NP-MRD: Showing NP-Card for isocaloploicin (NP0332831)

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Record Information

Version

2.0

Created at

2024-04-22 23:56:14 UTC

Updated at

2024-09-16 20:03:33 UTC

NP-MRD ID

NP0332831

Natural Product DOI

https://doi.org/10.57994/2105

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isocaloploicin

Description

Isocaloploicin belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). isocaloploicin was first documented in 2024 (PMID: 38780134). Based on a literature review very few articles have been published on isocaloploicin.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01052302332D          

 25 27  0  0  0  0            999 V2000
    4.5741    3.0436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162    2.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305    1.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189    1.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237    1.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9120    1.5805    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9401    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517    0.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9682   -0.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470    0.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    0.4930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604    0.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    0.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6392   -0.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837    1.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6953    1.5805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0906    1.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884    1.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9049    2.7028    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0625   -0.0281    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    1.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912    2.3003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5448   -0.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7025    2.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 15 21  1  0  0  0  0
 12 22  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
  7 24  1  0  0  0  0
  4 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332831

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(Cl)C2=C(OC3=C(C)C(O)=C(Cl)C(C)=C3C(=O)O2)C(C)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C17H13Cl3O5/c1-5-8-13(7(3)12(21)9(5)18)24-14-6(2)10(19)15(23-4)11(20)16(14)25-17(8)22/h21H,1-4H3

> <INCHI_KEY>
QQWOARUTFKFAHP-UHFFFAOYSA-N

> <FORMULA>
C17H13Cl3O5

> <MOLECULAR_WEIGHT>
403.64

> <EXACT_MASS>
401.9828566

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
37.82149663142167

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7,13-trichloro-14-hydroxy-6-methoxy-4,12,15-trimethyl-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one

> <JCHEM_LOGP>
5.852884205333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.154864712376839

> <JCHEM_PKA_STRONGEST_BASIC>
-3.751588782332767

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
96.0258

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5,7,13-trichloro-14-hydroxy-6-methoxy-4,12,15-trimethyl-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JAN-23         0                                  
HETATM    1  O   UNK     0       8.538   5.681   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.870   4.294   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.830   3.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.302   3.544   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.431   2.496   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0      12.902   2.950   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0      11.088   0.995   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.617   0.541   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.274  -0.960   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.488   1.588   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.100   0.920   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.713   1.588   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.584   0.541   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.926  -0.960   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.112   0.995   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.770   2.496   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.298   2.950   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.169   1.903   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.898   3.544   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0       3.556   5.045   0.000  0.00  0.00          Cl+0
HETATM   21 Cl   UNK     0       1.983  -0.053   0.000  0.00  0.00          Cl+0
HETATM   22  C   UNK     0       5.370   3.090   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.330   4.294   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      12.217  -0.053   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.645   5.045   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   24                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   22                                                  
CONECT   20   19                                                            
CONECT   21   15                                                            
CONECT   22   12   19   23                                                  
CONECT   23   22    2                                                       
CONECT   24    7                                                            
CONECT   25    4                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₃Cl₃O₅

Average Mass

403.6400 Da

Monoisotopic Mass

401.98286 Da

IUPAC Name

5,7,13-trichloro-14-hydroxy-6-methoxy-4,12,15-trimethyl-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one

Traditional Name

5,7,13-trichloro-14-hydroxy-6-methoxy-4,12,15-trimethyl-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one

CAS Registry Number

Not Available

SMILES

COC1=C(Cl)C2=C(OC3=C(C)C(O)=C(Cl)C(C)=C3C(=O)O2)C(C)=C1Cl

InChI Identifier

InChI=1S/C17H13Cl3O5/c1-5-8-13(7(3)12(21)9(5)18)24-14-6(2)10(19)15(23-4)11(20)16(14)25-17(8)22/h21H,1-4H3

InChI Key

QQWOARUTFKFAHP-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	Not Available	Université de Rennes	Solenn Ferron	2024-04-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	Not Available	Université de Rennes	Solenn Ferron	2024-04-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	Not Available	Université de Rennes	Solenn Ferron	2024-04-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	Not Available	Université de Rennes	Solenn Ferron	2024-04-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C3D6O, experimental)	Not Available	Université de Rennes	Solenn Ferron	2024-04-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C3D6O, experimental)	Not Available	Université de Rennes	Solenn Ferron	2024-04-22	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.12300072, C3D6O, simulated)	solenn.ferron@univ-rennes.fr	Université de Rennes	Solenn	2024-04-22	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
flavicans		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depsidone
Anisole
Fatty acid ester
Dioxepine
Alkyl aryl ether
1,4-dioxepine
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enol ester
Lactone
Carboxylic acid ester
Oxacycle
Chloroalkene
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen 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	5.85	ChemAxon
pKa (Strongest Acidic)	7.15	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	96.03 m³·mol⁻¹	ChemAxon
Polarizability	37.82 Å³	ChemAxon
Number of Rings	3	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ferron S, Ismed F, Elyashberg ME, Buevich AV, Arifa N, Boustie J, Uriac P, Le Pogam P, Le Devehat F: CASE-DFT Structure Elucidation of Proton-Deficient Chlorodepsidones from the Indonesian Lichen Teloschistes flavicans and Structure Revision of Flavicansone. J Nat Prod. 2024 Sep 27;87(9):2148-2159. doi: 10.1021/acs.jnatprod.4c00277. Epub 2024 May 23. [PubMed:38780134 ]

Showing NP-Card for isocaloploicin (NP0332831)

MOL for NP0332831 (isocaloploicin)

3D MOL for NP0332831 (isocaloploicin)

3D SDF for NP0332831 (isocaloploicin)

3D-SDF for NP0332831 (isocaloploicin)

PDB for NP0332831 (isocaloploicin)

3D PDB for NP0332831 (isocaloploicin)

SMILES for NP0332831 (isocaloploicin)

INCHI for NP0332831 (isocaloploicin)

Structure for NP0332831 (isocaloploicin)

3D Structure for NP0332831 (isocaloploicin)