NP-MRD: Showing NP-Card for (9s,9'r)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid (NP0322602)

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Record Information

Version

2.0

Created at

2022-09-12 01:27:55 UTC

Updated at

2022-09-12 01:27:56 UTC

NP-MRD ID

NP0322602

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9s,9'r)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid

Description

(9S,9'R)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9H,9'H,10H,10'H-[9,9'-bianthracene]-2,2'-dicarboxylic acid belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. (9s,9'r)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid is found in Senna alexandrina. Based on a literature review very few articles have been published on (9S,9'R)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9H,9'H,10H,10'H-[9,9'-bianthracene]-2,2'-dicarboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122203272D          

 40 45  0  0  1  0            999 V2000
    7.8592    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    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
    5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309122203272D          

 40 45  0  0  1  0            999 V2000
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 32 38  1  0  0  0  0
 38 39  1  0  0  0  0
  8 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0322602

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC(O)=C2C(=C1)[C@H]([C@H]1C3=C(O)C=CC=C3C(=O)C3=CC=C(C(O)=O)C(O)=C13)C1=CC=CC(O)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H18O10/c31-17-5-2-4-13-21(17)25(24-14(26(13)34)7-8-15(27(24)35)30(39)40)20-12-3-1-6-18(32)22(12)28(36)23-16(20)9-11(29(37)38)10-19(23)33/h1-10,20,25,31-33,35H,(H,37,38)(H,39,40)/t20-,25+/m1/s1

> <INCHI_KEY>
UVVHNHMVTQRBOM-NLFFAJNJSA-N

> <FORMULA>
C30H18O10

> <MOLECULAR_WEIGHT>
538.464

> <EXACT_MASS>
538.08999678

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
50.54284421296097

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9S,9'R)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9H,9'H,10H,10'H-[9,9'-bianthracene]-2,2'-dicarboxylic acid

> <JCHEM_LOGP>
6.374373618

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.5629870855138677

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.419584473702468

> <JCHEM_PKA_STRONGEST_BASIC>
-5.617359798444025

> <JCHEM_POLAR_SURFACE_AREA>
189.65999999999997

> <JCHEM_REFRACTIVITY>
141.1544

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9S,9'R)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9H,9'H-[9,9'-bianthracene]-2,2'-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0      14.670   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.575   1.246   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.430   1.246   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   39                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12   32                                                  
CONECT   12   11   13   31                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   12                                                  
CONECT   32   11   33   38                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   32   39                                                  
CONECT   39   38    8   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
(9S,9'r)-1,4',5',8-Tetrahydroxy-10,10'-dioxo-9H,9'H,10H,10'H-[9,9'-bianthracene]-2,2'-dicarboxylate	Generator

Chemical Formula

C₃₀H₁₈O₁₀

Average Mass

538.4640 Da

Monoisotopic Mass

538.09000 Da

IUPAC Name

(9S,9'R)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9H,9'H,10H,10'H-[9,9'-bianthracene]-2,2'-dicarboxylic acid

Traditional Name

(9S,9'R)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9H,9'H-[9,9'-bianthracene]-2,2'-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(O)=C2C(=C1)[C@H]([C@H]1C3=C(O)C=CC=C3C(=O)C3=CC=C(C(O)=O)C(O)=C13)C1=CC=CC(O)=C1C2=O

InChI Identifier

InChI=1S/C30H18O10/c31-17-5-2-4-13-21(17)25(24-14(26(13)34)7-8-15(27(24)35)30(39)40)20-12-3-1-6-18(32)22(12)28(36)23-16(20)9-11(29(37)38)10-19(23)33/h1-10,20,25,31-33,35H,(H,37,38)(H,39,40)/t20-,25+/m1/s1

InChI Key

UVVHNHMVTQRBOM-NLFFAJNJSA-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
Senna alexandrina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthracenecarboxylic acids and derivatives

Direct Parent

Anthracenecarboxylic acids

Alternative Parents

Substituents

Anthracene carboxylic acid
2-naphthalenecarboxylic acid or derivatives
2-naphthalenecarboxylic acid
Salicylic acid or derivatives
Hydroxybenzoic acid
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Dicarboxylic acid or derivatives
Vinylogous acid
Ketone
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	6.37	ChemAxon
pKa (Strongest Acidic)	2.42	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	189.66 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	141.15 m³·mol⁻¹	ChemAxon
Polarizability	50.54 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

162956695

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (9s,9'r)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid (NP0322602)

MOL for NP0322602 ((9s,9'r)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

3D MOL for NP0322602 ((9s,9'r)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

3D SDF for NP0322602 ((9s,9'r)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

3D-SDF for NP0322602 ((9s,9'r)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

PDB for NP0322602 ((9s,9'r)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

3D PDB for NP0322602 ((9s,9'r)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

SMILES for NP0322602 ((9s,9'r)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

INCHI for NP0322602 ((9s,9'r)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

Structure for NP0322602 ((9s,9'r)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

3D Structure for NP0322602 ((9s,9'r)-1,4',5',8-tetrahydroxy-10,10'-dioxo-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)