NP-MRD: Showing NP-Card for Salonitenolide (NP0051959)

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Record Information

Version

1.0

Created at

2022-04-27 23:10:09 UTC

Updated at

2022-04-27 23:10:09 UTC

NP-MRD ID

NP0051959

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Salonitenolide

Description

(3AR,4S,11aS)-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Salonitenolide is found in Berkheya speciosa, Brachylaena discolor, Centaurea alba, Centaurea aspera, Centaurea bombycina, Centaurea calcitrapa, Centaurea iberica, Centaurea melitensis, Centaurea paui, Centaurea salonitana, Centaurea stoebe, Cheirolophus intybaceus, Cnicus benedictus , Cousinia canescens, family Asteraceae spp., Heliomeris longifolia, Jurinea leptoloba, Jurinea maxima, Jurinea suffruticosa and Jurinella moschus. Based on a literature review a significant number of articles have been published on (3aR,4S,11aS)-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -2.4926    3.2561   -0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2496    2.8575   -0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0169    3.5853   -0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0393    4.6109    0.6412 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9791    2.9097   -0.7726 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6688    1.5229   -0.8727 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3204    0.8653    0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9662   -0.2872    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5731   -0.8382    1.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -0.9430    1.2016 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0771   -0.9882   -1.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8207   -1.6686   -1.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1112   -2.3732   -0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454   -1.9956    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7026   -2.7588    1.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7778   -0.7854   -0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2573    0.4726    0.2887 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2424    1.0925    1.0719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8263    1.4854   -0.7429 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3156    2.6047   -0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7132    4.2866    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417    1.1868   -1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2327    1.3954    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4172   -0.1808    2.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2272   -1.8709    1.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2622   -0.3357    0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8851   -1.7725   -0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4227   -0.3100   -1.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713   -1.0276   -2.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1586   -2.4899   -2.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5815   -3.2654   -0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7823   -2.8535    0.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3151   -3.7744    1.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6738   -2.2272    2.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8662   -0.8454   -0.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7194   -0.6707   -1.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4602    0.1682    0.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128    0.7135    1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2409    1.2491   -1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  1  0
 11  8  1  0
  8  9  1  0
  9 10  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 19  1  0
 19 17  1  0
 17 18  1  0
 17 16  1  0
 16 14  1  0
 19  6  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 13 31  1  0
 12 29  1  0
 12 30  1  0
 11 27  1  0
 11 28  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
  7 23  1  0
  6 22  1  6
  1 20  1  0
  1 21  1  0
 19 39  1  6
 17 37  1  1
 18 38  1  0
 16 35  1  0
 16 36  1  0
M  END


  Mrv1652304282201102D          

 19 20  0  0  1  0            999 V2000
    2.9012    1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871    1.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817    0.2983    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4589    0.9365    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7502    1.7084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5643    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556    2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697    2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925    2.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3328    3.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6241    4.0240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061    2.2240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5832    1.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551    2.0620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652    0.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8808    0.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904   -0.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393    2.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  5 16  1  1  0  0  0
 16 17  2  0  0  0  0
  4 18  1  6  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051959

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/CC\C(CO)=C\[C@@H]2OC(=O)C(=C)[C@@H]2[C@@H](O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-9-4-3-5-11(8-16)7-13-14(12(17)6-9)10(2)15(18)19-13/h4,7,12-14,16-17H,2-3,5-6,8H2,1H3/b9-4+,11-7-/t12-,13-,14+/m0/s1

> <INCHI_KEY>
BLDTUWFMPJJRPR-KPACVMPWSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.608278231248192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,11aS)-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
1.1902336900000001

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.28026817922364

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.570030591049036

> <JCHEM_PKA_STRONGEST_BASIC>
-2.734788390658264

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
73.29180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,11aS)-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.416   2.497   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.896   2.247   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.352   0.806   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.832   0.557   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.857   1.748   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.400   3.189   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.920   3.438   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.464   4.879   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.983   5.129   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.959   3.937   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.488   6.071   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.032   7.511   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.198   4.151   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.089   3.305   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.529   3.849   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.682   1.820   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.644   0.618   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.289  -0.884   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.807   3.785   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    1                                                       
CONECT   11    8   12                                                       
CONECT   12   11                                                            
CONECT   13    6   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    5   17                                                  
CONECT   17   16                                                            
CONECT   18    4                                                            
CONECT   19    2                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3210 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

(3aR,4S,11aS)-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

Traditional Name

(3aR,4S,11aS)-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

CAS Registry Number

Not Available

SMILES

C\C1=C/CC\C(CO)=C\[C@@H]2OC(=O)C(=C)[C@@H]2[C@@H](O)C1

InChI Identifier

InChI=1S/C15H20O4/c1-9-4-3-5-11(8-16)7-13-14(12(17)6-9)10(2)15(18)19-13/h4,7,12-14,16-17H,2-3,5-6,8H2,1H3/b9-4+,11-7-/t12-,13-,14+/m0/s1

InChI Key

BLDTUWFMPJJRPR-KPACVMPWSA-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
Berkheya speciosa	Plant	KNApSAcK
Brachylaena discolor	LOTUS Database	35616633
Centaurea alba	LOTUS Database	35616633
Centaurea aspera	LOTUS Database	35616633
Centaurea bombycina	LOTUS Database	35616633
Centaurea calcitrapa	LOTUS Database	35616633
Centaurea iberica	LOTUS Database	35616633
Centaurea melitensis	LOTUS Database	35616633
Centaurea paui	LOTUS Database	35616633
Centaurea salonitana	Plant	KNApSAcK
Centaurea stoebe	LOTUS Database	35616633
Cheirolophus intybaceus	LOTUS Database	35616633
Cnicus benedictus	Plant	KNApSAcK
Cousinia canescens	LOTUS Database	35616633
family Asteraceae spp.	-	KNApSAcK
Heliomeris longifolia	LOTUS Database	35616633
Jurinea leptoloba	LOTUS Database	35616633
Jurinea maxima	Plant	KNApSAcK
Jurinea suffruticosa	LOTUS Database	35616633
Jurinella moschus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Sesquiterpenoid
Germacrane sesquiterpenoid
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	1.2	ALOGPS
logP	1.19	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.57	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.29 m³·mol⁻¹	ChemAxon
Polarizability	27.61 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

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

163069585

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Salonitenolide (NP0051959)

MOL for NP0051959 (Salonitenolide)

3D MOL for NP0051959 (Salonitenolide)

3D SDF for NP0051959 (Salonitenolide)

3D-SDF for NP0051959 (Salonitenolide)

PDB for NP0051959 (Salonitenolide)

3D PDB for NP0051959 (Salonitenolide)

SMILES for NP0051959 (Salonitenolide)

INCHI for NP0051959 (Salonitenolide)

Structure for NP0051959 (Salonitenolide)

3D Structure for NP0051959 (Salonitenolide)