NP-MRD: Showing NP-Card for methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate (NP0195074)

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Record Information

Version

1.0

Created at

2022-09-04 12:51:50 UTC

Updated at

2022-09-04 12:51:50 UTC

NP-MRD ID

NP0195074

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate

Description

Rhein methylester 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. methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate is found in Cassia fistula. Rhein methylester is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    5.9428    1.3465   -1.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7476    0.6343   -0.9379 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5269    1.2804   -0.8050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5205    2.5282   -0.9522 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2899    0.5594   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2840   -0.8111   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1078   -1.4751   -0.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0677   -2.8631    0.1101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804   -0.7760    0.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0582    0.5848   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226    1.2564   -0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3213    1.3000    0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2779    2.5559   -0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5604    0.5933    0.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7476    1.3009    0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9366    0.6678    0.7219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9603   -0.6820    0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7953   -1.4551    0.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8768   -2.7894    0.9508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6088   -0.7808    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3392   -1.4785    0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920   -2.7346    0.5002 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9510    1.6166   -2.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9534    2.2843   -0.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8240    0.7338   -0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2164   -1.3503   -0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9405   -3.3714    0.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0695    2.3477   -0.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7183    2.3811    0.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8611    1.2471    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9050   -1.1744    1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2252   -3.4769    0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 21  1  0
 21 22  2  0
 21 20  1  0
 20 18  2  0
 18 19  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 12  1  0
 12 13  2  0
 12 10  1  0
 10 11  2  0
 11  5  1  0
 10  9  1  0
 14 20  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  8 27  1  0
 19 32  1  0
 17 31  1  0
 16 30  1  0
 15 29  1  0
 11 28  1  0
M  END


  Mrv1533004201505032D          

 22 24  0  0  0  0            999 V2000
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
  5 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195074

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC(O)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O6/c1-22-16(21)7-5-9-13(11(18)6-7)15(20)12-8(14(9)19)3-2-4-10(12)17/h2-6,17-18H,1H3

> <INCHI_KEY>
SGDMEGYCHABPCQ-UHFFFAOYSA-N

> <FORMULA>
C16H10O6

> <MOLECULAR_WEIGHT>
298.25

> <EXACT_MASS>
298.047738042

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.87770263085655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
3.6150523953333327

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.398940090024807

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.692765834533387

> <JCHEM_PKA_STRONGEST_BASIC>
-5.199180083497876

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
77.13810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   21                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    9   22                                                  
CONECT   22   21    5                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid	Generator

Chemical Formula

C₁₆H₁₀O₆

Average Mass

298.2500 Da

Monoisotopic Mass

298.04774 Da

IUPAC Name

methyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

Traditional Name

methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC(O)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C1

InChI Identifier

InChI=1S/C16H10O6/c1-22-16(21)7-5-9-13(11(18)6-7)15(20)12-8(14(9)19)3-2-4-10(12)17/h2-6,17-18H,1H3

InChI Key

SGDMEGYCHABPCQ-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
Cassia fistula	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
9,10-anthraquinone
Anthraquinone
2-naphthalenecarboxylic acid or derivatives
2-naphthalenecarboxylic acid
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Methyl ester
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	2.84	ALOGPS
logP	3.62	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.69	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.14 m³·mol⁻¹	ChemAxon
Polarizability	28.88 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

44583637

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate (NP0195074)

MOL for NP0195074 (methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate)

3D MOL for NP0195074 (methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate)

3D SDF for NP0195074 (methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate)

3D-SDF for NP0195074 (methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate)

PDB for NP0195074 (methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate)

3D PDB for NP0195074 (methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate)

SMILES for NP0195074 (methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate)

INCHI for NP0195074 (methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate)

Structure for NP0195074 (methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate)

3D Structure for NP0195074 (methyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate)