NP-MRD: Showing NP-Card for 3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione (NP0333421)

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Record Information

Version

2.0

Created at

2024-06-18 03:47:41 UTC

Updated at

2024-09-03 04:22:23 UTC

NP-MRD ID

NP0333421

Natural Product DOI

https://doi.org/10.57994/2844

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione

Description

3,5,7-Trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Based on a literature review very few articles have been published on 3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03022306222D          

 29 32  0  0  0  0            999 V2000
   -0.0000    2.4750    0.0000 O   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
    1.4289    2.4750    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
    2.8579    2.4750    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
    1.4289    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
    0.7145   -0.4125    0.0000 C   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
   -0.2822   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428   -0.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1552   -0.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606   -1.2640    0.0000 O   0  0  0  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
    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
    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
    3.6425    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2498   -0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4794   -1.0637    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    0.8250    0.0000 C   0  0  0  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  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
  9 16  2  0  0  0  0
  8 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
  7 27  2  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END


  Mrv2104 03022306222D          

 29 32  0  0  0  0            999 V2000
   -0.0000    2.4750    0.0000 O   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
    1.4289    2.4750    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
    2.8579    2.4750    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
    1.4289    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
    0.7145   -0.4125    0.0000 C   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
   -0.2822   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428   -0.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1552   -0.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606   -1.2640    0.0000 O   0  0  0  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
    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
    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
    3.6425    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2498   -0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4794   -1.0637    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    0.8250    0.0000 C   0  0  0  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  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
  9 16  2  0  0  0  0
  8 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
  7 27  2  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333421

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC2=C(C(O)=C3C(=O)C(O)(CC(C)=O)C(=O)C4=C3C2=C(C)C=C4O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1/C22H22O7/c1-8-6-11(24)13-14-12(8)18-16(21(4,5)10(3)29-18)17(25)15(14)20(27)22(28,19(13)26)7-9(2)23/h6,10,24-25,28H,7H2,1-5H3

> <INCHI_KEY>
SJTGXQPVZQYOCL-UHFFFAOYNA-N

> <FORMULA>
C22H22O7

> <MOLECULAR_WEIGHT>
398.411

> <EXACT_MASS>
398.136553048

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
40.70386063341976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-4H,5H,6H,8H,9H-phenaleno[1,2-b]furan-4,6-dione

> <JCHEM_LOGP>
3.8470694959999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.540949680003306

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.842079072928213

> <JCHEM_PKA_STRONGEST_BASIC>
-4.579768034158092

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
104.71649999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-9H-phenaleno[1,2-b]furan-4,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-MAR-23         0                                  
HETATM    1  O   UNK     0      -0.000   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.527  -1.447   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.517   0.267   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.506  -0.912   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.023  -0.645   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.980  -2.359   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.799   2.016   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.705   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.245   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.799  -0.476   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.933  -1.518   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.495  -1.986   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   20                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   12   28                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    9                                                            
CONECT   17    8   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19    6   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   19   25   26                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    7    2   28                                                  
CONECT   28   27   10   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₇

Average Mass

398.4110 Da

Monoisotopic Mass

398.13655 Da

IUPAC Name

3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-4H,5H,6H,8H,9H-phenaleno[1,2-b]furan-4,6-dione

Traditional Name

3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-9H-phenaleno[1,2-b]furan-4,6-dione

CAS Registry Number

Not Available

SMILES

CC1OC2=C(C(O)=C3C(=O)C(O)(CC(C)=O)C(=O)C4=C3C2=C(C)C=C4O)C1(C)C

InChI Identifier

InChI=1/C22H22O7/c1-8-6-11(24)13-14-12(8)18-16(21(4,5)10(3)29-18)17(25)15(14)20(27)22(28,19(13)26)7-9(2)23/h6,10,24-25,28H,7H2,1-5H3

InChI Key

SJTGXQPVZQYOCL-UHFFFAOYNA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	livia.soman@unifesp.br	Unifesp - Universidade Federal de São Paulo	Lívia Soman	2024-06-18	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
sp. CML3020		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthofurans. These are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Phenalane
2-naphthol
Naphthalene
Coumaran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Acyloin
Beta-hydroxy ketone
Benzenoid
Vinylogous acid
Tertiary alcohol
Ketone
Oxacycle
Ether
Polyol
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	3.85	ChemAxon
pKa (Strongest Acidic)	7.84	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.72 m³·mol⁻¹	ChemAxon
Polarizability	40.7 Å³	ChemAxon
Number of Rings	4	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione (NP0333421)

MOL for NP0333421 (3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione)

3D MOL for NP0333421 (3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione)

3D SDF for NP0333421 (3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione)

3D-SDF for NP0333421 (3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione)

PDB for NP0333421 (3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione)

3D PDB for NP0333421 (3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione)

SMILES for NP0333421 (3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione)

INCHI for NP0333421 (3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione)

Structure for NP0333421 (3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione)

3D Structure for NP0333421 (3,5,7-trihydroxy-1,8,8,9-tetramethyl-5-(2-oxopropyl)-8,9-dihydro-4H-phenaleno[1,2-b]furan-4,6(5H)-dione)