NP-MRD: Showing NP-Card for Citreoisocoumarin (NP0073422)

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Record Information

Version

2.0

Created at

2022-04-28 18:40:53 UTC

Updated at

2022-04-28 18:40:53 UTC

NP-MRD ID

NP0073422

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Citreoisocoumarin

Description

Citreoisocoumarin 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. Citreoisocoumarin is found in Ampelomyces sp., Fusarium tricinctum and Penicillium nalgiovense. Citreoisocoumarin was first documented in 2016 (PMID: 28901109). Based on a literature review a small amount of articles have been published on Citreoisocoumarin (PMID: 28587090) (PMID: 28825620) (PMID: 32098474) (PMID: 29887844).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    4.9259    1.1889   -0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4956    0.8897    0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6907    1.6420   -0.4820 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9561   -0.2686    0.7936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5275   -1.3967   -0.0638 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0415   -2.4080    0.7961 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4320   -1.0812   -1.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1906   -0.6595   -0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8867   -0.2896   -1.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0733    0.1116   -0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1133    0.4685   -1.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2919    0.8668   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3646    1.2349   -1.6495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4136    0.9026    0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3555    0.5395    1.3195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4541    0.5674    2.7032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1607    0.1356    0.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0714   -0.2381    1.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1189   -0.2273    2.7402 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0566   -0.6193    0.8955 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5796    0.3154    0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0722    1.6257   -1.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2135    1.9716    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7618   -0.6069    1.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1216    0.0888    1.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572   -1.8635   -0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2925   -3.3070    0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296   -0.3029   -1.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2380   -1.9745   -1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854   -0.3196   -2.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0201    0.4414   -2.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0193    0.4986   -1.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3273    1.2115    1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3263    0.8624    3.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20  8  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  6
  6 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
M  END


  Mrv1652304282220402D          

 20 21  0  0  1  0            999 V2000
   -2.8579    2.4750    0.0000 C   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
   -2.1434    1.2375    0.0000 C   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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    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
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    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
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.8875    0.0000 O   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  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  1  0  0  0
  3 19  1  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073422

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C[C@@H](O)CC1=CC2=CC(O)=CC(O)=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O6/c1-7(15)2-9(16)5-11-4-8-3-10(17)6-12(18)13(8)14(19)20-11/h3-4,6,9,16-18H,2,5H2,1H3/t9-/m1/s1

> <INCHI_KEY>
OSPHTXUUCFLMQA-SECBINFHSA-N

> <FORMULA>
C14H14O6

> <MOLECULAR_WEIGHT>
278.26

> <EXACT_MASS>
278.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.34199141642825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,8-dihydroxy-3-[(2S)-2-hydroxy-4-oxopentyl]-1H-isochromen-1-one

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
1.4157708076666669

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.269088023511232

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.428039684673012

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8247561579819855

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
71.68130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,8-dihydroxy-3-[(2S)-2-hydroxy-4-oxopentyl]isochromen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -6.668   5.390   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13                                                            
CONECT   19    3                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₄O₆

Average Mass

278.2600 Da

Monoisotopic Mass

278.07904 Da

IUPAC Name

6,8-dihydroxy-3-[(2S)-2-hydroxy-4-oxopentyl]-1H-isochromen-1-one

Traditional Name

6,8-dihydroxy-3-[(2S)-2-hydroxy-4-oxopentyl]isochromen-1-one

CAS Registry Number

Not Available

SMILES

CC(=O)C[C@@H](O)CC1=CC2=CC(O)=CC(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C14H14O6/c1-7(15)2-9(16)5-11-4-8-3-10(17)6-12(18)13(8)14(19)20-11/h3-4,6,9,16-18H,2,5H2,1H3/t9-/m1/s1

InChI Key

OSPHTXUUCFLMQA-SECBINFHSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ampelomyces sp.	-	KNApSAcK
Fusarium tricinctum	LOTUS Database	35616633
Penicillium nalgiovense	Fungi	KNApSAcK

Chemical Taxonomy

Description

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
Benzopyran
2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Beta-hydroxy ketone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Ketone
Lactone
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen 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	1.05	ALOGPS
logP	1.42	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.68 m³·mol⁻¹	ChemAxon
Polarizability	27.34 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

C00033726

Chemspider ID

31143389

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15071544

PDB ID

Not Available

ChEBI ID

177816

Good Scents ID

Not Available

References

General References

Shi T, Qi J, Shao CL, Zhao DL, Hou XM, Wang CY: Bioactive Diphenyl Ethers and Isocoumarin Derivatives from a Gorgonian-Derived Fungus Phoma sp. (TA07-1). Mar Drugs. 2017 May 25;15(6). pii: md15060146. doi: 10.3390/md15060146. [PubMed:28587090 ]
Fang F, Zhao J, Ding L, Huang C, Naman CB, He S, Wu B, Zhu P, Luo Q, Gerwick WH, Yan X, Wang Q, Zhang Z, Cui W: 5-Hydroxycyclopenicillone, a New beta-Amyloid Fibrillization Inhibitor from a Sponge-Derived Fungus Trichoderma sp. HPQJ-34. Mar Drugs. 2017 Aug 19;15(8). pii: md15080260. doi: 10.3390/md15080260. [PubMed:28825620 ]
Mallampudi NA, Choudhury UM, Mohapatra DK: Total Synthesis of (-)-Citreoisocoumarin, (-)-Citreoisocoumarinol, (-)-12-epi-Citreoisocoumarinol, and (-)-Mucorisocoumarins A and B Using a Gold(I)-Catalyzed Cyclization Strategy. J Org Chem. 2020 Mar 20;85(6):4122-4129. doi: 10.1021/acs.joc.9b03278. Epub 2020 Mar 10. [PubMed:32098474 ]
Son SY, Lee S, Singh D, Lee NR, Lee DY, Lee CH: Comprehensive Secondary Metabolite Profiling Toward Delineating the Solid and Submerged-State Fermentation of Aspergillus oryzae KCCM 12698. Front Microbiol. 2018 May 25;9:1076. doi: 10.3389/fmicb.2018.01076. eCollection 2018. [PubMed:29887844 ]
Wang M, Chen YC, Sun ZH, Tan GH, Li HH, Liu HX, Yan HJ, Guo XL, Zhang WM: [Study on cytotoxic secondary metabolites of endophytic fungus Diaporthe longicolla A616 from Pogostemon cablin]. Zhongguo Zhong Yao Za Zhi. 2016 Jun;41(11):2112-2117. doi: 10.4268/cjcmm20161122. [PubMed:28901109 ]

Showing NP-Card for Citreoisocoumarin (NP0073422)

MOL for NP0073422 (Citreoisocoumarin)

3D MOL for NP0073422 (Citreoisocoumarin)

3D SDF for NP0073422 (Citreoisocoumarin)

3D-SDF for NP0073422 (Citreoisocoumarin)

PDB for NP0073422 (Citreoisocoumarin)

3D PDB for NP0073422 (Citreoisocoumarin)

SMILES for NP0073422 (Citreoisocoumarin)

INCHI for NP0073422 (Citreoisocoumarin)

Structure for NP0073422 (Citreoisocoumarin)

3D Structure for NP0073422 (Citreoisocoumarin)