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Showing NP-Card for (1r,3s)-1,3,8-trihydroxy-6-methoxy-3-methyl-2,4-dihydro-1h-anthracene-9,10-dione (NP0329991)

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Record Information
Version2.0
Created at2022-09-12 14:55:36 UTC
Updated at2022-09-12 14:55:37 UTC
NP-MRD IDNP0329991
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,3s)-1,3,8-trihydroxy-6-methoxy-3-methyl-2,4-dihydro-1h-anthracene-9,10-dione
Description(1R,3S)-Austrocortilutein 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. Based on a literature review very few articles have been published on (1R,3S)-Austrocortilutein.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0329991 ((1r,3s)-1,3,8-trihydroxy-6-methoxy-3-methyl-2,4-dihydro-1h-anthracene-9,10-dione)


  Mrv1652309122216552D          

 22 24  0  0  1  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    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
    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
    2.1434    2.0625    0.0000 O   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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8125    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    1.6002    0.0000 O   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
  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
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 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
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  1  0  0  0
 19 22  1  0  0  0  0
 12 22  1  0  0  0  0
M  END
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3D MOL for NP0329991 ((1r,3s)-1,3,8-trihydroxy-6-methoxy-3-methyl-2,4-dihydro-1h-anthracene-9,10-dione)

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3D SDF for NP0329991 ((1r,3s)-1,3,8-trihydroxy-6-methoxy-3-methyl-2,4-dihydro-1h-anthracene-9,10-dione)

  Mrv1652309122216552D          

 22 24  0  0  1  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    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
    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
    2.1434    2.0625    0.0000 O   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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8125    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    1.6002    0.0000 O   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
  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
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 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
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  1  0  0  0
 19 22  1  0  0  0  0
 12 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329991

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C3=C(C[C@](C)(O)C[C@H]3O)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-16(21)5-9-13(11(18)6-16)15(20)12-8(14(9)19)3-7(22-2)4-10(12)17/h3-4,11,17-18,21H,5-6H2,1-2H3/t11-,16+/m1/s1

> <INCHI_KEY>
LRHFZXBVDMVFCW-BZNIZROVSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.298

> <EXACT_MASS>
304.094688235

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.400709780523602

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S)-1,3,8-trihydroxy-6-methoxy-3-methyl-1,2,3,4,9,10-hexahydroanthracene-9,10-dione

> <JCHEM_LOGP>
0.4898468376666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.163449367680617

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.143981097821849

> <JCHEM_PKA_STRONGEST_BASIC>
-2.854450184035855

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
78.5209

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S)-1,3,8-trihydroxy-6-methoxy-3-methyl-2,4-dihydro-1H-anthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0329991 ((1r,3s)-1,3,8-trihydroxy-6-methoxy-3-methyl-2,4-dihydro-1h-anthracene-9,10-dione)
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PDB for NP0329991 ((1r,3s)-1,3,8-trihydroxy-6-methoxy-3-methyl-2,4-dihydro-1h-anthracene-9,10-dione)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.517   1.273   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.527   2.987   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   22                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13    7   15                                                  
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   12                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

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3D PDB for NP0329991 ((1r,3s)-1,3,8-trihydroxy-6-methoxy-3-methyl-2,4-dihydro-1h-anthracene-9,10-dione)
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SMILES for NP0329991 ((1r,3s)-1,3,8-trihydroxy-6-methoxy-3-methyl-2,4-dihydro-1h-anthracene-9,10-dione)
COC1=CC(O)=C2C(=O)C3=C(C[C@](C)(O)C[C@H]3O)C(=O)C2=C1
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INCHI for NP0329991 ((1r,3s)-1,3,8-trihydroxy-6-methoxy-3-methyl-2,4-dihydro-1h-anthracene-9,10-dione)
InChI=1S/C16H16O6/c1-16(21)5-9-13(11(18)6-16)15(20)12-8(14(9)19)3-7(22-2)4-10(12)17/h3-4,11,17-18,21H,5-6H2,1-2H3/t11-,16+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC16H16O6
Average Mass304.2980 Da
Monoisotopic Mass304.09469 Da
IUPAC Name(1R,3S)-1,3,8-trihydroxy-6-methoxy-3-methyl-1,2,3,4,9,10-hexahydroanthracene-9,10-dione
Traditional Name(1R,3S)-1,3,8-trihydroxy-6-methoxy-3-methyl-2,4-dihydro-1H-anthracene-9,10-dione
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=C2C(=O)C3=C(C[C@](C)(O)C[C@H]3O)C(=O)C2=C1
InChI Identifier
InChI=1S/C16H16O6/c1-16(21)5-9-13(11(18)6-16)15(20)12-8(14(9)19)3-7(22-2)4-10(12)17/h3-4,11,17-18,21H,5-6H2,1-2H3/t11-,16+/m1/s1
InChI KeyLRHFZXBVDMVFCW-BZNIZROVSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassAnthracenes  
Sub ClassAnthraquinones  
Direct ParentHydroxyanthraquinones  
Alternative Parents
Substituents
  • Hydroxyanthraquinone
    • 

  • Anisole
    • 

  • Phenol ether
    • 

  • Aryl ketone
    • 

  • Quinone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • Vinylogous acid
    • 

  • Tertiary alcohol
    • 

  • Ketone
    • 

  • Secondary alcohol
    • 

  • Ether
    • 

  • Polyol
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.49ChemAxon
pKa (Strongest Acidic)8.14ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity78.52 m³·mol⁻¹ChemAxon
Polarizability30.4 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID30816829  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14466820  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]