NP-MRD: Showing NP-Card for methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate (NP0283276)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 10:28:24 UTC

Updated at

2022-09-09 10:28:24 UTC

NP-MRD ID

NP0283276

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate

Description

Methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadecan-18-yl]acetate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate is found in Xylocarpus granatum. Methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadecan-18-yl]acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241511082D          

 47 52  0  0  0  0            999 V2000
   -3.5322    0.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612    1.1828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1214    0.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525   -0.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3504    0.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2193    1.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6234   -0.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4104   -0.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127    0.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3742   -0.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890   -0.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6184   -0.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1964   -1.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5251   -1.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448   -2.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6736   -2.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8357   -1.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4677   -0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -1.5565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163   -2.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1009   -2.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7958   -2.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7991   -0.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3099   -0.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6123    0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1392   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524   -0.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793   -1.1065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2387    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7118    0.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981    1.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5405    2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0519    3.0444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8256    2.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924    1.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8986    0.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1849    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    1.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5585    1.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721    0.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692    0.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3385    1.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6580    2.2065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311    2.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3179    2.7024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174    3.6150    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 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
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 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
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 32 36  1  0  0  0  0
 31 37  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 24 41  1  0  0  0  0
 41 42  1  0  0  0  0
  7 42  1  0  0  0  0
 11 42  1  0  0  0  0
 42 43  1  0  0  0  0
 39 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
M  END


  Mrv1533004241511082D          

 47 52  0  0  0  0            999 V2000
   -3.5322    0.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612    1.1828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1214    0.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525   -0.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3504    0.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2193    1.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6234   -0.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4104   -0.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127    0.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3742   -0.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890   -0.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6184   -0.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1964   -1.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5251   -1.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448   -2.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6736   -2.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8357   -1.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4677   -0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -1.5565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163   -2.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1009   -2.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7958   -2.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7991   -0.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3099   -0.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6123    0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1392   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524   -0.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793   -1.1065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2387    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7118    0.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981    1.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5405    2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0519    3.0444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8256    2.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924    1.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8986    0.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1849    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    1.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5585    1.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721    0.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692    0.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3385    1.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6580    2.2065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311    2.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3179    2.7024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174    3.6150    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 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
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 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
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 32 36  1  0  0  0  0
 31 37  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 24 41  1  0  0  0  0
 41 42  1  0  0  0  0
  7 42  1  0  0  0  0
 11 42  1  0  0  0  0
 42 43  1  0  0  0  0
 39 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283276

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(O)C1C2(C)CC3(O)C(C2OC(C)=O)C(OC(C)=O)C2(O)C(CC(OC(C)=O)C4(C)C(OC(=O)CC24)C2=COC=C2)C13C

> <INCHI_IDENTIFIER>
InChI=1S/C33H42O14/c1-14(34)44-20-10-19-31(6)24(23(38)28(39)42-7)29(4)13-32(31,40)22(26(29)45-15(2)35)27(46-16(3)36)33(19,41)18-11-21(37)47-25(30(18,20)5)17-8-9-43-12-17/h8-9,12,18-20,22-27,38,40-41H,10-11,13H2,1-7H3

> <INCHI_KEY>
QKTBSFGBXSKROA-UHFFFAOYSA-N

> <FORMULA>
C33H42O14

> <MOLECULAR_WEIGHT>
662.685

> <EXACT_MASS>
662.257456032

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
65.37012768713774

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
-0.5928532519999998

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.30491538664307

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.368953514280346

> <JCHEM_PKA_STRONGEST_BASIC>
-2.888729104288032

> <JCHEM_POLAR_SURFACE_AREA>
205.32999999999996

> <JCHEM_REFRACTIVITY>
153.9265

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate

> <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      -6.593   1.660   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.154   2.208   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.960   1.236   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.205  -0.285   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.521   1.784   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.276   3.304   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.326   0.812   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.164  -0.742   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.633  -1.204   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.397   0.804   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.698  -0.366   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.220  -0.125   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.154  -1.801   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.367  -2.183   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.980  -3.595   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.510  -3.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.124  -5.182   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.427  -2.532   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.740  -1.659   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.644  -2.905   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.017  -4.312   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.922  -5.558   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.485  -4.472   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.358  -0.214   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.312  -1.423   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.876   0.045   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.860  -1.140   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.378  -0.881   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.361  -2.066   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       7.912   0.564   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.929   1.749   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.463   3.193   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.609   4.474   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.563   5.683   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.008   5.148   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.946   3.610   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.411   1.489   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.945   2.934   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.427   2.674   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.909   2.415   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.375   0.971   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.689   1.014   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.632   2.553   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       4.962   4.119   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       3.978   5.304   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       2.460   5.044   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       4.512   6.748   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   42                                                  
CONECT    8    7    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13   42                                             
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   13   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   26   41                                             
CONECT   25   24                                                            
CONECT   26   24   27   37                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   32                                                       
CONECT   37   31   26   38   39                                             
CONECT   38   37                                                            
CONECT   39   37   40   44                                                  
CONECT   40   39   41                                                       
CONECT   41   40   24   42                                                  
CONECT   42   41    7   11   43                                             
CONECT   43   42                                                            
CONECT   44   39   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  104    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0,.0,.0,]octadecan-18-yl]acetic acid	Generator
Methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetic acid	Generator

Chemical Formula

C₃₃H₄₂O₁₄

Average Mass

662.6850 Da

Monoisotopic Mass

662.25746 Da

IUPAC Name

methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate

Traditional Name

methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C(O)C1C2(C)CC3(O)C(C2OC(C)=O)C(OC(C)=O)C2(O)C(CC(OC(C)=O)C4(C)C(OC(=O)CC24)C2=COC=C2)C13C

InChI Identifier

InChI=1S/C33H42O14/c1-14(34)44-20-10-19-31(6)24(23(38)28(39)42-7)29(4)13-32(31,40)22(26(29)45-15(2)35)27(46-16(3)36)33(19,41)18-11-21(37)47-25(30(18,20)5)17-8-9-43-12-17/h8-9,12,18-20,22-27,38,40-41H,10-11,13H2,1-7H3

InChI Key

QKTBSFGBXSKROA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xylocarpus granatum	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
Mexicanolide
Prostaglandin skeleton
Steroid lactone
Eicosanoid
Oxosteroid
2-oxosteroid
3-oxasteroid
Steroid
Pentacarboxylic acid or derivatives
Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Pyran
Fatty acyl
Oxane
Heteroaromatic compound
Cyclic alcohol
Methyl ester
Furan
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	1.74	ALOGPS
logP	-0.59	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	205.33 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	153.93 m³·mol⁻¹	ChemAxon
Polarizability	65.37 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

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 methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate (NP0283276)

MOL for NP0283276 (methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate)

3D MOL for NP0283276 (methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate)

3D SDF for NP0283276 (methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate)

3D-SDF for NP0283276 (methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate)

PDB for NP0283276 (methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate)

3D PDB for NP0283276 (methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate)

SMILES for NP0283276 (methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate)

INCHI for NP0283276 (methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate)

Structure for NP0283276 (methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate)

3D Structure for NP0283276 (methyl 2-hydroxy-2-[4,12,14-tris(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]acetate)