NP-MRD: Showing NP-Card for Annuionone B (NP0047370)

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Record Information

Version

2.0

Created at

2022-03-17 20:39:05 UTC

Updated at

2022-03-17 20:39:05 UTC

NP-MRD ID

NP0047370

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Annuionone B

Description

Annuionone B belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Annuionone B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Annuionone B has been detected, but not quantified in, fats and oils and sunflowers. Annuionone B is found in Helianthus annuus, Helianthus annuus cv.Stella and SH0222 and Hilanthus annuus. This could make annuionone b a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218302D          

 16 17  0  0  0  0            999 V2000
   -1.7859    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012   -1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3555    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0707    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7859    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7859    1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4848   -0.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -0.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3555   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 14  1  0  0  0  0
  4 15  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6 13  1  0  0  0  0
  6 16  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047370

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)\C=C\C1C2(C)COC1(C)CC(=O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O3/c1-9(14)4-5-11-12(2)6-10(15)7-13(11,3)16-8-12/h4-5,11H,6-8H2,1-3H3/b5-4+

> <INCHI_KEY>
LYMNQFZEIGCRGT-SNAWJCMRSA-N

> <FORMULA>
C13H18O3

> <MOLECULAR_WEIGHT>
222.2802

> <EXACT_MASS>
222.125594442

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.056258241751085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5-dimethyl-8-[(1E)-3-oxobut-1-en-1-yl]-6-oxabicyclo[3.2.1]octan-3-one

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
1.2672759016666668

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.862597729677905

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.314528191791776

> <JCHEM_PKA_STRONGEST_BASIC>
-4.111780303212414

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
61.6728

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,5-dimethyl-8-[(1E)-3-oxobut-1-en-1-yl]-6-oxabicyclo[3.2.1]octan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.334   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.334  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.001  -2.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.671  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.671   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.001   0.768   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.669  -2.311   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.664   0.768   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.999   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.334   0.768   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.669   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.334   2.311   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.772  -0.567   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.001  -1.617   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.664  -2.311   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.001   2.308   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14   15                                             
CONECT    5    4    6    8                                                  
CONECT    6    1    5   13   16                                             
CONECT    7    2                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    6   14                                                       
CONECT   14    4   13                                                       
CONECT   15    4                                                            
CONECT   16    6                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
(-)-Annuionone b	HMDB
Annuionone b	MeSH

Chemical Formula

C₁₃H₁₈O₃

Average Mass

222.2802 Da

Monoisotopic Mass

222.12559 Da

IUPAC Name

1,5-dimethyl-8-[(1E)-3-oxobut-1-en-1-yl]-6-oxabicyclo[3.2.1]octan-3-one

Traditional Name

1,5-dimethyl-8-[(1E)-3-oxobut-1-en-1-yl]-6-oxabicyclo[3.2.1]octan-3-one

CAS Registry Number

211183-73-2

SMILES

CC(=O)\C=C\C1C2(C)COC1(C)CC(=O)C2

InChI Identifier

InChI=1S/C13H18O3/c1-9(14)4-5-11-12(2)6-10(15)7-13(11,3)16-8-12/h4-5,11H,6-8H2,1-3H3/b5-4+

InChI Key

LYMNQFZEIGCRGT-SNAWJCMRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Helianthus annuus	LOTUS Database	35616633
Helianthus annuus cv.Stella and SH0222	Plant	KNApSAcK
Helianthus annuus L.	FooDB	KNAPSACK
Hilanthus annuus	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Acryloyl-group
Enone
Tetrahydrofuran
Alpha,beta-unsaturated ketone
Cyclic ketone
Ketone
Ether
Dialkyl ether
Oxacycle
Carbonyl group
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.44	ALOGPS
logP	1.27	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	18.31	ChemAxon
pKa (Strongest Basic)	-4.1	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	2	ChemAxon
Refractivity	61.67 m³·mol⁻¹	ChemAxon
Polarizability	24.06 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

HMDB0032121

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008843

KNApSAcK ID

C00035807

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

101417753

PDB ID

Not Available

ChEBI ID

143059

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Annuionone B (NP0047370)

MOL for NP0047370 (Annuionone B)

3D MOL for NP0047370 (Annuionone B)

3D SDF for NP0047370 (Annuionone B)

3D-SDF for NP0047370 (Annuionone B)

PDB for NP0047370 (Annuionone B)

3D PDB for NP0047370 (Annuionone B)

SMILES for NP0047370 (Annuionone B)

INCHI for NP0047370 (Annuionone B)

Structure for NP0047370 (Annuionone B)

3D Structure for NP0047370 (Annuionone B)