Np mrd loader

Showing NP-Card for 6,8-Di-O-methylaverufin (NP0336245)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2024-09-11 05:22:30 UTC
Updated at2024-09-11 05:22:30 UTC
NP-MRD IDNP0336245
Secondary Accession NumbersNone
Natural Product Identification
Common Name6,8-Di-O-methylaverufin
Description6,8-Di-O-methylaverufin 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. 6,8-Di-O-methylaverufin was first documented in 2012 (PMID: 22363226). Based on a literature review very few articles have been published on 6,8-Di-O-methylaverufin (PMID: 29174381).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0336245 (6,8-Di-O-methylaverufin)


  Mrv2104 05262307542D          

 29 33  0  0  0  0            999 V2000
   -1.0673    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7825    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7825   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0728   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0728    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2115   -0.2056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2115    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992    1.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130    1.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7825   -1.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534    1.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534   -1.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0728   -1.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2115   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2115    1.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9267    0.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977   -1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  3 22  2  0  0  0  0
  4  5  2  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  5 14  1  0  0  0  0
  6 21  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 19  1  0  0  0  0
  9 10  2  0  0  0  0
 10 20  1  0  0  0  0
 11 12  2  0  0  0  0
 11 23  1  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 15 16  1  0  0  0  0
 15 25  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 24  1  0  0  0  0
 17 27  1  0  0  0  0
 19 28  1  0  0  0  0
 20 29  1  0  0  0  0
 24 26  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
Download

3D MOL for NP0336245 (6,8-Di-O-methylaverufin)

Download
3D SDF for NP0336245 (6,8-Di-O-methylaverufin)

  Mrv2104 05262307542D          

 29 33  0  0  0  0            999 V2000
   -1.0673    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7825    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7825   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0728   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0728    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2115   -0.2056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2115    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992    1.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130    1.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7825   -1.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534    1.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534   -1.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0728   -1.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2115   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2115    1.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9267    0.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977   -1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  3 22  2  0  0  0  0
  4  5  2  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  5 14  1  0  0  0  0
  6 21  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 19  1  0  0  0  0
  9 10  2  0  0  0  0
 10 20  1  0  0  0  0
 11 12  2  0  0  0  0
 11 23  1  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 15 16  1  0  0  0  0
 15 25  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 24  1  0  0  0  0
 17 27  1  0  0  0  0
 19 28  1  0  0  0  0
 20 29  1  0  0  0  0
 24 26  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336245

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(=O)C3=C(C=C4OC5(C)CCCC(O5)C4=C3O)C2=O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1/C22H20O7/c1-22-6-4-5-13(28-22)18-15(29-22)9-12-17(21(18)25)20(24)16-11(19(12)23)7-10(26-2)8-14(16)27-3/h7-9,13,25H,4-6H2,1-3H3

> <INCHI_KEY>
UOWSTUZKQCORDT-UHFFFAOYNA-N

> <FORMULA>
C22H20O7

> <MOLECULAR_WEIGHT>
396.395

> <EXACT_MASS>
396.120902984

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
40.84464016272305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-7,9-dimethoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0^{2,15}.0^{4,13}.0^{6,11}]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione

> <JCHEM_LOGP>
3.751751280666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.646404296745385

