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Showing NP-Card for 2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1,4,7,9(13),11-pentaene-6,10-dione (NP0285317)

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Record Information
Version2.0
Created at2022-09-09 13:26:14 UTC
Updated at2022-09-09 13:26:14 UTC
NP-MRD IDNP0285317
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1,4,7,9(13),11-pentaene-6,10-dione
DescriptionLamellicolic anhydride belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. 2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1,4,7,9(13),11-pentaene-6,10-dione is found in Neosetophoma cerealis and Simplicillium lamellicola. Based on a literature review very few articles have been published on Lamellicolic anhydride.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0285317 (2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1,4,7,9(13),11-pentaene-6,10-dione)


  Mrv1652309092215262D          

 19 21  0  0  0  0            999 V2000
    3.5724   -2.8875    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
    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   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
    1.4289    0.8250    0.0000 O   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    2.1434   -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  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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  1  0  0  0  0
 10 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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
  6 19  1  0  0  0  0
M  END
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3D MOL for NP0285317 (2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1,4,7,9(13),11-pentaene-6,10-dione)

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3D SDF for NP0285317 (2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1,4,7,9(13),11-pentaene-6,10-dione)

  Mrv1652309092215262D          

 19 21  0  0  0  0            999 V2000
    3.5724   -2.8875    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
    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   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
    1.4289    0.8250    0.0000 O   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    2.1434   -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  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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  1  0  0  0  0
 10 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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
  6 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285317

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)C2=C(O)OC(O)=C3C(O)=CC(=O)C1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C13H8O6/c1-4-2-5(14)9-11-8(4)6(15)3-7(16)10(11)13(18)19-12(9)17/h2-3,16-18H,1H3

> <INCHI_KEY>
NVARQLOCVDEUPQ-UHFFFAOYSA-N

> <FORMULA>
C13H8O6

> <MOLECULAR_WEIGHT>
260.201

> <EXACT_MASS>
260.032087978

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
23.71987879101534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0^{5,13}]trideca-1,4,7,9(13),11-pentaene-6,10-dione

> <JCHEM_LOGP>
0.6139090403333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.205731382640977

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.565737496741545

> <JCHEM_PKA_STRONGEST_BASIC>
2.906333366275301

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
86.08819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0^{5,13}]trideca-1,4,7,9(13),11-pentaene-6,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0285317 (2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1,4,7,9(13),11-pentaene-6,10-dione)
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PDB for NP0285317 (2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1,4,7,9(13),11-pentaene-6,10-dione)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   19                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   19                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    2   19                                                  
CONECT   19   18   12    6                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

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3D PDB for NP0285317 (2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1,4,7,9(13),11-pentaene-6,10-dione)
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SMILES for NP0285317 (2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1,4,7,9(13),11-pentaene-6,10-dione)
CC1=CC(=O)C2=C(O)OC(O)=C3C(O)=CC(=O)C1=C23
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INCHI for NP0285317 (2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1,4,7,9(13),11-pentaene-6,10-dione)
InChI=1S/C13H8O6/c1-4-2-5(14)9-11-8(4)6(15)3-7(16)10(11)13(18)19-12(9)17/h2-3,16-18H,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC13H8O6
Average Mass260.2010 Da
Monoisotopic Mass260.03209 Da
IUPAC Name2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0^{5,13}]trideca-1,4,7,9(13),11-pentaene-6,10-dione
Traditional Name2,4,12-trihydroxy-8-methyl-3-oxatricyclo[7.3.1.0^{5,13}]trideca-1,4,7,9(13),11-pentaene-6,10-dione
CAS Registry NumberNot Available
SMILES
CC1=CC(=O)C2=C(O)OC(O)=C3C(O)=CC(=O)C1=C23
InChI Identifier
InChI=1S/C13H8O6/c1-4-2-5(14)9-11-8(4)6(15)3-7(16)10(11)13(18)19-12(9)17/h2-3,16-18H,1H3
InChI KeyNVARQLOCVDEUPQ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Neosetophoma cerealisLOTUS Database
Simplicillium lamellicolaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassNaphthalenes  
Sub ClassNaphthols and derivatives  
Direct ParentNaphthols and derivatives  
Alternative Parents
Substituents
  • 2-naphthol
    • 

  • 2-benzopyran
    • 

  • Benzopyran
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen 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
logP0.61ChemAxon
pKa (Strongest Acidic)5.57ChemAxon
pKa (Strongest Basic)2.91ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.09 m³·mol⁻¹ChemAxon
Polarizability23.72 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 ID78436056  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound135779135  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]