NP-MRD: Showing NP-Card for Anisatin (NP0046756)

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Record Information

Version

2.0

Created at

2022-03-17 20:29:03 UTC

Updated at

2022-03-17 20:29:03 UTC

NP-MRD ID

NP0046756

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Anisatin

Description

Anisatin belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Anisatin is found in Illicium anisatum , Illicium fargesii, Illicium floridanum, Illicium majus, Illicium oligandrum, Illicium religiosum and Illicium simonsii. Anisatin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
    3.4392    0.1923   -0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466   -0.2287    0.6573 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0721   -1.7369    0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6264   -1.9323   -0.0005 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1926   -3.0940    0.6818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0142   -0.7028    0.5056 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0232   -0.8120    1.9241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9572    0.3851    0.1923 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4876    1.5408    1.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8379    1.9643    0.5334 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6174    2.5618   -0.7311 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0644    1.7934   -1.6574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628    1.9040   -2.8900 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716    0.8308   -1.2016 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1553   -0.1888   -2.1419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8748    0.9202    0.4128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8944    1.4102   -0.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6019    0.9163    1.6274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4214   -0.4608    0.1113 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9518   -1.1328   -1.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2752   -2.2850   -0.3025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3045   -1.4551    0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8495   -1.4876    1.9049 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3215   -0.3550    0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3672   -0.1901   -1.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902    1.2571   -0.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4510   -0.0033    1.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3050   -2.2798    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7131   -2.1138   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5123   -2.1522   -1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6086   -3.0941    1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8389   -1.1425    2.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4209    1.1606    2.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1916    2.3744    0.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021    2.7921    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0636    1.3735   -1.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3884    0.2646   -3.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0501    2.5144   -0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8486    0.8521   -0.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367    1.2941   -1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5426    0.6898    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9046   -0.7005   -1.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2716   -1.4440   -1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  1
  6 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 19 16  1  0
 16 17  1  0
 16 18  1  1
 16 10  1  0
 10  9  1  0
  8  9  1  1
  8 14  1  0
 14 15  1  0
 14 12  1  0
 12 13  2  0
 12 11  1  0
  8  2  1  0
  8  6  1  0
 19 22  1  1
 11 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  1
  3 28  1  0
  3 29  1  0
  4 30  1  6
  5 31  1  0
  7 32  1  0
 20 42  1  0
 20 43  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 10 35  1  1
  9 33  1  0
  9 34  1  0
 14 36  1  1
 15 37  1  0
M  END


  Mrv0541 02241220502D          

 23 26  0  0  1  0            999 V2000
   -0.9514   -1.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1945   -0.9938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4931   -1.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375   -0.9328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8502   -0.1417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0273   -0.1600    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0084    0.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    1.3293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8558    1.3286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3018    0.6038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8680    1.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4609    0.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8947    0.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9135   -0.7821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761    2.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5437    1.7748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8545    1.3702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3240    0.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    0.7018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9073   -0.0822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3539   -0.7698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6662   -0.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9268   -1.1546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  2  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 13  1  6  0  0  0
 13 14  2  0  0  0  0
  9 15  1  1  0  0  0
  9 16  1  6  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  1  0  0  0
  5 22  1  6  0  0  0
  4 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0046756

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H](O)[C@]2(O)[C@]3(COC3=O)[C@@](C)(O)[C@H]3C[C@@]12[C@@H](O)C(=O)O3

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O8/c1-6-3-7(16)15(21)13(6)4-8(23-10(18)9(13)17)12(2,20)14(15)5-22-11(14)19/h6-9,16-17,20-21H,3-5H2,1-2H3/t6-,7-,8?,9+,12+,13+,14+,15-/m1/s1

