NP-MRD: Showing NP-Card for methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate (NP0227029)

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Record Information

Version

2.0

Created at

2022-09-06 06:14:38 UTC

Updated at

2022-09-06 06:14:38 UTC

NP-MRD ID

NP0227029

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate

Description

Methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]Nonadec-10-ene-17-carboxylate belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate is found in Brucea javanica. Methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]Nonadec-10-ene-17-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241505262D          

 48 53  0  0  0  0            999 V2000
   -0.5396    1.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0436    0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7753    1.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0982    1.7985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2713    0.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5553    0.0580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817   -0.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0811   -0.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5048   -1.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3238   -1.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681   -0.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6822   -1.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9734   -1.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2051   -0.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9139    0.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4367    0.9937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1456    1.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3315    1.8994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0403    2.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2262    2.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9350    3.5770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5632    3.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2720    4.0814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3773    3.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9001    3.8138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6684    2.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4825    2.2700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0998    0.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086    1.2613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769   -0.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2764    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7558   -0.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5891    0.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2032    1.3194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8138    1.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882    1.8132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0556   -2.0558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2321   -2.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7719   -2.6997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8865   -1.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687   -1.1664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4343   -1.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2521   -1.7117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1195   -2.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6225   -3.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3076   -3.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4403   -3.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811   -0.5706    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
  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
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 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  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 11 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  8 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  0  0  0  0
  9 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  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
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 40 48  1  0  0  0  0
  5 48  1  0  0  0  0
  8 48  1  0  0  0  0
M  END


  Mrv1533004241505262D          

 48 53  0  0  0  0            999 V2000
   -0.5396    1.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0436    0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7753    1.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0982    1.7985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2713    0.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5553    0.0580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817   -0.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0811   -0.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5048   -1.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3238   -1.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681   -0.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6822   -1.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9734   -1.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2051   -0.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9139    0.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4367    0.9937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1456    1.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3315    1.8994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0403    2.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2262    2.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9350    3.5770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5632    3.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2720    4.0814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3773    3.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9001    3.8138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6684    2.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4825    2.2700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0998    0.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086    1.2613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769   -0.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2764    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7558   -0.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5891    0.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2032    1.3194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8138    1.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882    1.8132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0556   -2.0558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2321   -2.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7719   -2.6997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8865   -1.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687   -1.1664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4343   -1.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2521   -1.7117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1195   -2.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6225   -3.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3076   -3.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4403   -3.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811   -0.5706    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
  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
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 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  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 11 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  8 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  0  0  0  0
  9 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  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
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 40 48  1  0  0  0  0
  5 48  1  0  0  0  0
  8 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227029

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C12OCC34C1C(OC(=O)CC(C)C)C(=O)OC3CC1C(C)C=C(OC3OC(CO)C(O)C(O)C3O)C(=O)C1(C)C4C(O)C2O

> <INCHI_IDENTIFIER>
InChI=1S/C32H44O16/c1-11(2)6-17(34)48-22-24-31-10-44-32(24,29(42)43-5)26(40)21(38)23(31)30(4)13(8-16(31)47-27(22)41)12(3)7-14(25(30)39)45-28-20(37)19(36)18(35)15(9-33)46-28/h7,11-13,15-16,18-24,26,28,33,35-38,40H,6,8-10H2,1-5H3

> <INCHI_KEY>
NLCZJLRVAIBIDP-UHFFFAOYSA-N

> <FORMULA>
C32H44O16

> <MOLECULAR_WEIGHT>
684.688

> <EXACT_MASS>
684.262935337

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
67.87955001804308

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate

> <ALOGPS_LOGP>
0.19

> <JCHEM_LOGP>
-1.6947432196666667

> <ALOGPS_LOGS>
-2.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.720321826829547

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.090679044328143

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092357098258

> <JCHEM_POLAR_SURFACE_AREA>
245.03999999999996

> <JCHEM_REFRACTIVITY>
156.82230000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate

> <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      -1.007   2.984   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.081   1.754   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.447   1.940   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.050   3.357   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.373   0.710   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.037   0.108   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.832  -1.254   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.885  -1.135   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.676  -2.542   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.204  -2.870   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.220  -1.719   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.740  -1.968   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.284  -3.409   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.716  -0.777   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.173   0.664   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.149   1.855   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.605   3.296   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.085   3.546   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.542   4.986   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.022   5.236   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.479   6.677   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.518   6.178   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.974   7.619   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.038   5.928   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.014   7.119   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.581   4.487   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.101   4.237   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.653   0.914   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.109   2.354   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.677  -0.278   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.116   1.157   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.144  -0.064   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.833   1.435   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.979   2.463   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.386   1.903   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.965   3.385   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       3.837  -3.837   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.300  -3.761   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.441  -5.040   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       1.655  -2.380   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.128  -2.177   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.811  -3.398   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -2.337  -3.195   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -0.223  -4.821   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -1.162  -6.042   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -0.574  -7.466   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -2.688  -5.839   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       2.765  -1.065   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   35   48                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   32   48                                             
CONECT    9    8   10   37                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   30                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26                                                            
CONECT   28   15   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   11   31   32                                             
CONECT   31   30                                                            
CONECT   32   30    8   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    5   36                                                  
CONECT   36   35                                                            
CONECT   37    9   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   48                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   40    5    8                                                  
MASTER        0    0    0    0    0    0    0    0   48    0  106    0
END

View in JSmol

Synonyms

Value	Source
Methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0,.0,.0,]nonadec-10-ene-17-carboxylic acid	Generator
Methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylic acid	Generator

Chemical Formula

C₃₂H₄₄O₁₆

Average Mass

684.6880 Da

Monoisotopic Mass

684.26294 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C12OCC34C1C(OC(=O)CC(C)C)C(=O)OC3CC1C(C)C=C(OC3OC(CO)C(O)C(O)C3O)C(=O)C1(C)C4C(O)C2O

InChI Identifier

InChI=1S/C32H44O16/c1-11(2)6-17(34)48-22-24-31-10-44-32(24,29(42)43-5)26(40)21(38)23(31)30(4)13(8-16(31)47-27(22)41)12(3)7-14(25(30)39)45-28-20(37)19(36)18(35)15(9-33)46-28/h7,11-13,15-16,18-24,26,28,33,35-38,40H,6,8-10H2,1-5H3

InChI Key

NLCZJLRVAIBIDP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Brucea javanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

C-20 quassinoid skeleton
Quassinoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Naphthopyran
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Naphthalene
Furopyran
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Delta valerolactone
Fatty acid ester
Cyclohexenone
Delta_valerolactone
Oxepane
Oxane
Pyran
Hydroxy acid
Monosaccharide
Fatty acyl
Tetrahydrofuran
Cyclic alcohol
Furan
Methyl ester
Lactone
Ketone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Carboxylic acid derivative
Acetal
Dialkyl ether
Ether
Carbonyl group
Alcohol
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.19	ALOGPS
logP	-1.7	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.09	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	245.04 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	156.82 m³·mol⁻¹	ChemAxon
Polarizability	67.88 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

85155955

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate (NP0227029)

MOL for NP0227029 (methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate)

3D MOL for NP0227029 (methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate)

3D SDF for NP0227029 (methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate)

3D-SDF for NP0227029 (methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate)

PDB for NP0227029 (methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate)

3D PDB for NP0227029 (methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate)

SMILES for NP0227029 (methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate)

INCHI for NP0227029 (methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate)

Structure for NP0227029 (methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate)

3D Structure for NP0227029 (methyl 15,16-dihydroxy-9,13-dimethyl-3-[(3-methylbutanoyl)oxy]-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate)