NP-MRD: Showing NP-Card for kitrinomycin B (NP0331890)

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Record Information

Version

2.0

Created at

2023-09-27 04:02:39 UTC

Updated at

2024-09-03 04:17:19 UTC

NP-MRD ID

NP0331890

Natural Product DOI

https://doi.org/10.57994/0996

Secondary Accession Numbers

None

Natural Product Identification

Common Name

kitrinomycin B

Description

Kitrinomycin B belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. kitrinomycin B was first documented in 2023 (PMID: 37737825). Based on a literature review very few articles have been published on kitrinomycin B.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 09272304022D          

 21 22  0  0  0  0            999 V2000
    1.4289   -2.4750    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
    0.7145   -1.2375    0.0000 O   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
    0.0000    0.8250    0.0000 O   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 O   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
    1.4289    0.8250    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
    2.8579    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
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  4  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  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
 16 18  2  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 11 21  1  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331890

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C(O)C2=CC(O)=C(C(O)=O)C(O)=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C12H8O9/c1-20-12(19)9-7(14)3-2-4(13)6(10(16)17)8(15)5(3)11(18)21-9/h2,13-15H,1H3,(H,16,17)

> <INCHI_KEY>
SUXCSEWUNYMJLR-UHFFFAOYSA-N

> <FORMULA>
C12H8O9

> <MOLECULAR_WEIGHT>
296.187

> <EXACT_MASS>
296.016831838

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.734428534479534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,6,8-trihydroxy-3-(methoxycarbonyl)-1-oxo-1H-isochromene-7-carboxylic acid

> <JCHEM_LOGP>
2.3071495853333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.401868026103002

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2486431889233842

> <JCHEM_PKA_STRONGEST_BASIC>
-4.367715909905057

> <JCHEM_POLAR_SURFACE_AREA>
150.59

> <JCHEM_REFRACTIVITY>
66.67070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4,6,8-trihydroxy-3-(methoxycarbonyl)-1-oxoisochromene-7-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-23         0                                  
HETATM    1  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   1.540   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  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    4   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   15   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   11    2                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₈O₉

Average Mass

296.1870 Da

Monoisotopic Mass

296.01683 Da

IUPAC Name

4,6,8-trihydroxy-3-(methoxycarbonyl)-1-oxo-1H-isochromene-7-carboxylic acid

Traditional Name

4,6,8-trihydroxy-3-(methoxycarbonyl)-1-oxoisochromene-7-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C(O)C2=CC(O)=C(C(O)=O)C(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C12H8O9/c1-20-12(19)9-7(14)3-2-4(13)6(10(16)17)8(15)5(3)11(18)21-9/h2,13-15H,1H3,(H,16,17)

InChI Key

SUXCSEWUNYMJLR-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	andrew.piggott@mq.edu.au	Not Available	Not Available	2023-09-27	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	andrew.piggott@mq.edu.au	Not Available	Not Available	2023-09-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	andrew.piggott@mq.edu.au	Not Available	Not Available	2023-09-27	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	andrew.piggott@mq.edu.au	Not Available	Not Available	2023-09-27	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	andrew.piggott@mq.edu.au	Not Available	Not Available	2023-09-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	andrew.piggott@mq.edu.au	Not Available	Not Available	2023-09-27	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isocoumarins and derivatives

Sub Class

Not Available

Direct Parent

Isocoumarins and derivatives

Alternative Parents

Substituents

Isocoumarin
2-benzopyran
Salicylic acid or derivatives
Hydroxybenzoic acid
Benzopyran
1-carboxy-2-haloaromatic compound
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Fatty acid ester
Dihydropyranone
Fatty acyl
Benzenoid
Pyran
Dicarboxylic acid or derivatives
Heteroaromatic compound
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	2.31	ChemAxon
pKa (Strongest Acidic)	1.25	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	66.67 m³·mol⁻¹	ChemAxon
Polarizability	25.73 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cowled MS, Kalaitzis JA, Crombie A, Chen R, Sbaraini N, Lacey E, Piggott AM: Fungal Duel between Penicillium brasilianum and Aspergillus nomius Results in Dual Induction of Miktospiromide A and Kitrinomycin A. J Nat Prod. 2023 Oct 27;86(10):2398-2406. doi: 10.1021/acs.jnatprod.3c00593. Epub 2023 Sep 22. [PubMed:37737825 ]

Showing NP-Card for kitrinomycin B (NP0331890)

MOL for NP0331890 (kitrinomycin B)

3D MOL for NP0331890 (kitrinomycin B)

3D SDF for NP0331890 (kitrinomycin B)

3D-SDF for NP0331890 (kitrinomycin B)

PDB for NP0331890 (kitrinomycin B)

3D PDB for NP0331890 (kitrinomycin B)

SMILES for NP0331890 (kitrinomycin B)

INCHI for NP0331890 (kitrinomycin B)

Structure for NP0331890 (kitrinomycin B)

3D Structure for NP0331890 (kitrinomycin B)