NP-MRD: Showing NP-Card for Inujaponin C (NP0044107)

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Record Information

Version

1.0

Created at

2021-11-12 23:50:25 UTC

Updated at

2021-11-26 17:45:30 UTC

NP-MRD ID

NP0044107

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Inujaponin C

Description

It was first documented in 2016 (PMID: 27452450).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 47  0  0  0  0  0  0  0  0999 V2000
    2.5408    1.9515   -0.8246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4184    1.2778    0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294    1.0879    1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315    0.4614    2.2018 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8685    1.5887    0.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1412    0.7261    0.7900 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0227    1.2316   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2578    0.8136    0.6116 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4566    1.3790   -0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4203    2.3484   -1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6377    0.9808    0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5592    0.0021    1.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6006   -1.1098    1.3379 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2414   -2.1673    0.6756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3405   -0.6765    0.6158 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4811   -1.1744   -0.8290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1688   -1.3728    1.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1608   -0.7610    0.9398 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6948   -1.3129   -0.2478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8672   -2.0434   -0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629   -2.5926   -1.6262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5177   -2.2439    0.7399 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583    2.1061   -1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4681    2.3585   -1.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9273    2.5972    0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9842    1.1876    1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1243    0.8228   -1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0755    2.3286   -0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2073    1.1633    1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4307    1.8459   -2.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5761    3.0620   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3475    2.9935   -1.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5875    1.3282    0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5673   -0.4050    1.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2893    0.5572    2.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3195   -1.5357    2.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0400   -1.8072    0.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1694   -2.0158   -0.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8037   -0.3803   -1.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844   -1.5267   -1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3376   -1.4559    2.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1604   -2.4144    0.8616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8598   -1.0121    1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8938   -3.5784   -1.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4409   -2.7455   -1.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1964   -1.8680   -2.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  6
 15  8  1  0
  8  7  1  0
  7  6  1  0
  6  2  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  2  1  2  3
  6 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 17  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 17 15  1  0
 13 15  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
  8 29  1  1
  7 27  1  0
  7 28  1  0
  6 26  1  1
  5 25  1  0
  1 23  1  0
  1 24  1  0
 18 43  1  1
 21 44  1  0
 21 45  1  0
 21 46  1  0
 17 41  1  0
 17 42  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  1
 14 37  1  0
M  END


  Mrv1652311132100502D          

 23 24  0  0  1  0            999 V2000
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  2  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
   -2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  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
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  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
    1.4289   -0.8250    0.0000 H   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  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  6 10  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 11 16  1  0  0  0  0
  2 16  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  1  0  0  0
  3 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044107

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@H]([C@@H](C[C@@]1(C)[C@H](O)CC=C2C)OC(C)=O)C(=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O5/c1-9-5-6-15(19)17(4)8-14(22-11(3)18)12(7-13(9)17)10(2)16(20)21/h5,12-15,19H,2,6-8H2,1,3-4H3,(H,20,21)/t12-,13+,14-,15-,17-/m1/s1

> <INCHI_KEY>
WRSFGXCUJBXGHX-JRBZFYFNSA-N

> <FORMULA>
C17H24O5

> <MOLECULAR_WEIGHT>
308.374

> <EXACT_MASS>
308.162373873

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
32.68648379471517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2R,3R,4aR,5R,8aS)-3-(acetyloxy)-5-hydroxy-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
1.6125515370000005

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.625868450998968

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.583801403914137

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9624456845226765

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
81.42909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2R,3R,4aR,5R,8aS)-3-(acetyloxy)-5-hydroxy-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   16   21                                             
CONECT    3    2    4   17   23                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6                                                            
CONECT   11    5   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11    2                                                       
CONECT   17    3   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    2   22                                                  
CONECT   22   21                                                            
CONECT   23    3                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₄O₅

Average Mass

308.3740 Da

Monoisotopic Mass

308.16237 Da

IUPAC Name

2-[(2R,3R,4aR,5R,8aS)-3-(acetyloxy)-5-hydroxy-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl]prop-2-enoic acid

Traditional Name

2-[(2R,3R,4aR,5R,8aS)-3-(acetyloxy)-5-hydroxy-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@H]([C@@H](C[C@@]1(C)[C@H](O)CC=C2C)OC(C)=O)C(=C)C(O)=O

InChI Identifier

InChI=1S/C17H24O5/c1-9-5-6-15(19)17(4)8-14(22-11(3)18)12(7-13(9)17)10(2)16(20)21/h5,12-15,19H,2,6-8H2,1,3-4H3,(H,20,21)/t12-,13+,14-,15-,17-/m1/s1

InChI Key

WRSFGXCUJBXGHX-JRBZFYFNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Inula japonica

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	2.42	ALOGPS
logP	1.61	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.43 m³·mol⁻¹	ChemAxon
Polarizability	32.69 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

Not Available

References

General References

Wu XD, Ding LF, Tu WC, Yang H, Su J, Peng LY, Li Y, Zhao QS: Bioactive sesquiterpenoids from the flowers of Inula japonica. Phytochemistry. 2016 Sep;129:68-76. doi: 10.1016/j.phytochem.2016.07.008. Epub 2016 Jul 21. [PubMed:27452450 ]

Showing NP-Card for Inujaponin C (NP0044107)

MOL for NP0044107 (Inujaponin C)

3D MOL for NP0044107 (Inujaponin C)

3D SDF for NP0044107 (Inujaponin C)

3D-SDF for NP0044107 (Inujaponin C)

PDB for NP0044107 (Inujaponin C)

3D PDB for NP0044107 (Inujaponin C)

SMILES for NP0044107 (Inujaponin C)

INCHI for NP0044107 (Inujaponin C)

Structure for NP0044107 (Inujaponin C)

3D Structure for NP0044107 (Inujaponin C)