NP-MRD: Showing NP-Card for 7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione (NP0219364)

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Record Information

Version

2.0

Created at

2022-09-05 20:19:48 UTC

Updated at

2022-09-05 20:19:48 UTC

NP-MRD ID

NP0219364

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

Description

7-(Furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]Icosane-5,15,20-trione 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. 7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione is found in Citrus hanaju. 7-(Furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]Icosane-5,15,20-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004261504172D          

 45 51  0  0  0  0            999 V2000
    5.2964    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7219    1.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2725    2.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270    0.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5316    0.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3143   -0.1488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9571   -0.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1360   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076   -1.1050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1040   -1.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9288   -1.8471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3252   -2.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500   -2.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5463   -3.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8968   -3.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2932   -3.9992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0720   -3.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6436   -3.9622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6756   -2.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8508   -2.5152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6866    0.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3681   -0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474    1.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3999    1.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917    1.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    0.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2508    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784    0.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176   -0.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8094   -0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2619   -0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0012   -0.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537   -0.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    0.2470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1670    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3804    1.6469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9752    1.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7835    1.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1929   -1.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729   -1.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1830   -2.4878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5997   -2.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5936   -1.4020    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  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 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
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 27 40  1  0  0  0  0
 32 40  1  0  0  0  0
 38 40  1  0  0  0  0
 34 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 41 45  1  0  0  0  0
M  END


  Mrv1533004261504172D          

 45 51  0  0  0  0            999 V2000
    5.2964    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7219    1.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2725    2.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270    0.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5316    0.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3143   -0.1488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9571   -0.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1360   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076   -1.1050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1040   -1.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9288   -1.8471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3252   -2.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500   -2.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5463   -3.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8968   -3.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2932   -3.9992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0720   -3.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6436   -3.9622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6756   -2.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8508   -2.5152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6866    0.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3681   -0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474    1.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3999    1.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917    1.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    0.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2508    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784    0.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176   -0.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8094   -0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2619   -0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0012   -0.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537   -0.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    0.2470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1670    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3804    1.6469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9752    1.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7835    1.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1929   -1.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729   -1.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1830   -2.4878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5997   -2.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5936   -1.4020    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  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 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
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 27 40  1  0  0  0  0
 32 40  1  0  0  0  0
 38 40  1  0  0  0  0
 34 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 41 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219364

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC3C4(C)C(CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1)C(C)(C)OC(=O)CC4OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C32H42O13/c1-28(2)17-10-18(34)31(5)16(6-8-29(3)24(14-7-9-40-13-14)43-26(39)25-32(29,31)45-25)30(17,4)19(11-20(35)44-28)42-27-23(38)22(37)21(36)15(12-33)41-27/h7,9,13,15-17,19,21-25,27,33,36-38H,6,8,10-12H2,1-5H3

> <INCHI_KEY>
NHGZHAZTFBKTSU-UHFFFAOYSA-N

> <FORMULA>
C32H42O13

> <MOLECULAR_WEIGHT>
634.675

> <EXACT_MASS>
634.262541412

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
63.59384623602759

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

> <ALOGPS_LOGP>
1.32

> <JCHEM_LOGP>
0.8054230796666635

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200070864990945

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210528683902748

> <JCHEM_PKA_STRONGEST_BASIC>
-2.859077265875839

> <JCHEM_POLAR_SURFACE_AREA>
194.72000000000003

> <JCHEM_REFRACTIVITY>
148.86789999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       9.887   3.641   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.814   2.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.975   3.828   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.130   1.737   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.326   0.209   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      11.787  -0.278   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.253  -0.896   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.720  -0.747   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.921  -2.063   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.661  -3.413   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.200  -3.448   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.940  -4.798   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.480  -4.833   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.220  -6.183   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.141  -6.115   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.881  -7.465   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.601  -6.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.801  -7.396   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.861  -4.729   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.321  -4.695   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.882   0.545   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.287  -0.876   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.368   2.006   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.346   3.158   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.838   2.849   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.816   4.001   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.351   1.388   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.201   2.921   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.373   0.236   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.886  -1.225   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.378  -1.534   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.356  -0.382   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.869  -1.843   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.847  -0.691   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.175   0.461   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.312   1.922   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.710   3.074   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.820   2.231   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.329   2.540   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.842   1.079   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.360  -2.152   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.256  -3.405   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       0.342  -4.644   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -1.119  -4.157   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -1.108  -2.617   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   23                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22   23   29                                             
CONECT   22   21                                                            
CONECT   23   21    2   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   40                                             
CONECT   28   27                                                            
CONECT   29   27   21   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34   40                                             
CONECT   33   32                                                            
CONECT   34   32   35   41                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38   40                                                       
CONECT   40   39   27   32   38                                             
CONECT   41   34   42   45                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   41                                                       
MASTER        0    0    0    0    0    0    0    0   45    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₂O₁₃

Average Mass

634.6750 Da

Monoisotopic Mass

634.26254 Da

IUPAC Name

7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

Traditional Name

7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

CAS Registry Number

Not Available

SMILES

CC12CCC3C4(C)C(CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1)C(C)(C)OC(=O)CC4OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C32H42O13/c1-28(2)17-10-18(34)31(5)16(6-8-29(3)24(14-7-9-40-13-14)43-26(39)25-32(29,31)45-25)30(17,4)19(11-20(35)44-28)42-27-23(38)22(37)21(36)15(12-33)41-27/h7,9,13,15-17,19,21-25,27,33,36-38H,6,8,10-12H2,1-5H3

InChI Key

NHGZHAZTFBKTSU-UHFFFAOYSA-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
Citrus hanaju	LOTUS Database	35616633

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

Limonoid skeleton
Naphthopyran
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Naphthalene
Caprolactone
1,4-dioxepane
Delta_valerolactone
Delta valerolactone
Dioxepane
Oxepane
Dicarboxylic acid or derivatives
Monosaccharide
Pyran
Oxane
Heteroaromatic compound
Furan
Ketone
Carboxylic acid ester
Secondary alcohol
Lactone
Acetal
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Organoheterocyclic compound
Oxirane
Ether
Polyol
Alcohol
Organic oxide
Primary alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	1.32	ALOGPS
logP	0.81	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	194.72 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	148.87 m³·mol⁻¹	ChemAxon
Polarizability	63.59 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione (NP0219364)

MOL for NP0219364 (7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

3D MOL for NP0219364 (7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

3D SDF for NP0219364 (7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

3D-SDF for NP0219364 (7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

PDB for NP0219364 (7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

3D PDB for NP0219364 (7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

SMILES for NP0219364 (7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

INCHI for NP0219364 (7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

Structure for NP0219364 (7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

3D Structure for NP0219364 (7-(furan-3-yl)-1,8,12,17,17-pentamethyl-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)