> <INCHI_KEY>
GEVWHIDSUOMVRI-QHRGTXDDSA-N

> <FORMULA>
C15H20O8

> <MOLECULAR_WEIGHT>
328.3145

> <EXACT_MASS>
328.115817616

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.368209685560657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2'R,3S,4'R,5'R,7'R,8'R,11'R)-4',5',7',11'-tetrahydroxy-2',7'-dimethyl-9'-oxaspiro[oxetane-3,6'-tricyclo[6.3.1.0¹,⁵]dodecane]-4,10'-dione

> <ALOGPS_LOGP>
-0.89

> <JCHEM_LOGP>
-2.057976409

> <ALOGPS_LOGS>
-0.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.726228295196805

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.01498940895532

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2698134866479807

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
71.9123

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.85e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
anisatin

> <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      -1.776  -2.443   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.363  -1.855   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.920  -2.703   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.123  -1.741   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.587  -0.265   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.051  -0.299   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.016   1.078   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.001   2.481   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.597   2.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.430   1.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.487   2.234   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.594   1.177   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.537   0.070   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.572  -1.460   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.635   4.010   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.882   3.313   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.595   2.558   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.471   1.247   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001   1.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.694  -0.153   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.527  -1.437   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.110  -0.414   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.597  -2.155   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6   10   22                                             
CONECT    6    5    2    7   20                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   15   16                                             
CONECT   10    9    5   11   13                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   10   14                                                  
CONECT   14   13                                                            
CONECT   15    9                                                            
CONECT   16    9                                                            
CONECT   17    8   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    6   21                                                  
CONECT   21   20                                                            
CONECT   22    5                                                            
CONECT   23    4                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₈

Average Mass

328.3145 Da

Monoisotopic Mass

328.11582 Da

IUPAC Name

(1'S,2'R,3S,4'R,5'R,7'R,8'R,11'R)-4',5',7',11'-tetrahydroxy-2',7'-dimethyl-9'-oxaspiro[oxetane-3,6'-tricyclo[6.3.1.0¹,⁵]dodecane]-4,10'-dione

Traditional Name

anisatin

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H](O)[C@]2(O)[C@]3(COC3=O)[C@@](C)(O)[C@H]3C[C@@]12[C@@H](O)C(=O)O3

InChI Identifier

InChI=1S/C15H20O8/c1-6-3-7(16)15(21)13(6)4-8(23-10(18)9(13)17)12(2,20)14(15)5-22-11(14)19/h6-9,16-17,20-21H,3-5H2,1-2H3/t6-,7-,8?,9+,12+,13+,14+,15-/m1/s1

InChI Key

GEVWHIDSUOMVRI-QHRGTXDDSA-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
Illicium anisatum	Plant	KNApSAcK
Illicium fargesii	Plant	KNApSAcK
Illicium floridanum	LOTUS Database	35616633
Illicium majus	LOTUS Database	35616633
Illicium oligandrum	Plant	KNApSAcK
Illicium religiosum	Plant	KNApSAcK
Illicium simonsii	LOTUS Database	35616633
Illicium verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Prezizaane sesquiterpenoid
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Tertiary alcohol
Beta_propiolactone
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxetane
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

delta-lactone (CHEBI:2733 )
Sesquiterpenoids (C15) (C09294 )
Sesquiterpenes (C09294 )

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	-0.89	ALOGPS
logP	-2.1	ChemAxon
logS	-0.62	ALOGPS
pKa (Strongest Acidic)	12.01	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.91 m³·mol⁻¹	ChemAxon
Polarizability	30.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

FDB005800

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C09294

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Anisatin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

2733

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Anisatin (NP0046756)

MOL for NP0046756 (Anisatin)

3D MOL for NP0046756 (Anisatin)

3D SDF for NP0046756 (Anisatin)

3D-SDF for NP0046756 (Anisatin)

PDB for NP0046756 (Anisatin)

3D PDB for NP0046756 (Anisatin)

SMILES for NP0046756 (Anisatin)

INCHI for NP0046756 (Anisatin)

Structure for NP0046756 (Anisatin)

3D Structure for NP0046756 (Anisatin)