NP-MRD: Showing NP-Card for 6,7-iso-felinone A (NP0341955)

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Record Information

Version

2.0

Created at

2024-11-13 10:45:15 UTC

Updated at

2024-11-13 12:01:07 UTC

NP-MRD ID

NP0341955

Natural Product DOI

https://doi.org/10.57994/3445

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,7-iso-felinone A

Description

6,7-Iso-felinone A belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center. Based on a literature review very few articles have been published on 6,7-iso-felinone A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02102310562D          

 15 16  0  0  1  0            999 V2000
   -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  2  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
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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
    0.7145   -0.4125    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  2  0  0  0  0  0  0  0  0  0
    2.4256    0.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  6  0  0  0
  9 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  6 14  1  0  0  0  0
  8 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0341955

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC2=C(CO1)C(=O)[C@@](C)(O)[C@H](O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C11H16O4/c1-6-3-7-4-9(12)11(2,14)10(13)8(7)5-15-6/h6,9,12,14H,3-5H2,1-2H3/t6-,9+,11-/m0/s1

> <INCHI_KEY>
WUTMPUKLLJPVCV-OIVXANJASA-N

> <FORMULA>
C11H16O4

> <MOLECULAR_WEIGHT>
212.245

> <EXACT_MASS>
212.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
21.73544835401495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6R,7S)-6,7-dihydroxy-3,7-dimethyl-3,4,5,6,7,8-hexahydro-1H-2-benzopyran-8-one

> <JCHEM_LOGP>
-0.08287663766666656

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.555409283468698

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.29128592713758

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3435032842676233

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
54.759899999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6R,7S)-6,7-dihydroxy-3,7-dimethyl-3,4,5,6-tetrahydro-1H-2-benzopyran-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-FEB-23         0                                  
HETATM    1  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   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       1.334  -0.770   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.528   0.677   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.518  -1.037   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    2    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    4    8                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    6                                                       
CONECT   15    8                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₆O₄

Average Mass

212.2450 Da

Monoisotopic Mass

212.10486 Da

IUPAC Name

(3S,6R,7S)-6,7-dihydroxy-3,7-dimethyl-3,4,5,6,7,8-hexahydro-1H-2-benzopyran-8-one

Traditional Name

(3S,6R,7S)-6,7-dihydroxy-3,7-dimethyl-3,4,5,6-tetrahydro-1H-2-benzopyran-8-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CC2=C(CO1)C(=O)[C@@](C)(O)[C@H](O)C2

InChI Identifier

InChI=1S/C11H16O4/c1-6-3-7-4-9(12)11(2,14)10(13)8(7)5-15-6/h6,9,12,14H,3-5H2,1-2H3/t6-,9+,11-/m0/s1

InChI Key

WUTMPUKLLJPVCV-OIVXANJASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹³C, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	hmasaru@hirosaki-u.ac.jp	HIrosaki Univ.	Masaru Hashimoto	2024-11-13	View Spectrum
HMBC NMR	[¹³C, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	hmasaru@hirosaki-u.ac.jp	HIrosaki Univ.	Masaru Hashimoto	2024-11-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	hmasaru@hirosaki-u.ac.jp	HIrosaki Univ.	Masaru Hashimoto	2024-11-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	hmasaru@hirosaki-u.ac.jp	HIrosaki Univ.	Masaru Hashimoto	2024-11-13	View Spectrum
1DNOESY NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	hmasaru@hirosaki-u.ac.jp	HIrosaki Univ.	Masaru Hashimoto	2024-11-13	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	hmasaru@hirosaki-u.ac.jp	HIrosaki Univ.	Masaru Hashimoto	2024-11-13	View Spectrum
1DNOESY NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	hmasaru@hirosaki-u.ac.jp	HIrosaki Univ.	Masaru Hashimoto	2024-11-13	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.15991521, CDCl₃, simulated)	hmasaru@hirosaki-u.ac.jp	HIrosaki Univ.	Masaru Hashimoto	2024-11-13	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
sp. KT3922		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaphilones

Sub Class

Not Available

Direct Parent

Azaphilones

Alternative Parents

Substituents

Azaphilone
Benzopyran
Cyclohexenone
Pyran
Acyloin
Tertiary alcohol
Secondary alcohol
Ketone
1,2-diol
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.083	ChemAxon
pKa (Strongest Acidic)	12.29	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	54.76 m³·mol⁻¹	ChemAxon
Polarizability	21.74 Å³	ChemAxon
Number of Rings	2	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

132822016

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6,7-iso-felinone A (NP0341955)

MOL for NP0341955 (6,7-iso-felinone A)

3D MOL for NP0341955 (6,7-iso-felinone A)

3D SDF for NP0341955 (6,7-iso-felinone A)

3D-SDF for NP0341955 (6,7-iso-felinone A)

PDB for NP0341955 (6,7-iso-felinone A)

3D PDB for NP0341955 (6,7-iso-felinone A)

SMILES for NP0341955 (6,7-iso-felinone A)

INCHI for NP0341955 (6,7-iso-felinone A)

Structure for NP0341955 (6,7-iso-felinone A)

3D Structure for NP0341955 (6,7-iso-felinone A)