NP-MRD: Showing NP-Card for (+)-Granatumin F (NP0081607)

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Record Information

Version

2.0

Created at

2022-04-29 02:37:03 UTC

Updated at

2022-04-29 02:37:03 UTC

NP-MRD ID

NP0081607

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Granatumin F

Description

Methyl (2R)-2-(acetyloxy)-2-[(1R,2S,4S,5S,6R,11R,12S,13S,14R,15R,17S,18S)-4,14-bis(acetyloxy)-6-(furan-3-yl)-2,11,12,17-tetrahydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadec-9-en-18-yl]acetate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. (+)-Granatumin F is found in Xylocarpus granatum . Based on a literature review very few articles have been published on methyl (2R)-2-(acetyloxy)-2-[(1R,2S,4S,5S,6R,11R,12S,13S,14R,15R,17S,18S)-4,14-bis(acetyloxy)-6-(furan-3-yl)-2,11,12,17-tetrahydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadec-9-en-18-yl]acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204372D          

 48 53  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292204372D          

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   -0.7079    0.4403    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3425    0.9675    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1163    0.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2556   -0.1317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509    1.2087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5248    0.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2032    1.7806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8378    2.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6117    2.0218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6986    3.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3729    0.5378    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2466    0.5415    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7672   -0.0985    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5817    0.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1023   -0.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9169   -0.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4374   -1.1169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2109    0.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903    0.9339    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8757    0.8031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3552    1.4432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5406    1.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6492    2.2140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1286    2.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140    2.7232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4226    3.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1697    1.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843    1.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5335    2.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0513    3.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8221    2.7440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7807    1.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4571   -0.9050    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6071   -0.9726    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3706   -0.2012    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2100    0.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1867   -0.0803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2097   -1.1689    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5459   -1.9222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0616   -2.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7590   -2.5046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979   -3.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9508   -1.5659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2869   -0.7392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7772    1.2199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3341    1.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4184   -0.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  2 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  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
 22 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 21 28  1  6  0  0  0
 20 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 33  2  0  0  0  0
 14 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 12 36  1  0  0  0  0
 36 37  1  0  0  0  0
  1 37  1  0  0  0  0
 36 38  1  6  0  0  0
 35 39  1  0  0  0  0
  1 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 34 44  1  1  0  0  0
 14 45  1  6  0  0  0
 13 46  1  6  0  0  0
 12 47  1  6  0  0  0
  1 48  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0081607

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H](OC(C)=O)[C@H]1[C@@]2(C)C[C@]3(O)[C@H]([C@H]2OC(C)=O)[C@H](O)[C@]2(O)C4=CC(=O)O[C@@H](C5=COC=C5)[C@]4(C)[C@H](C[C@]2(O)[C@]13C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H40O15/c1-14(34)45-19-11-32(41)30(6)23(22(27(39)43-7)46-15(2)35)28(4)13-31(30,40)21(26(28)47-16(3)36)24(38)33(32,42)18-10-20(37)48-25(29(18,19)5)17-8-9-44-12-17/h8-10,12,19,21-26,38,40-42H,11,13H2,1-7H3/t19-,21-,22+,23-,24-,25-,26+,28+,29-,30+,31-,32-,33+/m0/s1

> <INCHI_KEY>
XXWTYPBCQPFLFB-HZEHRPOGSA-N

> <FORMULA>
C33H40O15

> <MOLECULAR_WEIGHT>
676.668

> <EXACT_MASS>
676.236720588

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
64.10526510319863

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2R)-2-(acetyloxy)-2-[(1R,2S,4S,5S,6R,11R,12S,13S,14R,15R,17S,18S)-4,14-bis(acetyloxy)-6-(furan-3-yl)-2,11,12,17-tetrahydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0^{2,11}.0^{5,10}.0^{13,17}]octadec-9-en-18-yl]acetate

> <ALOGPS_LOGP>
1.04

> <JCHEM_LOGP>
-1.3256331046666658

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.465510294934035

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.089814349713102

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8888575557656613

> <JCHEM_POLAR_SURFACE_AREA>
225.55999999999997

> <JCHEM_REFRACTIVITY>
155.92970000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(R)-(methyl (acetyloxy)[(1R,2S,4S,5S,6R,11R,12S,13S,14R,15R,17S,18S)-4,14-bis(acetyloxy)-6-(furan-3-yl)-2,11,12,17-tetrahydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0^{2,11}.0^{5,10}.0^{13,17}]octadec-9-en-18-yl]acetate)