> <JCHEM_PKA_STRONGEST_BASIC>
-4.11760480099229

> <JCHEM_POLAR_SURFACE_AREA>
91.29

> <JCHEM_REFRACTIVITY>
103.80159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-7,9-dimethoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0^{2,15}.0^{4,13}.0^{6,11}]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0336245 (6,8-Di-O-methylaverufin)
Download
PDB for NP0336245 (6,8-Di-O-methylaverufin)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -1.992   1.157   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.992  -0.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.660  -1.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.670  -0.384   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.670   1.157   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.660   1.924   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.327   1.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.662   1.157   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.662  -0.384   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.327  -1.154   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.003  -1.154   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.333  -0.384   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.333   1.157   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.003   1.924   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.665  -1.154   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.995  -0.384   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.995   1.157   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.665   1.924   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -5.998   1.924   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.327  -2.694   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.660   3.465   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.660  -2.694   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.003  -2.694   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.330   0.386   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.995  -1.924   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.330  -1.154   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.995   2.697   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.330   1.151   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.662  -3.465   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6   14                                                  
CONECT    6    1    5   21                                                  
CONECT    7    1    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    2    9   20                                                  
CONECT   11    4   12   23                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14   18                                                  
CONECT   14    5   13                                                       
CONECT   15   12   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24   27                                             
CONECT   18   13   17                                                       
CONECT   19    8   28                                                       
CONECT   20   10   29                                                       
CONECT   21    6                                                            
CONECT   22    3                                                            
CONECT   23   11                                                            
CONECT   24   17   26                                                       
CONECT   25   15   26                                                       
CONECT   26   24   25                                                       
CONECT   27   17                                                            
CONECT   28   19                                                            
CONECT   29   20                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

Download
3D PDB for NP0336245 (6,8-Di-O-methylaverufin)
Download
SMILES for NP0336245 (6,8-Di-O-methylaverufin)
COC1=CC2=C(C(=O)C3=C(C=C4OC5(C)CCCC(O5)C4=C3O)C2=O)C(OC)=C1
Download
INCHI for NP0336245 (6,8-Di-O-methylaverufin)
InChI=1/C22H20O7/c1-22-6-4-5-13(28-22)18-15(29-22)9-12-17(21(18)25)20(24)16-11(19(12)23)7-10(26-2)8-14(16)27-3/h7-9,13,25H,4-6H2,1-3H3
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC22H20O7
Average Mass396.3950 Da
Monoisotopic Mass396.12090 Da
IUPAC Name3-hydroxy-7,9-dimethoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0^{2,15}.0^{4,13}.0^{6,11}]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione
Traditional Name3-hydroxy-7,9-dimethoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0^{2,15}.0^{4,13}.0^{6,11}]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C(=O)C3=C(C=C4OC5(C)CCCC(O5)C4=C3O)C2=O)C(OC)=C1
InChI Identifier
InChI=1/C22H20O7/c1-22-6-4-5-13(28-22)18-15(29-22)9-12-17(21(18)25)20(24)16-11(19(12)23)7-10(26-2)8-14(16)27-3/h7-9,13,25H,4-6H2,1-3H3
InChI KeyUOWSTUZKQCORDT-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassAnthracenes  
Sub ClassAnthraquinones  
Direct ParentAnthraquinones  
Alternative Parents
Substituents
  • 9,10-anthraquinone
    • 

  • Anthraquinone
    • 

  • Anisole
    • 

  • Aryl ketone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Ketal
    • 

  • Oxane
    • 

  • Vinylogous acid
    • 

  • Ketone
    • 

  • Organoheterocyclic compound
    • 

  • Acetal
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP3.75ChemAxon
pKa (Strongest Acidic)7.65ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area91.29 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity103.8 m³·mol⁻¹ChemAxon
Polarizability40.84 ųChemAxon
Number of Rings5ChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Miao FP, Li XD, Liu XH, Cichewicz RH, Ji NY: Secondary metabolites from an algicolous Aspergillus versicolor strain. Mar Drugs. 2012 Jan;10(1):131-9. doi: 10.3390/md10010131. Epub 2012 Jan 16. [PubMed:22363226  ] 
  2. Kim KW, Kim HJ, Sohn JH, Yim JH, Kim YC, Oh H: Anti-neuroinflammatory effect of 6,8,1'-tri-O-methylaverantin, a metabolite from a marine-derived fungal strain Aspergillus sp., via upregulation of heme oxygenase-1 in lipopolysaccharide-activated microglia. Neurochem Int. 2018 Feb;113:8-22. doi: 10.1016/j.neuint.2017.11.010. Epub 2017 Nov 22. [PubMed:29174381  ]