NP-MRD: Showing NP-Card for 2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid (NP0289819)

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Record Information

Version

2.0

Created at

2022-09-09 20:11:49 UTC

Updated at

2022-09-09 20:11:49 UTC

NP-MRD ID

NP0289819

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid

Description

2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid is found in Ligularia sagitta. Based on a literature review very few articles have been published on 2-{2-hydroxy-1b-dimethyl-4-oxo-octahydro-H-naphtho[1,8a-b]oxiren-3-ylidene}propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    4.0289   -0.3583    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8831    0.4290   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2186    1.6266   -0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4076    2.0230   -0.9317 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2432    2.3951   -1.3831 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6582   -0.0104    0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -1.2460    0.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1705   -1.5646    1.7912 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085   -2.1655    0.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7947   -1.3952   -0.2124 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0088   -1.7932   -1.5089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0391   -2.0499   -0.4411 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2706   -1.2145   -0.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8111    0.1070   -1.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9887    0.8068   -0.2158 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6643    2.2228   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    0.0373    0.2082 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6626    0.1286    1.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589    0.6875   -0.4045 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4371    0.5234   -1.7831 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9080   -1.4280    0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9632   -0.0267    0.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1043   -0.1687    1.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258    2.6482   -2.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7469   -2.9628   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1327   -2.6550    1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1350   -3.1362   -0.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9938   -1.7350   -1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7784   -1.0269    0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2706   -0.1400   -2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7238    0.7164   -1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847    0.9432    0.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2057    2.7630    0.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0810    2.2851   -1.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6628    2.7341   -0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1609    0.8171    1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    0.5848    2.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5816   -0.8561    2.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372    1.7504   -0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566   -0.2965   -2.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 10 11  1  6
 10  9  1  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6 19  1  0
 19 20  1  0
 19 17  1  0
 17 18  1  1
  6  2  2  0
  2  1  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
 17 15  1  0
 10 12  1  0
 17 10  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 15 32  1  1
 14 30  1  0
 14 31  1  0
 13 28  1  0
 13 29  1  0
 12 27  1  1
  9 25  1  0
  9 26  1  0
 19 39  1  6
 20 40  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
M  END


  Mrv1652309092222112D          

 20 22  0  0  0  0            999 V2000
    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 C   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
   -1.4289   -1.6500    0.0000 O   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   -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
    0.0000    0.0000    0.0000 O   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
    2.1434   -0.4125    0.0000 C   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
    2.8579    0.0000    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
    3.5724   -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
    2.8579   -2.4750    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
    2.1434   -2.0625    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
  2  1  1  4  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 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  1  0  0  0  0
 15 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289819

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2OC22CC(=O)C(C(O)C12C)=C(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O5/c1-7-4-5-10-15(20-10)6-9(16)11(8(2)13(18)19)12(17)14(7,15)3/h7,10,12,17H,4-6H2,1-3H3,(H,18,19)

> <INCHI_KEY>
YLSDOVQJJLALFS-UHFFFAOYSA-N

> <FORMULA>
C15H20O5

> <MOLECULAR_WEIGHT>
280.32

> <EXACT_MASS>
280.131073744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.61802242473391

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{5-hydroxy-4,4a-dimethyl-7-oxo-octahydro-2H-naphtho[4,4a-b]oxiren-6-ylidene}propanoic acid

> <JCHEM_LOGP>
1.3562106689999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.826737286146283

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.658159779986647

> <JCHEM_PKA_STRONGEST_BASIC>
-3.334724497626815

> <JCHEM_POLAR_SURFACE_AREA>
87.13

> <JCHEM_REFRACTIVITY>
70.40570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -4.620   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       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7   19                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   17                                             
CONECT   11   10   12                                                       
CONECT   12   11   10   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    6   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
2-{2-hydroxy-1b-dimethyl-4-oxo-octahydro-H-naphtho[1,8a-b]oxiren-3-ylidene}propanoate	Generator

Chemical Formula

C₁₅H₂₀O₅

Average Mass

280.3200 Da

Monoisotopic Mass

280.13107 Da

IUPAC Name

2-{5-hydroxy-4,4a-dimethyl-7-oxo-octahydro-2H-naphtho[4,4a-b]oxiren-6-ylidene}propanoic acid

Traditional Name

2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid

CAS Registry Number

Not Available

SMILES

CC1CCC2OC22CC(=O)C(C(O)C12C)=C(C)C(O)=O

InChI Identifier

InChI=1S/C15H20O5/c1-7-4-5-10-15(20-10)6-9(16)11(8(2)13(18)19)12(17)14(7,15)3/h7,10,12,17H,4-6H2,1-3H3,(H,18,19)

InChI Key

YLSDOVQJJLALFS-UHFFFAOYSA-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
Ligularia sagitta	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	1.36	ChemAxon
pKa (Strongest Acidic)	3.66	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.41 m³·mol⁻¹	ChemAxon
Polarizability	28.62 Å³	ChemAxon
Number of Rings	3	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

Not Available

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

163023230

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid (NP0289819)

MOL for NP0289819 (2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid)

3D MOL for NP0289819 (2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid)

3D SDF for NP0289819 (2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid)

3D-SDF for NP0289819 (2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid)

PDB for NP0289819 (2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid)

3D PDB for NP0289819 (2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid)

SMILES for NP0289819 (2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid)

INCHI for NP0289819 (2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid)

Structure for NP0289819 (2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid)

3D Structure for NP0289819 (2-{5-hydroxy-4,4a-dimethyl-7-oxo-hexahydronaphtho[4,4a-b]oxiren-6-ylidene}propanoic acid)