NP-MRD: Showing NP-Card for 8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate (NP0166023)

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Record Information

Version

2.0

Created at

2022-09-03 01:18:27 UTC

Updated at

2022-09-03 01:18:27 UTC

NP-MRD ID

NP0166023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate

Description

8-Hydroxy-7-methyl-6-oxo-3-propyl-6,7,8,8a-tetrahydro-1H-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate 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. 8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate is found in Aspergillus falconensis. Based on a literature review very few articles have been published on 8-hydroxy-7-methyl-6-oxo-3-propyl-6,7,8,8a-tetrahydro-1H-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032203182D          

 30 32  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309032203182D          

 30 32  0  0  0  0            999 V2000
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    0.0000    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
    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
    2.8579    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
    4.2868   -0.0000    0.0000 O   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
    4.3848   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -2.0127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6670   -2.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1973   -1.5240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7616   -3.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2919   -2.4425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0166023

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1=CC2=CC(=O)C(C)(OC(=O)C3=C(OC)C=C(O)C(Cl)=C3C)C(O)C2CO1

> <INCHI_IDENTIFIER>
InChI=1S/C22H25ClO7/c1-5-6-13-7-12-8-17(25)22(3,20(26)14(12)10-29-13)30-21(27)18-11(2)19(23)15(24)9-16(18)28-4/h7-9,14,20,24,26H,5-6,10H2,1-4H3

> <INCHI_KEY>
ZGNHKNQTDPXJQE-UHFFFAOYSA-N

> <FORMULA>
C22H25ClO7

> <MOLECULAR_WEIGHT>
436.89

> <EXACT_MASS>
436.1288808

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.56837704162896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-7-methyl-6-oxo-3-propyl-6,7,8,8a-tetrahydro-1H-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate

> <ALOGPS_LOGP>
3.68

> <JCHEM_LOGP>
3.5585587503333334

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.754557620528914

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.134449058108959

> <JCHEM_PKA_STRONGEST_BASIC>
-3.486038614240778

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
113.6601

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1H-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.185  -2.043   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.195  -3.757   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.712  -4.025   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.702  -2.845   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.238  -5.472   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.755  -5.739   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.745  -4.559   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.262  -4.827   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.282  -7.186   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.292  -8.366   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.819  -9.813   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.775  -8.099   0.000  0.00  0.00           C+0
HETATM   23 Cl   UNK     0       7.785  -9.278   0.000  0.00  0.00          Cl+0
HETATM   24  C   UNK     0       8.249  -6.651   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.732  -6.384   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   30                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   26                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   24                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   15   25                                                  
CONECT   25   24                                                            
CONECT   26   10   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    6   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29    4                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
8-Hydroxy-7-methyl-6-oxo-3-propyl-6,7,8,8a-tetrahydro-1H-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoic acid	Generator

Chemical Formula

C₂₂H₂₅ClO₇

Average Mass

436.8900 Da

Monoisotopic Mass

436.12888 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCCC1=CC2=CC(=O)C(C)(OC(=O)C3=C(OC)C=C(O)C(Cl)=C3C)C(O)C2CO1

InChI Identifier

InChI=1S/C22H25ClO7/c1-5-6-13-7-12-8-17(25)22(3,20(26)14(12)10-29-13)30-21(27)18-11(2)19(23)15(24)9-16(18)28-4/h7-9,14,20,24,26H,5-6,10H2,1-4H3

InChI Key

ZGNHKNQTDPXJQE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Emericella falconensis	LOTUS Database	35616633

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
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-methoxybenzoic acid or derivatives
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzoate ester
Methoxyphenol
Benzoic acid or derivatives
Methoxybenzene
2-chlorophenol
M-cresol
Anisole
2-halophenol
Benzoyl
Phenoxy compound
Phenol ether
Chlorobenzene
1-hydroxy-2-unsubstituted benzenoid
Halobenzene
Alkyl aryl ether
Cyclohexenone
Toluene
Phenol
Aryl chloride
Aryl halide
Benzenoid
Monocyclic benzene moiety
Cyclic ketone
Ketone
Secondary alcohol
Carboxylic acid ester
Oxacycle
Ether
Carboxylic acid derivative
Organohalogen compound
Organochloride
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
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	3.68	ALOGPS
logS	-4.6	ALOGPS

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

85162735

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate (NP0166023)

MOL for NP0166023 (8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate)

3D MOL for NP0166023 (8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate)

3D SDF for NP0166023 (8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate)

3D-SDF for NP0166023 (8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate)

PDB for NP0166023 (8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate)

3D PDB for NP0166023 (8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate)

SMILES for NP0166023 (8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate)

INCHI for NP0166023 (8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate)

Structure for NP0166023 (8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate)

3D Structure for NP0166023 (8-hydroxy-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3-chloro-4-hydroxy-6-methoxy-2-methylbenzoate)