NP-MRD: Showing NP-Card for (1s,2r,3r,4s,5r,7s,8r,9r,10r,13r,15r)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl (2e)-3-phenylprop-2-enoate (NP0212158)

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Record Information

Version

2.0

Created at

2022-09-05 10:43:50 UTC

Updated at

2022-09-05 10:43:51 UTC

NP-MRD ID

NP0212158

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,4s,5r,7s,8r,9r,10r,13r,15r)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl (2e)-3-phenylprop-2-enoate

Description

(15R,17R)-6alpha-Acetoxy-4alpha-formyl-3alpha-hydroxy-1alpha-(cinnamoyloxy)-7alpha,15-epoxy-4-demethyl-12,13-secomeliacan-13-en-12-oic acid methyl ester 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. (1s,2r,3r,4s,5r,7s,8r,9r,10r,13r,15r)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl (2e)-3-phenylprop-2-enoate is found in Melia azedarach. Based on a literature review very few articles have been published on (15R,17R)-6alpha-Acetoxy-4alpha-formyl-3alpha-hydroxy-1alpha-(cinnamoyloxy)-7alpha,15-epoxy-4-demethyl-12,13-secomeliacan-13-en-12-oic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052212432D          

 48 53  0  0  1  0            999 V2000
    2.7166    3.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3447    2.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955    2.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236    1.5185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4182    1.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2690    0.9655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8971    0.4306    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1303    1.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7149    0.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3126    1.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2037    1.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0381    0.7155    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7823    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9315    1.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7493    1.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1055    1.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5079    0.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8889   -0.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0712   -0.2047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4735   -0.7735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3004   -2.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3426   -0.1224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.9471    1.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4918    0.6890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6410    1.5004    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
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  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
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  9 19  1  0  0  0  0
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  7 21  1  0  0  0  0
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 35 47  1  0  0  0  0
 27 47  1  0  0  0  0
  6 47  1  0  0  0  0
 47 48  1  1  0  0  0
M  END

     RDKit          3D

 92 97  0  0  0  0  0  0  0  0999 V2000
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   -1.4185   -1.5227   -0.3762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5546   -0.9199   -1.5997 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2875   -1.0805   -2.4184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0906   -2.4655   -2.5164 O   0  0  0  0  0  0  0  0  0  0  0  0
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 19 67  1  1
 18 65  1  0
 18 66  1  0
 12 61  1  1
 11 58  1  0
 11 59  1  0
 11 60  1  0
 17 64  1  0
 15 63  1  0
 14 62  1  0
 22 69  1  6
 25 70  1  0
 25 71  1  0
 25 72  1  0
 27 73  1  1
 29 74  1  0
 29 75  1  0
 29 76  1  0
 30 77  1  0
 32 78  1  6
 33 79  1  0
 34 80  1  0
 34 81  1  0
 35 82  1  1
 39 83  1  0
 40 84  1  0
 42 85  1  0
 43 86  1  0
 44 87  1  0
 45 88  1  0
 46 89  1  0
 48 90  1  0
 48 91  1  0
 48 92  1  0
M  END


  Mrv1652309052212432D          

 48 53  0  0  1  0            999 V2000
    2.7166    3.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3447    2.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955    2.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236    1.5185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4182    1.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2690    0.9655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8971    0.4306    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1303    1.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7149    0.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3126    1.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2037    1.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0381    0.7155    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7823    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9315    1.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7493    1.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1055    1.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5079    0.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8889   -0.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0712   -0.2047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4735   -0.7735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -0.3808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9707   -0.6573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8215   -1.4687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4496   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2268   -1.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3004   -2.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3426   -0.1224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5653   -0.3989    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9725   -1.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0706   -0.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667   -1.7381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628    0.1360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8401   -0.1405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0864    0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637    1.2239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0129    2.0353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3848    2.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5340    3.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925    2.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417    1.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3190    1.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4682    0.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455    0.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8736    0.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7244    1.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9471    1.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4918    0.6890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6410    1.5004    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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  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  1  0  0  0
 21 20  1  6  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 27 22  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  6  0  0  0
 30 31  2  0  0  0  0
 28 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 41 46  1  0  0  0  0
 35 47  1  0  0  0  0
 27 47  1  0  0  0  0
  6 47  1  0  0  0  0
 47 48  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0212158

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1[C@@]2(C)[C@H](O[C@@H]3C[C@H](C(C)=C23)C2=COC=C2)[C@H](OC(C)=O)[C@H]2[C@](C)(C=O)[C@H](O)C[C@H](OC(=O)\C=C\C3=CC=CC=C3)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C38H44O10/c1-21-25(24-14-15-45-19-24)16-26-32(21)38(5)27(17-31(43)44-6)37(4)29(48-30(42)13-12-23-10-8-7-9-11-23)18-28(41)36(3,20-39)34(37)33(35(38)47-26)46-22(2)40/h7-15,19-20,25-29,33-35,41H,16-18H2,1-6H3/b13-12+/t25-,26-,27-,28-,29+,33-,34+,35-,36-,37+,38-/m1/s1

> <INCHI_KEY>
PDYSCTLBKPHLJG-CUNMOGCISA-N

> <FORMULA>
C38H44O10

> <MOLECULAR_WEIGHT>
660.76

> <EXACT_MASS>
660.293447617

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
68.94943434574884

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,4S,5R,7S,8R,9R,10R,13R,15R)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0^{3,8}.0^{11,15}]hexadec-11-en-7-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
3.930938679666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.452291866771453

