NP-MRD: Showing NP-Card for β-santonin (NP0302017)

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Record Information

Version

1.0

Created at

2022-09-10 15:18:53 UTC

Updated at

2022-09-10 15:18:53 UTC

NP-MRD ID

NP0302017

Secondary Accession Numbers

None

Natural Product Identification

Common Name

β-santonin

Description

Beta-santonin belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Thus, beta-santonin is considered to be an isoprenoid. β-santonin is found in Artemisia caerulescens, Artemisia schrenkiana and Artemisia sericea. It was first documented in 2018 (PMID: 29109061). Based on a literature review very few articles have been published on beta-santonin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.9741    2.8057   -0.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641    1.5014   -0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8457    0.4042   -0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5399    0.3461   -0.7030 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1067    1.5352   -1.0717 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732    1.4885   -0.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3504    2.2735   -1.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7015    0.3454    0.2254 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5983   -0.6355   -0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3458   -0.0522    0.5512 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0161   -1.4600    0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4404   -1.6601    1.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776   -0.8991    0.2538 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4800   -1.7274   -1.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7405   -0.8784    0.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4801    0.2014    0.8897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176    1.4627    0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6048    2.5132    0.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7653    2.7895   -1.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733    3.5946   -0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1484    3.1426    0.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6058   -0.4352   -1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864    0.8266    1.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6384   -0.4675   -0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6699   -0.4899   -1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3710   -1.6955   -0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9599    0.5658    1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2177   -2.0560   -0.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6863   -1.8576    1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7322   -2.7291    1.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821   -1.2861    2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1704   -2.5692   -0.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4730   -2.1511   -1.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7266   -1.0728   -1.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1679   -1.8288    1.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5033    0.1547    1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4 10  1  0
  3 13  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
  8 23  1  1
 10 27  1  1
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  6
M  END


  Mrv1652309102217182D          

 18 20  0  0  1  0            999 V2000
    2.2089    0.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781   -0.7735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6108   -0.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -0.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0758   -0.0207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3140   -1.2781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9440   -1.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -1.4747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1228   -2.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982   -2.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -1.5262    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4736   -2.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597    0.5775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0302017

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H]2CC[C@@]3(C)C=CC(=O)C(C)=C3[C@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10+,13+,15+/m1/s1

> <INCHI_KEY>
XJHDMGJURBVLLE-OMSPQPPYSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.306

> <EXACT_MASS>
246.12559444

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.46439704748918

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aS,5aS,9bS)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione

> <JCHEM_LOGP>
2.6011767110000004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.0724997274601344

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
68.83239999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
β-santonin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       4.123   1.174   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.395  -0.183   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.207  -1.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.746  -1.444   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.740  -0.268   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.166  -0.850   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.475  -0.039   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.053  -2.386   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.229  -3.380   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.557  -2.753   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.829  -4.110   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.290  -4.158   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.479  -2.849   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.751  -4.206   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.939  -2.897   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.128  -1.588   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.856  -0.231   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.045   1.078   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    3   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    2   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
b-Santonin	Generator
Β-santonin	Generator

Chemical Formula

C₁₅H₁₈O₃

Average Mass

246.3060 Da

Monoisotopic Mass

246.12559 Da

IUPAC Name

(3R,3aS,5aS,9bS)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione

Traditional Name

β-santonin

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H]2CC[C@@]3(C)C=CC(=O)C(C)=C3[C@H]2OC1=O

InChI Identifier

InChI=1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10+,13+,15+/m1/s1

InChI Key

XJHDMGJURBVLLE-OMSPQPPYSA-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
Artemisia caerulescens	LOTUS Database	35616633
Artemisia schrenkiana	LOTUS Database	35616633
Artemisia sericea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

santonin (CHEBI:28356 )
Eudesmane sesquiterpenoids (C09545 )
Eudesmanes (C09545 )
Eudesmane sesquiterpenoids (LMPR0103190004 )

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	2.6	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.83 m³·mol⁻¹	ChemAxon
Polarizability	26.46 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

C00003365

Chemspider ID

207478

KEGG Compound ID

C09545

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

237619

PDB ID

Not Available

ChEBI ID

28356

Good Scents ID

Not Available

References

General References

Sahu N, Meena S, Shukla V, Chaturvedi P, Kumar B, Datta D, Arya KR: Extraction, fractionation and re-fractionation of Artemisia nilagirica for anticancer activity and HPLC-ESI-QTOF-MS/MS determination. J Ethnopharmacol. 2018 Mar 1;213:72-80. doi: 10.1016/j.jep.2017.10.029. [PubMed:29109061 ]
LOTUS database [Link]

Showing NP-Card for β-santonin (NP0302017)

MOL for NP0302017 (β-santonin)

3D MOL for NP0302017 (β-santonin)

3D SDF for NP0302017 (β-santonin)

3D-SDF for NP0302017 (β-santonin)

PDB for NP0302017 (β-santonin)

3D PDB for NP0302017 (β-santonin)

SMILES for NP0302017 (β-santonin)

INCHI for NP0302017 (β-santonin)

Structure for NP0302017 (β-santonin)

3D Structure for NP0302017 (β-santonin)