NP-MRD: Showing NP-Card for 1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione (NP0304057)

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Record Information

Version

2.0

Created at

2022-09-10 18:52:54 UTC

Updated at

2022-09-10 18:52:54 UTC

NP-MRD ID

NP0304057

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione

Description

SCHEMBL5981388 belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. 1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione is found in Hemerocallis fulva. SCHEMBL5981388 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
    0.6273    2.7854   -0.6941 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7258    1.5578   -0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0510    0.9367   -0.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1508    1.7528   -0.4901 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3880    1.1718   -0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5534   -0.1557   -0.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4428   -1.0023    0.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6629   -2.3317    0.3423 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893   -0.4204   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9975   -1.2386    0.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0592   -2.4659    0.3767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3467   -0.6384    0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4366    0.7026   -0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7195    1.2370   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8307    0.4505   -0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1896    1.0222   -0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0653    2.3796   -0.5987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7294   -0.9029    0.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003   -1.6699    0.2275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4757   -1.4352    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935   -2.7711    0.4454 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0378    2.8095   -0.7055 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2541    1.8409   -0.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297   -0.5845   -0.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006   -3.1017    0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752    2.3018   -0.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7852    0.8815    0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7676    0.5460   -1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6474    2.4343   -1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8196   -2.6339    0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9880   -3.4582    0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 20  1  0
 20 21  1  0
 20 18  2  0
 18 19  1  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  3  2  1  0
  2  1  2  0
 18 15  1  0
  7  9  1  0
  2 13  1  0
 17 29  1  0
 16 27  1  0
 16 28  1  0
 14 26  1  0
 21 31  1  0
 19 30  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
M  END


  Mrv1652310081720242D          

 21 23  0  0  0  0            999 V2000
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    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
    3.5724    1.2375    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
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   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
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  3  2  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16  5  1  0  0  0  0
 17  9  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 20 14  2  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304057

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=CC2=C(C(O)=C1O)C(=O)C1=C(C=CC=C1O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O6/c16-5-6-4-8-11(15(21)12(6)18)14(20)10-7(13(8)19)2-1-3-9(10)17/h1-4,16-18,21H,5H2

> <INCHI_KEY>
FWDJFYYRADDLPT-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.239

> <EXACT_MASS>
286.047738042

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.402660063774192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,8-trihydroxy-3-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
2.540660342333333

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.349797762312637

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.638608950567931

> <JCHEM_PKA_STRONGEST_BASIC>
-3.075295015945181

> <JCHEM_POLAR_SURFACE_AREA>
115.05999999999999

> <JCHEM_REFRACTIVITY>
73.9096

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-17         0                                  
HETATM    1  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   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  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    7                                                       
CONECT    3    1    9                                                       
CONECT    4    6    8                                                       
CONECT    5    6   16                                                       
CONECT    6    4    5   12                                                  
CONECT    7    2   10   13                                                  
CONECT    8    4   11   13                                                  
CONECT    9    3   10   17                                                  
CONECT   10    7    9   14                                                  
CONECT   11    8   14   15                                                  
CONECT   12    6   15   18                                                  
CONECT   13    7    8   19                                                  
CONECT   14   10   11   20                                                  
CONECT   15   11   12   21                                                  
CONECT   16    5                                                            
CONECT   17    9                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₀O₆

Average Mass

286.2390 Da

Monoisotopic Mass

286.04774 Da

IUPAC Name

1,2,8-trihydroxy-3-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

OCC1=CC2=C(C(O)=C1O)C(=O)C1=C(C=CC=C1O)C2=O

InChI Identifier

InChI=1S/C15H10O6/c16-5-6-4-8-11(15(21)12(6)18)14(20)10-7(13(8)19)2-1-3-9(10)17/h1-4,16-18,21H,5H2

InChI Key

FWDJFYYRADDLPT-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
Hemerocallis fulva	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Ketone
Polyol
Alcohol
Primary alcohol
Aromatic alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen 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	ALOGPS
logP	2.54	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.64	ChemAxon
pKa (Strongest Basic)	-3.1	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	1	ChemAxon
Refractivity	73.91 m³·mol⁻¹	ChemAxon
Polarizability	27.4 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

HMDB0166435

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

10125440

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione (NP0304057)

MOL for NP0304057 (1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione)

3D MOL for NP0304057 (1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione)

3D SDF for NP0304057 (1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione)

3D-SDF for NP0304057 (1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione)

PDB for NP0304057 (1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione)

3D PDB for NP0304057 (1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione)

SMILES for NP0304057 (1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione)

INCHI for NP0304057 (1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione)

Structure for NP0304057 (1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione)

3D Structure for NP0304057 (1,2,8-trihydroxy-3-(hydroxymethyl)anthracene-9,10-dione)