> <JCHEM_PKA_STRONGEST_BASIC>
-2.859473719465121

> <JCHEM_POLAR_SURFACE_AREA>
138.57

> <JCHEM_REFRACTIVITY>
174.35179999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4S,5R,7S,8R,9R,10R,13R,15R)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0^{3,8}.0^{11,15}]hexadec-11-en-7-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.071   6.346   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.243   5.348   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.965   3.833   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.137   2.834   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.514   3.317   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.236   1.802   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.408   0.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.843   2.281   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.935   1.007   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.050   2.069   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.847   3.595   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.405   1.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.794   2.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.072   3.515   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.599   3.718   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.264   2.329   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.148   1.268   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.126  -0.179   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.599  -0.382   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.484  -1.444   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.129  -0.711   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.679  -1.227   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.400  -2.742   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.572  -3.740   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.023  -3.224   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.294  -5.255   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.506  -0.228   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.055  -0.745   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.815  -2.084   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.132  -1.726   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.125  -3.244   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.117   0.254   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.568  -0.262   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.161   1.768   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.612   2.285   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.891   3.799   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.718   4.798   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.997   6.312   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -0.733   4.282   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.011   2.767   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.462   2.251   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -2.741   0.736   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -4.192   0.220   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -5.364   1.219   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -5.086   2.733   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -3.635   3.249   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.785   1.286   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       3.063   2.801   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                                                       
CONECT    6    5    7   47                                                  
CONECT    7    6    8    9   21                                             
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    7   22                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28   47                                                  
CONECT   28   27   29   30   32                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   28   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   47                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   41                                                       
CONECT   47   35   27    6   48                                             
CONECT   48   47                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  106    0
END

View in JSmol

Synonyms

Value	Source
(15R,17R)-6a-Acetoxy-4a-formyl-3a-hydroxy-1a-(cinnamoyloxy)-7a,15-epoxy-4-demethyl-12,13-secomeliacan-13-en-12-Oate methyl ester	Generator
(15R,17R)-6a-Acetoxy-4a-formyl-3a-hydroxy-1a-(cinnamoyloxy)-7a,15-epoxy-4-demethyl-12,13-secomeliacan-13-en-12-Oic acid methyl ester	Generator
(15R,17R)-6alpha-Acetoxy-4alpha-formyl-3alpha-hydroxy-1alpha-(cinnamoyloxy)-7alpha,15-epoxy-4-demethyl-12,13-secomeliacan-13-en-12-Oate methyl ester	Generator
(15R,17R)-6Α-acetoxy-4α-formyl-3α-hydroxy-1α-(cinnamoyloxy)-7α,15-epoxy-4-demethyl-12,13-secomeliacan-13-en-12-Oate methyl ester	Generator
(15R,17R)-6Α-acetoxy-4α-formyl-3α-hydroxy-1α-(cinnamoyloxy)-7α,15-epoxy-4-demethyl-12,13-secomeliacan-13-en-12-Oic acid methyl ester	Generator

Chemical Formula

C₃₈H₄₄O₁₀

Average Mass

660.7600 Da

Monoisotopic Mass

660.29345 Da

IUPAC Name

(1S,2R,3R,4S,5R,7S,8R,9R,10R,13R,15R)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0^{3,8}.0^{11,15}]hexadec-11-en-7-yl (2E)-3-phenylprop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1[C@@]2(C)[C@H](O[C@@H]3C[C@H](C(C)=C23)C2=COC=C2)[C@H](OC(C)=O)[C@H]2[C@](C)(C=O)[C@H](O)C[C@H](OC(=O)\C=C\C3=CC=CC=C3)[C@]12C

InChI Identifier

InChI=1S/C38H44O10/c1-21-25(24-14-15-45-19-24)16-26-32(21)38(5)27(17-31(43)44-6)37(4)29(48-30(42)13-12-23-10-8-7-9-11-23)18-28(41)36(3,20-39)34(37)33(35(38)47-26)46-22(2)40/h7-15,19-20,25-29,33-35,41H,16-18H2,1-6H3/b13-12+/t25-,26-,27-,28-,29+,33-,34+,35-,36-,37+,38-/m1/s1

InChI Key

PDYSCTLBKPHLJG-CUNMOGCISA-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
Naphthofuran
Cinnamic acid or derivatives
Cinnamic acid ester
Tricarboxylic acid or derivatives
Styrene
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Cyclic alcohol
Furan
Heteroaromatic compound
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Carboxylic acid derivative
Aldehyde
Hydrocarbon derivative
Alcohol
Organic oxide
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	3.93	ChemAxon
pKa (Strongest Acidic)	14.45	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	138.57 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	174.35 m³·mol⁻¹	ChemAxon
Polarizability	68.95 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

9506234

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11331284

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,4s,5r,7s,8r,9r,10r,13r,15r)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl (2e)-3-phenylprop-2-enoate (NP0212158)

MOL for NP0212158 ((1s,2r,3r,4s,5r,7s,8r,9r,10r,13r,15r)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0212158 ((1s,2r,3r,4s,5r,7s,8r,9r,10r,13r,15r)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0212158 ((1s,2r,3r,4s,5r,7s,8r,9r,10r,13r,15r)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0212158 ((1s,2r,3r,4s,5r,7s,8r,9r,10r,13r,15r)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0212158 ((1s,2r,3r,4s,5r,7s,8r,9r,10r,13r,15r)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0212158 ((1s,2r,3r,4s,5r,7s,8r,9r,10r,13r,15r)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0212158 ((1s,2r,3r,4s,5r,7s,8r,9r,10r,13r,15r)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0212158 ((1s,2r,3r,4s,5r,7s,8r,9r,10r,13r,15r)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0212158 ((1s,2r,3r,4s,5r,7s,8r,9r,10r,13r,15r)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0212158 ((1s,2r,3r,4s,5r,7s,8r,9r,10r,13r,15r)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadec-11-en-7-yl (2e)-3-phenylprop-2-enoate)