NP-MRD: Showing NP-Card for diaporthin (NP0304628)

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Record Information

Version

2.0

Created at

2022-09-10 19:51:55 UTC

Updated at

2022-09-10 19:51:55 UTC

NP-MRD ID

NP0304628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

diaporthin

Description

Diaporthin 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. diaporthin is found in Aspergillus ochraceus. diaporthin was first documented in 2016 (PMID: 27559694). Based on a literature review a small amount of articles have been published on Diaporthin (PMID: 31861107) (PMID: 31782665) (PMID: 29497981) (PMID: 36000162).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -5.5028    0.3330   -0.9223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2911   -0.1330   -1.5010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1328    0.0275   -0.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1191    0.5965    0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9551    0.7650    1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0436    1.3444    2.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7610    0.3344    0.7643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4407    0.4503    1.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4708    0.9703    2.5785 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5222    0.0011    0.8530 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6011   -0.5492   -0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9168   -1.0254   -0.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9892   -0.7249    0.1569 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0603    0.7496    0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2076   -1.2451   -0.2679 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4370   -0.6877   -1.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7562   -0.2466   -0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9289   -0.4023   -1.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3960    1.4369   -0.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3746    0.1864   -1.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6152   -0.1290    0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0553    0.9471    0.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730    1.5858    3.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1454   -0.4524   -1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9152   -2.1026   -1.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6983   -1.2768    1.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1295    1.1039    0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6994    1.0063    1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900    1.3654   -0.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0964   -2.2197   -0.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4335   -1.1394   -2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8486   -0.8697   -2.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 11 16  2  0
 16 17  1  0
 17 18  2  0
 18  3  1  0
 17  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
 12 24  1  0
 12 25  1  0
 13 26  1  1
 14 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
M  END


  Mrv1652309102221512D          

 18 19  0  0  1  0            999 V2000
   -0.7145   -1.2375    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 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
    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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    4.2868   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    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
    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  2  1  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  2  0  0  0  0
  8 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  1  6  0  0  0
 11 16  2  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  2  0  0  0  0
  3 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304628

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)OC(C[C@H](C)O)=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O5/c1-7(14)3-10-5-8-4-9(17-2)6-11(15)12(8)13(16)18-10/h4-7,14-15H,3H2,1-2H3/t7-/m0/s1

> <INCHI_KEY>
ORLHWDAVUBPRKN-ZETCQYMHSA-N

> <FORMULA>
C13H14O5

> <MOLECULAR_WEIGHT>
250.25

> <EXACT_MASS>
250.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.369260499571354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-3-[(2S)-2-hydroxypropyl]-6-methoxy-1H-isochromen-1-one

> <JCHEM_LOGP>
1.873851251

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.524653612683007

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.478207245811669

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5693166975644752

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
66.5771

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-3-[(2S)-2-hydroxypropyl]-6-methoxyisochromen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   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  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   17                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17                                                       
CONECT   17   16    7   18                                                  
CONECT   18   17    3                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₄O₅

Average Mass

250.2500 Da

Monoisotopic Mass

250.08412 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)OC(C[C@H](C)O)=CC2=C1

InChI Identifier

InChI=1S/C13H14O5/c1-7(14)3-10-5-8-4-9(17-2)6-11(15)12(8)13(16)18-10/h4-7,14-15H,3H2,1-2H3/t7-/m0/s1

InChI Key

ORLHWDAVUBPRKN-ZETCQYMHSA-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
Aspergillus ochraceus	LOTUS Database	35616633

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
Anisole
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Pyran
Benzenoid
Vinylogous acid
Heteroaromatic compound
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
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

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

4481110

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5323561

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liao HX, Shao TM, Mei RQ, Huang GL, Zhou XM, Zheng CJ, Wang CY: Bioactive Secondary Metabolites from the Culture of the Mangrove-Derived Fungus Daldinia eschscholtzii HJ004. Mar Drugs. 2019 Dec 17;17(12). pii: md17120710. doi: 10.3390/md17120710. [PubMed:31861107 ]
Lai D, Li J, Zhao S, Gu G, Gong X, Proksch P, Zhou L: Chromone and isocoumarin derivatives from the endophytic fungus Xylomelasma sp. Samif07, and their antibacterial and antioxidant activities. Nat Prod Res. 2019 Nov 29:1-5. doi: 10.1080/14786419.2019.1696333. [PubMed:31782665 ]
de Medeiros AG, Savi DC, Mitra P, Shaaban KA, Jha AK, Thorson JS, Rohr J, Glienke C: Bioprospecting of Diaporthe terebinthifolii LGMF907 for antimicrobial compounds. Folia Microbiol (Praha). 2018 Jul;63(4):499-505. doi: 10.1007/s12223-018-0587-2. Epub 2018 Mar 1. [PubMed:29497981 ]
Shi JY, Wang CF, Xie MM, Hao YJ, Wang N, Ma HB, Yang XW: Brefeldin A from the Deep-Sea-Derived Fungus Fusarium sp. Targets on RIPK3 to Inhibit TNFalpha-Induced Necroptosis. Chem Biodivers. 2022 Oct;19(10):e202200696. doi: 10.1002/cbdv.202200696. Epub 2022 Sep 16. [PubMed:36000162 ]
Chankhamjon P, Tsunematsu Y, Ishida-Ito M, Sasa Y, Meyer F, Boettger-Schmidt D, Urbansky B, Menzel KD, Scherlach K, Watanabe K, Hertweck C: Regioselective Dichlorination of a Non-Activated Aliphatic Carbon Atom and Phenolic Bismethylation by a Multifunctional Fungal Flavoenzyme. Angew Chem Int Ed Engl. 2016 Sep 19;55(39):11955-9. doi: 10.1002/anie.201604516. Epub 2016 Aug 25. [PubMed:27559694 ]
LOTUS database [Link]

Showing NP-Card for diaporthin (NP0304628)

MOL for NP0304628 (diaporthin)

3D MOL for NP0304628 (diaporthin)

3D SDF for NP0304628 (diaporthin)

3D-SDF for NP0304628 (diaporthin)

PDB for NP0304628 (diaporthin)

3D PDB for NP0304628 (diaporthin)

SMILES for NP0304628 (diaporthin)

INCHI for NP0304628 (diaporthin)

Structure for NP0304628 (diaporthin)

3D Structure for NP0304628 (diaporthin)