NP-MRD: Showing NP-Card for 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid (NP0046040)

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Record Information

Version

2.0

Created at

2022-03-17 19:47:24 UTC

Updated at

2022-03-17 19:47:25 UTC

NP-MRD ID

NP0046040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid

Description

3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid, also known as dmac-3,8, 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. 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid has been detected, but not quantified in, saffrons. 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid is found in Streptomyces albidoflavus. This could make 3,8-dihydroxy-1-methylanthraquinone-2-carboxylic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305322D          

 22 24  0  0  0  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    4.2868   -1.6500    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
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  1  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13  7  2  0  0  0  0
 13  9  1  0  0  0  0
 14  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 14  2  0  0  0  0
 20 15  2  0  0  0  0
 21 16  2  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=CC(O)=C1C(O)=O

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

> <INCHI_KEY>
MHABMANUFPZXEB-UHFFFAOYSA-N

> <FORMULA>
C16H10O6

> <MOLECULAR_WEIGHT>
298.247

> <EXACT_MASS>
298.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
28.566830184834107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,8-dihydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
3.7825797286666667

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.359698600588086

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2268323426401606

> <JCHEM_PKA_STRONGEST_BASIC>
-4.444766738132524

> <JCHEM_POLAR_SURFACE_AREA>
111.89999999999999

> <JCHEM_REFRACTIVITY>
77.41019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,8-dihydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   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       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    2    9                                                       
CONECT    5    8   10                                                       
CONECT    6    1   11   12                                                  
CONECT    7    3   13   14                                                  
CONECT    8    5   11   14                                                  
CONECT    9    4   13   17                                                  
CONECT   10    5   12   18                                                  
CONECT   11    6    8   15                                                  
CONECT   12    6   10   16                                                  
CONECT   13    7    9   15                                                  
CONECT   14    7    8   19                                                  
CONECT   15   11   13   20                                                  
CONECT   16   12   21   22                                                  
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   16                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylate	Generator
DMAC-3,8	MeSH
3,8-Dihydroxymethylanthraquinone carboxylic acid	MeSH
9,10-dihydro-3,8-Dihydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic acid, 9ci	HMDB
3,8-Dihydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate	Generator
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid	MeSH

Chemical Formula

C₁₆H₁₀O₆

Average Mass

298.2470 Da

Monoisotopic Mass

298.04774 Da

IUPAC Name

3,8-dihydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Traditional Name

3,8-dihydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid

CAS Registry Number

69119-31-9

SMILES

CC1=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=CC(O)=C1C(O)=O

InChI Identifier

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

InChI Key

MHABMANUFPZXEB-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Crocus sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Streptomyces albidoflavus	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
Hydroxyanthraquinone
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
Vinylogous acid
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen 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	2.27	ALOGPS
logP	3.78	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.23	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.41 m³·mol⁻¹	ChemAxon
Polarizability	28.57 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

HMDB0030830

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002786

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

14379528

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid (NP0046040)

MOL for NP0046040 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

3D MOL for NP0046040 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

3D SDF for NP0046040 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

3D-SDF for NP0046040 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

PDB for NP0046040 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

3D PDB for NP0046040 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

SMILES for NP0046040 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

INCHI for NP0046040 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

Structure for NP0046040 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

3D Structure for NP0046040 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)