NP-MRD: Showing NP-Card for 1,4,5,8-Tetrahydroxy-2-methylanthraquinone (NP0062080)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 06:45:19 UTC

Updated at

2022-04-28 06:45:19 UTC

NP-MRD ID

NP0062080

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,4,5,8-Tetrahydroxy-2-methylanthraquinone

Description

1,4,5,8-Tetrahydroxy-2-methyl-9,10-dihydroanthracene-9,10-dione belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. 1,4,5,8-Tetrahydroxy-2-methylanthraquinone is found in Asahinea chrysantha, Drechslera setariae, Drechslera spicifera, Curvularia geniculata, Curvularia lunata, Curvularia lunata NRRL 2380, Curvularia ramosa, Curvularia trifolii, Drechslera avenae, Drechslera dematioidea, Drechslera halodes, Drechslera sorokiniana, Maesopsis eminii, Pyrenochaeta terrestris, Pyrenophora chaetomioides, Rhamnus wightii and Setophoma terrestris. 1,4,5,8-Tetrahydroxy-2-methyl-9,10-dihydroanthracene-9,10-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -4.5485   -0.9461    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2062   -0.3117    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863    1.0045    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8289    1.6569    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7782    2.9759    0.6866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6874    0.9020    0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7785   -0.4583   -0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0319   -1.0532   -0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2255   -2.3735   -0.3706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359   -1.2404   -0.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3093   -2.4512   -0.5155 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7553   -0.6355   -0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867   -1.4041   -0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8794   -2.7298   -0.7028 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1469   -0.7769   -0.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2612    0.5471   -0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1209    1.3505    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2872    2.6709    0.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8909    0.7242    0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542    1.4626    0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603    2.6715    0.4957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8618   -1.1283    1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2942   -0.3308   -0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4813   -1.9568   -0.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9509    1.6454    0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0864    3.6286    0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7380   -3.1646   -0.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1802   -3.3519   -0.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0083   -1.4211   -0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2239    1.0420   -0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7832    3.4520    0.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6 20  1  0
 20 21  2  0
 20 19  1  0
 19 17  2  0
 17 18  1  0
 17 16  1  0
 16 15  2  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 10  1  0
 10 11  2  0
 10  7  1  0
  7  8  2  0
  8  9  1  0
  8  2  1  0
  7  6  1  0
 12 19  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  0
 18 31  1  0
 16 30  1  0
 15 29  1  0
 14 28  1  0
  9 27  1  0
M  END


  Mrv1533004261501522D          

 21 23  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
    5.0013   -3.7125    0.0000 O   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
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  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
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062080

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C2C(=O)C3=C(O)C=CC(O)=C3C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O6/c1-5-4-8(18)11-12(13(5)19)15(21)10-7(17)3-2-6(16)9(10)14(11)20/h2-4,16-19H,1H3

> <INCHI_KEY>
NFQXCHAJWVRYND-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.239

> <EXACT_MASS>
286.047738042

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.192876818885118

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4,5,8-tetrahydroxy-2-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
4.817866177333333

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.870745502333806

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.224265429813501

> <JCHEM_PKA_STRONGEST_BASIC>
-5.55746003894602

> <JCHEM_POLAR_SURFACE_AREA>
115.06000000000002

> <JCHEM_REFRACTIVITY>
74.11580000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4,5,8-tetrahydroxy-2-methylanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-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  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   19                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    6   20                                                  
CONECT   20   19    2   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
3-Methyl-1,4,5,8-tetrahydroxyanthraquinone	MeSH

Chemical Formula

C₁₅H₁₀O₆

Average Mass

286.2390 Da

Monoisotopic Mass

286.04774 Da

IUPAC Name

1,4,5,8-tetrahydroxy-2-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,4,5,8-tetrahydroxy-2-methylanthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(=O)C3=C(O)C=CC(O)=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C15H10O6/c1-5-4-8(18)11-12(13(5)19)15(21)10-7(17)3-2-6(16)9(10)14(11)20/h2-4,16-19H,1H3

InChI Key

NFQXCHAJWVRYND-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
Asahinea chrysantha	LOTUS Database	35616633
Cochliobolus setariae	Fungi	KNApSAcK
Cochliobolus spicifer	Fungi	KNApSAcK
Curvularia geniculata	Fungi	KNApSAcK
Curvularia lunata	LOTUS Database	35616633
Curvularia lunata NRRL 2380	Fungi	KNApSAcK
Curvularia ramosa	Fungi	KNApSAcK
Curvularia trifolii	Fungi	KNApSAcK
Drechslera avenae	LOTUS Database	35616633
Drechslera dematioidea	Fungi	KNApSAcK
Drechslera halodes	Fungi	KNApSAcK
Drechslera sorokiniana	Fungi	KNApSAcK
Maesopsis eminii	LOTUS Database	35616633
Pyrenochaeta terrestris	Fungi	KNApSAcK
Pyrenophora chaetomioides	LOTUS Database	35616633
Rhamnus wightii	Plant	KNApSAcK
Setophoma terrestris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anthraquinone
9,10-anthraquinone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	2.15	ALOGPS
logP	4.82	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.22	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	74.12 m³·mol⁻¹	ChemAxon
Polarizability	27.19 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

10148

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1,4,5,8-Tetrahydroxy-2-methylanthraquinone (NP0062080)

MOL for NP0062080 (1,4,5,8-Tetrahydroxy-2-methylanthraquinone)

3D MOL for NP0062080 (1,4,5,8-Tetrahydroxy-2-methylanthraquinone)

3D SDF for NP0062080 (1,4,5,8-Tetrahydroxy-2-methylanthraquinone)

3D-SDF for NP0062080 (1,4,5,8-Tetrahydroxy-2-methylanthraquinone)

PDB for NP0062080 (1,4,5,8-Tetrahydroxy-2-methylanthraquinone)

3D PDB for NP0062080 (1,4,5,8-Tetrahydroxy-2-methylanthraquinone)

SMILES for NP0062080 (1,4,5,8-Tetrahydroxy-2-methylanthraquinone)

INCHI for NP0062080 (1,4,5,8-Tetrahydroxy-2-methylanthraquinone)

Structure for NP0062080 (1,4,5,8-Tetrahydroxy-2-methylanthraquinone)

3D Structure for NP0062080 (1,4,5,8-Tetrahydroxy-2-methylanthraquinone)