NP-MRD: Showing NP-Card for Meliazedarine O (NP0331865)

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Record Information

Version

2.0

Created at

2023-09-26 21:28:32 UTC

Updated at

2024-09-03 04:17:15 UTC

NP-MRD ID

NP0331865

Natural Product DOI

https://doi.org/10.57994/0971

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Meliazedarine O

Description

Meliazedarine O 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. Based on a literature review very few articles have been published on Meliazedarine O.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 09262321282D          

 50 57  0  0  1  0            999 V2000
    4.8165   -1.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5613   -2.5296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3818   -2.6161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9950   -2.0642    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7094   -2.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5376   -3.2838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0895   -3.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9100   -3.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2453   -4.5648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6321   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9177   -4.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2105   -1.8091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7171   -3.3698    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1294   -4.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2320   -4.0372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5674   -4.7909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2260   -1.7759    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7111   -1.1085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3757   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8608    0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5254    1.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0106    1.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6752    2.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1603    3.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9808    3.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3161    2.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8310    1.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5552   -0.2683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3753   -1.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9204   -2.3567    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2705   -2.8649    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442   -1.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5360   -1.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391   -1.4528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9393   -0.6339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2803   -0.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5210   -0.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805    0.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5573   -1.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780   -2.6537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4994   -2.2534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3720   -3.3719    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5771   -3.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8589   -3.1866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6382   -2.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8193   -2.2915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0762   -3.1969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8967   -3.2834    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4116   -3.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9265   -4.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  7 11  1  0  0  0  0
  3 12  1  6  0  0  0
  4 12  1  6  0  0  0
  3 13  1  0  0  0  0
 13  6  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
  2 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 19 28  2  0  0  0  0
 17 29  1  0  0  0  0
 30 29  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 32  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 34 39  1  0  0  0  0
 40 39  1  0  0  0  0
 40 41  1  6  0  0  0
 42 40  1  0  0  0  0
 42 30  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 32 45  1  0  0  0  0
 45 46  1  0  0  0  0
 47 42  1  0  0  0  0
  2 47  1  0  0  0  0
 47 48  1  1  0  0  0
 47 49  1  0  0  0  0
 15 49  1  0  0  0  0
 49 50  2  0  0  0  0
M  END


  Mrv2104 09262321282D          

 50 57  0  0  1  0            999 V2000
    4.8165   -1.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5613   -2.5296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3818   -2.6161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9950   -2.0642    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7094   -2.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5376   -3.2838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0895   -3.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9100   -3.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2453   -4.5648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6321   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9177   -4.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2105   -1.8091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7171   -3.3698    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1294   -4.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2320   -4.0372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5674   -4.7909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2260   -1.7759    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7111   -1.1085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3757   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8608    0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5254    1.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0106    1.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6752    2.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1603    3.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9808    3.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3161    2.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8310    1.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5552   -0.2683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3753   -1.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9204   -2.3567    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2705   -2.8649    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442   -1.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5360   -1.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391   -1.4528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9393   -0.6339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2803   -0.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5210   -0.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805    0.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5573   -1.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780   -2.6537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4994   -2.2534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3720   -3.3719    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5771   -3.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8589   -3.1866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6382   -2.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8193   -2.2915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0762   -3.1969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8967   -3.2834    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4116   -3.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9265   -4.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  7 11  1  0  0  0  0
  3 12  1  6  0  0  0
  4 12  1  6  0  0  0
  3 13  1  0  0  0  0
 13  6  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
  2 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 19 28  2  0  0  0  0
 17 29  1  0  0  0  0
 30 29  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 32  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 34 39  1  0  0  0  0
 40 39  1  0  0  0  0
 40 41  1  6  0  0  0
 42 40  1  0  0  0  0
 42 30  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 32 45  1  0  0  0  0
 45 46  1  0  0  0  0
 47 42  1  0  0  0  0
  2 47  1  0  0  0  0
 47 48  1  1  0  0  0
 47 49  1  0  0  0  0
 15 49  1  0  0  0  0
 49 50  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331865

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@H](OC(=O)\C=C\C3=CC=CC=C3)[C@]3(C)[C@]([H])(C(=O)[C@H](O)[C@@]4(C)[C@@H](C[C@H]5O[C@@]345)C3=COC=C3)[C@]11COC(O)C2(C)[C@@H](C[C@@H]1O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H42O11/c1-19(38)46-25-16-24(39)36-18-45-32(43)33(25,2)23(36)15-26(47-28(40)11-10-20-8-6-5-7-9-20)35(4)30(36)29(41)31(42)34(3)22(21-12-13-44-17-21)14-27-37(34,35)48-27/h5-13,17,22-27,30-32,39,42-43H,14-16,18H2,1-4H3/b11-10+/t22-,23-,24-,25+,26+,27+,30-,31-,32?,33?,34+,35+,36+,37+/m0/s1

> <INCHI_KEY>
JHWAKPYQAQESPR-MOBBBFQNSA-N

> <FORMULA>
C37H42O11

> <MOLECULAR_WEIGHT>
662.732

> <EXACT_MASS>
662.272712172

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
68.66263835779625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4R,5R,6S,8R,10R,11S,12R,14R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-4,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0^{1,14}.0^{2,11}.0^{5,10}.0^{8,10}]henicosan-12-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
2.6601932456666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.88753780303457

