NP-MRD: Showing NP-Card for 5,10-dihydroxy-4-(hydroxymethyl)-1h-anthra[1,2-c]furan-3,6,11-trione (NP0144963)

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Record Information

Version

2.0

Created at

2022-09-02 00:03:41 UTC

Updated at

2022-09-02 00:03:41 UTC

NP-MRD ID

NP0144963

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,10-dihydroxy-4-(hydroxymethyl)-1h-anthra[1,2-c]furan-3,6,11-trione

Description

5,10-Dihydroxy-4-(hydroxymethyl)-1H,3H,6H,11H-anthra[1,2-c]furan-3,6,11-trione 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. 5,10-dihydroxy-4-(hydroxymethyl)-1h-anthra[1,2-c]furan-3,6,11-trione is found in Berchemia discolor. 5,10-Dihydroxy-4-(hydroxymethyl)-1H,3H,6H,11H-anthra[1,2-c]furan-3,6,11-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -4.5214    1.7132    1.3334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2719    1.7881    1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4684    2.8825    1.4780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252    2.6410    1.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1346    1.2672    0.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4244    0.7567    0.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6605   -0.5206    0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9697   -1.1610    0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0613   -0.4917    0.5563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5874   -1.2989   -0.2842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8002   -2.5807   -0.7513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3230   -0.7655   -0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0697    0.5062    0.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2857    1.0447    0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4904    2.2103    0.6168 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4311    0.2761   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7184    0.8111   -0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9024    2.1061    0.2110 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899    0.0677   -0.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5631   -1.2152   -1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2797   -1.7245   -1.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891   -1.0007   -0.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358   -1.5409   -0.7454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138   -2.6977   -1.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7185    3.3467    0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5608    2.7108    2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1386   -1.4727   -0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9403   -2.1371    0.7165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7294   -1.0221    1.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297   -2.9692   -0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8243    2.5054    0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7966    0.4711   -0.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4122   -1.7793   -1.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1026   -2.7272   -1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13  5  1  0
  5  6  2  0
  6  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
  6  7  1  0
 22 16  1  0
 23 12  1  0
  4  5  1  0
  9 29  1  0
  8 27  1  0
  8 28  1  0
 11 30  1  0
  4 25  1  0
  4 26  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
 21 34  1  0
M  END


  Mrv1533004151517182D          

 24 27  0  0  0  0            999 V2000
    2.4544   -0.1565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2602    0.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8164   -0.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222   -0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8717    0.3747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9842   -0.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2337   -0.0576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5404   -1.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3462   -1.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9024   -1.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6528   -2.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8471   -2.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5975   -3.6352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2908   -2.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4851   -2.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2355   -3.2030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9288   -1.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1231   -1.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7155   -2.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9073   -2.5356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8155   -1.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0982   -1.3082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5668   -1.3751    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
  4  5  1  0  0  0  0
  4  6  1  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
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  6 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  3 24  1  0  0  0  0
 19 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0144963

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=C(O)C2=C(C3=C1C(=O)OC3)C(=O)C1=C(O)C=CC=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H10O7/c18-4-7-10-8(5-24-17(10)23)12-13(15(7)21)14(20)6-2-1-3-9(19)11(6)16(12)22/h1-3,18-19,21H,4-5H2

> <INCHI_KEY>
VAFJYSQYZZTBIY-UHFFFAOYSA-N

> <FORMULA>
C17H10O7

> <MOLECULAR_WEIGHT>
326.26

> <EXACT_MASS>
326.042652662

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
30.697854202689342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,10-dihydroxy-4-(hydroxymethyl)-1H,3H,6H,11H-anthra[1,2-c]furan-3,6,11-trione

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
2.3989299293333337

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.352777317072626

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.626556877085685

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2417345631239263

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000002

> <JCHEM_REFRACTIVITY>
82.5086

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,10-dihydroxy-4-(hydroxymethyl)-1H-anthra[1,2-c]furan-3,6,11-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  O   UNK     0       4.582  -0.292   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.086   0.038   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.124  -1.099   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.628  -0.768   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.094   0.699   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.666  -1.906   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.170  -1.575   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.636  -0.107   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.209  -2.713   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.713  -2.382   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.751  -3.520   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.285  -4.987   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.781  -5.318   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.315  -6.786   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.743  -4.180   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.239  -4.511   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.773  -5.979   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.201  -3.374   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.696  -3.704   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.936  -5.043   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.427  -4.733   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.256  -3.203   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.917  -2.442   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.658  -2.567   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   18                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    6   19                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    3   19                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₀O₇

Average Mass

326.2600 Da

Monoisotopic Mass

326.04265 Da

IUPAC Name

5,10-dihydroxy-4-(hydroxymethyl)-1H,3H,6H,11H-anthra[1,2-c]furan-3,6,11-trione

Traditional Name

5,10-dihydroxy-4-(hydroxymethyl)-1H-anthra[1,2-c]furan-3,6,11-trione

CAS Registry Number

Not Available

SMILES

OCC1=C(O)C2=C(C3=C1C(=O)OC3)C(=O)C1=C(O)C=CC=C1C2=O

InChI Identifier

InChI=1S/C17H10O7/c18-4-7-10-8(5-24-17(10)23)12-13(15(7)21)14(20)6-2-1-3-9(19)11(6)16(12)22/h1-3,18-19,21H,4-5H2

InChI Key

VAFJYSQYZZTBIY-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
Berchemia discolor	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

9,10-anthraquinone
Anthraquinone
Isobenzofuranone
Phthalide
Isocoumaran
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Carboxylic acid ester
Ketone
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.1	ALOGPS
logP	2.4	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.63	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	82.51 m³·mol⁻¹	ChemAxon
Polarizability	30.7 Å³	ChemAxon
Number of Rings	4	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

14704557

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,10-dihydroxy-4-(hydroxymethyl)-1h-anthra[1,2-c]furan-3,6,11-trione (NP0144963)

MOL for NP0144963 (5,10-dihydroxy-4-(hydroxymethyl)-1h-anthra[1,2-c]furan-3,6,11-trione)

3D MOL for NP0144963 (5,10-dihydroxy-4-(hydroxymethyl)-1h-anthra[1,2-c]furan-3,6,11-trione)

3D SDF for NP0144963 (5,10-dihydroxy-4-(hydroxymethyl)-1h-anthra[1,2-c]furan-3,6,11-trione)

3D-SDF for NP0144963 (5,10-dihydroxy-4-(hydroxymethyl)-1h-anthra[1,2-c]furan-3,6,11-trione)

PDB for NP0144963 (5,10-dihydroxy-4-(hydroxymethyl)-1h-anthra[1,2-c]furan-3,6,11-trione)

3D PDB for NP0144963 (5,10-dihydroxy-4-(hydroxymethyl)-1h-anthra[1,2-c]furan-3,6,11-trione)

SMILES for NP0144963 (5,10-dihydroxy-4-(hydroxymethyl)-1h-anthra[1,2-c]furan-3,6,11-trione)

INCHI for NP0144963 (5,10-dihydroxy-4-(hydroxymethyl)-1h-anthra[1,2-c]furan-3,6,11-trione)

Structure for NP0144963 (5,10-dihydroxy-4-(hydroxymethyl)-1h-anthra[1,2-c]furan-3,6,11-trione)

3D Structure for NP0144963 (5,10-dihydroxy-4-(hydroxymethyl)-1h-anthra[1,2-c]furan-3,6,11-trione)