NP-MRD: Showing NP-Card for Spiciferone A (NP0084409)

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Record Information

Version

2.0

Created at

2022-04-29 05:08:38 UTC

Updated at

2022-04-29 05:08:39 UTC

NP-MRD ID

NP0084409

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Spiciferone A

Description

Spiciferone A belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Spiciferone A is found in Cochliobolus spicifer and Curvularia hawaiiensis. Spiciferone A was first documented in 2006 (PMID: 16808526). Based on a literature review a small amount of articles have been published on Spiciferone A (PMID: 29366851) (PMID: 29540777) (PMID: 19630376).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.8189   -2.1747    0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4146   -0.8128    0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7370    0.0651   -0.5065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8137   -0.5255   -1.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4782    1.3399   -0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261    1.2481   -0.8199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8847    2.6359   -0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6029    2.6826    0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2095    1.4830    0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3123    0.2571   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000   -0.7957   -0.1036 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7703   -0.7216    0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367   -1.9470    0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3361    0.5019    0.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7938    0.6157    0.7767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5728    1.6404    0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123    2.7875    0.6151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6475   -2.9238    0.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2116   -2.2339    1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1610   -2.4473   -0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5070   -0.8711    0.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3122   -0.2672    1.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9944    0.2786   -2.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6127   -1.2606   -2.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8320   -0.9799   -2.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083    3.5216   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637    3.6750    0.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9199   -2.1518    1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5168   -1.7612   -0.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0592   -2.8139   -0.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500    0.9368   -0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8823    1.3665    1.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1788   -0.3479    1.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 10  3  1  0
 16  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  7 26  1  0
  8 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
M  END


  Mrv1652304292207082D          

 17 18  0  0  1  0            999 V2000
    0.0000    0.0000    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 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  1  0  0  0  0  0  0  0  0  0
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060    1.4072    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
    2.8579   -1.6500    0.0000 C   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
    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
    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 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 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  1  0  0  0
  7  8  1  0  0  0  0
  4  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084409

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]1(C)C(=O)C=CC2=C1OC(C)=C(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O3/c1-5-14(4)11(15)7-6-10-12(16)8(2)9(3)17-13(10)14/h6-7H,5H2,1-4H3/t14-/m0/s1

> <INCHI_KEY>
QMMMQWRPZIJGPT-AWEZNQCLSA-N

> <FORMULA>
C14H16O3

> <MOLECULAR_WEIGHT>
232.279

> <EXACT_MASS>
232.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.935157369008994

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8R)-8-ethyl-2,3,8-trimethyl-7,8-dihydro-4H-chromene-4,7-dione

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
2.8078735829999992

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.2481217106796425

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
68.86789999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8R)-8-ethyl-2,3,8-trimethylchromene-4,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.798   2.627   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7   12                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₆O₃

Average Mass

232.2790 Da

Monoisotopic Mass

232.10994 Da

IUPAC Name

(8R)-8-ethyl-2,3,8-trimethyl-7,8-dihydro-4H-chromene-4,7-dione

Traditional Name

(8R)-8-ethyl-2,3,8-trimethylchromene-4,7-dione

CAS Registry Number

Not Available

SMILES

CC[C@@]1(C)C(=O)C=CC2=C1OC(C)=C(C)C2=O

InChI Identifier

InChI=1S/C14H16O3/c1-5-14(4)11(15)7-6-10-12(16)8(2)9(3)17-13(10)14/h6-7H,5H2,1-4H3/t14-/m0/s1

InChI Key

QMMMQWRPZIJGPT-AWEZNQCLSA-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
Cochliobolus spicifer	Fungi	KNApSAcK
Curvularia hawaiiensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Pyranone
Heteroaromatic compound
Cyclic ketone
Ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.64	ALOGPS
logP	2.81	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.87 m³·mol⁻¹	ChemAxon
Polarizability	24.94 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

C00053797

Chemspider ID

156826

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

180199

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stierle AA, Stierle DB, Kelly K: Berkelic acid, a novel spiroketal with selective anticancer activity from an acid mine waste fungal extremophile. J Org Chem. 2006 Jul 7;71(14):5357-60. doi: 10.1021/jo060018d. [PubMed:16808526 ]
Rusman Y, Held BW, Blanchette RA, He Y, Salomon CE: Cadopherone and colomitide polyketides from Cadophora wood-rot fungi associated with historic expedition huts in Antarctica. Phytochemistry. 2018 Apr;148:1-10. doi: 10.1016/j.phytochem.2017.12.019. Epub 2018 Feb 6. [PubMed:29366851 ]
Tan XM, Li LY, Sun LY, Sun BD, Niu SB, Wang MH, Zhang XY, Sun WS, Zhang GS, Deng H, Xing XK, Zou ZM, Ding G: Spiciferone analogs from an endophytic fungus Phoma betae collected from desert plants in West China. J Antibiot (Tokyo). 2018 Jun;71(6):613-617. doi: 10.1038/s41429-018-0037-z. Epub 2018 Mar 14. [PubMed:29540777 ]
Wu X, Zhou J, Snider BB: Introduction of the (-)-berkelic acid side chain and assignment of the C-22 stereochemistry. J Org Chem. 2009 Aug 21;74(16):6245-52. doi: 10.1021/jo901221a. [PubMed:19630376 ]

Showing NP-Card for Spiciferone A (NP0084409)

MOL for NP0084409 (Spiciferone A)

3D MOL for NP0084409 (Spiciferone A)

3D SDF for NP0084409 (Spiciferone A)

3D-SDF for NP0084409 (Spiciferone A)

PDB for NP0084409 (Spiciferone A)

3D PDB for NP0084409 (Spiciferone A)

SMILES for NP0084409 (Spiciferone A)

INCHI for NP0084409 (Spiciferone A)

Structure for NP0084409 (Spiciferone A)

3D Structure for NP0084409 (Spiciferone A)