NP-MRD: Showing NP-Card for (1r,4r,5r,7s,8r,9r,10r,11s,12s)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate (NP0223825)

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Record Information

Version

1.0

Created at

2022-09-06 02:01:56 UTC

Updated at

2022-09-06 02:01:56 UTC

NP-MRD ID

NP0223825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4r,5r,7s,8r,9r,10r,11s,12s)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate

Description

(1R,4R,5R,7S,8R,9R,10R,11S,12S)-5,7-bis(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]Dodecan-11-yl 2-methylpropanoate 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. (1r,4r,5r,7s,8r,9r,10r,11s,12s)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate is found in Melia azedarach. Based on a literature review very few articles have been published on (1R,4R,5R,7S,8R,9R,10R,11S,12S)-5,7-bis(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]Dodecan-11-yl 2-methylpropanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204012D          

 49 53  0  0  1  0            999 V2000
    1.6541   -4.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -3.4800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9716   -2.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2677   -1.8252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6452   -2.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8492   -1.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269   -0.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2005   -1.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4175   -2.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -1.5274    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4863   -2.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3108   -2.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382   -3.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8542   -3.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2041   -2.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3071   -0.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6570   -0.2442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6759    0.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    1.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0261    2.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9111    0.8779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3713    0.8779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3291    1.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9733    2.4100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5911    2.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460    2.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8862    2.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6523    1.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5210   -1.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8570   -1.8274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713   -2.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4334   -1.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804   -3.0653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6751    0.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5097   -0.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691    0.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7720   -0.9547    0.0000 O   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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 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
 13 17  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  0  0  0
 36 34  1  6  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 39 44  1  0  0  0  0
 44 45  1  0  0  0  0
 34 45  1  0  0  0  0
 45 46  1  6  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  2  0  0  0  0
M  END


  Mrv1652309062204012D          

 49 53  0  0  1  0            999 V2000
    1.6541   -4.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -3.4800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9716   -2.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2677   -1.8252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6452   -2.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8492   -1.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269   -0.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2005   -1.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4175   -2.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -1.5274    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4863   -2.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3108   -2.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382   -3.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8542   -3.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2041   -2.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3071   -0.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6570   -0.2442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6759    0.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    1.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0261    2.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9111    0.8779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3713    0.8779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3291    1.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9733    2.4100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5911    2.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460    2.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8862    2.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6523    1.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5210   -1.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8570   -1.8274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713   -2.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4334   -1.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804   -3.0653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6751    0.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5097   -0.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691    0.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7720   -0.9547    0.0000 O   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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 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
 13 17  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  0  0  0
 36 34  1  6  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 39 44  1  0  0  0  0
 44 45  1  0  0  0  0
 34 45  1  0  0  0  0
 45 46  1  6  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0223825

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@@H]1[C@]2(C)[C@@H]3[C@@H](OC[C@]3(C)[C@@H](C[C@@H]2OC(C)=O)OC(C)=O)[C@@H](OC(=O)C(C)C)[C@@]1(C)C1=C(C)[C@@H](C[C@@H]1OC(C)=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C37H50O12/c1-18(2)34(42)49-33-31-32-35(7,17-45-31)27(47-21(5)39)15-28(48-22(6)40)36(32,8)26(14-29(41)43-10)37(33,9)30-19(3)24(23-11-12-44-16-23)13-25(30)46-20(4)38/h11-12,16,18,24-28,31-33H,13-15,17H2,1-10H3/t24-,25+,26-,27-,28+,31-,32-,33-,35-,36+,37-/m1/s1

> <INCHI_KEY>
OVMLYMIACVFLEH-TYDWBPNSSA-N

> <FORMULA>
C37H50O12

> <MOLECULAR_WEIGHT>
686.795

> <EXACT_MASS>
686.33022705

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
69.96749987214773

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4R,5R,7S,8R,9R,10R,11S,12S)-5,7-bis(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-11-yl 2-methylpropanoate

