                                                            
CONECT   30   17   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   30   37                                                  
CONECT   37   36   14   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₆H₃₀O₁₂

Average Mass

534.5140 Da

Monoisotopic Mass

534.17373 Da

IUPAC Name

[(9R)-4,5,9-trihydroxy-10-oxo-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracen-2-yl]methyl (2R,3S)-3-hydroxy-2-methylbutanoate

Traditional Name

[(9R)-4,5,9-trihydroxy-10-oxo-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2R,3S)-3-hydroxy-2-methylbutanoate

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](CO)[C@@H](O)[C@H](O)[C@H]3O)C2=C1

InChI Identifier

InChI=1S/C26H30O12/c1-10(11(2)28)25(35)37-9-12-6-14-19(16(30)7-12)21(32)18-13(4-3-5-15(18)29)26(14,36)24-23(34)22(33)20(31)17(8-27)38-24/h3-7,10-11,17,20,22-24,27-31,33-34,36H,8-9H2,1-2H3/t10-,11+,17-,20-,22+,23-,24-,26-/m1/s1

InChI Key

LHIPKJMQYMTREZ-LIEJRACDSA-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
Hexose monosaccharide
C-glycosyl compound
Glycosyl compound
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Fatty acid ester
Fatty acyl
Hydroxy acid
Monosaccharide
Oxane
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Primary 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	0.33	ChemAxon
pKa (Strongest Acidic)	8.16	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	214.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.68 m³·mol⁻¹	ChemAxon
Polarizability	53.18 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

163001539

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(9r)-4,5,9-trihydroxy-10-oxo-9-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate (NP0235364)

MOL for NP0235364 ([(9r)-4,5,9-trihydroxy-10-oxo-9-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D MOL for NP0235364 ([(9r)-4,5,9-trihydroxy-10-oxo-9-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D SDF for NP0235364 ([(9r)-4,5,9-trihydroxy-10-oxo-9-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D-SDF for NP0235364 ([(9r)-4,5,9-trihydroxy-10-oxo-9-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

PDB for NP0235364 ([(9r)-4,5,9-trihydroxy-10-oxo-9-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D PDB for NP0235364 ([(9r)-4,5,9-trihydroxy-10-oxo-9-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

SMILES for NP0235364 ([(9r)-4,5,9-trihydroxy-10-oxo-9-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

INCHI for NP0235364 ([(9r)-4,5,9-trihydroxy-10-oxo-9-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

Structure for NP0235364 ([(9r)-4,5,9-trihydroxy-10-oxo-9-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D Structure for NP0235364 ([(9r)-4,5,9-trihydroxy-10-oxo-9-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracen-2-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate)