NP-MRD: Showing NP-Card for methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate (NP0247257)

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Record Information

Version

1.0

Created at

2022-09-07 09:02:36 UTC

Updated at

2022-09-07 09:02:36 UTC

NP-MRD ID

NP0247257

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate

Description

Methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]Octadeca-12,16-diene-15-carboxylate 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. methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate is found in Trichilia pallida. Methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]Octadeca-12,16-diene-15-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 04121518192D          

 45 50  0  0  0  0            999 V2000
    2.8086    4.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0889    3.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5571    2.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399    2.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449    3.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4646    3.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2131    2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4934    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3055    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373    2.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495    1.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1813    2.5951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3323    1.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5858    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1176    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2063   -1.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2038   -0.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2019   -1.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9153   -2.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6782   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4267   -1.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8025   -1.3344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -0.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3547   -0.5998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0923    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1370    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4742    2.3670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    2.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400    2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6017    1.7357    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  1  0  0  0  0
  3  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  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 14 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
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 39 43  1  0  0  0  0
 38 44  1  0  0  0  0
  8 44  1  0  0  0  0
 34 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END


  Mrv0541 04121518192D          

 45 50  0  0  0  0            999 V2000
    2.8086    4.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0889    3.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5571    2.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399    2.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449    3.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4646    3.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2131    2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4934    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3055    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373    2.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495    1.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1813    2.5951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3323    1.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5858    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1176    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2063   -1.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2038   -0.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2019   -1.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9153   -2.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6782   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4267   -1.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8025   -1.3344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -0.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3547   -0.5998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0923    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1370    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4742    2.3670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    2.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400    2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6017    1.7357    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  1  0  0  0  0
  3  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  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 14 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
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 39 43  1  0  0  0  0
 38 44  1  0  0  0  0
  8 44  1  0  0  0  0
 34 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247257

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)OC1C(OC(C)=O)C2C3(C)C=CC(=O)C(C)(C(=O)OC)C3=C(O)C(=O)C2(C)C23OC2CC(C2=COC=C2)C13C

> <INCHI_IDENTIFIER>
InChI=1S/C34H40O11/c1-9-16(2)28(39)44-27-23(43-17(3)35)25-30(4)12-10-20(36)31(5,29(40)41-8)24(30)22(37)26(38)33(25,7)34-21(45-34)14-19(32(27,34)6)18-11-13-42-15-18/h10-13,15-16,19,21,23,25,27,37H,9,14H2,1-8H3

> <INCHI_KEY>
WCANMRDCBZNWSJ-UHFFFAOYSA-N

> <FORMULA>
C34H40O11

> <MOLECULAR_WEIGHT>
624.683

> <EXACT_MASS>
624.257062108

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
63.21920258573482

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
4.131808083666666

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.973111729958494

> <JCHEM_PKA_STRONGEST_BASIC>
-2.85813049061275

> <JCHEM_POLAR_SURFACE_AREA>
158.94

> <JCHEM_REFRACTIVITY>
157.99299999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       5.243   8.012   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.766   6.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.773   5.386   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.048   4.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.257   5.657   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.734   7.106   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.264   4.480   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.788   3.032   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.304   2.761   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.296   3.938   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.812   3.667   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.805   4.844   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.087   2.803   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.827   1.312   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.343   1.041   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.820   2.489   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.336   2.218   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.852   1.947   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.375   0.499   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.891   0.228   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.382  -0.678   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.852  -2.124   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.714  -1.452   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.049  -0.685   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.710  -2.992   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.042  -3.765   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.866  -0.407   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.873  -1.585   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.397  -3.033   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.357  -1.314   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.365  -2.491   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.834   0.135   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.254  -1.292   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.318   0.406   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.529  -1.120   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.102  -0.539   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.172   0.325   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.256   1.804   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.689   3.020   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.229   2.970   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -2.752   4.418   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -1.536   5.364   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.261   4.499   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.795   1.854   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       1.123   3.240   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   44                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   32                                                  
CONECT   15   14   16   17   27                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   27                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   21   15   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   14   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35   36   44                                             
CONECT   35   34   36                                                       
CONECT   36   35   34   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   44                                                  
CONECT   39   38   40   43                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   39                                                       
CONECT   44   38    8   34   45                                             
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Value	Source
Methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0,.0,.0,]octadeca-12,16-diene-15-carboxylic acid	Generator
Methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylic acid	Generator

Chemical Formula

C₃₄H₄₀O₁₁

Average Mass

624.6830 Da

Monoisotopic Mass

624.25706 Da

IUPAC Name

methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate

Traditional Name

methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)OC1C(OC(C)=O)C2C3(C)C=CC(=O)C(C)(C(=O)OC)C3=C(O)C(=O)C2(C)C23OC2CC(C2=COC=C2)C13C

InChI Identifier

InChI=1S/C34H40O11/c1-9-16(2)28(39)44-27-23(43-17(3)35)25-30(4)12-10-20(36)31(5,29(40)41-8)24(30)22(37)26(38)33(25,7)34-21(45-34)14-19(32(27,34)6)18-11-13-42-15-18/h10-13,15-16,19,21,23,25,27,37H,9,14H2,1-8H3

InChI Key

WCANMRDCBZNWSJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trichilia pallida	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
17-furanylsteroid skeleton
Steroid ester
3-oxo-delta-1-steroid
Hydroxysteroid
Oxosteroid
7-hydroxysteroid
7-oxosteroid
Delta-1-steroid
Steroid
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Fatty acid ester
Cyclohexenone
Fatty acyl
Pyran
Oxane
Heteroaromatic compound
Furan
Methyl ester
Ketone
Carboxylic acid ester
Cyclic ketone
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Enol
Oxirane
Ether
Organoheterocyclic compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	3.78	ALOGPS
logP	4.13	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.97	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	158.94 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	157.99 m³·mol⁻¹	ChemAxon
Polarizability	63.22 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

73197344

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate (NP0247257)

MOL for NP0247257 (methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D MOL for NP0247257 (methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D SDF for NP0247257 (methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D-SDF for NP0247257 (methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

PDB for NP0247257 (methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D PDB for NP0247257 (methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

SMILES for NP0247257 (methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

INCHI for NP0247257 (methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

Structure for NP0247257 (methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D Structure for NP0247257 (methyl 9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-14,18-dioxo-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)