NP-MRD: Showing NP-Card for 4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate (NP0292855)

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Record Information

Version

2.0

Created at

2022-09-10 00:35:22 UTC

Updated at

2022-09-10 00:35:22 UTC

NP-MRD ID

NP0292855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate

Description

4,5-Dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl)oxan-3-yl benzoate belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. 4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate is found in Picramnia latifolia. 4,5-Dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl)oxan-3-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171518032D          

 36 40  0  0  0  0            999 V2000
    0.7145   -2.8875    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0421   -3.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296   -3.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993   -4.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9815   -4.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4512   -5.4154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3565   -4.4969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084   -5.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  4  6  2  0  0  0  0
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  9 10  2  0  0  0  0
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M  END

     RDKit          3D

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   -4.7327   -2.9010   -2.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8 42  1  0
M  END


  Mrv1533004171518032D          

 36 40  0  0  0  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0292855

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C2C(=O)C3=C(O)C=CC=C3C(O)(C3OCC(OC(=O)C4=CC=CC=C4)C(O)C3O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H24O9/c1-13-10-16-21(18(29)11-13)23(31)20-15(8-5-9-17(20)28)27(16,34)25-24(32)22(30)19(12-35-25)36-26(33)14-6-3-2-4-7-14/h2-11,19,22,24-25,28-30,32,34H,12H2,1H3

> <INCHI_KEY>
HESXYYVNWWHMEB-UHFFFAOYSA-N

> <FORMULA>
C27H24O9

> <MOLECULAR_WEIGHT>
492.48

> <EXACT_MASS>
492.142032353

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
48.759914756259604

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl)oxan-3-yl benzoate

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
3.9131449526666664

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.95413921718885

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.301903184545246

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6557853621934218

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
127.22200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.335  -3.080   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  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.658  -6.570   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.679  -6.570   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.162  -6.302   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.172  -7.482   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.699  -8.929   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.709 -10.109   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.192  -9.841   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.666  -8.394   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.202 -11.021   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.729 -12.468   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.261 -13.648   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.777 -13.381   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.304 -11.933   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.314 -10.754   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.215  -9.197   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.742 -10.644   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.205  -8.017   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.722  -8.284   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   35                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15   17   18   35                                             
CONECT   17   16                                                            
CONECT   18   16   19   33                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   31                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   21   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   18   34                                                  
CONECT   34   33                                                            
CONECT   35   16    6   36                                                  
CONECT   36   35    2                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
4,5-Dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl)oxan-3-yl benzoic acid	Generator

Chemical Formula

C₂₇H₂₄O₉

Average Mass

492.4800 Da

Monoisotopic Mass

492.14203 Da

IUPAC Name

4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl)oxan-3-yl benzoate

Traditional Name

4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(=O)C3=C(O)C=CC=C3C(O)(C3OCC(OC(=O)C4=CC=CC=C4)C(O)C3O)C2=C1

InChI Identifier

InChI=1S/C27H24O9/c1-13-10-16-21(18(29)11-13)23(31)20-15(8-5-9-17(20)28)27(16,34)25-24(32)22(30)19(12-35-25)36-26(33)14-6-3-2-4-7-14/h2-11,19,22,24-25,28-30,32,34H,12H2,1H3

InChI Key

HESXYYVNWWHMEB-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
Picramnia latifolia	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
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Oxane
Vinylogous acid
Tertiary alcohol
Ketone
Carboxylic acid ester
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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
logP	2.14	ALOGPS
logP	3.91	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.3	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	127.22 m³·mol⁻¹	ChemAxon
Polarizability	48.76 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

72794129

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate (NP0292855)

MOL for NP0292855 (4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate)

3D MOL for NP0292855 (4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate)

3D SDF for NP0292855 (4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate)

3D-SDF for NP0292855 (4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate)

PDB for NP0292855 (4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate)

3D PDB for NP0292855 (4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate)

SMILES for NP0292855 (4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate)

INCHI for NP0292855 (4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate)

Structure for NP0292855 (4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate)

3D Structure for NP0292855 (4,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-3-yl benzoate)