NP-MRD: Showing NP-Card for 2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate (NP0151816)

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Record Information

Version

2.0

Created at

2022-09-02 08:11:26 UTC

Updated at

2022-09-02 08:11:26 UTC

NP-MRD ID

NP0151816

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate

Description

2-(Acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]Hexadec-11-en-7-yl benzoate 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. 2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate is found in Melia azedarach. 2-(Acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]Hexadec-11-en-7-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241510522D          

 46 51  0  0  0  0            999 V2000
    3.6399   -0.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0118   -0.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1610   -1.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5329   -1.9588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9383   -1.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875   -2.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8647   -2.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7156   -1.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4928   -2.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2701   -2.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4193   -3.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1966   -3.6177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7912   -3.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3840   -4.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4271   -4.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2002   -4.1140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -3.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859   -4.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5350   -4.9459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3123   -5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9404   -4.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4615   -6.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6086   -3.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8830   -4.2507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2854   -3.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4676   -3.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184   -2.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0439   -2.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6416   -2.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4594   -3.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2262   -2.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1528   -1.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5742   -2.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1513   -2.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7490   -2.2294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3927   -1.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250   -1.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3436   -1.4419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9717   -0.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7490   -1.1835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8225   -0.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0452    0.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8961    0.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5241    1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3014    1.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4506    0.4393    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 13 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  0  0  0  0
  6 30  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 28 32  1  0  0  0  0
 27 33  1  0  0  0  0
 33 34  2  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
 33 37  1  0  0  0  0
  9 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 41 46  1  0  0  0  0
M  END


  Mrv1533004241510522D          

 46 51  0  0  0  0            999 V2000
    3.6399   -0.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0118   -0.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1610   -1.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5329   -1.9588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9383   -1.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875   -2.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8647   -2.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7156   -1.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4928   -2.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2701   -2.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4193   -3.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1966   -3.6177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7912   -3.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3840   -4.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4271   -4.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2002   -4.1140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -3.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859   -4.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5350   -4.9459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3123   -5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9404   -4.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4615   -6.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6086   -3.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8830   -4.2507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2854   -3.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4676   -3.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184   -2.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0439   -2.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6416   -2.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4594   -3.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2262   -2.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1528   -1.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5742   -2.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1513   -2.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7490   -2.2294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3927   -1.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250   -1.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3436   -1.4419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9717   -0.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7490   -1.1835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8225   -0.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0452    0.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8961    0.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5241    1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3014    1.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4506    0.4393    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 13 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  0  0  0  0
  6 30  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 28 32  1  0  0  0  0
 27 33  1  0  0  0  0
 33 34  2  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
 33 37  1  0  0  0  0
  9 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 41 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0151816

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1C2(C)C(OC3CC(C(C)=C23)C2=COC=C2)C(OC(C)=O)C2C(C)(C=O)C(O)CC(OC(=O)C3=CC=CC=C3)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C36H42O10/c1-19-23(22-12-13-43-17-22)14-24-29(19)36(5)25(15-28(40)42-6)35(4)27(46-33(41)21-10-8-7-9-11-21)16-26(39)34(3,18-37)31(35)30(32(36)45-24)44-20(2)38/h7-13,17-18,23-27,30-32,39H,14-16H2,1-6H3

> <INCHI_KEY>
PONWNFBYSMNLAS-UHFFFAOYSA-N

> <FORMULA>
C36H42O10

> <MOLECULAR_WEIGHT>
634.722

> <EXACT_MASS>
634.277797552

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
66.70257165016994

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
3.3923478103333355

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.452291429035984

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8594819105349183

> <JCHEM_POLAR_SURFACE_AREA>
138.57000000000002

> <JCHEM_REFRACTIVITY>
164.60609999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.794  -0.145   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.622  -1.143   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.900  -2.658   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.728  -3.656   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.351  -3.174   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.630  -4.689   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.081  -5.205   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.802  -3.690   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.253  -4.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.704  -4.722   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.983  -6.237   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.434  -6.753   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.810  -7.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.050  -8.575   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.997  -8.217   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.440  -7.679   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.359  -6.719   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.187  -7.718   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.465  -9.232   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.916  -9.749   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.089  -8.750   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.195 -11.263   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.736  -7.202   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.382  -7.935   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.266  -6.873   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.739  -6.670   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.461  -5.155   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.815  -4.422   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.931  -5.484   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.457  -5.687   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.022  -4.210   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.019  -2.896   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.072  -4.490   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.283  -5.223   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.398  -4.162   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -0.733  -2.772   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.793  -2.976   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.975  -2.692   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      11.147  -1.693   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      12.598  -2.209   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      10.869  -0.179   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.418   0.338   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.139   1.852   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      10.312   2.851   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      11.763   2.335   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      12.041   0.820   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8    9   17                                             
CONECT    8    7                                                            
CONECT    9    7   10   38                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   17                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   13    7   18                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29   32                                                  
CONECT   29   28   25   30                                                  
CONECT   30   29    6   23   31                                             
CONECT   31   30                                                            
CONECT   32   28                                                            
CONECT   33   27   34   37                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   33                                                       
CONECT   38    9   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   41                                                       
MASTER        0    0    0    0    0    0    0    0   46    0  102    0
END

View in JSmol

Synonyms

Value	Source
2-(Acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0,.0,]hexadec-11-en-7-yl benzoic acid	Generator
2-(Acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoic acid	Generator

Chemical Formula

C₃₆H₄₂O₁₀

Average Mass

634.7220 Da

Monoisotopic Mass

634.27780 Da

IUPAC Name

2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate

Traditional Name

2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate

CAS Registry Number

Not Available

SMILES

COC(=O)CC1C2(C)C(OC3CC(C(C)=C23)C2=COC=C2)C(OC(C)=O)C2C(C)(C=O)C(O)CC(OC(=O)C3=CC=CC=C3)C12C

InChI Identifier

InChI=1S/C36H42O10/c1-19-23(22-12-13-43-17-22)14-24-29(19)36(5)25(15-28(40)42-6)35(4)27(46-33(41)21-10-8-7-9-11-21)16-26(39)34(3,18-37)31(35)30(32(36)45-24)44-20(2)38/h7-13,17-18,23-27,30-32,39H,14-16H2,1-6H3

InChI Key

PONWNFBYSMNLAS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melia azedarach	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
Naphthofuran
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Methyl ester
Tetrahydrofuran
Cyclic alcohol
Heteroaromatic compound
Furan
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Ether
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aldehyde
Organooxygen compound
Alcohol
Organic oxygen 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	4.06	ALOGPS
logP	3.39	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	14.45	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	138.57 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	164.61 m³·mol⁻¹	ChemAxon
Polarizability	66.7 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

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 2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate (NP0151816)

MOL for NP0151816 (2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate)

3D MOL for NP0151816 (2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate)

3D SDF for NP0151816 (2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate)

3D-SDF for NP0151816 (2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate)

PDB for NP0151816 (2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate)

3D PDB for NP0151816 (2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate)

SMILES for NP0151816 (2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate)

INCHI for NP0151816 (2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate)

Structure for NP0151816 (2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate)

3D Structure for NP0151816 (2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl benzoate)