NP-MRD: Showing NP-Card for Norobtusifolin (NP0051628)

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Record Information

Version

2.0

Created at

2022-04-27 22:55:34 UTC

Updated at

2022-04-27 22:55:35 UTC

NP-MRD ID

NP0051628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Norobtusifolin

Description

1,2,8-Trihydroxy-3-methylanthraquinone, also known as norobtusifolin or 2-hydroxychrysophanol, 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. Thus, 1,2,8-trihydroxy-3-methylanthraquinone is considered to be an aromatic polyketide lipid molecule. Norobtusifolin is found in Hemerocallis fulva and Myrsine africana . 1,2,8-Trihydroxy-3-methylanthraquinone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -3.9738    1.5107    1.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7111    0.7673    1.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8455    1.2911    0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6341    0.6996   -0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116   -0.4494    0.4794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1633   -0.9867    1.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7871   -2.1318    2.1048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3626   -0.3712    1.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2507   -0.8736    2.6908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9608   -1.0833    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047   -2.1326    0.7579 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8249   -0.5030   -0.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0441   -1.1347   -1.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4046   -2.2265   -0.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8692   -0.5699   -2.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4992    0.5738   -2.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132    1.1978   -2.5400 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5154    0.6366   -1.5668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2246    1.2760   -1.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0910    2.3427   -1.8658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4978    1.6979    0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6506    1.0210    2.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6919    2.5118    1.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0876    2.1911   -0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2611   -2.6369    2.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0063   -1.7098    3.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4188   -2.9222   -0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061   -1.0985   -2.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1453    1.0052   -3.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9952    2.1071   -3.0439 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
 12 18  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 18 19  1  0
 19 20  2  0
  8  2  1  0
 13 12  1  0
 19  4  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  7 25  1  0
  9 26  1  0
 17 30  1  0
 16 29  1  0
 15 28  1  0
 14 27  1  0
M  END


  Mrv0541 05061307212D          

 20 22  0  0  0  0            999 V2000
    0.0000    0.8250    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
    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
    0.7145    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
    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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  1  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  4  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  9  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  2  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051628

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2=C(C(O)=C1O)C(=O)C1=C(C=CC=C1O)C2=O

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

> <INCHI_KEY>
CQNVSNFEXPKHGW-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.2369

> <EXACT_MASS>
270.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.431500706347425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,8-trihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
3.821431499

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.418449822264439

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.930018051689951

> <JCHEM_PKA_STRONGEST_BASIC>
-4.446928852572625

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
72.1349

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxychrysophanol

> <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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   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       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   6.160   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    6    8                                                       
CONECT    6    1    5   12                                                  
CONECT    7    3   10   13                                                  
CONECT    8    5   11   13                                                  
CONECT    9    4   10   16                                                  
CONECT   10    7    9   14                                                  
CONECT   11    8   14   15                                                  
CONECT   12    6   15   17                                                  
CONECT   13    7    8   18                                                  
CONECT   14   10   11   19                                                  
CONECT   15   11   12   20                                                  
CONECT   16    9                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
Norobtusifolin	ChEBI
2-Hydroxychrysophanol	Kegg
1,2,8-Trihydroxy-3-methyl-9,10-anthracenedione, 9ci	HMDB

Chemical Formula

C₁₅H₁₀O₅

Average Mass

270.2369 Da

Monoisotopic Mass

270.05282 Da

IUPAC Name

1,2,8-trihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

2-hydroxychrysophanol

CAS Registry Number

Not Available

SMILES

CC1=CC2=C(C(O)=C1O)C(=O)C1=C(C=CC=C1O)C2=O

InChI Identifier

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

InChI Key

CQNVSNFEXPKHGW-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
Hemerocallis fulva	LOTUS Database	35616633
Myrsine africana	Plant	KNApSAcK

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
Vinylogous acid
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:7635 )
Anthracenes and phenanthrenes (C10379 )
Anthraquinone type (C10379 )
Anthracenes and phenanthrenes (LMPK13040011 )

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	2.71	ALOGPS
logP	3.82	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.93	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.13 m³·mol⁻¹	ChemAxon
Polarizability	26.43 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