NP-MRD: Showing NP-Card for Purpurin 1-methyl ether (NP0051636)

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Record Information

Version

1.0

Created at

2022-04-27 22:55:52 UTC

Updated at

2022-04-27 22:55:52 UTC

NP-MRD ID

NP0051636

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Purpurin 1-methyl ether

Description

2,4-Dihydroxy-1-methoxy-9,10-dihydroanthracene-9,10-dione 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. Purpurin 1-methyl ether is found in Cinchona calisaya, Cinchona pubescens, Cinchona spp., Galium aparine and Morinda citrifolia. 2,4-Dihydroxy-1-methoxy-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

 30 32  0  0  0  0  0  0  0  0999 V2000
   -2.1255    2.9980   -0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9683    2.1772    0.5346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    0.7914    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0321    0.0423    0.4654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2424    0.7010    0.6204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9407   -1.3291    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7016   -1.9170    0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563   -3.2857    0.0853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5379   -1.1488    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    0.2327    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978    1.0369    0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4839    2.2832    0.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051    0.4140    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0520    1.1621    0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2677    0.5446   -0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3783   -0.8380   -0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2229   -1.5769   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0059   -0.9649   -0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7835   -1.7405   -0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8606   -2.9873   -0.1020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5449    3.9297   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7760    2.4757   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2096    3.2733   -0.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0760    0.1286    0.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8291   -1.9447    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3475   -3.9179    0.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745    2.2387    0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1860    1.1479   -0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3639   -1.2789   -0.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2939   -2.6478   -0.2876 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
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 10  3  1  0
 18 13  1  0
 19  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END


  Mrv1533004251509522D          

 20 22  0  0  0  0            999 V2000
    1.4289   -4.1250    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
    2.1434   -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
    0.7145   -2.8875    0.0000 O   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
    5.7158   -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
  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  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  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
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  3 20  1  0  0  0  0
  9 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051636

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O5/c1-20-15-10(17)6-9(16)11-12(15)14(19)8-5-3-2-4-7(8)13(11)18/h2-6,16-17H,1H3

> <INCHI_KEY>
NLORVHQRZMJFEZ-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.24

> <EXACT_MASS>
270.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
26.158658080538736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4-dihydroxy-1-methoxy-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
2.8039041656666663

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.532373477468925

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.915793966865846

> <JCHEM_PKA_STRONGEST_BASIC>
-4.932185015315642

> <JCHEM_POLAR_SURFACE_AREA>
83.82999999999998

> <JCHEM_REFRACTIVITY>
71.57600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
purpurin 1-methyl ether

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+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  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   20                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    3    9                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₀O₅

Average Mass

270.2400 Da

Monoisotopic Mass

270.05282 Da

IUPAC Name

2,4-dihydroxy-1-methoxy-9,10-dihydroanthracene-9,10-dione

Traditional Name

purpurin 1-methyl ether

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O

InChI Identifier

InChI=1S/C15H10O5/c1-20-15-10(17)6-9(16)11-12(15)14(19)8-5-3-2-4-7(8)13(11)18/h2-6,16-17H,1H3

InChI Key

NLORVHQRZMJFEZ-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
Cinchona calisaya	LOTUS Database	35616633
Cinchona pubescens	LOTUS Database	35616633
Cinchona spp.	Plant	KNApSAcK
Galium aparine	LOTUS Database	35616633
Morinda citrifolia	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
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Ketone
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:8646 )
Anthraquinone type (C10397 )

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	2.88	ALOGPS
logP	2.8	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.92	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.58 m³·mol⁻¹	ChemAxon
Polarizability	26.16 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

C00002858

Chemspider ID

Not Available

KEGG Compound ID

C10397

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442766

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Purpurin 1-methyl ether (NP0051636)

MOL for NP0051636 (Purpurin 1-methyl ether)

3D MOL for NP0051636 (Purpurin 1-methyl ether)

3D SDF for NP0051636 (Purpurin 1-methyl ether)

3D-SDF for NP0051636 (Purpurin 1-methyl ether)

PDB for NP0051636 (Purpurin 1-methyl ether)

3D PDB for NP0051636 (Purpurin 1-methyl ether)

SMILES for NP0051636 (Purpurin 1-methyl ether)

INCHI for NP0051636 (Purpurin 1-methyl ether)

Structure for NP0051636 (Purpurin 1-methyl ether)

3D Structure for NP0051636 (Purpurin 1-methyl ether)