NP-MRD: Showing NP-Card for Demethoxyviridiol (NP0141230)

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Record Information

Version

1.0

Created at

2022-06-29 22:18:49 UTC

Updated at

2022-06-29 22:18:49 UTC

NP-MRD ID

NP0141230

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Demethoxyviridiol

Description

Demethoxyviridiol belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. Demethoxyviridiol is found in Hypoxylon hinnuleum. It was first documented in 2013 (PMID: 23098903). Based on a literature review very few articles have been published on Demethoxyviridiol (PMID: 31661270).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 44  0  0  0  0  0  0  0  0999 V2000
   -1.3717   -0.9719   -1.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463   -0.4440    0.0360 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5142   -0.4746    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765   -1.6994    0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5490   -1.8112    0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140   -0.6702   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6830    0.5417   -0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3056    0.6575   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7273    2.0236   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4371    3.0128   -0.2450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7364    2.0836   -0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5999    3.0840    0.0081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8443    2.5944    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8032    1.2169    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4528    0.9474    0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7907    0.1304    0.3965 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6013   -0.0361   -0.7327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1635   -1.1762    0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6902   -1.1635    1.1122 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3109   -2.4587    1.3298 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7302    1.5682   -0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9345    0.8382   -0.7680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855   -0.5022   -0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6640   -1.3183    0.2285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7183   -2.0153   -1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884   -1.0103   -2.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1347   -0.3331   -1.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6136   -2.6179    0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0198   -2.8011    0.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7531    3.1769    0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4883    0.4081    1.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4659   -0.4010   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3310   -1.9177   -0.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6863   -1.6030    1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108   -0.5756    2.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840   -2.7532    2.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9507    1.9472    0.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4799    2.4501   -0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8936    0.7884   -1.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8936    1.2852   -0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2 19  1  0
 19 20  1  0
 19 18  1  0
 18 16  1  0
 16 17  1  0
 16 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  1  0
 11 15  2  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 15  2  1  0
  7  8  1  0
  3  2  1  0
 23  6  1  0
 15 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 19 35  1  1
 20 36  1  0
 18 33  1  0
 18 34  1  0
 16 31  1  1
 17 32  1  0
 13 30  1  0
  4 28  1  0
  5 29  1  0
 21 37  1  0
 21 38  1  0
 22 39  1  0
 22 40  1  0
M  END


  Mrv1652306302200182D          

 24 28  0  0  1  0            999 V2000
    2.6313   -1.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3791   -0.6266    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7449   -1.1542    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9709   -0.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8311   -0.0557    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4653    0.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4976    1.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2916    1.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500    0.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393    0.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5665    0.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0772    1.3640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8723   -0.0502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3616   -0.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6674   -1.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4839   -1.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9945   -0.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6888   -0.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230    0.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0208   -0.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8178   -0.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3454   -1.5149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0570    0.2298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8847   -1.9673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  6 10  1  0  0  0  0
  2 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
  5 23  1  6  0  0  0
  3 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0141230

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12[C@H](O)C[C@H](O)C3=COC(=C13)C(=O)C1=C2C=CC2=C1CCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H16O5/c1-19-11-4-2-8-9(3-5-12(8)20)15(11)17(23)18-16(19)10(7-24-18)13(21)6-14(19)22/h2,4,7,13-14,21-22H,3,5-6H2,1H3/t13-,14+,19-/m0/s1

> <INCHI_KEY>
OSSCBUARECIOCW-KSMMKXTCSA-N

> <FORMULA>
C19H16O5

> <MOLECULAR_WEIGHT>
324.332

> <EXACT_MASS>
324.099773615

$$$$

HEADER    PROTEIN                                 30-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-22         0                                  
HETATM    1  C   UNK     0       4.912  -2.636   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.441  -1.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.257  -2.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.812  -1.622   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.551  -0.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.735   0.881   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.796   2.420   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.278   2.838   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.133   1.557   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.180   0.348   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.657   1.337   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.611   2.546   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.228  -0.094   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.275  -1.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.846  -2.733   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.370  -2.954   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.323  -1.745   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.752  -0.315   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.936   0.670   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.239  -0.151   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.860  -1.644   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.845  -2.828   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.106   0.429   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.518  -3.672   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10   14                                             
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    6    2                                                  
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13    2   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17   22                                                  
CONECT   22   21                                                            
CONECT   23    5                                                            
CONECT   24    3                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₆O₅

Average Mass

324.3320 Da

Monoisotopic Mass

324.09977 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@]12[C@H](O)C[C@H](O)C3=COC(=C13)C(=O)C1=C2C=CC2=C1CCC2=O

InChI Identifier

InChI=1S/C19H16O5/c1-19-11-4-2-8-9(3-5-12(8)20)15(11)17(23)18-16(19)10(7-24-18)13(21)6-14(19)22/h2,4,7,13-14,21-22H,3,5-6H2,1H3/t13-,14+,19-/m0/s1

InChI Key

OSSCBUARECIOCW-KSMMKXTCSA-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
Hypoxylon hinnuleum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Naphthofuran
Indanone
Naphthalene
Indane
Aryl alkyl ketone
Aryl ketone
Heteroaromatic compound
Furan
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
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

149946

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

171531

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Andersson PF, Bengtsson S, Cleary M, Stenlid J, Broberg A: Viridin-like steroids from Hymenoscyphus pseudoalbidus. Phytochemistry. 2013 Feb;86:195-200. doi: 10.1016/j.phytochem.2012.09.012. Epub 2012 Oct 22. [PubMed:23098903 ]
Masi M, Di Lecce R, Tuzi A, Linaldeddu BT, Montecchio L, Maddau L, Evidente A: Hyfraxinic Acid, a Phytotoxic Tetrasubstituted Octanoic Acid, Produced by the Ash (Fraxinus excelsior L.) Pathogen Hymenoscyphus fraxineus Together with Viridiol and Some of Its Analogues. J Agric Food Chem. 2019 Dec 11;67(49):13617-13623. doi: 10.1021/acs.jafc.9b06055. Epub 2019 Nov 25. [PubMed:31661270 ]

Showing NP-Card for Demethoxyviridiol (NP0141230)

MOL for NP0141230 (Demethoxyviridiol)

3D MOL for NP0141230 (Demethoxyviridiol)

3D SDF for NP0141230 (Demethoxyviridiol)

3D-SDF for NP0141230 (Demethoxyviridiol)

PDB for NP0141230 (Demethoxyviridiol)

3D PDB for NP0141230 (Demethoxyviridiol)

SMILES for NP0141230 (Demethoxyviridiol)

INCHI for NP0141230 (Demethoxyviridiol)

Structure for NP0141230 (Demethoxyviridiol)

3D Structure for NP0141230 (Demethoxyviridiol)