> <JCHEM_LOGP>
3.150098814666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.857115878933511

> <JCHEM_POLAR_SURFACE_AREA>
153.87

> <JCHEM_REFRACTIVITY>
172.42289999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,5R,7S,8R,9R,10R,11S,12S)-5,7-bis(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-11-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       3.088  -7.696   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.001  -6.496   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.814  -4.809   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.500  -3.407   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.071  -3.826   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.835  -2.168   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.589  -1.263   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.585  -2.890   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.050  -1.317   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.374  -2.797   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.779  -4.408   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.913  -2.851   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.774  -4.128   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.313  -4.182   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.738  -5.662   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.461  -6.523   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.248  -5.575   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.440  -1.404   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.226  -0.456   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.262   1.296   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.002   2.473   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.049   4.250   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.701   1.639   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.750   0.268   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.693   1.639   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.614   3.372   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.817   4.499   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.103   4.024   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.699   3.929   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.654   5.582   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.157   0.895   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.633   2.359   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.173   2.359   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.649   0.895   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.818   2.058   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.403  -0.010   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.242  -1.542   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.706  -3.068   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.971  -2.168   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       7.200  -3.411   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       8.720  -4.132   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.142  -3.335   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       8.923  -5.722   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       7.217  -1.263   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       7.056   0.268   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       8.727   0.405   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      10.285  -0.148   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      11.516   0.839   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      10.774  -1.782   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   37                                                  
CONECT    7    6    8    9   24                                             
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
CONECT   18   12   19                                                       
CONECT   19   18    9   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    7   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   24   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36   45                                             
CONECT   35   34                                                            
CONECT   36   34   31   37                                                  
CONECT   37   36    6   38   39                                             
CONECT   38   37                                                            
CONECT   39   37   40   44                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   39   45                                                       
CONECT   45   44   34   46                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  106    0
END

View in JSmol

Synonyms

Value	Source
(1R,4R,5R,7S,8R,9R,10R,11S,12S)-5,7-Bis(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0,]dodecan-11-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₃₇H₅₀O₁₂

Average Mass

686.7950 Da

Monoisotopic Mass

686.33023 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@@H]1[C@]2(C)[C@@H]3[C@@H](OC[C@]3(C)[C@@H](C[C@@H]2OC(C)=O)OC(C)=O)[C@@H](OC(=O)C(C)C)[C@@]1(C)C1=C(C)[C@@H](C[C@@H]1OC(C)=O)C1=COC=C1

InChI Identifier

InChI=1S/C37H50O12/c1-18(2)34(42)49-33-31-32-35(7,17-45-31)27(47-21(5)39)15-28(48-22(6)40)36(32,8)26(14-29(41)43-10)37(33,9)30-19(3)24(23-11-12-44-16-23)13-25(30)46-20(4)38/h11-12,16,18,24-28,31-33H,13-15,17H2,1-10H3/t24-,25+,26-,27-,28+,31-,32-,33-,35-,36+,37-/m1/s1

InChI Key

OVMLYMIACVFLEH-TYDWBPNSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melia azedarach	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Pentacarboxylic acid or derivatives
Furan
Heteroaromatic compound
Tetrahydrofuran
Methyl ester
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	3.15	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	153.87 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	172.42 m³·mol⁻¹	ChemAxon
Polarizability	69.97 Å³	ChemAxon
Number of Rings	5	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

163195556

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4r,5r,7s,8r,9r,10r,11s,12s)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate (NP0223825)

MOL for NP0223825 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate)

3D MOL for NP0223825 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate)

3D SDF for NP0223825 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate)

3D-SDF for NP0223825 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate)

PDB for NP0223825 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate)

3D PDB for NP0223825 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate)

SMILES for NP0223825 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate)

INCHI for NP0223825 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate)

Structure for NP0223825 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate)

3D Structure for NP0223825 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate)