NP-MRD: Showing NP-Card for (1s,3br,4r,5ar,7s,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-2-methoxy-5-[(1s,2s)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl 3-methylbut-2-enoate (NP0217464)

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Record Information

Version

2.0

Created at

2022-09-05 17:49:27 UTC

Updated at

2022-09-05 17:49:27 UTC

NP-MRD ID

NP0217464

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3br,4r,5ar,7s,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-2-methoxy-5-[(1s,2s)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl 3-methylbut-2-enoate

Description

(1R,2S,5S,7R,9R,10R,14S,15S)-9-hydroxy-14-[(2R,3S,5R)-2-methoxy-5-[(1S,2S)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-11-en-5-yl 3-methylbut-2-enoate 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,3br,4r,5ar,7s,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-2-methoxy-5-[(1s,2s)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl 3-methylbut-2-enoate is found in Toona sinensis. Based on a literature review very few articles have been published on (1R,2S,5S,7R,9R,10R,14S,15S)-9-hydroxy-14-[(2R,3S,5R)-2-methoxy-5-[(1S,2S)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-11-en-5-yl 3-methylbut-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052219492D          

 44 48  0  0  1  0            999 V2000
   -0.5092   -3.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8690   -2.6772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4061   -1.9944    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6864   -1.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0350   -0.7121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0618    0.1125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6388    0.5480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893    0.5015    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1784   -0.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4003    1.2290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5168    0.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436    1.7152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -1.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -1.9676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9249   -2.6189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6955   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -3.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3895   -1.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737   -2.8825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1858   -3.0277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9055   -2.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -3.3182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6221   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9024   -4.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3706   -4.8700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7146   -4.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9949   -5.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8070   -5.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4630   -5.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -4.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942   -4.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -3.8037    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9343   -4.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -4.2891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5903   -4.9199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -3.5132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3100   -4.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  0  0  0
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  3 14  1  0  0  0  0
 14 15  1  1  0  0  0
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 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  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  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 24 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 18 43  1  0  0  0  0
 23 43  1  0  0  0  0
 43 44  1  6  0  0  0
M  END


  Mrv1652309052219492D          

 44 48  0  0  1  0            999 V2000
   -0.5092   -3.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8690   -2.6772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4061   -1.9944    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6864   -1.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0350   -0.7121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0618    0.1125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6388    0.5480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893    0.5015    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1784   -0.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4003    1.2290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5168    0.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436    1.7152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -1.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -1.9676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9249   -2.6189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6955   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -3.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3895   -1.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737   -2.8825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1858   -3.0277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9055   -2.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -3.3182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6221   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9024   -4.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3706   -4.8700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7146   -4.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9949   -5.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8070   -5.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4630   -5.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -4.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942   -4.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -3.8037    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9343   -4.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -4.2891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5903   -4.9199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -3.5132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3100   -4.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  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  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 24 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 18 43  1  0  0  0  0
 23 43  1  0  0  0  0
 43 44  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0217464

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1O[C@H](C[C@H]1[C@@H]1CC=C2[C@@]1(C)CC[C@@H]1[C@@]3(C)CC[C@H](OC(=O)C=C(C)C)C(C)(C)[C@@H]3C[C@@H](O)[C@@]21C)[C@H](O)[C@@](C)(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C36H58O8/c1-20(2)16-29(39)44-28-13-15-34(6)25-12-14-33(5)22(21-17-23(43-31(21)42-9)30(40)35(7,41)19-37)10-11-24(33)36(25,8)27(38)18-26(34)32(28,3)4/h11,16,21-23,25-28,30-31,37-38,40-41H,10,12-15,17-19H2,1-9H3/t21-,22-,23+,25+,26-,27+,28-,30-,31+,33-,34+,35-,36-/m0/s1

> <INCHI_KEY>
TXZJJNHNQOUAAI-LQSMXYKHSA-N

> <FORMULA>
C36H58O8

> <MOLECULAR_WEIGHT>
618.852

> <EXACT_MASS>
618.413168828

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
71.31419014336997

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,7R,9R,10R,14S,15S)-9-hydroxy-14-[(2R,3S,5R)-2-methoxy-5-[(1S,2S)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl 3-methylbut-2-enoate

> <JCHEM_LOGP>
4.285545425999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.080539508027297