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.174  -0.733   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.321   0.822   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.506   1.806   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.950   1.272   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.210  -0.246   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -5.135   2.256   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -6.580   1.722   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.246   3.324   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.431   4.308   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.875   3.774   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.171   5.826   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.696   1.004   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.327   1.011   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.299  -0.184   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.819   0.060   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.791  -1.134   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.311  -0.890   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.283  -2.085   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.860   0.549   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.889   1.743   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.368   1.499   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.396   2.694   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.876   2.450   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.945   4.133   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.973   5.328   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.453   5.083   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.522   6.766   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.917   2.938   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.437   3.182   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.596   4.472   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.562   5.671   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.001   5.122   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.924   3.584   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.720  -1.689   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.133  -1.815   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.692  -0.376   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.392   0.805   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.215  -0.150   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -0.391  -2.182   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.019  -3.588   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -0.115  -4.835   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.417  -4.675   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -0.743  -6.241   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       3.642  -2.923   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       4.269  -1.380   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       1.451   2.277   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       0.624   2.542   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -2.648  -1.180   0.000  0.00  0.00           C+0
CONECT    1    2   37   39   48                                             
CONECT    2    1    3   12                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    2   13   36   47                                             
CONECT   13   12   14   23   46                                             
CONECT   14   13   15   34   45                                             
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   15   22   28                                             
CONECT   22   21   23   24                                                  
CONECT   23   22   13                                                       
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   21                                                            
CONECT   29   20   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   29                                                       
CONECT   34   14   35   44                                                  
CONECT   35   34   36   39                                                  
CONECT   36   35   12   37   38                                             
CONECT   37   36    1                                                       
CONECT   38   36                                                            
CONECT   39   35    1   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   34                                                            
CONECT   45   14                                                            
CONECT   46   13                                                            
CONECT   47   12                                                            
CONECT   48    1                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  106    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2R)-2-(acetyloxy)-2-[(1R,2S,4S,5S,6R,11R,12S,13S,14R,15R,17S,18S)-4,14-bis(acetyloxy)-6-(furan-3-yl)-2,11,12,17-tetrahydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0,.0,.0,]octadec-9-en-18-yl]acetic acid	Generator

Chemical Formula

C₃₃H₄₀O₁₅

Average Mass

676.6680 Da

Monoisotopic Mass

676.23672 Da

IUPAC Name

methyl (2R)-2-(acetyloxy)-2-[(1R,2S,4S,5S,6R,11R,12S,13S,14R,15R,17S,18S)-4,14-bis(acetyloxy)-6-(furan-3-yl)-2,11,12,17-tetrahydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0^{2,11}.0^{5,10}.0^{13,17}]octadec-9-en-18-yl]acetate

Traditional Name

(R)-(methyl (acetyloxy)[(1R,2S,4S,5S,6R,11R,12S,13S,14R,15R,17S,18S)-4,14-bis(acetyloxy)-6-(furan-3-yl)-2,11,12,17-tetrahydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0^{2,11}.0^{5,10}.0^{13,17}]octadec-9-en-18-yl]acetate)

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H](OC(C)=O)[C@H]1[C@@]2(C)C[C@]3(O)[C@H]([C@H]2OC(C)=O)[C@H](O)[C@]2(O)C4=CC(=O)O[C@@H](C5=COC=C5)[C@]4(C)[C@H](C[C@]2(O)[C@]13C)OC(C)=O

InChI Identifier

InChI=1S/C33H40O15/c1-14(34)45-19-11-32(41)30(6)23(22(27(39)43-7)46-15(2)35)28(4)13-31(30,40)21(26(28)47-16(3)36)24(38)33(32,42)18-10-20(37)48-25(29(18,19)5)17-8-9-44-12-17/h8-10,12,19,21-26,38,40-42H,11,13H2,1-7H3/t19-,21-,22+,23-,24-,25-,26+,28+,29-,30+,31-,32-,33+/m0/s1

InChI Key

XXWTYPBCQPFLFB-HZEHRPOGSA-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
Xylocarpus granatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Mexicanolide
Limonoid skeleton
Steroid lactone
11-hydroxysteroid
11-beta-hydroxysteroid
2-oxosteroid
Oxosteroid
Hydroxysteroid
Steroid
3-oxasteroid
Pentacarboxylic acid or derivatives
Naphthopyran
Naphthalene
Dihydropyranone
Pyran
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Furan
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.04	ALOGPS
logP	-1.3	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.09	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	225.56 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	155.93 m³·mol⁻¹	ChemAxon
Polarizability	64.11 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162938833

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Granatumin F (NP0081607)

MOL for NP0081607 ((+)-Granatumin F)

3D MOL for NP0081607 ((+)-Granatumin F)

3D SDF for NP0081607 ((+)-Granatumin F)

3D-SDF for NP0081607 ((+)-Granatumin F)

PDB for NP0081607 ((+)-Granatumin F)

3D PDB for NP0081607 ((+)-Granatumin F)

SMILES for NP0081607 ((+)-Granatumin F)

INCHI for NP0081607 ((+)-Granatumin F)

Structure for NP0081607 ((+)-Granatumin F)

3D Structure for NP0081607 ((+)-Granatumin F)