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.836672936112402

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8442985587595135

> <JCHEM_POLAR_SURFACE_AREA>
165.26000000000002

> <JCHEM_REFRACTIVITY>
167.62430000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,5R,6S,8R,10R,11S,12R,14R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-4,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0^{1,14}.0^{2,11}.0^{5,10}.0^{8,10}]henicosan-12-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-SEP-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-SEP-23         0                                  
HETATM    1  C   UNK     0       8.991  -3.257   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.514  -4.722   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.046  -4.883   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.191  -3.853   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.524  -4.624   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.204  -6.130   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.234  -7.275   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.765  -7.114   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      15.391  -8.521   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.247  -9.551   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.913  -8.781   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.726  -3.377   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.672  -6.290   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.442  -7.624   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.766  -7.536   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.392  -8.943   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.888  -3.315   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.794  -2.069   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.168  -0.662   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.073   0.583   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.448   1.990   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.353   3.236   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.727   4.643   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.633   5.889   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.164   5.727   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.790   4.320   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.885   3.075   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.636  -0.501   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.301  -2.943   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.451  -4.399   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       4.238  -5.348   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0       3.816  -3.124   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.867  -1.911   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.300  -2.712   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.487  -1.183   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.256  -0.257   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.839  -0.859   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.444   1.272   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.640  -3.470   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.052  -4.954   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       8.399  -4.206   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.294  -6.294   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.811  -6.706   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       3.470  -5.948   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       3.058  -4.465   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       1.529  -4.277   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       7.609  -5.968   0.000  0.00  0.00           C+0
HETATM   48  H   UNK     0       9.140  -6.129   0.000  0.00  0.00           H+0
HETATM   49  C   UNK     0       8.235  -7.375   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       7.329  -8.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17   47                                             
CONECT    3    2    4   12   13                                             
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7                                                       
CONECT   12    3    4                                                       
CONECT   13    3    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   49                                                  
CONECT   16   15                                                            
CONECT   17    2   18   29                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   19                                                            
CONECT   29   17   30                                                       
CONECT   30   29   31   32   42                                             
CONECT   31   30                                                            
CONECT   32   30   33   34   45                                             
CONECT   33   32                                                            
CONECT   34   32   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   34   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   30   43   47                                             
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   32   46                                                  
CONECT   46   45                                                            
CONECT   47   42    2   48   49                                             
CONECT   48   47                                                            
CONECT   49   47   15   50                                                  
CONECT   50   49                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  114    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₄₂O₁₁

Average Mass

662.7320 Da

Monoisotopic Mass

662.27271 Da

IUPAC Name

(1S,2R,4R,5R,6S,8R,10R,11S,12R,14R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-4,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0^{1,14}.0^{2,11}.0^{5,10}.0^{8,10}]henicosan-12-yl (2E)-3-phenylprop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@H](OC(=O)\C=C\C3=CC=CC=C3)[C@]3(C)[C@]([H])(C(=O)[C@H](O)[C@@]4(C)[C@@H](C[C@H]5O[C@@]345)C3=COC=C3)[C@]11COC(O)C2(C)[C@@H](C[C@@H]1O)OC(C)=O

InChI Identifier

InChI=1S/C37H42O11/c1-19(38)46-25-16-24(39)36-18-45-32(43)33(25,2)23(36)15-26(47-28(40)11-10-20-8-6-5-7-9-20)35(4)30(36)29(41)31(42)34(3)22(21-12-13-44-17-21)14-27-37(34,35)48-27/h5-13,17,22-27,30-32,39,42-43H,14-16,18H2,1-4H3/b11-10+/t22-,23-,24-,25+,26+,27+,30-,31-,32?,33?,34+,35+,36+,37+/m0/s1

InChI Key

JHWAKPYQAQESPR-MOBBBFQNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	15521328343@163.com	Not Available	Not Available	2023-09-26	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	15521328343@163.com	Not Available	Not Available	2023-09-26	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	15521328343@163.com	Not Available	Not Available	2023-09-26	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	15521328343@163.com	Not Available	Not Available	2023-09-26	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	15521328343@163.com	Not Available	Not Available	2023-09-26	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	15521328343@163.com	Not Available	Not Available	2023-09-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	15521328343@163.com	Not Available	Not Available	2023-09-26	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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
Thromboxane
Steroid ester
Eicosanoid
Steroid
Naphthopyran
Cinnamic acid ester
Fatty alcohol ester
Cinnamic acid or derivatives
Secoiridoid-skeleton
Naphthalene
Fatty acid ester
Fatty acyl
Benzenoid
Pyran
Oxane
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Acyloin
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Furan
Cyclic alcohol
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	2.66	ChemAxon
pKa (Strongest Acidic)	11.84	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	165.26 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	167.62 m³·mol⁻¹	ChemAxon
Polarizability	68.66 Å³	ChemAxon
Number of Rings	8	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

Showing NP-Card for Meliazedarine O (NP0331865)

MOL for NP0331865 (Meliazedarine O)

3D MOL for NP0331865 (Meliazedarine O)

3D SDF for NP0331865 (Meliazedarine O)

3D-SDF for NP0331865 (Meliazedarine O)

PDB for NP0331865 (Meliazedarine O)

3D PDB for NP0331865 (Meliazedarine O)

SMILES for NP0331865 (Meliazedarine O)

INCHI for NP0331865 (Meliazedarine O)

Structure for NP0331865 (Meliazedarine O)

3D Structure for NP0331865 (Meliazedarine O)