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.786203141966201

> <JCHEM_PKA_STRONGEST_BASIC>
-0.351813239028849

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
169.51220000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,7R,9R,10R,14S,15S)-9-hydroxy-14-[(2R,3S,5R)-2-methoxy-5-[(1S,2S)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl 3-methylbut-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      -0.950  -6.383   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.622  -4.997   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.758  -3.723   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.281  -2.274   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.065  -1.329   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.115   0.210   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.193   1.023   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.473   0.936   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.200  -0.422   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.747   2.294   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.831   1.662   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.881   3.202   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.209  -2.193   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.781  -3.673   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.594  -3.453   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.290  -4.203   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.885  -7.913   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.892  -9.091   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.400  -8.184   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.924  -9.633   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.440  -9.904   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.931 -10.810   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.184  -8.144   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.322  -8.817   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       4.835  -9.184   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.312  -7.735   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   43                                                  
CONECT   19   18   15   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   43                                                  
CONECT   24   23   25   26   39                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   28   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36   24   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   18   23   44                                             
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,5S,7R,9R,10R,14S,15S)-9-Hydroxy-14-[(2R,3S,5R)-2-methoxy-5-[(1S,2S)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0,.0,]heptadec-11-en-5-yl 3-methylbut-2-enoic acid	Generator

Chemical Formula

C₃₆H₅₈O₈

Average Mass

618.8520 Da

Monoisotopic Mass

618.41317 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@@H]1O[C@H](C[C@H]1[C@@H]1CC=C2[C@@]1(C)CC[C@@H]1[C@@]3(C)CC[C@H](OC(=O)C=C(C)C)C(C)(C)[C@@H]3C[C@@H](O)[C@@]21C)[C@H](O)[C@@](C)(O)CO

InChI Identifier

InChI=1S/C36H58O8/c1-20(2)16-29(39)44-28-13-15-34(6)25-12-14-33(5)22(21-17-23(43-31(21)42-9)30(40)35(7,41)19-37)10-11-24(33)36(25,8)27(38)18-26(34)32(28,3)4/h11,16,21-23,25-28,30-31,37-38,40-41H,10,12-15,17-19H2,1-9H3/t21-,22-,23+,25+,26-,27+,28-,30-,31+,33-,34+,35-,36-/m0/s1

InChI Key

TXZJJNHNQOUAAI-LQSMXYKHSA-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
Toona sinensis	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
Dihydroxy bile acid, alcohol, or derivatives
24-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid ester
Hydroxysteroid
7-hydroxysteroid
Steroid
Fatty acid ester
Fatty acyl
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

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

163103293

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3br,4r,5ar,7s,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-2-methoxy-5-[(1s,2s)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl 3-methylbut-2-enoate (NP0217464)

MOL for NP0217464 ((1s,3br,4r,5ar,7s,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-2-methoxy-5-[(1s,2s)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl 3-methylbut-2-enoate)

3D MOL for NP0217464 ((1s,3br,4r,5ar,7s,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-2-methoxy-5-[(1s,2s)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl 3-methylbut-2-enoate)

3D SDF for NP0217464 ((1s,3br,4r,5ar,7s,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-2-methoxy-5-[(1s,2s)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl 3-methylbut-2-enoate)

3D-SDF for NP0217464 ((1s,3br,4r,5ar,7s,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-2-methoxy-5-[(1s,2s)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl 3-methylbut-2-enoate)

PDB for NP0217464 ((1s,3br,4r,5ar,7s,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-2-methoxy-5-[(1s,2s)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl 3-methylbut-2-enoate)

3D PDB for NP0217464 ((1s,3br,4r,5ar,7s,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-2-methoxy-5-[(1s,2s)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl 3-methylbut-2-enoate)

SMILES for NP0217464 ((1s,3br,4r,5ar,7s,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-2-methoxy-5-[(1s,2s)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl 3-methylbut-2-enoate)

INCHI for NP0217464 ((1s,3br,4r,5ar,7s,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-2-methoxy-5-[(1s,2s)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl 3-methylbut-2-enoate)

Structure for NP0217464 ((1s,3br,4r,5ar,7s,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-2-methoxy-5-[(1s,2s)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl 3-methylbut-2-enoate)

3D Structure for NP0217464 ((1s,3br,4r,5ar,7s,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-2-methoxy-5-[(1s,2s)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl 3-methylbut-2-enoate)