NP-MRD: Showing NP-Card for 5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid (NP0192257)

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Record Information

Version

2.0

Created at

2022-09-04 09:25:13 UTC

Updated at

2022-09-04 09:25:14 UTC

NP-MRD ID

NP0192257

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid

Description

5-{[5-Chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid 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. 5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid is found in Bartalinia robillardoides. Based on a literature review very few articles have been published on 5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042211252D          

 35 36  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1652309042211252D          

 35 36  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0192257

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(O)C(C)(O)C=CC1=CC2=C(Cl)C(=O)C(C)(OC(=O)C=C(C)CC(O)=O)C(=O)C2=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C25H29ClO9/c1-6-14(3)21(30)24(4,33)8-7-15-11-16-17(12-34-15)22(31)25(5,23(32)20(16)26)35-19(29)10-13(2)9-18(27)28/h7-8,10-12,14,21,30,33H,6,9H2,1-5H3,(H,27,28)

> <INCHI_KEY>
KRQJBTNVZHCANM-UHFFFAOYSA-N

> <FORMULA>
C25H29ClO9

> <MOLECULAR_WEIGHT>
508.95

> <EXACT_MASS>
508.1500102

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
50.511714061939315

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid

> <JCHEM_LOGP>
2.817424774

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.396992633506667

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8546612316532674

> <JCHEM_PKA_STRONGEST_BASIC>
-3.344185483085849

> <JCHEM_POLAR_SURFACE_AREA>
147.43

> <JCHEM_REFRACTIVITY>
130.94559999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -6.160   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      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.206  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.874  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       5.335   1.540   0.000  0.00  0.00          Cl+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.185  -2.043   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.195  -3.757   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.712  -4.025   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.238  -5.472   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.702  -2.845   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.218  -3.112   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.745  -4.559   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.208  -1.933   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.725  -2.200   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.715  -1.020   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      14.251  -3.647   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   35  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    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   35                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   33                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   31                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   19   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   14   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   12                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoate	Generator

Chemical Formula

C₂₅H₂₉ClO₉

Average Mass

508.9500 Da

Monoisotopic Mass

508.15001 Da

IUPAC Name

5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid

Traditional Name

5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid

CAS Registry Number

Not Available

SMILES

CCC(C)C(O)C(C)(O)C=CC1=CC2=C(Cl)C(=O)C(C)(OC(=O)C=C(C)CC(O)=O)C(=O)C2=CO1

InChI Identifier

InChI=1S/C25H29ClO9/c1-6-14(3)21(30)24(4,33)8-7-15-11-16-17(12-34-15)22(31)25(5,23(32)20(16)26)35-19(29)10-13(2)9-18(27)28/h7-8,10-12,14,21,30,33H,6,9H2,1-5H3,(H,27,28)

InChI Key

KRQJBTNVZHCANM-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
Bartalinia robillardoides	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
Branched fatty acid
Fatty acid ester
Halogenated fatty acid
Heterocyclic fatty acid
Cyclohexenone
Hydroxy fatty acid
Methyl-branched fatty acid
Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
Pyran
Unsaturated fatty acid
Fatty acyl
Enoate ester
Alpha-haloketone
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Alpha-chloroketone
Tertiary alcohol
Cyclic ketone
Carboxylic acid ester
1,2-diol
Ketone
Secondary alcohol
Oxacycle
Vinyl halide
Chloroalkene
Carboxylic acid
Haloalkene
Carboxylic acid derivative
Vinyl chloride
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
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	2.82	ChemAxon
pKa (Strongest Acidic)	3.85	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	147.43 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	130.95 m³·mol⁻¹	ChemAxon
Polarizability	50.51 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

163066115

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid (NP0192257)

MOL for NP0192257 (5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid)

3D MOL for NP0192257 (5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid)

3D SDF for NP0192257 (5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid)

3D-SDF for NP0192257 (5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid)

PDB for NP0192257 (5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid)

3D PDB for NP0192257 (5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid)

SMILES for NP0192257 (5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid)

INCHI for NP0192257 (5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid)

Structure for NP0192257 (5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid)

3D Structure for NP0192257 (5-{[5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid)